52:
641:
377:
38:
461:; etc. In the body, toxic substances are often bonded to glucuronic acid to increase their water solubility; the resulting glucuronides are then excreted. Compounds can also be generally defined based on the class of glycone; for example, biosides are glycosides with a disaccharide (biose) glycone.
144:
butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.
673:
formation, carbon and nitrogen transport, and possibly act as antioxidants. The production of cyanogenic glycosides is an evolutionarily conserved function, appearing in species as old as
1209:
Nahrstedt, A.; Davis, R.H. (1983). "Occurrence, variation and biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in species of the
Heliconiini (Insecta: Lepidoptera)".
976:. Saponins are also natural ruminal antiprotozoal agents that are potential to improve ruminal microbial fermentation reducing ammonia concentrations and methane production in ruminant
681:. These compounds are made by around 3,000 species. In screens they are found in about 11% of cultivated plants but only 5% of plants overall; humans seem to have selected for them.
277:
510:
Glycosides are also classified according to the chemical nature of the aglycone. For purposes of biochemistry and pharmacology, this is the most useful classification.
351:
refers to the synthesis of glycosides by the reaction of unprotected monosaccharides with alcohols (usually as solvent) in the presence of a strong acid catalyst. The
127:. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by
754:, have evolved to use the cyanogenic glycosides found in their host plants as a form of protection against predators through their unpalatability.
1281:
1256:
1193:
1622:
469:
Depending on whether the glycosidic bond lies "below" or "above" the plane of the cyclic sugar molecule, glycosides are classified as
416:
1409:
Benson, Woodruff W. (1971). "Evidence for the
Evolution of Unpalatability Through Kin Selection in the Heliconinae (Lepidoptera)".
1841:
1536:"The effect and mode of action of saponins on the microbial populations and fermentation in the rumen and ruminant production"
134:, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as
398:
1595:
928:). In general, the use of the term saponin in organic chemistry is discouraged, because many plant constituents can produce
1298:
880:
and anti-inflammatory effects. Steroid saponins are important starting material for the production of semi-synthetic
394:
387:
662:. These remove the sugar part of the molecule, allowing the cyanohydrin structure to collapse and release toxic
1615:
1021:
666:. Storing them in inactive forms in the vacuole prevents them from damaging the plant under normal conditions.
1453:
961:
1329:
Gleadow, RM; Møller, BL (2014). "Cyanogenic glycosides: synthesis, physiology, and phenotypic plasticity".
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1144:
352:
561:
348:
1455:
The roles of temperature and host plant interactions in larval development and population ecology of
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736:
620:
253:
1024:(historically as now recognised does not improve survivability; other agents are now preferred) and
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Glycosides can be classified by the glycone, by the type of glycosidic bond, and by the aglycone.
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1070:-glucose combinations are bound to the ends of the aglycone to form the different compounds.
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Along with playing a role in deterring herbivores, in some plants they control germination,
663:
356:
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is the condensation of glycosyl halides and alcohols in the presence of metal salts such as
276:
and group them with the glycosides; this is considered a misnomer and is discouraged by the
120:
76:
1299:"Nouvelles expériences sur les amandes amères et sur l'huile volatile qu'elles fournissent"
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In formal terms, a glycoside is any molecule in which a sugar group is bonded through its
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that can form and break glycosidic bonds. The most important cleavage enzymes are the
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1301:[New experiments on bitter almonds and the volatile oil that they provide].
735:, were investigated as potential drugs to treat cancer and were heavily promoted as
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1054:. The two primary glycosides, stevioside and rebaudioside A, are used as natural
968:
and vaccines directed against intracellular pathogens as well as for therapeutic
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651:
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316:. For example, the glycone and aglycone portions can be chemically separated by
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These compounds give a permanent froth when shaken with water. They also cause
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27:"Bioside" redirects here. For the poisonous substance or microorganism, see
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Comparative
Biochemistry and Physiology Part B: Comparative Biochemistry
960:
Molina, to stimulate both the Th1 immune response and the production of
704:, the first cyanogenic glycoside to be identified, was first isolated),
233:
part of the glycoside. The glycone can consist of a single sugar group (
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401: in this section. Unsourced material may be challenged and removed.
344:
have been developed that can form glycosidic bonds in excellent yield.
45:
41:
28:
488:
There are four type of linkages present between glycone and aglycone:
1672:
1111:
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1006:
949:
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329:
325:
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species. Anthron and anthranol are reduced forms of anthraquinone.
