770:: (i) Foods containing at least 1.7 g per serving of plant stanol esters, eaten twice a day with meals for a total daily intake of at least 3.4 g, as part of a diet low in saturated fat and cholesterol, may reduce the risk of heart disease. A serving of supplies ___grams of plant stanol esters. Reviewing clinical trials involving phytosterol supplementation, the FDA concluded that when consumed in the range of 1 to 3 grams in enriched foods, phytosterols resulted in statistically significant (5-15%) reductions in blood LDL cholesterol levels relative to placebo. The FDA also concluded that a daily dietary intake of 2 grams a day of phytosterols (expressed as non-esterified phytosterols) is required to demonstrate a relationship between phytosterol consumption and cholesterol lowering for reduced CVD risk.
851:, a rare genetic disorder which results in a 50- to 100-fold increase in blood plant sterol levels and is associated with rapid development of coronary atherosclerosis. Phytosterolaemia has been linked to mutations in the ABCG5/G8 proteins which pump plant sterols out of enterocytes and hepatocytes into the lumen and bile ducts, respectively. Plant sterol levels in the blood have been shown to be positively, negatively or not associated with CVD risk, depending on the study population investigated.
195:
31:
265:
100:
279:
237:
223:
298:
251:
209:
312:
825:. Phytosterols reduce cholesterol levels by competing with cholesterol absorption in the gut via one or several possible mechanisms, an effect that complements statins. Phytosterols further reduce cholesterol levels by about 9% to 17% in statin users. The type or dose of statin does not appear to affect the cholesterol-lowering efficacy of phytosterols.
787:
material: "Plant sterols help reduce cholesterol." This statement when used, shall be shown in letters up to twice the size and prominence as those of the primary statement. "High cholesterol is a risk factor for heart disease." This statement when used, shall be shown in letters up to the same size and prominence as those of the primary statement.
871:
of 0.6 to 2.5 g/day showed no difference between the two forms on total cholesterol, LDL cholesterol, HDL cholesterol, or triglyceride levels. Trials looking at high doses (> 4 g/day) of plant sterols or stanols are very limited, and none have yet to be completed comparing the same high dose of plant sterol to plant stanol.
810:(CVD) and overall mortality under well-defined circumstances, the evidence has been inconsistent for phytosterol-enriched foods or supplements to lower risk of CVD, with two reviews indicating no or marginal effect, and another review showing evidence for use of dietary phytosterols to attain a cholesterol-lowering effect.
766:: (i) Foods containing at least 0.65 g per serving of plant sterol esters, eaten twice a day with meals for a daily total intake of at least 1.3 g, as part of a diet low in saturated fat and cholesterol, may reduce the risk of heart disease. A serving of supplies ___grams of vegetable oil sterol esters.
2261:
Assmann, Gerd; Cullen, Paul; Erbey, John; Ramey, Dena R.; Kannenberg, Frank; Schulte, Helmut (2006). "Plasma sitosterol elevations are associated with an increased incidence of coronary events in men: Results of a nested case-control analysis of the
Prospective Cardiovascular Münster (PROCAM) study".
781:
reviewed the evidence of 84 randomized controlled trials published between 1994 and 2007 involving phytosterol supplementation. An average 8.8% reduction in LDL-cholesterol was observed at a mean intake of 2 grams per day. Health Canada concluded that sufficient scientific evidence exists to support
1755:
Gylling, H; Plat, J; Turley, S; Ginsberg, H. N; Ellegård, L; Jessup, W; Jones, P. J; Lütjohann, D; Maerz, W; Masana, L; Silbernagel, G; Staels, B; Borén, J; Catapano, A. L; De Backer, G; Deanfield, J; Descamps, O. S; Kovanen, P. T; Riccardi, G; Tokgözoglu, L; Chapman, M. J; European
Atherosclerosis
870:
to lower cholesterol continues to be a hotly debated topic. Plant sterols and stanols, when compared head-to-head in clinical trials, have been shown to equally reduce cholesterol levels. A meta-analysis of 14 randomized, controlled trials comparing plant sterols to plant stanols directly at doses
742:
can be reduced on average by 7 to 10.5% if a person consumes 1.5 to 2.4 grams of plant sterols and stanols per day, an effect usually established within 2–3 weeks. Longer-term studies extending up to 85 weeks showed that the cholesterol-lowering effect could be sustained. Based on this and other
899:
predominate. Sitosterol regulates membrane fluidity and permeability in a similar manner to cholesterol in mammalian cell membranes. Plant sterols can also modulate the activity of membrane-bound enzymes. Phytosterols are also linked to plant adaptation to temperature and plant immunity against
786:
individuals: Primary statement: " of provides X% of the daily amount* of plant sterols shown to help reduce/lower cholesterol in adults." Two additional statements that could be used in combination or alone, adjacent to the primary statement, without any intervening printed, written or graphic
874:
The debate regarding sterol vs. stanol safety is centered on their differing intestinal absorption and resulting plasma concentrations. Phytostanols have a lower estimated intestinal absorption rate (0.02 - 0.3%) than phytosterols (0.4 - 5%) and consequently blood phytostanol concentration is
360:
The intake of naturally occurring phytosterols ranges between ~200–300 mg/day depending on eating habits. Specially designed vegetarian experimental diets have been produced yielding upwards of 700 mg/day. The most commonly occurring phytosterols in the human diet are β-sitosterol,
1388:
Andersson, S W; Skinner, J; Ellegård, L; Welch, A A; Bingham, S; Mulligan, A; Andersson, H; Khaw, K-T (2004). "Intake of dietary plant sterols is inversely related to serum cholesterol concentration in men and women in the EPIC Norfolk population: A cross-sectional study".
2190:
Fassbender, Klaus; Lütjohann, Dieter; Dik, Miranda G.; Bremmer, Marijke; König, Jochem; Walter, Silke; Liu, Yang; Letièmbre, Maryse; Von
Bergmann, Klaus (2008). "Moderately elevated plant sterol levels are associated with reduced cardiovascular risk—The LASA study".
919:
Moreau, Robert A.; Nyström, Laura; Whitaker, Bruce D.; Winkler-Moser, Jill K.; Baer, David J.; Gebauer, Sarah K.; Hicks, Kevin B. (2018). "Phytosterols and their derivatives: Structural diversity, distribution, metabolism, analysis, and health-promoting uses".
1483:"Plant Sterols and Blood Cholesterol - Scientific substantiation of a health claim related to plant sterols and lower/reduced blood cholesterol and reduced risk of (coronary) heart disease pursuant to Article 14 of Regulation (EC) No 1924/2006[1]"
1512:
2498:
Talati, Ripple; Sobieraj, Diana M.; Makanji, Sagar S.; Phung, Olivia J.; Coleman, Craig I. (2010). "The
Comparative Efficacy of Plant Sterols and Stanols on Serum Lipids: A Systematic Review and Meta-Analysis".
356:
products highlighting phytosterol content. Cereal products, vegetables, fruit and berries, which are not as rich in phytosterols, may also be significant sources of phytosterols due to their higher intakes.
1838:
Trautwein, Elke A.; Duchateau, Guus S. M. J. E.; Lin, Yuguang; Mel'nikov, Sergey M.; Molhuizen, Henry O.F.; Ntanios, Fady Y. (2003). "Proposed mechanisms of cholesterol-lowering action of plant sterols".
813:
Coadministration of statins with phytosterol-enriched foods increases the cholesterol-lowering effect of phytosterols, again without any proof of clinical benefit and with anecdotal evidence of potential
5987:
172:(ergosta-5,7,22-trien-3β-ol). Important: Ergosterol is not a plant sterol. Ergosterol is a component of fungal cell membranes, serving the same function in fungi that cholesterol serves in animal cells.
2155:
Strandberg, Timo E.; Gylling, Helena; Tilvis, Reijo S.; Miettinen, Tatu A. (2010). "Serum plant and other noncholesterol sterols, cholesterol metabolism and 22-year mortality among middle-aged men".
2226:
Rajaratnam, Radhakrishnan A; Gylling, Helena; Miettinen, Tatu A (2000). "Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women".
743:
efficacy data, the EFSA scientific panel provided the following health advisory: "Plant sterols have been shown to lower/reduce blood cholesterol. Blood cholesterol lowering may reduce the risk of
111:(saturation). They are divided into 4,4-dimethyl phytosterols, 4-monomethyl phytosterols, and 4-desmethyl phytosterols based on the location of methyl groups at the carbon-4 position. Stanols are
799:
levels was first demonstrated in humans in 1953. From 1954 to 1982, phytosterols were subsequently marketed as a pharmaceutical under the name
Cytellin as a treatment for elevated cholesterol.
1901:
Scholle, JM; Baker, WL; Talati, R; Coleman, CI (2009). "The effect of adding plant sterols or stanols to statin therapy in hypercholesterolemic patients: Systematic review and meta-analysis".
1069:"Effects of Phytosterols supplementation on blood glucose, glycosylated hemoglobin (HbA1c) and insulin levels in humans: a systematic review and meta-analysis of randomized controlled trials"
2422:
O'Neill, F.H.; Brynes, A.; Mandeno, R.; Rendell, N.; Taylor, G.; Seed, M.; Thompson, G.R. (2004). "Comparison of the effects of dietary plant sterol and stanol esters on lipid metabolism".
2375:"Comparison of the effects of plant sterol ester and plant stanol ester-enriched margarines in lowering serum cholesterol concentrations in hypercholesterolaemic subjects on a low-fat diet"
1516:
782:
a relationship between phytosterol consumption and blood cholesterol lowering. Based on this evidence, Health Canada approved the following statements for qualifying foods intended for
64:. More than 250 sterols and related compounds have been identified. Free phytosterols extracted from oils are insoluble in water, relatively insoluble in oil, and soluble in alcohols.
6201:
836:
Phytosterols have a long history of safe use, dating back to
Cytellin, the pharmaceutical preparation of phytosterols marketed in the US from 1954 to 1982. Phytosterol esters have
5980:
1433:
1018:
Genser, B.; Silbernagel, G.; De Backer, G.; Bruckert, E.; Carmena, R.; Chapman, M. J.; Deanfield, J.; Descamps, O. S.; Rietzschel, E. R.; Dias, K. C.; März, W. (2012).
6211:
2564:
De Smet, E; Mensink, R. P; Plat, J (2012). "Effects of plant sterols and stanols on intestinal cholesterol metabolism: Suggested mechanisms from past to present".
2332:
Pinedo, S.; Vissers, M. N.; Bergmann, K. v.; Elharchaoui, K.; Lutjohann, D.; Luben, R.; Wareham, N. J.; Kastelein, J. J. P.; Khaw, K.-T.; Boekholdt, S. M. (2006).
6206:
5973:
1866:
De Smet, E; Mensink, RP; Plat, J (2012). "Effects of plant sterols and stanols on intestinal cholesterol metabolism: suggested mechanisms from past to present".
1556:
3849:
329:
The richest naturally occurring sources of phytosterols are vegetable oils and products made from them. Sterols can be present in the free form and as
5025:
2752:
6196:
5834:
2297:
Sudhop, Thomas; Gottwald, Britta M.; Von
Bergmann, Klaus (2002). "Serum plant sterols as a potential risk factor for coronary heart disease".
3936:
2026:
Lea, L.J.; Hepburn, P.A. (2006). "Safety evaluation of phytosterol-esters. Part 9: Results of a
European post-launch monitoring programme".
6039:
3982:
2798:
6044:
963:
Akhisa, T.; Kokke, W. (1991). "Naturally occurring sterols and related compounds from plants". In
Patterson, G. W.; Nes, W. D. (eds.).
5261:
3777:
1451:
1067:
Salehi-Sahlabadi A, Varkaneh HK, Shahdadian F, Ghaedi E, Nouri M, Singh A, Farhadnejad H, Găman MA, Hekmatdoost A, Mirmiran P (2020).
844:
were subject to postlaunch monitoring after being introduced to the EU market in 2000, and no unpredicted side effects were reported.
