1243:(invocation). European settlers of New Zealand used the wood for wharf piles, bridges, railway sleepers, telegraph poles, lighthouses, mining equipment, fence posts and foundation blocks. The durability stems from the anti-bacterial activity of totarol. Houses, churches, grave markers, and even cobbles and kerbs were made of totara; strips of the bark were used as a roofing material. The presence of totarol means totara wood resists decay and insect attack in the heart timber. Totarol has been found in organic matter in the embankments of a
300:
207:
1260:. Leaf extract from the flowering plant has been used historically as a medicine known as "El Rayhan". It was used as a decoction, infusion and health remedy for bathing newborns with inflamed skin and washing sores. Additionally, it was used to treat oral wounds, disorders of the digestive and urinary systems, diarrhea, peptic ulcers, hemorrhoids and inflammations. Totarol was detected in a 2024 Myrtus Communis leaf extract study and described as having considerable
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Easterfield observed no other compound had been cited in chemical literature before with this formula. Easterfield and his colleague J.C McDowell proposed the name “totarol” in a follow-up paper in 1915, as the crystalline substance was believed to possess a tertiary alcohol group. In 1937 Short and
1406:
followed by debromination to yield (±)-totarol. The main downfall of this synthesis was that in multiple steps, complete conversion of reactant to products was not observed and undesirable side products were often not separable by chromatography. However, since this was the first total synthesis of
1314:
The biosynthesis of totarol was difficult to determine. The main reason for the challenge in determining how the secondary metabolite is produced is because totarol does not follow the isoprene rule: the isopropyl group of totarol is in the “wrong” place at C14. Initially, it was hypothesized that
1903:
Products for sale containing totarol include toothpastes, tooth tablets, mouthwash, toners, cleansers, moisturisers, face masks, concealers, blemish control, anti-acne, pimple patches, face cream, eye cream, sun screen, deodorants, face mists, facial wash, anti-wrinkle, restorative serum, renew
1894:
Totarol is extracted by supercritical extraction. The process uses high pressure carbon dioxide under specific temperature, pressure and gas flow conditions to extract totarol from powdered totara wood. Totarol can be extracted from dead wood, negating the need to cut down live trees. Although
1167:
of bacteria by weakening Van der Waals interactions with its phenolic group, which also results in bacterial cells unable to synthesize ATP. Motivation for totarol functioning via disruption of membrane structure is due to its high phospholipid/water partition coefficient. However, totarol's
1904:
cream, scar removal serum, dandruff control, scalp treatment, shampoo bar, pet skin cream, hand wash, hand cream, pressed powder makeup, mascara, rescue cream, skin whitener, lip tint, pregnancy body oil, mouth freshener, sore throat relief, cold and flu nasal spray.
787:, crustaceous foulers (Table 1). In addition to inhibiting microorganisms by itself, totarol exhibits inhibitory synergy with currently used antimicrobial drugs: totarol potentiates isonicotinic acid hydrazide against various Mycobacteria.; methicillin against
1264:
potential. Despite totarol's demonstrated antimicrobial efficacy, its commercial application remains primarily confined to the cosmetic industry. For totarol to be considered for clinical use, a comprehensive understanding of its mode of action is essential.
1323:(Scheme 1). This hypothesis was motivated by the well known santonin-desmotroposantonin rearrangement of steroid dienones into aromatic compounds. It is now accepted that totarol is synthesized biologically from ferruginol. Geranyl geranyl pyrophosphate
1168:
partitioning capability was only observed at concentrations 10 to 100 fold higher than required for antibacterial activity. Thus it is unlikely that totarol is an uncoupler of bacterial respiration at the low levels observed in antimicrobial studies.
1151:
strains through inhibition of MsrA, although it is unclear if MsrA is an efflux pump. Totarol may also gain its antibacterial properties by inhibiting bacterial respiratory transport but this is very unlikely because totarol is also effective against
2164:
Le Métayer P, Schaeffer P, Adam P, Albrecht P, Roussé S, Duringer P (June 2008). "An unprecedented condensation pathway leading to the formation of phenolic C40 bis-diterpenoids in sediments from the Lower
Oligocene of the Rhine Rift Valley".