560:
These glycosides contain an aglycone group that is a derivative of
312:
Much of the chemistry of glycosides is explained in the article on
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36:
936:-glycosides are amphipolar under certain conditions, acting as a
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group. Plants that make cyanogenic glycosides store them in the
590:
492:
C-linkage/glycosidic bond, "nonhydrolysable by acids or enzymes"
321:
1604:
347:
There are many ways to chemically synthesize glycosidic bonds.
211:
Many authors require in addition that the sugar be bonded to a
670:
618:. Other coumarin glycosides are obtained from dried leaves of
370:
196:-glycosyl compound". The given definition is the one used by
34:
Molecule in which a sugar is bound to another functional group
1600:
964:(CTLs) against exogenous antigens make them ideal for use in
696:
tree; other species that produce cyanogenic glycosides are
215:
for the molecule to qualify as a glycoside, thus excluding
100:
94:
88:
632:
In this case, the aglycone is called benzo-gamma-pyrone.
336:, and the most important synthetic enzymes in nature are
82:
998:
nucleus. These glycosides are found in the plant genera
280:. Glycosylamines and glycosides are grouped together as
940:. More modern uses of saponins in biotechnology are as
264:
Molecules containing an N-glycosidic bond are known as
766:. Examples of this large group of glycosides include:
1274:
97:
91:
815:
Among the important effects of flavonoids are their
103:
85:
1747:
1704:
1671:
1638:
79:
278:International Union of Pure and Applied Chemistry
1491:Sun, Hong-Xiang; Xie, Yong; Ye, Yi-Ping (2009).
1324:
1322:
1320:
1318:
1316:
481:can only hydrolyze α-linkages; others, such as
1459:Doubleday, the Rocky Mountain Apollo butterfly
1793:
1616:
8:
1186:Synthesis and Characterization of Glycosides
994:In these glycosides, the aglycone part is a
906:, in the form of its glycoside dioscin. The
1370:The Cochrane Database of Systematic Reviews
1050:Bertoni have 40–300 times the sweetness of
972:but with the aforementioned side-effect of
1778:
1623:
1609:
1601:
1803:
1756:
1588:Compendium of Chemical Terminology, the "
1551:
1510:
1385:
1364:Milazzo, S; Horneber, M (28 April 2015).
1058:in many countries. These glycosides have
417:Learn how and when to remove this message
1798:
1788:
872:. Their medicinal value is due to their
819:effect. They are also known to decrease
532:. Salicin is converted in the body into
248:The first glycoside ever identified was
156:. Glycosides can be linked by an O- (an
1176:
984:Steroid glycosides (cardiac glycosides)
437:If the glycone group of a glycoside is
256:and Antoine Boutron-Charlard, in 1830.
219:. The sugar group is then known as the
846:. It has a urinary antiseptic effect.
739:; they are ineffective and dangerous.
731:Amygdalin and a synthetic derivative,
650:In this case, the aglycone contains a
1493:"Advances in saponin-based adjuvants"
1343:10.1146/annurev-arplant-050213-040027
914:glycosides and ginseng saponins from
340:. Genetically altered enzymes termed
7:
1042:These sweet glycosides found in the
1016:. They are used in the treatment of
742:Some butterfly species, such as the
399:adding citations to reliable sources
180:) glycosidic bond. According to the
1820:
1297:Robiquet; Boutron-Charlard (1830).
868:. Saponin glycosides are found in
25:
1596:IUPAC naming rules for glycosides
568:effect. They are mainly found in
1303:Annales de Chimie et de Physique
1106:As the name contains the prefix
610:which is reported to dilate the
375:
284:; other glycoconjugates include
75:
1366:"Laetrile treatment for cancer"
831:Here, the aglycone is a simple
807:(aglycone: quercetin, glycone:
606:or a derivative. An example is
386:needs additional citations for
223:and the non-sugar group as the
1465:(MSc). University of Alberta.
1378:10.1002/14651858.CD005476.pub4
1331:Annual Review of Plant Biology
536:, which is closely related to
526:, which is found in the genus
485:, can only affect β-linkages.
1:
1534:Patra, AK; Saxena, J (2009).
1512:10.1016/j.vaccine.2009.01.091
1241:IUPAC Gold Book - Glycosides
1223:10.1016/0305-0491(83)90041-x
956:, isolated from the bark of
433:By glycone/presence of sugar
241:), or several sugar groups (
1184:Brito-Arias, Marco (2007).
1863:
1540:Nutrition Research Reviews
1305:. 2nd series (in French).
1110:, these compounds contain
1035:
987:
853:
465:By type of glycosidic bond
328:. There are also numerous
26:
1553:10.1017/S0954422409990163
835:structure. An example is
572:plants except the family
501:S-linkage/glycosidic bond
498:N-linkage/glycosidic bond
495:O-linkage/glycosidic bond
457:, then the molecule is a
449:, then the molecule is a
441:, then the molecule is a
324:and can be hydrolyzed by
252:, by the French chemists
192:; the preferred term is "
44:, a glycoside related to
1582:Definition of glycosides
1272:Lindhorst, T.K. (2007).