2657:
1986:
854:
The link between plant sterols and CVD or CHD risk is complicated because phytosterol levels reflect cholesterol absorption. (See
6191:
4604:
3842:
1171:
Moreau RA, Hicks KB (2004). "The in vitro hydrolysis of phytosterol conjugates in food matrices by mammalian digestive enzymes".
6373:
5092:
345:
and fats, without, however, changing their relative composition. Sterols are therefore a useful tool in checking authenticity.
990:
6186:
5803:
5208:
4419:
361:
campesterol and stigmasterol, which account for about 65%, 30% and 3% of diet contents, respectively. The most common plant
6530:
2459:"Unesterified plant sterols and stanols lower LDL-cholesterol concentrations equivalently in hypercholesterolemic persons"
2063:
Silbernagel, G.; Fauler, G.; Renner, W.; Landl, E. M.; Hoffmann, M. M.; Winkelmann, B. R.; Boehm, B. O.; Marz, W. (2008).
1987:"The New Low-Cholesterol Diet: Plant Sterols and Stanols: What are sterols and stanols, and does anyone like to eat them?"
6137:
5018:
3254:
2745:
2028:
837:
756:
2334:"Plasma levels of plant sterols and the risk of coronary artery disease: The prospective EPIC-Norfolk Population Study"
6221:
6116:
6088:
3835:
3804:
828:
Because of their cholesterol reducing properties, some manufacturers are using sterols or stanols as a food additive.
1944:
Katan, M. B.; Grundy, S. M.; Jones, P.; Law, M.; Miettinen, T.; Paoletti, R.; Stresa
Workshop, Participants (2003).
5827:
4744:
2065:"The relationships of cholesterol metabolism and plasma plant sterols with the severity of coronary artery disease"
1497:
342:
6450:
6383:
6216:
6111:
6106:
5130:
5125:
5120:
5114:
3929:
3798:
2601:"Connecting growth and defense: The emerging roles of brassinosteroids and gibberellins in plant innate immunity"
2106:"The associations of cholesterol metabolism and plasma plant sterols with all-cause and cardiovascular mortality"
1757:
1468:"Blood cholesterol reduction health claims on phytosterols can now be judged against EFSA new scientific advice"
1216:"Estimation of plant sterol and cholesterol intake in Finland: Quality of new values and their effect on intake"
6077:
5585:
5507:
4707:
3975:
2791:
2104:
Silbernagel, G.; Fauler, G.; Hoffmann, M. M.; Lutjohann, D.; Winkelmann, B. R.; Boehm, B. O.; Marz, W. (2010).
5560:
1306:"Divergent changes in serum sterols during a strict uncooked vegan diet in patients with rheumatoid arthritis"
75:-lowering effects from long-term consumption of phytosterols, there is insufficient evidence for an effect on
6325:
6276:
1758:"Plant sterols and plant stanols in the management of dyslipidaemia and prevention of cardiovascular disease"
6535:
6525:
6155:
5051:
5011:
4307:
2738:
1214:
Valsta, L. M.; Lemström, A.; Ovaskainen, M.-L.; Lampi, A.-M.; Toivo, J.; Korhonen, T.; Piironen, V. (2007).
807:
744:
180:
Esterification of the hydroxyl group at carbon 3 with fatty/organic acids or carbohydrates results in plant
6271:
6425:
6364:
6244:
6174:
6003:
5165:
4871:
4469:
4429:
4424:
3209:
365:
in the human diet are sitostanol and campestanol, which combined make up about 5% of dietary phytosterol.
161:
Removing carbon 24 and hydrogens from carbons 22 and 23, and inverting the stereochemistry at C-24 yields
76:
2776:
194:
6520:
6132:
6101:
5820:
5135:
5106:
5071:
5066:
4807:
3056:
2650:
891:
cells, which contain only one major sterol, plant cells synthesize an array of sterol mixtures in which
107:
They have a fused polycyclic structure and vary in carbon side chains and / or presence or absence of a
2009:
6485:
5944:
5914:
6435:
6330:
6308:
5939:
5575:
5502:
5253:
4840:
4739:
4734:
4597:
4514:
4284:
3922:
3082:
2600:
783:
6415:
5954:
5883:
5349:
5316:
5155:
4622:
4128:
3968:
2784:
264:
84:
80:
5965:
5934:
6281:
6011:
4196:
3867:
2704:
2404:
1926:
1598:
1414:
1370:
1196:
1153:
68:
6298:
5873:
1946:"Efficacy and Safety of Plant Stanols and Sterols in the Management of Blood Cholesterol Levels"
278:
236:
222:
6254:
5555:
5541:
5145:
4904:
4889:
4881:
4702:
4679:
4378:
3859:
3821:
2622:
2581:
2516:
2480:
2439:
2396:
2355:
2314:
2279:
2243:
2208:
2172:
2137:
2086:
2045:
1967:
1918:
1883:
1820:
1779:
1737:
1683:
1639:
1590:
1447:
1406:
1362:
1327:
1286:
1237:
1188:
1145:
1137:
1118:"Health benefits of 4,4-dimethyl phytosterols: an exploration beyond 4-desmethyl phytosterols"
1098:
1049:
945:
937:
819:
739:
338:
4772:
1539:"Food Labeling; Health Claim; Phytosterols and Risk of Coronary Heart Disease; Proposed Rule"
6072:
5281:
4802:
4729:
4721:
4208:
4099:
3396:
3172:
3112:
2643:
2612:
2573:
2543:
2508:
2470:
2431:
2386:
2345:
2306:
2271:
2235:
2200:
2164:
2127:
2117:
2076:
2037:
1957:
1910:
1875:
1848:
1810:
1769:
1727:
1719:
1673:
1629:
1582:
1439:
1398:
1354:
1317:
1276:
1268:
1227:
1180:
1129:
1088:
1080:
1039:
1031:
929:
330:
297:
250:
208:
6034:
5909:
5477:
5417:
5286:
5150:
4954:
4926:
4850:
4590:
4444:
4439:
4434:
4389:
3515:
3430:
3388:
2896:
2690:
2204:
2168:
1774:
841:
815:
572:
311:
72:
4777:
396:
200:
119:
34:
2635:
1538:
6495:
6480:
6462:
6096:
5878:
5857:
5745:
5728:
5690:
5492:
5467:
5381:
5368:
5306:
5076:
4948:
4932:
4876:
4449:
4319:
4275:
3781:
3735:
3648:
3643:
3633:
3610:
3572:
3562:
3143:
2694:
2670:
2132:
2105:
1732:
1707:
1281:
1256:
1093:
1068:
1044:
1019:
848:
482:
381:
270:
162:
88:
2547:
2435:
2239:
1708:"Controversial role of plant sterol esters in the management of hypercholesterolaemia"
1358:
1116:
Zhang, Tao; Liu, Ruijie; Chang, Ming; Jin, Qingzhe; Zhang, Hui; Wang, Xingguo (2020).
6514:
6430:
6059:
5904:
5710:
5705:
5700:
5685:
5647:
5622:
5526:
5482:
5458:
5324:
5291:
5276:
5271:
5213:
5188:
5183:
5178:
5140:
5042:
5034:
4999:
4899:
4855:
4827:
4544:
4481:
4204:
4156:
3726:
3692:
3687:
3638:
2868:
2762:
1157:
818:. Statins work by reducing cholesterol synthesis via inhibition of the rate-limiting
778:
696:
407:
349:
112:
2408:
2373:
Hallikainen, M A; Sarkkinen, E S; Gylling, H; Erkkilä, A T; Uusitupa, M I J (2000).
1930:
1513:"Health claims: plant sterol/stanol esters and risk of coronary heart disease (CHD)"
1498:"Health claims: plant sterol/stanol esters and risk of coronary heart disease (CHD)"
1467:
1418:
1374:
30:
6420:
6410:
5949:
5929:
5720:
5657:
5627:
5497:
5441:
5301:
5266:
5239:
4894:
4812:
4792:
4759:
4631:
4509:
4315:
4260:
4091:
4009:
3880:
3740:
3658:
3577:
3567:
3510:
3493:
3478:
3447:
3407:
3377:
3303:
2982:
2962:
2709:
1914:
1602:
1482:
1200:
896:
762:
634:
413:
391:
284:
242:
228:
181:
141:
61:
45:
933:
2275:
1020:"Plant sterols and cardiovascular disease: A systematic review and meta-analysis"
847:
A potential safety concern regarding phytosterol consumption is in patients with
154:
By hydrogenating the double bond between carbons 5 and 6 and removing carbon 24,
6351:
6340:
6335:
6313:
6303:
6236:
5996:
5924:
5899:
5862:
5750:
5680:
5673:
5668:
5639:
5617:
5536:
5519:
5386:
5203:
5198:
5193:
4970:
4943:
4787:
4694:
4684:
4659:
4639:
4564:
4549:
4539:
4519:
4296:
4237:
4167:
4138:
4064:
3875:
3712:
3702:
3678:
3663:
3505:
3470:
3354:
3349:
3217:
3181:
3158:
3097:
3046:
3036:
2986:
2906:
2699:
796:
665:
420:
402:
386:
376:
334:
303:
256:
214:
155:
134:
127:
108:
99:
49:
2512:
2350:
2333:
2081:
2064:
1723:
1084:
1035:
6490:
6470:
6440:
6402:
6320:
6293:
6286:
6266:
6259:
6147:
6029:
5919:
5867:
5695:
5605:
5391:
5329:
5218:
4987:
4960:
4937:
4649:
4644:
4554:
4529:
4454:
4347:
4342:
4247:
4232:
4227:
4185:
4053:
3946:
3910:
3900:
3827:
3697:
3615:
3541:
3500:
3488:
3483:
3369:
3359:
3153:
3148:
3101:
2714:
2666:
2041:
1345:
Weihrauch, JL; Gardner, JM (1978). "Sterol content of foods of plant origin".
1184:
892:
603:
317:
169:
148:
2534:
Hartmann, Marie-Andrée (1998). "Plant sterols and the membrane environment".
2475:
2458:
1815:
1798:
1678:
1661:
1443:
1272:
1141:
941:
168:
Further removal of hydrogens from carbons 7 and 8 from brassicasterol yields
6475:
5407:
5344:
5334:
4822:
4674:
4669:
4664:
4487:
4397:
4357:
4255:
4219:
4076:
4049:
4041:
4000:
3992:
3954:
3895:
3324:
3233:
3186:
3117:
2957:
2812:
2770:
2685:
2391:
2374:
2310:
1402:
1304:Ågren, J. J.; Tvrzicka, E.; Nenonen, M. T.; Helve, T.; Hänninen, O. (2007).
884:
513:
353:
17:
2626:
2585:
2577:
2520:
2484:
2443:
2400:
2359:
2318:
2283:
2247:
2212:
2176:
2141:
2090:
2049:
1971:
1922:
1887:
1879:
1852:
1824:
1783:
1741:
1687:
1634:
1617:
1594:
1586:
1410:
1331:
1290:
1241:
1192:
1149:
1102:
1053:
949:
2730:
1643:
369:
Sterol composition in crude oils (as percentage of total sterol fraction)
6249:
6160:
5760:
5597:
5580:
5472:
5412:
5339:
5296:
5234:
5173:
4966:
4817:
4749:
4654:
4570:
4366:
4292:
4181:
4172:
4152:
4143:
4072:
4026:
3890:
3668:
3653:
3625:
3554:
3520:
3319:
3191:
3092:
3066:
3051:
3002:
2992:
2952:
2877:
2816:
1366:
542:
451:
2617:
2122:
1232:
1215:
855:
6356:
6067:
6049:
6021:
6000:
5767:
5738:
5610:
5565:
5531:
5514:
5376:
4797:
4782:
4334:
4030:
4018:
3546:
3536:
3457:
3278:
3273:
3201:
3196:
3138:
3133:
3087:
3061:
2997:
2936:
2931:
2857:
2848:
2808:
1322:
1305:
1133:
1117:
5784:
5779:
5772:
5755:
5733:
5570:
5550:
5436:
5354:
4614:
4578:
4495:
4374:
4113:
4080:
3885:
3707:
3249:
3107:
3041:
3007:
2978:
2891:
2674:
1962:
1945:
888:
867:
822:
803:
57:
341:. Some of the sterols are removed during the deodorization step of
4767:
1618:"Serum plant sterols and their relation to cholesterol absorption"
967:. Champaign, IL: American Oil Chemists' Society. pp. 172–228.