1916:
including totarol are used for the aromatization and production of some gins. Consequently, totarol can aid in the characterization of different types of gin or commercial brands, vouching for the authenticity and quality of the product.
3960:
1225:
as it reaches down to Papatūānuku (Mother Earth) and up towards
Ranginui (Sky Father). The roots in the symbolism of the totara mark out a genealogical reference point which Māori believe ties them to the natural world, the
1220:
can be viewed as a representation of ancestry and historical and mythological events. The totara can also be seen to represent a connection between the past and the present, the secular and the spiritual. It has a strong link to
2247:
Mossa JS, El-Feraly FS, Muhammad I (November 2004). "Antimycobacterial constituents from
Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide".
1238:
and the forest godess
Mumuwhango and is considered a noble tree. According to tradition, felling a totara wasn't possible without seeking permission from Tāne-Mahuta. This involved performing specific rituals and chanting
450:
422:
735:
of the family
Podocarpaceae and the subfamily Cupressoideae of the family Cupressaceae. Outside Podocarpus and Cupressoideae, totarol is rarely found in the plant kingdom. However, totarol has recently been isolated in
4191:
Reddy PJ, Ray S, Sathe GJ, Gajbhiye A, Prasad TS, Rapole S, et al. (January 2015). "A comprehensive proteomic analysis of totarol induced alterations in
Bacillus subtilis by multipronged quantitative proteomics".
1931:
collect resin to create a protective barrier around the opening of their nest to ward off insects from settling near the nest's entrance. The presence of totarol can aid in the determination of this bee species.
4147:
Gao Y, Xu X, Chang S, Wang Y, Xu Y, Ran S, et al. (December 2015). "Totarol prevents neuronal injury in vitro and ameliorates brain ischemic stroke: Potential roles of Akt activation and HO-1 induction".
1251:
resin at the site was used for its antibacterial and antifungal properties to preserve meat, as well as for its ability to repel insects. Totarol has also been identified in the leaves of
Algerian grown
3647:
Antibacterial properties of diterpenes and their derivatives: a thesis presented in partial fulfilment of the requirements for the degree of Master of
Science in Microbiology at Massey University
2759:
Mateo CR, Prieto M, Micol V, Shapiro S, Villalaín J (December 2000). "A fluorescence study of the interaction and location of (+)-totarol, a diterpenoid bioactive molecule, in model membranes".
1156:. Recently totarol was also hypothesized to inhibit gram-positive and acid-fast bacteria via inhibition of FtsZ protein, which forms the Z-ring, a polymer necessary for efficient bacterial cell
4787:"Chemical Composition Antioxidant and Anti-Inflammatory Activities of Myrtus communis L. Leaf Extract: Forecasting ADMET Profiling and Anti-Inflammatory Targets Using Molecular Docking Tools"
3134:"Chemical Composition Antioxidant and Anti-Inflammatory Activities of Myrtus communis L. Leaf Extract: Forecasting ADMET Profiling and Anti-Inflammatory Targets Using Molecular Docking Tools"
3663:
Evans GB, Furneaux RH, Gravestock MB, Lynch GP, Scott GK (September 1999). "The synthesis and antibacterial activity of totarol derivatives. Part 1: modifications of ring-C and pro-drugs".
2484:
Evans GB, Furneaux RH, Gravestock MB, Lynch GP, Scott GK (September 1999). "The synthesis and antibacterial activity of totarol derivatives. Part 1: modifications of ring-C and pro-drugs".
516:
1454:, a lamdane diterpene named zamoranic acid (Scheme 5). The addition of the isopropyl group in the chemical synthesis was achieved with complete stereoselectivity. Acetylation to yield
3147:
Minami T, Iwamoto M, Ohtsu H, Ohishi H, Tanaka R, Yoshitake A (August 2002). "Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii".