1022:congestive heart failure
762:Here, the aglycone is a
556:Anthraquinone glycosides
1794:Anthraquinone glycoside
1411:The American Naturalist
1249:10.1351/goldbook.G02661
962:cytotoxic T-lymphocytes
844:Arctostaphylos uva-ursi
477:. Some enzymes such as
200:, which recommends the
152:to another group via a
1842:Carbohydrate chemistry
1452:Doyle, Amanda (2011).
1150:Chemical glycosylation
1145:Carbohydrate chemistry
1062:as the aglycone part.
920:(Chinese ginseng) and
692:which are made by the
647:
602:Here, the aglycone is
580:. They are present in
353:Koenigs-Knorr reaction
63:
55:Chemical structure of
48:
643:
636:Cyanogenic glycosides
349:Fischer glycosidation
272:call these compounds
237:), two sugar groups (
138:. Several species of
54:
40:
1779:Cyanogenic glycoside
1457:Parnassius smintheus
801:, glycone: rutinose)
791:, glycone: rutinose)
758:Flavonoid glycosides
751:Parnassius smintheus
737:alternative medicine
621:Psoralea corylifolia
514:Alcoholic glycosides
395:improve this article
338:glycosyltransferases
334:glycoside hydrolases
204:to correctly assign
119:is bound to another
1804:Flavonoid glycoside
1757:Alcoholic glycoside
1114:. Examples include
952:and its derivative
922:Panax quinquefolius
827:Phenolic glycosides
628:Chromone glycosides
598:Coumarin glycosides
320:in the presence of
302:lipopolysaccharides
1799:Coumarin glycoside
1789:Phenolic glycoside
1155:Glycorandomization
1074:Iridoid glycosides
1032:Steviol glycosides
958:Quillaja saponaria
648:
268:. Many authors in
202:Haworth projection
64:
49:
1829:
1828:
1816:Steviol glycoside
1762:Cardiac glycoside
1663:C-glycosidic bond
1658:S-glycosidic bond
1653:N-glycosidic bond
1648:O-glycosidic bond
1505:(12): 1787–1796.
1283:978-3-527-31528-4
1258:978-0-9678550-9-7
1195:978-0-387-26251-2
1090:, theviridoside,
1078:These contain an
1048:Stevia rebaudiana
1038:Steviol glycoside
990:Cardiac glycoside
892:; for example in
720:, which produces
684:Examples include
677:and as recent as
614:as well as block
612:coronary arteries
550:anti-inflammatory
518:An example of an
427:
426:
419:
260:Related compounds
188:-glycoside" is a
61:cardiac glycoside
16:(Redirected from
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841:Common Bearberry
664:hydrogen cyanide
616:calcium channels
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243:oligosaccharide
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150:anomeric carbon
125:glycosidic bond
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917:Panax ginseng
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867:
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849:
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839:found in the
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694:bitter almond
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567:
563:
562:anthraquinone
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531:
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525:
522:glycoside is
521:
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390:
389:
384:This section
382:
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343:
339:
335:
331:
327:
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307:
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299:
295:
291:
290:glycopeptides
287:
286:glycoproteins
283:
279:
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259:
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187:
183:
179:
178:
173:
172:
171:thioglycoside
167:
166:
165:glycosylamine
161:
160:
155:
151:
146:
143:
142:
137:
133:
130:
126:
122:
118:
114:
108:
73:
69:
62:
58:
53:
47:
43:
39:
30:
19:
18:Thioglycoside
1705:
1631:
1571:
1543:
1539:
1529:
1502:
1496:
1486:
1474:. Retrieved
1458:
1454:
1447:
1414:
1410:
1404:
1369:
1359:
1334:
1330:
1306:
1302:
1292:
1273:
1267:
1240:
1237:"Glycosides"
1231:
1217:(1): 65–73.
1214:
1210:
1204:
1188:. Springer.
1185:
1179:
1140:Carbohydrate
1105:
1082:group; e.g.