337:. The bound form is usually hydrolyzed in the small intestines by
103:
Nomenclature of the structure of a tetracyclic damarane triterpene
98:
53:
29:
52:, that serve as structural components of biological membranes of
5969:
5816:
5812:
5007:
4586:
3964:
3918:
3831:
2780:
2734:
2639:
2457:
Vanstone, CA; Raeini-Sarjaz, M; Parsons, WE; Jones, PJ (2002).
806:, where cholesterol lowering has been proven to reduce risk of
115:
sterols, having no double bonds in the sterol ring structure.
866:
The equivalent ability and safety of plant sterols and plant
5804:
List of phytochemicals and foods in which they are prominent
1573:
Pollak, OJ (1953). "Reduction of blood cholesterol in man".
147:
By hydrogenating the double bond between carbons 5 and 6, β-
738:
The European Foods Safety Authority (EFSA) concluded that
1799:"The Cholesterol-Lowering Action of Plant Stanol Esters"
1662:"Ingestion of phytosterols is not potentially hazardous"
996:. Agriculture and Agri-Food Canada, Government of Canada
71:
have been marketed for decades. Despite well-documented
1257:"Food Ingredients That Inhibit Cholesterol Absorption"
3776:
Terpene synthase enzymes (many), having in common a
2599:
De Bruyne, L; Höfte, M; De Vleesschauwer, D (2014).
1701:
1699:
1697:
759:has approved the following claim for phytosterols:
6460:
6400:
6393:
6349:
6234:
6173:
6146:
6125:
6086:
6058:
6019:
6010:
5892:
5850:
5795:
5719:
5656:
5638:
5596:
5457:
5426:
5400:
5367:
5315:
5252:
5227:
5164:
5105:
5085:
5059:
5050:
5041:
4998:
4979:
4919:
4864:
4839:
4758:
4720:
4693:
4630:
4621:
4577:
4563:
4528:
4494:
4480:
4410:
4388:
4365:
4356:
4333:
4306:
4283:
4274:
4246:
4218:
4195:
4166:
4137:
4121:
4112:
4090:
4063:
4040:
4017:
4008:
3999:
3953:
3909:
3866:
3820:
3791:
3769:
3752:
3725:
3677:
3624:
3609:
3592:
3529:
3456:
3446:
3429:
3368:
3342:
3312:
3287:
3266:
3242:
3232:
3171:
3126:
3075:
3029:
3020:
2971:
2945:
2924:
2905:
2867:
2824:
2769:
856:
Phytosterols as a marker for cholesterol absorption
140:Removing a hydrogen from carbons 22 and 23 yields
2424:Nutrition, Metabolism and Cardiovascular Diseases
2264:Nutrition, Metabolism and Cardiovascular Diseases
292:Structures of some common sterols, for comparison
1841:European Journal of Lipid Science and Technology
1756:Society Consensus Panel on Phytosterols (2014).
875:generally lower than phytosterol concentration.
840:(GRAS) status in the US. Phytosterol-containing
184:, i.e. oleates, ferulates and (acyl) glycosides.
2854:Iridoid glycosides (iridoids bound to a sugar)
1557:"Plant Sterols and Blood Cholesterol Lowering"
1435:Ullmann's Encyclopedia of Industrial Chemistry
5981:
5828:
5019:
4598:
3976:
3930:
3843:
2792:
2746:
2651:
2228:Journal of the American College of Cardiology
1706:Weingartner, O.; Bohm, M.; Laufs, U. (2008).
1481:European Food Safety Authority (2008-08-21).
1466:European Food Safety Authority (2009-07-31).
1432:Alfred Thomas (2007), "Fats and Fatty Oils",
1013:
1011:
8:
2501:Journal of the American Dietetic Association
1903:Journal of the American College of Nutrition
1655:
1653:
1347:Journal of the American Dietetic Association
6397:
6179:
6016:
5988:
5974:
5966:
5835:
5821:
5813:
5056:
5047:
5026:
5012:
5004:
4627:
4605:
4591:
4583:
4362:
4280:
4118:
4014:
4005:
3983:
3969:
3961:
3937:
3923:
3915:
3850:
3836:
3828:
3621:
3453:
3239:
3026:
2921:
2799:
2785:
2777:
2753:
2739:
2731:
2658:
2644:
2636:
2463:The American Journal of Clinical Nutrition
1622:The American Journal of Clinical Nutrition
122:. The nomenclature is shown on the right.
2616:
2474:
2390:
2349:
2131:
2121:
2080:
1961:
1814:
1773:
1731:
1677:
1633:
1321:
1280:
1231:
1092:
1043:
991:"Phytosterols and stanols: Topic 10075E"
914:
912:
367:
2566:Molecular Nutrition & Food Research
2559:
2557:
1868:Molecular Nutrition & Food Research
908:
290:
187:
2379:European Journal of Clinical Nutrition
1391:European Journal of Clinical Nutrition
984:
982:
980:
978:
976:
974:
965:Physiology and Biochemistry of Sterols
795:The ability of phytosterols to reduce
189:Structures of some common phytosterols
2205:10.1016/j.atherosclerosis.2006.10.032
2169:10.1016/j.atherosclerosis.2009.11.007
1775:10.1016/j.atherosclerosis.2013.11.043
27:Class of steroids derived from plants
7:
118:The molecule in the article lead is
348:As common sources of phytosterols,
3778:terpene synthase N terminal domain
2010:"GRAS Notice 000181: Phytosterols"
1616:Tilvis, RS; Miettinen, TA (1986).
1438:(7th ed.), Wiley, p. 9,
25:
310:
296:
277:
263:
249:
235:
221:
207:
193:
5093:p-Hydroxybenzoic acid glucoside
1672:(11): 2485, author reply 2486.
133:By removing carbons 24 and 24,
67:Phytosterol-enriched foods and
5262:α-Cyano-4-hydroxycinnamic acid
5209:Phloroglucinol carboxylic acid
4420:List of phytochemicals in food
1915:10.1080/07315724.2009.10719784
883:Sterols are essential for all
1:
2548:10.1016/S1360-1385(98)01233-3
2436:10.1016/S0939-4753(04)80033-4
2338:The Journal of Lipid Research
2240:10.1016/S0735-1097(00)00527-1
2110:The Journal of Lipid Research
2069:The Journal of Lipid Research
1359:10.1016/S0002-8223(21)05668-6
934:10.1016/j.plipres.2018.04.001
6138:Geranylgeranyl pyrophosphate
3255:Geranylgeranyl pyrophosphate
2276:10.1016/j.numecd.2005.04.001
2029:Food and Chemical Toxicology
1310:British Journal of Nutrition
1220:British Journal of Nutrition
887:. In contrast to animal and
838:generally recognized as safe
144:(stigmasta-5,22-dien-3β-ol).
37:, a prototypical phytosterol
6117:Dimethylallyl pyrophosphate
4745:Pyrocatecollic type tannins
3805:Dimethylallyl pyrophosphate
1985:Griffin, RM (Feb 2, 2009).
989:Patterson, CA (July 2006).
151:(Stigmastanol) is obtained.
6552:
2513:10.1016/j.jada.2010.02.011
2351:10.1194/jlr.M600371-JLR200
2082:10.1194/jlr.P800013-JLR200
1255:Jesch ED, Carr TP (2017).
1085:10.1007/s40200-020-00526-z
922:Progress in Lipid Research
165:(ergosta-5,22-dien-3β-ol).
6182:
6112:Isopentenyl pyrophosphate
6107:5-Diphosphomevalonic acid
5131:3,5-Dihydroxybenzoic acid
5126:2,6-Dihydroxybenzoic acid
5121:2,4-Dihydroxybenzoic acid
5115:2,3-Dihydroxybenzoic acid
4467:
3799:Isopentenyl pyrophosphate
3753:Norisoprenoids (modified)
2681:
2042:10.1016/j.fct.2006.01.017
1185:10.1007/s11745-004-1294-3
5586:Syn-propanethial-S-oxide
5508:Phenethyl Isothiocyanate
5052:Monohydroxybenzoic acids
4708:1,3,6-Trigalloyl glucose
3792:Activated isoprene forms
3593:Sesquarterpenes/oids (7)
2842:Monocyclic (single ring)
1803:The Journal of Nutrition
1724:10.1093/eurheartj/ehn580
1666:The Journal of Nutrition
1496:FDA (8 September 2000).
1444:10.1002/14356007.a10_173
1273:10.3746/pnf.2017.22.2.67
1036:10.1093/eurheartj/ehr441
6326:Cholesta-7,24-dien-3-ol
6277:4alpha-Methylzymosterol
6156:Prephytoene diphosphate
6004:metabolic intermediates
5665:Saturated cyclic acids
5166:Trihydroxybenzoic acids
4430:O-methylated flavonoids
4425:C-methylated flavonoids
3415:Secodehydroabietic acid
2536:Trends in Plant Science
2392:10.1038/sj.ejcn.1601083
2311:10.1053/meta.2002.36298
1950:Mayo Clinic Proceedings
1403:10.1038/sj.ejcn.1601980
1073:J Diabetes Metab Disord
808:cardiovascular diseases
768:For plant stanol esters
352:have been developed as
126:By removing carbon 24,
77:cardiovascular diseases
56:. They encompass plant
6245:Farnesyl pyrophosphate
6175:Non-mevalonate pathway
5107:Dihydroxybenzoic acids
4470:Flavonoid biosynthesis
4308:3-hydroxyanthocyanidin
3210:Farnesyl pyrophosphate
2578:10.1002/mnfr.201100722
2476:10.1093/ajcn/76.6.1272
1880:10.1002/mnfr.201100722
1853:10.1002/ejlt.200390033
1816:10.1093/jn/129.12.2109
1797:Nguyen, Tu T. (1999).
1712:European Heart Journal
1679:10.1093/jn/137.11.2485
1587:10.1161/01.CIR.7.5.702
1024:European Heart Journal
745:coronary heart disease
104:
38:
6378:-Dihydroxycholesterol
6272:14-demethyllanosterol
6133:Geranyl pyrophosphate
6102:Phosphomevalonic acid
6078:β-Hydroxybutyric acid
5561:3,3'-Diindolylmethane
5489:Aglycone derivatives
5254:Hydroxycinnamic acids
5136:Ethyl protocatechuate
5072:4-Hydroxybenzoic acid
5067:3-Hydroxybenzoic acid
4841:Flavono-ellagitannins
4832:Phlorofucofuroeckol B
4808:Phlorofucofuroeckol A
4740:Catechol-type tannins
4735:Polyflavonoid tannins
4285:3-deoxyanthocyanidins
3412:Sandaracopimaric acid
3057:Geranyl pyrophosphate
102:
33:
6531:Hypolipidemic agents
6436:24-Methylenelophenol
6331:7-Dehydrodesmosterol
6309:7-Dehydrocholesterol
5576:Allyl isothiocyanate
5503:Allyl isothiocyanate
5317:Aromatic amino acids
5228:Other phenolic acids
4623:Hydrolysable tannins
4515:Secoisolariciresinol
3602:Tetraprenylcurcumene
3083:Grapefruit mercaptan
1635:10.1093/ajcn/43.1.92
791:Cholesterol lowering
784:hypercholesterolemic
325:Dietary phytosterols
6426:4α-methylfecosterol
6369:-Hydroxycholesterol
5350:5-hydroxytryptophan
5156:Protocatechuic acid
4865:Other Miscellaneous
3868:Natural monophenols
3385:Dehydroabietic acid
2851:(cyclopentane ring)
2123:10.1194/jlr.P002899
1233:10.1079/BJN20041234
1122:Food & Function
879:Functions in plants
370:
85:glycated hemoglobin
81:fasting blood sugar
69:dietary supplements
6012:Mevalonate pathway
5437:Phenolic compounds
4680:Tellimagrandin IIs
3860:phenolic compounds
3822:Phenolic compounds
2845:Bicyclic (2 rings)
2705:Dihydrotachysterol
1660:Jones, PJ (2007).