2121:
Sharp H, Latif Z, Bartholomew B, Bright C, Jones CD, Sarker SD, et al. (February 2001). "Totarol, totaradiol and ferruginol: three diterpenes from Thuja plicata (Cupressaceae)".
3554:
Muroi H, Kubo I (April 1996). "Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant
Staphylococcus aureus".
2570:
Muroi H, Kubo I (April 1996). "Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant
Staphylococcus aureus".
5067:
Patricio EF, Cruz-López L, Maile R, Tentschert J, Jones GR, Morgan ED (February 2002). "The propolis of stingless bees: terpenes from the tibia of three Frieseomelitta species".
3857:
Patricio EF, Cruz-López L, Maile R, Tentschert J, Jones GR, Morgan ED (February 2002). "The propolis of stingless bees: terpenes from the tibia of three Frieseomelitta species".
579:
4520:
Minimum Inhibitory and Bactericidal Concentrations of a Totarol™ formulation against Staphylococcus aureus strains obtained from bovine intramammary infections in New Zealand
2436:
Samoylenko V, Dunbar DC, Gafur MA, Khan SI, Ross SA, Mossa JS, et al. (December 2008). "Antiparasitic, nematicidal and antifouling constituents from Juniperus berries".
3900:
Clarkson C, Musonda CC, Chibale K, Campbell WE, Smith P (October 2003). "Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity".
771:
Totarol motivates research in drug discovery due to its ability to inhibit numerous microorganisms. Totarol exhibits antimicrobial properties in numerous species including
3190:
Lee MK, Yang H, Yoon JS, Jeong EJ, Kim DY, Ha NR, et al. (July 2008). "Antifibrotic activity of diterpenes from Biota orientalis leaves on hepatic stellate cells".
1895:
totarol can be extracted from other Podocarpus, some trees in the cypress family (cypress, juniper, thuja) and from rosemary, it is most abundant in Podocarpus totara.
2794:
Bernabeu A, Shapiro S, Villalaín J (October 2002). "A MAS-NMR study of the location of (+)-totarol, a diterpenoid bioactive molecule, in phospholipid model membranes".
124:
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1439:
followed by intramolecular cyclization with aluminium chloride forms the B ring and totarylmethyl ether which is demethylated by boron tribromide to yield totarol.
2832:
Evans GB, Furneaux RH, Gainsford GJ, Murphy MP (July 2000). "The synthesis and antibacterial activity of totarol derivatives. Part 3: Modification of ring-B".
1303:
properties not possessed by totarol. Consequently, gymnosperms that produce totarol and nagilactones are able to defend themselves against bacteria and fungi.
3086:
346:
1204:
dates back to over 100 years. The timber of Podocarpus totara is renowned for its resilience against rotting, which made it valuable to Māori for housing,
3473:
Miyake T, Kigoshi H, Akita H (December 2007). "Chemoenzymatic synthesis of (+)-totarol,(+)-podototarin,(+)-sempervirol, and (+)-jolkinolides E and D.".
4112:
Jaiswal R, Beuria TK, Mohan R, Mahajan SK, Panda D (April 2007). "Totarol inhibits bacterial cytokinesis by perturbing the assembly dynamics of FtsZ".
2680:
Jaiswal R, Beuria TK, Mohan R, Mahajan SK, Panda D (April 2007). "Totarol inhibits bacterial cytokinesis by perturbing the assembly dynamics of FtsZ".
1212:
stockades, drinking vessels, shovels and carvings in chiefs houses. Totara bark was used to cover kelp bags containing preserved muttonbirds known as
1216:. The totara tree was accorded divine status by Māori based on its immense size and its use in making waka employed on long, dangerous voyages.
512:
4758:
Lu Y, Cui Y, Yang W, Meng F (July 11, 2023). "Design and synthesis of novel totarol derivatives bearing carbamate moiety as potential fungicides".