1077:
1047:
1041:
1013:Strophanthus
1011:
1005:
999:
993:
921:
915:
908:ginsenosides
890:progesterone
859:
843:
830:
814:
761:
749:
743:
741:
730:
726:lotaustralin
714:white clover
700:(from which
683:
668:
649:
631:
619:
601:
589:
559:
527:
517:
509:
487:
475:β-glycosides
474:
471:α-glycosides
470:
468:
436:
428:
413:
407:January 2021
404:
393:Please help
388:verification
385:
346:
311:
274:N-glycosides
273:
270:biochemistry
263:
247:
239:disaccharide
230:
224:
220:
212:
210:
193:
185:
184:, the name "
175:
174:), or C- (a
169:
163:
157:
147:
139:
71:
65:
1772:Cardenolide
1729:Glucuronide
1719:Galactoside
1686:β-Glycoside
1681:α-Glycoside
1584:, from the
1476:13 November
1126:, found in
1118:, found in
932:, and many
874:expectorant
823:fragility.
817:antioxidant
797:(aglycone:
787:(aglycone:
777:, glycone:
773:(aglycone:
745:Dryas iulia
679:angiosperms
652:cyanohydrin
546:antipyretic
506:By aglycone
459:glucuronide
453:; if it is
445:; if it is
298:glycolipids
177:C-glycoside
159:O-glycoside
136:medications
115:in which a
1847:Glycosides
1836:Categories
1734:Rhamnoside
1714:Fructoside
1632:Glycosides
1337:: 155–85.
1309:: 352–382.
1171:References
1056:sweeteners
1026:arrhythmia
938:surfactant
934:triterpene
912:triterpene
884:and other
805:Quercitrin
789:naringenin
775:hesperetin
771:Hesperidin
576:which are
451:fructoside
318:hydrolysis
141:Heliconius
132:hydrolysis
1724:Glucoside
1590:Gold Book
1001:Digitalis
974:hemolysis
942:adjuvants
904:diosgenin
901:sapogenin
894:Dioscorea
878:corticoid
870:liquorice
862:hemolysis
821:capillary
799:quercetin
764:flavonoid
722:linamarin
686:amygdalin
660:cytoplasm
645:Amygdalin
574:Liliaceae
552:effects.
542:analgesic
520:alcoholic
479:α-amylase
443:glucoside
308:Chemistry
250:amygdalin
213:non-sugar
162:), N- (a
72:glycoside
68:chemistry
57:oleandrin
1749:Aglycone
1739:Riboside
1673:Geometry
1562:20003589
1521:19208455
1439:84261089
1396:25918920
1351:24579992
1243:. 2009.
1134:See also
1124:sinalbin
1116:sinigrin
1096:catalpol
1068:rhamnose
1020:, e.g.,
946:vaccines
897:wild yam
888:such as
850:Saponins
833:phenolic
809:rhamnose
785:Naringin
779:rutinose
733:laetrile
690:prunasin
604:coumarin
578:monocots
566:laxative
540:and has
447:fructose
226:aglycone
190:misnomer
168:), S-(a
113:molecule
1811:Saponin
1706:Glycone
1498:Vaccine
1431:2459551
1387:6513327
1092:loganin
1084:aucubin
1080:iridoid
1064:Glucose
1060:steviol
1052:sucrose
996:steroid
978:animals
856:Saponin
837:arbutin
718:cassava
702:dhurrin
698:sorghum
656:vacuole
608:apterin
586:rhubarb
538:aspirin
524:salicin
483:emulsin
439:glucose
330:enzymes
221:glycone
46:aspirin
42:Salicin
29:Biocide
1560:
1519:
1437:
1429:
1394:
1384:
1349:
1280:
1255:
1192:
1122:, and
1112:sulfur
1046:plant
1044:stevia
1010:, and
1007:Scilla
950:Quil A
716:, and
706:barley
548:, and
326:alkali
300:, and
129:enzyme
123:via a
1586:IUPAC
1463:(PDF)
1435:S2CID
1427:JSTOR
1108:thio-
954:QS-21
795:Rutin
675:ferns
582:senna
570:dicot
529:Salix
231:genin
198:IUPAC
182:IUPAC
117:sugar
111:is a
1640:Bond
1558:PMID
1517:PMID
1478:2017
1392:PMID
1347:PMID
1278:ISBN
1253:ISBN
1190:ISBN
930:foam
910:are
899:the
748:and
724:and
710:flax
688:and
591:Aloe
588:and
322:acid
70:, a
59:, a
1548:doi
1507:doi
1467:doi
1419:doi
1415:105
1382:PMC
1374:doi
1339:doi
1245:doi
1219:doi
1066:or
944:in
864:of
671:bud
473:or
397:by
359:or
245:).
229:or
66:In
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1538:.
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1503:27
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1495:.
1433:.
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1380:.
1368:.
1345:.
1335:65
1333:.
1315:^
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1251:.
1239:.
1215:75
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1130:.
1098:.
1094:,
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1028:.
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948::
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712:,
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292:,
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1261:.
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20:)
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