1323:10.1079/BJN2000234
1261:Prev Nutr Food Sci
1134:10.1039/C9FO01205B
368:
339:pancreatic enzymes
105:
39:
6508:
6507:
6504:
6503:
6255:2,3-Oxidosqualene
6230:
6229:
6169:
6168:
5963:
5962:
5810:
5809:
5556:Indole-3-carbinol
5542:Diallyl disulfide
5451:
5450:
5363:
5362:
5248:
5247:
5146:Homogentisic acid
5117:(Hypogallic acid)
5101:
5100:
4994:
4993:
4915:
4914:
4882:Synthetic tannins
4844:(complex tannins)
4730:Proanthocyanidins
4722:Condensed tannins
4716:
4715:
4703:Digalloyl glucose
4613:Types of natural
4476:
4475:
4463:
4462:
4406:
4405:
4379:Isoliquiritigenin
4329:
4328:
4270:
4269:
4108:
4107:
3814:
3813:
3762:7,8-dihydroionone
3721:
3720:
3588:
3587:
3425:
3424:
3393:Lambertianic acid
3167:
3166:
3016:
3015:
2831:Acyclic (linear,
2728:
2727:
2618:10.1093/mp/ssu050
1809:(12): 2109–2112.
820:HMG-CoA reductase
740:blood cholesterol
726:
725:
331:fatty acid esters
16:(Redirected from
6543:
6486:Ergostatetraenol
6398:
6357:Steroid hormones
6180:
6073:Acetoacetic acid
6017:
5990:
5983:
5976:
5967:
5945:Stigmastadienone
5915:δ-7-stigmasterol
5837:
5830:
5823:
5814:
5418:Alkylresorcinols
5282:Chlorogenic acid
5057:
5048:
5028:
5021:
5014:
5005:
4955:Phenylpropanoids
4927:Diarylheptanoids
4803:Fucophlorethol A
4628:
4607:
4600:
4593:
4584:
4445:Prenylflavonoids
4440:Pyranoflavonoids
4435:Furanoflavonoids
4363:
4281:
4209:Leucodelphinidin
4197:Flavan-3,4-diols
4119:
4100:Dalbergichromene
4015:
4006:
3985:
3978:
3971:
3962:
3939:
3932:
3925:
3916:
3852:
3845:
3838:
3829:
3622:
3454:
3431:Sesterterpenoids
3397:Levopimaric acid
3259:Geranyl-linalool
3240:
3173:Sesquiterpenoids
3113:Perillyl alcohol
3027:
2922:
2801:
2794:
2787:
2778:
2755:
2748:
2741:
2732:
2660:
2653:
2646:
2637:
2631:
2630:
2620:
2596:
2590:
2589:
2561:
2552:
2551:
2531:
2525:
2524:
2495:
2489:
2488:
2478:
2454:
2448:
2447:
2419:
2413:
2412:
2394:
2370:
2364:
2363:
2353:
2329:
2323:
2322:
2294:
2288:
2287:
2258:
2252:
2251:
2223:
2217:
2216:
2187:
2181:
2180:
2152:
2146:
2145:
2135:
2125:
2101:
2095:
2094:
2084:
2060:
2054:
2053:
2023:
2017:
2016:
2014:
2005:
1999:
1998:
1996:
1994:
1982:
1976:
1975:
1965:
1963:10.4065/78.8.965
1941:
1935:
1934:
1898:
1892:
1891:
1863:
1857:
1856:
1847:(3–4): 171–185.
1835:
1829:
1828:
1818:
1794:
1788:
1787:
1777:
1752:
1746:
1745:
1735:
1703:
1692:
1691:
1681:
1657:
1648:
1647:
1637:
1613:
1607:
1606:
1570:
1564:
1563:
1561:
1552:
1546:
1545:
1543:
1534:
1528:
1527:
1525:
1524:
1515:. Archived from
1508:
1502:
1501:
1493:
1487:
1486:
1478:
1472:
1471:
1463:
1457:
1456:
1429:
1423:
1422:
1385:
1379:
1378:
1342:
1336:
1335:
1325:
1301:
1295:
1294:
1284:
1252:
1246:
1245:
1235:
1211:
1205:
1204:
1168:
1162:
1161:
1113:
1107:
1106:
1096:
1064:
1058:
1057:
1047:
1015:
1006:
1005:
1003:
1001:
995:
986:
969:
968:
960:
954:
953:
916:
862:Sterol vs stanol
849:phytosterolaemia
842:functional foods
371:
314:
300:
281:
267:
253:
239:
225:
211:
197:
21:
6551:
6550:
6546:
6545:
6544:
6542:
6541:
6540:
6511:
6510:
6509:
6500:
6456:
6389:
6354:
6345:
6226:
6165:
6142:
6121:
6082:
6054:
6035:Acetoacetyl-CoA
6006:
5994:
5964:
5959:
5940:Stigmastadienol
5905:δ-5-avenasterol
5900:δ-7-avenasterol
5888:
5846:
5841:
5811:
5806:
5791:
5746:Polysaccharides
5729:Monosaccharides
5715:
5652:
5634:
5592:
5493:Isothiocyanates
5478:Gluconasturtiin
5468:isothiocyanates
5453:
5452:
5447:
5422:
5396:
5369:Phenylethanoids
5359:
5311:
5287:Diferulic acids
5244:
5223:
5160:
5151:Orsellinic acid
5097:
5081:
5037:
5032:
4990:
4975:
4949:Naphthoquinones
4911:
4860:
4851:Epicutissimin A
4843:
4835:
4754:
4712:
4689:
4617:
4611:
4573:
4559:
4532:
4524:
4502:
4498:
4490:
4472:
4459:
4402:
4390:Dihydrochalcone
4384:
4352:
4325:
4302:
4266:
4242:
4214:
4191:
4170:
4162:
4141:
4133:
4104:
4086:
4059:
4036:
3995:
3989:
3957:
3949:
3943:
3905:
3862:
3856:
3816:
3815:
3810:
3787:
3765:
3748:
3717:
3673:
3613:
3611:Tetraterpenoids
3605:
3584:
3525:
3516:Cholecalciferol
3442:
3439:Geranylfarnesol
3421:
3404:Neoabietic acid
3389:Isopimaric acid
3364:
3338:
3308:
3283:
3262:
3228:
3163:
3122:
3071:
3022:
3021:Monoterpenoids
3012:
2967:
2941:
2917:
2913:
2909:
2901:
2897:Isovaleric acid
2887:
2883:
2863:
2820:
2805:
2765:
2759:
2729:
2724:
2695:Ergocalciferols
2691:Cholecalciferol
2677:
2671:membrane lipids
2664:
2634:
2605:Molecular Plant
2598:
2597:
2593:
2563:
2562:
2555:
2533:
2532:
2528:
2497:
2496:
2492:
2456:
2455:
2451:
2421:
2420:
2416:
2372:
2371:
2367:
2331:
2330:
2326:
2305:(12): 1519–21.
2296:
2295:
2291:
2260:
2259:
2255:
2225:
2224:
2220:
2193:Atherosclerosis
2189:
2188:
2184:
2157:Atherosclerosis
2154:
2153:
2149:
2103:
2102:
2098:
2062:
2061:
2057:
2025:
2024:
2020:
2012:
2007:
2006:
2002:
1992:
1990:
1984:
1983:
1979:
1943:
1942:
1938:
1900:
1899:
1895:
1865:
1864:
1860:
1837:
1836:
1832:
1796:
1795:
1791:
1762:Atherosclerosis
1754:
1753:
1749:
1705:
1704:
1695:
1659:
1658:
1651:
1615:
1614:
1610:
1572:
1571:
1567:
1559:
1555:Health Canada.
1554:
1553:
1549:
1541:
1536:
1535:
1531:
1522:
1520:
1510:
1509:
1505:
1495:
1494:
1490:
1480:
1479:
1475:
1465:
1464:
1460:
1454:
1431:
1430:
1426:
1397:(10): 1378–85.
1387:
1386:
1382:
1344:
1343:
1339:
1303:
1302:
1298:
1254:
1253:
1249:
1213:
1212:
1208:
1170:
1169:
1165:
1115:
1114:
1110:
1066:
1065:
1061:
1017:
1016:
1009:
999:
997:
993:
988:
987:
972:
962:
961:
957:
918:
917:
910:
906:
881:
864:
834:
816:adverse effects
793:
776:
753:
736:
731:
573:Palm kernel oil
327:
320:
315:
306:
301:
287:
282:
273:
268:
259:
254:
245:
240:
231:
226:
217:
212:
203:
198:
97:
73:LDL cholesterol
28:
23:
22:
15:
12:
11:
5:
6549:
6547:
6539:
6538:
6536:Phytochemicals
6533:
6528:
6526:Food additives
6523:
6513:
6512:
6506:
6505:
6502:
6501:
6499:
6498:
6496:Ergocalciferol
6493:
6488:
6483:
6481:Ergostatrienol
6478:
6473:
6467:
6465:
6463:Ergocalciferol
6458:
6457:
6455:
6454:
6443:
6438:
6433:
6428:
6423:
6418:
6416:Cycloeucalenol
6413:
6407:
6405:
6395:
6391:
6390:
6388:
6387:
6380:
6371:
6361:
6359:
6347:
6346:
6344:
6343:
6338:
6333:
6328:
6323:
6317:
6316:
6311:
6306:
6301:
6296:
6290:
6289:
6284:
6279:
6274:
6269:
6263:
6262:
6257:
6252:
6247:
6241:
6239:
6232:
6231:
6228:
6227:
6225:
6224:
6219:
6214:
6209:
6204:
6199:
6194:
6189:
6183:
6177:
6171:
6170:
6167:
6166:
6164:
6163:
6158:
6152:
6150:
6144:
6143:
6141:
6140:
6135:
6129:
6127:
6123:
6122:
6120:
6119:
6114:
6109:
6104:
6099:
6097:Mevalonic acid
6093:
6091:
6084:
6083:
6081:
6080:
6075:
6070:
6064:
6062:
6056:
6055:
6053:
6052:
6047:
6042:
6037:
6032:
6026:
6024:
6014:
6008:
6007:
5995:
5993:
5992:
5985:
5978:
5970:
5961:
5960:
5958:
5957:
5952:
5947:
5942:
5937:
5932:
5927:
5922:
5917:
5912:
5907:
5902:
5896:
5894:
5890:
5889:
5887:
5886:
5881:
5879:Ergostatrienol
5876:
5871:
5865:
5860:
5858:Brassicasterol
5854:
5852:
5848:
5847:
5842:
5840:
5839:
5832:
5825:
5817:
5808:
5807:
5802:
5800:
5793:
5792:
5790:
5789:
5788:
5787:
5782:
5777:
5776:
5775:
5765:
5764:
5763:
5758:
5743:
5742:
5741:
5736:
5725:
5723:
5717:
5716:
5714:
5713:
5708:
5703:
5698:
5693:
5691:Anacardic acid
5688:
5683:
5678:
5677:
5676:
5671:
5662:
5660:
5654:
5653:
5651:
5650:
5644:
5642:
5636:
5635:
5633:
5632:
5631:
5630:
5625:
5615:
5614:
5613:
5602:
5600:
5594:
5593:
5591:
5590:
5589:
5588:
5583:
5578:
5573:
5568:
5563:
5558:
5548:
5547:
5546:
5545:
5544:
5534:
5527:Organosulfides
5524:
5523:
5522:
5517:
5512:
5511:
5510:
5505:
5500:
5487:
5486:
5485:
5480:
5475:
5463:
5461:
5459:Glucosinolates
5455:
5454:
5449:
5448:
5446:
5445:
5439:
5433:
5431:
5424:
5423:
5421:
5420:
5415:
5410:
5404:
5402:
5398:
5397:
5395:
5394:
5389:
5384:
5382:Hydroxytyrosol
5379:
5373:
5371:
5365:
5364:
5361:
5360:
5358:
5357:
5352:
5347:
5342:
5337:
5332:
5327:
5321:
5319:
5313:
5312:
5310:
5309:
5307:Sinapinic acid
5304:
5299:
5294:
5289:
5284:
5279:
5274:
5269:
5264:
5258:
5256:
5250:
5249:
5246:
5245:
5243:
5242:
5237:
5231:
5229:
5225:
5224:
5222:
5221:
5216:
5211:
5206:
5201:
5196:
5191:
5186:
5181:
5176:
5170:
5168:
5162:
5161:
5159:
5158:
5153:
5148:
5143:
5138:
5133:
5128:
5123:
5118:
5111:
5109:
5103:
5102:
5099:
5098:
5096:
5095:
5089:
5087:
5083:
5082:
5080:
5079:
5077:Salicylic acid
5074:
5069:
5063:
5061:
5054:
5045:
5043:Phenolic acids
5039:
5038:
5035:Aromatic acids
5033:
5031:
5030:
5023:
5016:
5008:
5002:
5000:Aromatic acids
4996:
4995:
4992:
4991:
4986:
4984:
4977:
4976:
4974:
4973:
4964:
4958:
4952:
4946:
4941:
4935:
4933:Anthraquinones
4930:
4923:
4921:
4917:
4916:
4913:
4912:
4910:
4909:
4908:
4907:
4902:
4897:
4892:
4884:
4879:
4877:Pseudo tannins
4874:
4872:Tannin sources
4868:
4866:
4862:
4861:
4859:
4858:
4853:
4847:
4845:
4837:
4836:
4834:
4833:
4830:
4825:
4820:
4815:
4810:
4805:
4800:
4795:
4790:
4785:
4780:
4775:
4770:
4764:
4762:
4756:
4755:
4753:
4752:
4747:
4742:
4737:
4732:
4726:
4724:
4718:
4717:
4714:
4713:
4711:
4710:
4705:
4699:
4697:
4691:
4690:
4688:
4687:
4682:
4677:
4672:
4667:
4662:
4657:
4652:
4647:
4642:
4636:
4634:
4625:
4619:
4618:
4612:
4610:
4609:
4602:
4595:
4587:
4581:
4575:
4574:
4569:
4567:
4561:
4560:
4558:
4557:
4552:
4547:
4542:
4536:
4534:
4526:
4525:
4523:
4522:
4517:
4512:
4506:
4504:
4500:
4492:
4491:
4486:
4484:
4482:Flavonolignans
4478:
4477:
4474:
4473:
4468:
4465:
4464:
4461:
4460:
4458:
4457:
4452:
4450:Methylenedioxy
4447:
4442:
4437:
4432:
4427:
4422:
4416:
4414:
4408:
4407:
4404:
4403:
4401:
4400:
4394:
4392:
4386:
4385:
4383:
4382:
4371:
4369:
4360:
4354:
4353:
4351:
4350:
4345:
4339:
4337:
4331:
4330:
4327:
4326:
4324:
4323:
4320:Guibourtinidin
4312:
4310:
4304:
4303:
4301:
4300:
4289:
4287:
4278:
4276:Anthocyanidins
4272:
4271:
4268:
4267:
4265:
4264:
4258:
4252:
4250:
4244:
4243:
4241:
4240:
4235:
4230:
4224:
4222:
4216:
4215:
4213:
4212:
4201:
4199:
4193:
4192:
4190:
4189:
4178:
4176:
4164:
4163:
4161:
4160:
4149:
4147:
4135:
4134:
4132:
4131:
4125:
4123:
4116:
4110:
4109:
4106:
4105:
4103:
4102:
4096:
4094:
4088:
4087:
4085:
4084:
4069:
4067:
4061:
4060:
4058:
4057:
4046:
4044:
4038:
4037:
4035:
4034:
4023:
4021:
4012:
4003:
3997:
3996:
3990:
3988:
3987:
3980:
3973:
3965:
3959:
3951:
3950:
3944:
3942:
3941:
3934:
3927:
3919:
3913:
3907:
3906:
3904:
3903:
3898:
3893:
3888:
3883:
3878:
3872:
3870:
3864:
3863:
3857:
3855:
3854:
3847:
3840:
3832:
3826:
3824:
3818:
3817:
3812:
3811:
3809:
3808:
3802:
3795:
3793:
3789:
3788:
3786:
3785:
3782:protein domain
3773:
3771:
3767:
3766:
3764:
3763:
3760:
3756:
3754:
3750:
3749:
3747:
3746:
3743:
3738:
3736:Natural rubber
3732:
3730:
3727:Polyterpenoids
3723:
3722:
3719:
3718:
3716:
3715:
3710:
3705:
3700:
3695:
3690:
3684:
3682:
3675:
3674:
3672:
3671:
3666:
3661:
3656:
3651:
3649:Delta-Carotene
3646:
3644:Gamma-Carotene
3641:
3636:
3634:Alpha-Carotene
3630:
3628:
3619:
3607:
3606:
3604:
3603:
3600:
3596:
3594:
3590:
3589:
3586:
3585:
3583:
3582:
3581:
3580:
3575:
3573:Betulinic acid
3570:
3565:
3563:Oleanolic acid
3557:
3552:
3549:
3544:
3539:
3533:
3531:
3527:
3526:
3524:
3523:
3518:
3513:
3508:
3503:
3498:
3497:
3496:
3491:
3486:
3481:
3476:
3475:Citrostadienol
3473:
3462:
3460:
3451:
3444:
3443:
3441:
3440:
3436:
3434:
3427:
3426:
3423:
3422:
3420:
3419:
3418:Palustric acid
3416:
3413:
3410:
3405:
3402:
3399:
3394:
3391:
3386:
3383:
3380:
3374:
3372:
3366:
3365:
3363:
3362:
3357:
3352:
3346:
3344:
3340:
3339:
3337:
3336:
3333:
3330:
3327:
3322:
3316:
3314:
3310:
3309:
3307:
3306:
3301:
3298:
3291:
3289:
3285:
3284:
3282:
3281:
3276:
3270:
3268:
3264:
3263:
3261:
3260:
3257:
3252:
3246:
3244:
3237:
3230:
3229:
3227:
3226:
3223:
3220:
3215:
3212:
3207:
3204:
3199:
3194:
3189:
3184:
3178:
3176:
3169:
3168:
3165:
3164:
3162:
3161:
3156:
3151:
3146:
3144:Bornyl acetate
3141:
3136:
3130:
3128:
3124:
3123:
3121:
3120:
3115:
3110:
3105:
3095:
3090:
3085:
3079:
3077:
3073:
3072:
3070:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3033:
3031:
3024:
3018:
3017:
3014:
3013:
3011:
3010:
3005:
3000:
2995:
2990:
2975:
2973:
2969:
2968:
2966:
2965:
2960:
2955:
2949:
2947:
2943:
2942:
2940:
2939:
2934:
2928:
2926:
2919:
2915:
2911:
2903:
2902:
2900:
2899:
2894:
2889:
2885:
2881:
2874:
2872:
2869:Hemiterpenoids
2865:
2864:
2862:
2861:
2855:
2852:
2846:
2843:
2840:
2828:
2826:
2822:
2821:
2806:
2804:
2803:
2796:
2789:
2781:
2775:
2773:
2767:
2766:
2763:phytochemicals
2760:
2758:
2757:
2750:
2743:
2735:
2726:
2725:
2723:
2722:
2717:
2712:
2707:
2702:
2697:
2688:
2682:
2679:
2678:
2665:
2663:
2662:
2655:
2648:
2640:
2633:
2632:
2591:
2572:(7): 1058–72.
2553:
2542:(5): 170–175.
2526:
2490:
2449:
2414:
2365:
2324:
2289:
2253:
2234:(5): 1185–91.
2218:
2182:
2147:
2116:(8): 2384–93.
2096:
2055:
2036:(8): 1213–22.
2018:
2000:
1977:
1936:
1893:
1874:(7): 1058–72.
1858:
1830:
1789:
1747:
1693:
1649:
1608:
1565:
1547:
1529:
1503:
1488:
1473:
1458:
1453:978-3527306732
1452:
1424:
1380:
1337:
1296:
1247:
1206:
1163:
1108:
1079:(1): 625–632.
1059:
1030:(4): 444–451.
1007:
970:
955:
907:
905:
902:
880:
877:
863:
860:
833:
830:
792:
789:
775:
772:
752:
749:
735:
732:
730:
727:
724:
723:
720:
717:
714:
711:
708:
705:
702:
699:
693:
692:
689:
686:
683:
680:
677:
674:
671:
668:
662:
661:
658:
655:
652:
649:
646:
643:
640:
637:
631:
630:
627:
624:
621:
618:
615:
612:
609:
606:
600:
599:
596:
593:
590:
587:
584:
581:
578:
575:
569:
568:
565:
562:
559:
556:
553:
550:
548:
545:
539:
538:
535:
533:
530:
527:
524:
521:
519:
516:
510:
509:
506:
503:
500:
497:
494:
491:
488:
485:
483:Cottonseed oil
479:
478:
475:
472:
469:
466:
463:
460:
457:
454:
448:
447:
444:
441:
438:
435:
432:
429:
426:
423:
417:
416:
410:
408:∆7-Avenasterol
405:
399:
394:
389:
384:
382:Brassicasterol
379:
374:
350:vegetable oils
326:
323:
322:
321:
316:
309:
307:
302:
295:
293:
289:
288:
283:
276:
274:
271:Brassicasterol
269:
262:
260:
255:
248:
246:
241:
234:
232:
227:
220:
218:
213:
206:
204:
199:
192:
190:
186:
185:
174:
173:
166:
163:brassicasterol
159:
152:
145:
138:
131:
96:
93:
89:mortality rate
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
6548:
6537:
6534:
6532:
6529:
6527:
6524:
6522:
6519:
6518:
6516:
6497:
6494:
6492:
6489:
6487:
6484:
6482:
6479:
6477:
6474:
6472:
6469:
6468:
6466:
6464:
6459:
6452:
6448:
6444:
6442:
6439:
6437:
6434:
6432:
6431:Isofucosterol
6429:
6427:
6424:
6422:
6419:
6417:
6414:
6412:
6409:
6408:
6406:
6404:
6399:
6396:
6392:
6385:
6381:
6379:
6377:
6372:
6370:
6368:
6363:
6362:
6360:
6358:
6353:
6348:
6342:
6339:
6337:
6334:
6332:
6329:
6327:
6324:
6322:
6319:
6318:
6315:
6312:
6310:
6307:
6305:
6302:
6300:
6297:
6295:
6292:
6291:
6288:
6285:
6283:
6280:
6278:
6275:
6273:
6270:
6268:
6265:
6264:
6261:
6258:
6256:
6253:
6251:
6248:
6246:
6243:
6242:
6240:
6238:
6233:
6223:
6220:
6218:
6215:
6213:
6210:
6208:
6205:
6203:
6200:
6198:
6195:
6193:
6190:
6188:
6185:
6184:
6181:
6178:
6176:
6172:
6162:
6159:
6157:
6154:
6153:
6151:
6149:
6145:
6139:
6136:
6134:
6131:
6130:
6128:
6124:
6118:
6115:
6113:
6110:
6108:
6105:
6103:
6100:
6098:
6095:
6094:
6092:
6090:
6085:
6079:
6076:
6074:
6071:
6069:
6066:
6065:
6063:
6061:
6060:Ketone bodies
6057:
6051:
6048:
6046:
6043:
6041:
6038:
6036:
6033:
6031:
6028:
6027:
6025:
6023:
6018:
6015:
6013:
6009:
6005:
6002:
5998:
5991:
5986:
5984:
5979:
5977:
5972:
5971:
5968:
5956:
5955:Stigmastenone
5953:
5951:
5948:
5946:
5943:
5941:
5938:
5936:
5933:
5931:
5928:
5926:
5923:
5921:
5918:
5916:
5913:
5911:
5908:
5906:
5903:
5901:
5898:
5897:
5895:
5891:
5885:
5884:Ergostadienol
5882:
5880:
5877:
5875:
5872:
5869:
5866:
5864:
5861:
5859:
5856:
5855:
5853:
5849:
5845:
5838:
5833:
5831:
5826:
5824:
5819:
5818:
5815:
5805:
5801:
5798:
5794:
5786:
5783:
5781:
5778:
5774:
5771:
5770:
5769:
5766:
5762:
5759:
5757:
5754:
5753:
5752:
5749:
5748:
5747:
5744:
5740:
5737:
5735:
5732:
5731:
5730:
5727:
5726:
5724:
5722:
5721:Carbohydrates
5718:
5712:
5711:Fertaric acid
5709:
5707:
5706:Coutaric acid
5704:
5702:
5701:Caftaric acid
5699:
5697:
5694:
5692:
5689:
5687:
5686:Tartaric acid
5684:
5682:
5679:
5675:
5672:
5670:
5667:
5666:
5664:
5663:
5661:
5659:
5658:Organic acids
5655:
5649:
5648:Chlorophyllin
5646:
5645:
5643:
5641:
5637:
5629:
5626:
5624:
5623:Indicaxanthin
5621:
5620:
5619:
5616:
5612:
5609:
5608:
5607:
5604:
5603:
5601:
5599:
5595:
5587:
5584:
5582:
5579:
5577:
5574:
5572:
5569:
5567:
5564:
5562:
5559:
5557:
5554:
5553:
5552:
5549:
5543:
5540:
5539:
5538:
5535:
5533:
5530:
5529:
5528:
5525:
5521:
5518:
5516:
5513:
5509:
5506:
5504:
5501:
5499:
5496:
5495:
5494:
5491:
5490:
5488:
5484:
5483:Glucoraphanin
5481:
5479:
5476:
5474:
5471:
5470:
5469:
5466:Precursor to
5465:
5464:
5462:
5460:
5456:
5443:
5442:Phlorotannins
5440:
5438:
5435:
5434:
5432:
5429:
5425:
5419:
5416:
5414:
5411:
5409:
5406:
5405:
5403:
5399:
5393:
5390:
5388:
5385:
5383:
5380:
5378:
5375:
5374:
5372:
5370:
5366:
5356:
5353:
5351:
5348:
5346:
5343:
5341:
5338:
5336:
5333:
5331:
5328:
5326:
5325:phenylalanine
5323:
5322:
5320:
5318:
5314:
5308:
5305:
5303:
5300:
5298:
5295:
5293:
5292:Coumaric acid
5290:
5288:
5285:
5283:
5280:
5278:
5277:Cinnamic acid
5275:
5273:
5272:Chicoric acid
5270:
5268:
5265:
5263:
5260:
5259:
5257:
5255:
5251:
5241:
5238:
5236:
5233:
5232:
5230:
5226:
5220:
5217:
5215:
5214:Syringic acid
5212:
5210:
5207:
5205:
5202:
5200:
5197:
5195:
5192:
5190:
5189:Eudesmic acid
5187:
5185:
5184:Ethyl gallate
5182:
5180:
5179:Chebulic acid
5177:
5175:
5172:
5171:
5169:
5167:
5163:
5157:
5154:
5152:
5149:
5147:
5144:
5142:
5141:Gentisic acid
5139:
5137:
5134:
5132:
5129:
5127:
5124:
5122:
5119:
5116:
5113:
5112:
5110:
5108:
5104:
5094:
5091:
5090:
5088:
5084:
5078:
5075:
5073:
5070:
5068:
5065:
5064:
5062:
5058:
5055:
5053:
5049:
5046:
5044:
5040:
5036:
5029:
5024:
5022:
5017:
5015:
5010:
5009:
5006:
5003:
5001:
4997:
4989:
4985:
4982:
4978:
4972:
4968:
4965:
4962:
4959:
4956:
4953:
4950:
4947:
4945:
4942:
4939:
4936:
4934:
4931:
4928:
4925:
4924:
4922:
4918:
4906:
4903:
4901:
4898:
4896:
4893:
4891:
4888:
4887:
4885:
4883:
4880:
4878:
4875:
4873:
4870:
4869:
4867:
4863:
4857:
4856:Acutissimin A
4854:
4852:
4849:
4848:
4846:
4842:
4838:
4831:
4829:
4828:7-Phloroeckol
4826:
4824:
4821:
4819:
4816:
4814:
4811:
4809:
4806:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
4784:
4781:
4779:
4776:
4774:
4771:
4769:
4766:
4765:
4763:
4761:
4760:Phlorotannins
4757:
4751:
4748:
4746:
4743:
4741:
4738:
4736:
4733:
4731:
4728:
4727:
4725:
4723:
4719:
4709:
4706:
4704:
4701:
4700:
4698:
4696:
4692:
4686:
4683:
4681:
4678:
4676:
4673:
4671:
4668:
4666:
4663:
4661:
4658:
4656:
4653:
4651:
4648:
4646:
4643:
4641:
4638:
4637:
4635:
4633:
4632:Ellagitannins
4629:
4626:
4624:
4620:
4616:
4608:
4603:
4601:
4596:
4594:
4589:
4588:
4585:
4582:
4580:
4576:
4572:
4568:
4566:
4562:
4556:
4553:
4551:
4548:
4546:
4545:Pterostilbene
4543:
4541:
4538:
4537:
4535:
4531:
4527:
4521:
4518:
4516:
4513:
4511:
4508:
4507:
4505:
4497:
4493:
4489:
4485:
4483:
4479:
4471:
4466:
4456:
4453:
4451:
4448:
4446:
4443:
4441:
4438:
4436:
4433:
4431:
4428:
4426:
4423:
4421:
4418:
4417:
4415:
4413:
4412:Miscellaneous
4409:
4399:
4396:
4395:
4393:
4391:
4387:
4380:
4376:
4373:
4372:
4370:
4368:
4364:
4361:
4359:
4355:
4349:
4346:
4344:
4341:
4340:
4338:
4336:
4332:
4321:
4317:
4314:
4313:
4311:
4309:
4305:
4298:
4294:
4291:
4290:
4288:
4286:
4282:
4279:
4277:
4273:
4262:
4259:
4257:
4254:
4253:
4251:
4249:
4245:
4239:
4236:
4234:
4231:
4229:
4226:
4225:
4223:
4221:
4217:
4210:
4206:
4205:Leucocyanidin
4203:
4202:
4200:
4198:
4194:
4187:
4183:
4180:
4179:
4177:
4174:
4169:
4165:
4158:
4157:Gallocatechol
4154:
4151:
4150:
4148:
4145:
4140:
4136:
4130:
4129:Luteoliflavan
4127:
4126:
4124:
4120:
4117:
4115:
4111:
4101:
4098:
4097:
4095:
4093:
4092:Neoflavonoids
4089:
4082:
4078:
4074:
4071:
4070:
4068:
4066:
4062:
4055:
4051:
4048:
4047:
4045:
4043:
4039:
4032:
4028:
4025:
4024:
4022:
4020:
4016:
4013:
4011:
4010:Anthoxanthins
4007:
4004:
4002:
3998:
3994:
3986:
3981:
3979:
3974:
3972:
3967:
3966:
3963:
3960:
3956:
3952:
3948:
3940:
3935:
3933:
3928:
3926:
3921:
3920:
3917:
3914:
3912:
3908:
3902:
3899:
3897:
3894:
3892:
3889:
3887:
3884:
3882:
3881:Benzenetriols
3879:
3877:
3874:
3873:
3871:
3869:
3865:
3861:
3853:
3848:
3846:
3841:
3839:
3834:
3833:
3830:
3825:
3823:
3819:
3806:
3803:
3800:
3797:
3796:
3794:
3790:
3783:
3779:
3775:
3774:
3772:
3768:
3761:
3759:3-oxo-α-ionol
3758:
3757:
3755:
3751:
3744:
3742:
3739:
3737:
3734:
3733:
3731:
3728:
3724:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3693:Cryptoxanthin
3691:
3689:
3688:Canthaxanthin
3686:
3685:
3683:
3680:
3676:
3670:
3667:
3665:
3662:
3660:
3657:
3655:
3652:
3650:
3647:
3645:
3642:
3640:
3639:Beta-Carotene
3637:
3635:
3632:
3631:
3629:
3627:
3623:
3620:
3617:
3612:
3608:
3601:
3599:Ferrugicadiol
3598:
3597:
3595:
3591:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3560:
3558:
3556:
3553:
3551:Serratenediol
3550:
3548:
3545:
3543:
3540:
3538:
3535:
3534:
3532:
3528:
3522:
3519:
3517:
3514:
3512:
3509:
3507:
3504:
3502:
3499:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3474:
3472:
3469:
3468:
3467:
3464:
3463:
3461:
3459:
3455:
3452:
3449:
3448:Triterpenoids
3445:
3438:
3437:
3435:
3432:
3428:
3417:
3414:
3411:
3409:
3406:
3403:
3401:Mercusic acid
3400:
3398:
3395:
3392:
3390:
3387:
3384:
3382:Communic acid
3381:
3379:
3376:
3375:
3373:
3371:
3367:
3361:
3358:
3356:
3353:
3351:
3348:
3347:
3345:
3341:
3334:
3331:
3328:
3326:
3323:
3321:
3318:
3317:
3315:
3311:
3305:
3302:
3299:
3296:
3293:
3292:
3290:
3286:
3280:
3277:
3275:
3272:
3271:
3269:
3265:
3258:
3256:
3253:
3251:
3248:
3247:
3245:
3241:
3238:
3235:
3231:
3224:
3221:
3219:
3216:
3213:
3211:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3188:
3185:
3183:
3180:
3179:
3177:
3174:
3170:
3160:
3157:
3155:
3152:
3150:
3147:
3145:
3142:
3140:
3137:
3135:
3132:
3131:
3129:
3125:
3119:
3116:
3114:
3111:
3109:
3106:
3103:
3099:
3096:
3094:
3091:
3089:
3086:
3084:
3081:
3080:
3078:
3074:
3068:
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3035:
3034:
3032:
3028:
3025:
3019:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2988:
2984:
2980:
2977:
2976:
2974:
2970:
2964:
2961:
2959:
2956:
2954:
2951:
2950:
2948:
2944:
2938:
2935:
2933:
2930:
2929:
2927:
2923:
2920:
2908:
2904:
2898:
2895:
2893:
2890:
2879:
2876:
2875:
2873:
2870:
2866:
2859:
2856:
2853:
2850:
2847:
2844:
2841:
2838:
2834:
2830:
2829:
2827:
2823:
2818:
2814:
2810:
2802:
2797:
2795:
2790:
2788:
2783:
2782:
2779:
2774:
2772:
2768:
2764:
2756:
2751:
2749:
2744:
2742:
2737:
2736:
2733:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2692:
2689:
2687:
2684:
2683:
2680:
2676:
2672:
2668:
2661:
2656:
2654:
2649:
2647:
2642:
2641:
2638:
2628:
2624:
2619:
2614:
2611:(6): 943–59.
2610:
2606:
2602:
2595:
2592:
2587:
2583:
2579:
2575:
2571:
2567:
2560:
2558:
2554:
2549:
2545:
2541:
2537:
2530:
2527:
2522:
2518:
2514:
2510:
2507:(5): 719–26.
2506:
2502:
2494:
2491:
2486:
2482:
2477:
2472:
2469:(6): 1272–8.
2468:
2464:
2460:
2453:
2450:
2445:
2441:
2437:
2433:
2430:(3): 133–42.
2429:
2425:
2418:
2415:
2410:
2406:
2402:
2398:
2393:
2388:
2385:(9): 715–25.
2384:
2380:
2376:
2369:
2366:
2361:
2357:
2352:
2347:
2344:(1): 139–44.
2343:
2339:
2335:
2328:
2325:
2320:
2316:
2312:
2308:
2304:
2300:
2293:
2290:
2285:
2281:
2277:
2273:
2269:
2265:
2257:
2254:
2249:
2245:
2241:
2237:
2233:
2229:
2222:
2219:
2214:
2210:
2206:
2202:
2198:
2194:
2186:
2183:
2178:
2174:
2170:
2166:
2162:
2158:
2151:
2148:
2143:
2139:
2134:
2129:
2124:
2119:
2115:
2111:
2107:
2100:
2097:
2092:
2088:
2083:
2078:
2075:(2): 334–41.
2074:
2070:
2066:
2059:
2056:
2051:
2047:
2043:
2039:
2035:
2031:
2030:
2022:
2019:
2011:
2004:
2001:
1988:
1981:
1978:
1973:
1969:
1964:
1959:
1956:(8): 965–78.
1955:
1951:
1947:
1940:
1937:
1932:
1928:
1924:
1920:
1916:
1912:
1909:(5): 517–24.
1908:
1904:
1897:
1894:
1889:
1885:
1881:
1877:
1873:
1869:
1862:
1859:
1854:
1850:
1846:
1842:
1834:
1831:
1826:
1822:
1817:
1812:
1808:
1804:
1800:
1793:
1790:
1785:
1781:
1776:
1771:
1768:(2): 346–60.
1767:
1763:
1759:
1751:
1748:
1743:
1739:
1734:
1729:
1725:
1721:
1717:
1713:
1709:
1702:
1700:
1698:
1694:
1689:
1685:
1680:
1675:
1671:
1667:
1663:
1656:
1654:
1650:
1645:
1641:
1636:
1631:
1627:
1623:
1619:
1612:
1609:
1604:
1600:
1596:
1592:
1588:
1584:
1580:
1576:
1569:
1566:
1558:
1551:
1548:
1540:
1533:
1530:
1519:on 2012-10-09
1518:
1514:
1507:
1504:
1499:
1492:
1489:
1484:
1477:
1474:
1469:
1462:
1459:
1455:
1449:
1445:
1441:
1437:
1436:
1428:
1425:
1420:
1416:
1412:
1408:
1404:
1400:
1396:
1392:
1384:
1381:
1376:
1372:
1368:
1364:
1360:
1356:
1352:
1348:
1341:
1338:
1333:
1329:
1324:
1319:
1315:
1311:
1307:
1300:
1297:
1292:
1288:
1283:
1278:
1274:
1270:
1266:
1262:
1258:
1251:
1248:
1243:
1239:
1234:
1229:
1225:
1221:
1217:
1210:
1207:
1202:
1198:
1194:
1190:
1186:
1182:
1179:(8): 769–76.
1178:
1174:
1167:
1164:
1159:
1155:
1151:
1147:
1143:
1139:
1135:
1131:
1128:(1): 93–110.
1127:
1123:
1119:
1112:
1109:
1104:
1100:
1095:
1090:
1086:
1082:
1078:
1074:
1070:
1063:
1060:
1055:
1051:
1046:
1041:
1037:
1033:
1029:
1025:
1021:
1014:
1012:
1008:
992:
985:
983:
981:
979:
977:
975:
971:
966:
959:
956:
951:
947:
943:
939:
935:
931:
927:
923:
915:
913:
909:
903:
901:
898:
894:
890:
886:
878:
876:
872:
869:
861:
859:
857:
852:
850:
845:
843:
839:
831:
829:
826:
824:
821:
817:
811:
809:
805:
800:
798:
790:
788:
785:
780:
779:Health Canada
774:Health Canada
773:
771:
769:
765:
764:
763:sterol esters
758:
750:
748:
746:
741:
733:
729:Health claims
728:
721:
718:
715:
712:
709:
706:
703:
700:
698:
697:Sunflower oil
695:
694:
690:
687:
684:
681:
678:
675:
672:
669:
667:
664:
663:
659:
656:
653:
650:
647:
644:
641:
638:
636:
633:
632:
628:
625:
622:
619:
616:
613:
610:
607:
605:
602:
601:
597:
594:
591:
588:
585:
582:
579:
576:
574:
571:
570:
566:
563:
560:
557:
554:
551:
549:
546:
544:
541:
540:
536:
534:
531:
528:
525:
522:
520:
517:
515:
512:
511:
507:
504:
501:
498:
495:
492:
489:
486:
484:
481:
480:
476:
473:
470:
467:
464:
461:
458:
455:
453:
450:
449:
445:
442:
439:
436:
433:
430:
427:
424:
422:
419:
418:
415:
411:
409:
406:
404:
400:
398:
395:
393:
390:
388:
385:
383:
380:
378:
375:
373:
372:
366:
364:
358:
355:
351:
346:
344:
343:refining oils
340:
336:
332:
324:
319:
313:
308:
305:
299:
294:
291:
286:
280:
275:
272:
266:
261:
258:
252:
247:
244:
238:
233:
230:
224:
219:
216:
210:
205:
202:
196:
191:
188:
183:
182:sterol esters
179:
178:
177:
176:In addition:
171:
167:
164:
160:
157:
153:
150:
146:
143:
139:
136:
132:
129:
125:
124:
123:
121:
116:
114:
110:
101:
94:
92:
90:
87:, or overall
86:
82:
78:
74:
70:
65:
63:
59:
55:
51:
48:, similar to
47:
46:phytosteroids
43:
36:
32:
19:
6521:Phytosterols
6447:Phytosterols
6446:
6421:Obtusifoliol
6411:Cycloartenol
6375:
6366:
5950:Stigmasterol
5935:Stigmastenol
5930:Stigmastanol
5910:β-Sitosterol
5870:(Vitamin D2)
5844:Phytosterols
5843:
5796:
5640:Chlorophylls
5628:Vulgaxanthin
5618:Betaxanthins
5537:Polysulfides
5520:Thiocyanates
5498:Sulforaphane
5427:
5302:Ferulic acid
5267:Caffeic acid
5240:Ellagic acid
4980:
4971:isocoumarins
4944:Kavalactones
4886:Tannin uses
4813:Tetrafucol A
4793:Diphlorethol
4778:6,6'-Bieckol
4773:8,8′-Bieckol
4695:Gallotannins
4660:Casuarictins
4640:Punicalagins
4565:Curcuminoids
4510:Matairesinol
4411:
4316:Apigeninidin
4261:Aromadendrin
4168:Flavan-4-ols
4139:Flavan-3-ols
3876:Benzenediols
3745:Gutta-balatá
3741:Gutta percha
3679:Xanthophylls
3659:Neurosporene
3578:Moronic acid
3568:Ursolic acid
3511:Testosterone
3494:Stigmasterol
3479:Cycloartenol
3466:Phytosterols
3465:
3408:Pimaric acid
3378:Abietic acid
3329:Manoyl oxide
3304:Salvinorin A
3294:
3234:Diterpenoids
3098:Thujaplicins
3023:(2,modified)
2963:Phellandrene
2907:Monoterpenes
2836:
2832:
2825:Basic forms:
2720:Phytosterols
2719:
2710:Fusidic acid
2608:
2604:
2594:
2569:
2565:
2539:
2535:
2529:
2504:
2500:
2493:
2466:
2462:
2452:
2427:
2423:
2417:
2382:
2378:
2368:
2341:
2337:
2327:
2302:
2298:
2292:
2270:(1): 13–21.
2267:
2263:
2256:
2231:
2227:
2221:
2199:(1): 283–8.
2196:
2192:
2185:
2163:(1): 282–7.
2160:
2156:
2150:
2113:
2109:
2099:
2072:
2068:
2058:
2033:
2027:
2021:
2003:
1991:. Retrieved
1980:
1953:
1949:
1939:
1906:
1902:
1896:
1871:
1867:
1861:
1844:
1840:
1833:
1806:
1802:
1792:
1765:
1761:
1750:
1718:(4): 404–9.
1715:
1711:
1669:
1665:
1625:
1621:
1611:
1581:(5): 702–6.
1578:
1574:
1568:
1550:
1532:
1521:. Retrieved
1517:the original
1506:
1491:
1476:
1461:
1434:
1427:
1394:
1390:
1383:
1353:(1): 39–47.
1350:
1346:
1340:
1316:(2): 137–9.
1313:
1309:
1299:
1267:(2): 67–80.
1264:
1260:
1250:
1226:(4): 671–8.
1223:
1219:
1209:
1176:
1172:
1166:
1125:
1121:
1111:
1076:
1072:
1062:
1027:
1023:
998:. Retrieved
964:
958:
925:
921:
897:stigmasterol
882:
873:
865:
853:
846:
835:
827:
812:
801:
794:
777:
767:
760:
754:
737:
635:Rapeseed oil
589:62.6 – 70.4
586:12.3 – 16.1
558:50.2 – 62.1
552:18.7 – 29.1
414:Stigmasterol
397:β-Sitosterol
392:Stigmasterol
362:
359:
347:
328:
285:Cycloartenol
243:Stigmastanol
229:Stigmasterol
201:β-sitosterol
175:
158:is obtained.
142:stigmasterol
137:is obtained.
130:is obtained.
120:β-sitosterol
117:
106:
66:
42:Phytosterols
41:
40:
35:β-sitosterol
18:Plant sterol
6352:Cholesterol
6341:Cholesterol
6336:Desmosterol
6314:Cholesterol
6304:Lathosterol
6282:Zymosterone
6237:Cholesterol
5997:Cholesterol
5925:Spinasterol
5863:Campesterol
5751:Beta-glucan
5681:Oxalic acid
5674:Quinic acid
5669:Phytic acid
5606:Betacyanins
5387:Oleocanthal
5204:Norbergenin
5199:Tannic acid
5194:Gallic acid
4988:Polyphenols
4961:Xanthonoids
4938:Chalconoids
4788:Eckstolonol
4685:Terflavin B
4650:Vescalagins
4645:Castalagins
4550:Piceatannol
4540:Resveratrol
4530:Stilbenoids
4520:Pinoresinol
4455:Castavinols
4297:Delphinidin
4248:Flavanonols
4238:Eriodictyol
4065:Isoflavones
3947:polyphenols
3911:Polyphenols
3713:Rubixanthin
3703:Astaxanthin
3664:Phytofluene
3616:Carotenoids
3506:Cholesterol
3501:Tocopherols
3471:Campesterol
3370:Resin acids
3355:Gibberellin
3350:Aphidicolin
3343:Tetracyclic
3218:Longifolene
3182:Artemisinin
3159:Umbellulone
3047:Citronellol
3037:Citronellal
2700:Cholesterol
2667:Cholestanes
1628:(1): 92–7.
1575:Circulation
900:pathogens.
802:Unlike the
797:cholesterol
666:Soybean oil
583:8.4 – 12.7
555:8.9 – 13.9
421:Coconut oil
403:Avenasterol
387:Campesterol
377:Cholesterol
335:glycolipids
304:Cholesterol
257:Campestanol
215:Campesterol
156:campestanol
135:cholesterol
128:campesterol
109:double bond
50:cholesterol
6515:Categories
6491:Ergosterol
6471:Fecosterol
6441:Sitosterol
6403:Sitosterol
6321:Zymosterol
6299:Zymostenol
6294:Zymosterol
6287:Zymosterol
6267:Lanosterol
6260:Lanosterol
6148:Carotenoid
6030:Acetyl-CoA
5920:Momordenol
5874:Ergostenol
5868:Ergosterol
5696:Malic acid
5392:Oleuropein
5330:tryptophan
5219:Theogallin
5086:Glycosides
4963:(C6-C1-C6)
4940:(C6-C3-C6)
4929:(C6-C7-C6)
4890:Enological
4670:Punicalins
4665:Grandinins
4555:Pinosylvin
4533:(C6-C2-C6)
4348:Leptosidin
4343:Aureusidin
4233:Naringenin
4228:Hesperidin
4220:Flavanones
4186:Luteoforol
4054:Kaempferol
4001:Flavonoids
3993:flavonoids
3958:(C6-C3-C6)
3955:Flavonoids
3901:Dillapiole
3698:Zeaxanthin
3542:Lanosterol
3489:Sitosterol
3484:Sitostanol
3360:Paclitaxel
3267:Monocyclic
3154:Ascaridole
3149:Eucalyptol
3102:Hinokitiol
3076:Monocyclic
2946:Monocyclic
2813:terpenoids
2771:Terpenoids
2715:Lanosterol
2299:Metabolism
1523:2011-09-06
1000:7 November
904:References
893:sitosterol
885:eukaryotes
761:For plant
701:0.2 – 1.3
670:0.6 – 1.4
608:0.6 – 3.8
604:Peanut oil
567:0.2 – 2.4
547:2.2 – 6.7
529:75.6 – 90
523:2.3 – 3.6
508:0.7 – 1.4
505:1.4 – 3.3
502:1.9 – 3.8
496:1.2 – 1.8
493:7.2 – 8.4
490:0.1 – 0.9
487:0.7 – 2.3
456:0.2 – 0.6
318:Ergosterol
170:ergosterol
149:sitostanol
6476:Episterol
5598:Betalains
5408:Capsaicin
5345:thyroxine
5335:histidine
5060:Aglycones
4967:Coumarins
4823:Bifuhalol
4750:Flavolans
4675:Roburin A
4655:Castalins
4488:Silymarin
4398:Phloretin
4367:Chalcones
4358:Chalcones
4256:Taxifolin
4173:flavanols
4144:flavanols
4077:Genistein
4050:Quercetin
4042:Flavonols
3991:Types of
3945:Types of
3896:Carvacrol
3858:Types of
3770:Synthesis
3626:Carotenes
3521:Ecdysones
3325:Forskolin
3313:Tricyclic
3300:Epimanool
3225:Nootkatin
3222:Muurolene
3214:Juniperol
3206:Chanootin
3187:Bisabolol
3118:Carvacrol
2958:Terpinene
2860:(4 rings)
2807:Types of
2761:Types of
2686:Adosterol
1158:208646899
1142:2042-6496
942:1873-2194
928:: 35–61.
532:3.1 – 14
514:Olive oil
354:margarine
113:saturated
95:Structure
6453:instead.
6394:Nonhuman
6386:instead.
6250:Squalene
6161:Phytoene
6126:Geranyl-
5761:Lentinan
5739:Pentoses
5581:Piperine
5532:Sulfides
5515:Nitriles
5473:Sinigrin
5413:Gingerol
5340:tyrosine
5297:Coumarin
5235:Vanillin
5174:Bergenin
4895:Drilling
4818:Trifucol
4571:Curcumin
4499:((C6-C3)
4293:Cyanidin
4182:Apiforol
4153:Catechin
4073:Daidzein
4027:Apigenin
4019:Flavones
3891:Carnosol
3669:Phytoene
3654:Lycopene
3555:Squalane
3547:Saponins
3458:Steroids
3320:Cembrene
3297:-Abienol
3288:Bicyclic
3192:Cadinene
3127:Bicyclic
3093:p-Cymene
3067:Linalool
3052:Geraniol
3003:Sabinene
2993:Camphene
2972:Bicyclic
2953:Limonene
2937:Myrcenes
2878:Isoprene
2858:Steroids
2849:Iridoids
2817:isoprene
2809:terpenes
2627:24777987
2586:22623436
2521:20430133
2485:12450893
2444:15330272
2409:19548242
2401:11002384
2360:17074925
2319:12489060
2284:16399487
2248:10758959
2213:17137582
2177:19962145
2142:20228406
2091:18769018
2050:16542769
1972:12911045
1931:41438503
1923:20439548
1888:22623436
1825:10573535
1784:24468148
1742:19158117
1688:17951490
1595:13042924
1419:19049641
1411:15054420
1375:43470157
1332:11242480
1291:28702423
1242:15522137
1193:15638245
1150:31804642
1103:32550215
1054:22334625
950:29627611
713:56 – 63
704:0 – 0.2
691:1.5 – 5
688:1 – 4.5
682:52 – 58
679:16 – 19
676:16 – 24
673:0 – 0.3
657:0 – 0.8
654:0 – 6.6
651:45 – 58
648:0 – 0.7
645:18 – 39
639:0.4 – 2
620:48 – 65
614:12 – 20
611:0 – 0.2
598:0 – 2.1
595:0 – 1.4
580:0 – 0.3
577:1 – 3.7
564:0 – 5.1
561:0 – 2.8
543:Palm oil
526:0.6 – 2
518:0 – 0.5
499:80 – 90
468:55 – 67
462:18 – 24
459:0 – 0.2
452:Corn oil
443:0.6 – 2
437:50 – 70
434:12 – 18
428:0 – 0.9
425:0.6 – 2
6202:CDP-MEP
6068:Acetone
6050:HMG-CoA
6045:HMB-CoA
6022:HMG-CoA
6001:steroid
5773:Inulins
5768:Fructan
5734:Hexoses
5611:Betanin
5566:Allicin
5551:Indoles
5377:Tyrosol
4957:(C6-C3)
4951:(C6-C4)
4905:Tanning
4798:Difucol
4783:Dieckol
4615:tannins
4579:Tannins
4496:Lignans
4381:, et.c.
4335:Aurones
4322:, et.c.
4299:, et.c.
4263:, et.c.
4211:, et.c.
4188:, et.c.
4159:, et.c.
4114:Flavans
4056:, et.c.
4033:, et.c.
4031:Chrysin
3807:(DMAPP)
3537:Betulin
3335:Pimarol
3332:Pimaral
3279:Retinal
3274:Retinol
3243:Acyclic
3202:Cedrene
3197:Cadinol
3139:Borneol
3134:Camphor
3088:Menthol
3062:Halomon
3030:Acyclic
2998:Thujene
2932:Ocimene
2925:Acyclic
2675:sterols
2133:2903788
1989:. WebMD
1733:2642922
1644:3942097
1603:3165910
1282:5503415
1201:4043005
1094:7270433
1045:3279314
868:stanols
804:statins
719:7 – 13
710:8 – 11
707:7 – 13
642:5 – 13
617:5 – 13
440:5 – 16
431:7 – 10
363:stanols
62:stanols
58:sterols
6374:20α,22
6212:HMB-PP
6197:CDP-ME
5785:Pectin
5780:Lignin
5756:Chitin
5571:Alliin
5401:Others
5355:L-DOPA
4920:Others
4375:Butein
4122:Flavan
4081:Orobol
3886:Apiole
3729:(many)
3708:Lutein
3559:Acids
3250:Phytol
3108:Thymol
3042:Citral
3008:Carene
2979:Pinene
2892:Prenol
2839:forms)
2819:units)
2815:(# of
2625:
2584:
2519:
2483:
2442:
2407:
2399:
2358:
2317:
2282:
2246:
2211:
2175:
2140:
2130:
2089:
2048:
1993:6 July
1970:
1929:
1921:
1886:
1823:
1782:
1740:
1730:
1686:
1642:
1601:
1593:
1450:
1417:
1409:
1373:
1367:659760
1365:
1330:
1289:
1279:
1240:
1199:
1191:
1173:Lipids
1156:
1148:
1140:
1101:
1091:
1052:
1042:
948:
940:
889:fungal
832:Safety
823:enzyme
722:3 – 6
716:2 – 7
685:2 – 4
660:0 – 5
629:0 – 5
626:0 – 5
623:7 – 9
592:4 – 9
537:0 – 4
477:1 – 4
474:1 – 3
471:4 – 8
465:4 – 8
446:2 – 8
54:plants
6445:More
6350:From
6222:DMAPP
6207:MEcPP
6089:DMAPP
4768:Eckol
4083:et.c.
3801:(IPP)
3618:) (8)
3530:Other
2837:trans
2405:S2CID
2013:(PDF)
2008:FDA.
1927:S2CID
1599:S2CID
1560:(PDF)
1542:(PDF)
1537:FDA.
1511:FDA.
1415:S2CID
1371:S2CID
1197:S2CID
1154:S2CID
994:(PDF)
6451:here
6449:see
6384:here
6382:See
6187:DOXP
5999:and
5797:Misc
5428:Misc
4981:Misc
4969:and
2985:and
2918:)(2)
2835:and
2811:and
2623:PMID
2582:PMID
2517:PMID
2481:PMID
2440:PMID
2397:PMID
2356:PMID
2315:PMID
2280:PMID
2244:PMID
2209:PMID
2173:PMID
2138:PMID
2087:PMID
2046:PMID
1995:2013
1968:PMID
1919:PMID
1884:PMID
1821:PMID
1780:PMID
1738:PMID
1684:PMID
1640:PMID
1591:PMID
1448:ISBN
1407:PMID
1363:PMID
1328:PMID
1287:PMID
1238:PMID
1189:PMID
1146:PMID
1138:ISSN
1099:PMID
1050:PMID
1002:2017
946:PMID
938:ISSN
895:and
755:The
734:EFSA
333:and
60:and
44:are
6461:To
6401:To
6355:to
6235:To
6217:IPP
6192:MEP
6087:to
6040:HMB
6020:to
5893:C29
5851:C28
4900:Ink
3450:(6)
3433:(5)
3295:cis
3236:(4)
3175:(3)
2871:(1)
2833:cis
2613:doi
2574:doi
2544:doi
2509:doi
2505:110
2471:doi
2432:doi
2387:doi
2346:doi
2307:doi
2272:doi
2236:doi
2201:doi
2197:196
2165:doi
2161:210
2128:PMC
2118:doi
2077:doi
2038:doi
1958:doi
1911:doi
1876:doi
1849:doi
1845:105
1811:doi
1807:129
1770:doi
1766:232
1728:PMC
1720:doi
1674:doi
1670:137
1630:doi
1583:doi
1440:doi
1399:doi
1355:doi
1318:doi
1277:PMC
1269:doi
1228:doi
1181:doi
1130:doi
1089:PMC
1081:doi
1040:PMC
1032:doi
930:doi
858:).
757:FDA
751:FDA
747:".
412:∆7-
401:∆5-
6517::
6365:22
4377:,
4318:,
4295:,
4207:,
4184:,
4155:,
4079:,
4075:,
4052:,
4029:,
2916:16
2912:10
2910:(C
2880:(C
2673::
2669:,
2621:.
2607:.
2603:.
2580:.
2570:56
2568:.
2556:^
2538:.
2515:.
2503:.
2479:.
2467:76
2465:.
2461:.
2438:.
2428:14
2426:.
2403:.
2395:.
2383:54
2381:.
2377:.
2354:.
2342:48
2340:.
2336:.
2313:.
2303:51
2301:.
2278:.
2268:16
2266:.
2242:.
2232:35
2230:.
2207:.
2195:.
2171:.
2159:.
2136:.
2126:.
2114:51
2112:.
2108:.
2085:.
2073:50
2071:.
2067:.
2044:.
2034:44
2032:.
1966:.
1954:78
1952:.
1948:.
1925:.
1917:.
1907:28
1905:.
1882:.
1872:56
1870:.
1843:.
1819:.
1805:.
1801:.
1778:.
1764:.
1760:.
1736:.
1726:.
1716:30
1714:.
1710:.
1696:^
1682:.
1668:.
1664:.
1652:^
1638:.
1626:43
1624:.
1620:.
1597:.
1589:.
1577:.
1446:,
1413:.
1405:.
1395:58
1393:.
1369:.
1361:.
1351:73
1349:.
1326:.
1314:85
1312:.
1308:.
1285:.
1275:.
1265:22
1263:.
1259:.
1236:.
1224:92
1222:.
1218:.
1195:.
1187:.
1177:39
1175:.
1152:.
1144:.
1136:.
1126:11
1124:.
1120:.
1097:.
1087:.
1077:19
1075:.
1071:.
1048:.
1038:.
1028:33
1026:.
1022:.
1010:^
973:^
944:.
936:.
926:70
924:.
911:^
91:.
83:,
79:,
6376:R
6367:R
5989:e
5982:t
5975:v
5836:e
5829:t
5822:v
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5444:)
5430::
5027:e
5020:t
5013:v
4983::
4606:e
4599:t
4592:v
4503:)
4501:2
4175:)
4171:(
4146:)
4142:(
3984:e
3977:t
3970:v
3938:e
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3851:e
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3784:)
3780:(
3681::
3614:(
3104:)
3100:(
2989:)
2987:β
2983:α
2981:(
2914:H
2888:)
2886:8
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2882:5
2800:e
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