1135:
Although totarol exhibits antimicrobial properties, the mode of action is unclear and various methods of inhibitory action have been proposed. In
803:. In nature, totarol is a key player in gymnosperm's defense against harmful microbes: gymnosperms that produce totarol are resistant to rotting.
2056:
2033:
2653:
Shapiro S, Guggenheim B (August 1998). "Inhibition of oral bacteria by phenolic compounds. Part 1. QSAR analysis using molecular connectivity".
3419:
Das S, Sukanta B, Debabrata M (January 1992). "Stereocontrolled total synthesis of (±)-totaryl methyl ether and (±)-semperviryl methyl ether".
693:, Easterfield detected a "crystalline bloom" on totara boards a few hours after leaving the planing machine. After extraction of totarol from
3035:
3936:
2666:
1423:
The first total enantioselective synthesis of totarol was achieved in 1979 (Scheme 4). The key step in the synthesis is the formation of
4915:"Totarol exhibits antibacterial effects through antibiofilm and combined interaction against vancomycin-resistant Enterococcus faecalis"
3781:
Gordien AY, Gray AI, Franzblau SG, Seidel V (December 2009). "Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae)".
2528:
Gordien AY, Gray AI, Franzblau SG, Seidel V (December 2009). "Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae)".
2610:
Haraguchi H, Ishikawa H, Sakai S, Ying BP, Kubo I (June 1996). "Inhibition of lipid peroxidation by diterpenoid from Podocarpus nagi".
1291:
by acting as a hydrogen donor to peroxy radicals or reacting with other peroxy radicals to terminate undesirable radical reactions.
314:
5024:
Vichi S, Aumatell MR, Buxaderas S, López-Tamames E (November 2008). "Assessment of some diterpenoids in commercial distilled gin".
3233:
Van De Water RW, Pettus TR (July 2002). "o-Quinone methides: intermediates underdeveloped and underutilized in organic synthesis".
4229:"Effects of Ultrasound Treatment on Physiochemical Properties and Antimicrobial Activities of Whey Protein-Totarol Nanoparticles"
3652:
3262:"Anticancer Activities and Mechanism of Action of Nagilactones, a Group of Terpenoid Lactones Isolated from Podocarpus Species"
2936:
1387:
330:
InChI=1/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1
4843:"Efficacy of totarol against Staphylococcus pseudintermedius and Staphylococcus coagulans in dogs and cats: An in vitro study"
3369:
Barltrop JA, Rogers NA (1958). "520. Experiments on the synthesis of diterpenes. Part I. A total synthesis of (±)-totarol".
2971:"Ko te Rākau Hei Tohu Mō te Rangahau Me te Tuhi Whakapapa: Tree Symbolism as a Method for Researching and Writing Genealogy"
1458:
required high temperatures due to the steric hindrance of the isopropyl group. Cis-hydroxylation followed by cleavage with
3740:
1435:. This same cyclization can also be achieved via a Friedel-Crafts alkylation and cyclization. Subsequent hydrogenation of
504:
3025:
1512:
Chemoenzymatic synthesis of totarol has also been achieved with high yield (41.8%) (Scheme 6). A racemic beta-keto ester
1484:
to yield totarane diastereomers which were separated by column chromatography. The desired diastereomer was treated with
586:
5131:
486:
257:
3319:
Kubo I, Muroi H, Kubo A (December 1993). "Antibacterial activity of long-chain alcohols against Streptococcus mutans".
323:
InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,
4002:"The Antifungal Compound Totarol of Thujopsis dolabrata var. hondai Seeds Selects for Fungi on Seedling Root Surfaces"
1912:
Totarol may also be used as an indicator for the quality of juniper berry based spirits. Juniper berries that contain
1144:
278:
4802:"A balance of biocompatibility and antibacterial capability of 3D printed PEEK implants with natural totarol coating"
4478:"Formulation and Functional Properties of Whey Protein-Based Tissue Adhesive Using Totarol as an Antimicrobial Agent"
540:
441:
3446:
Marcos IS, Cubillo MA, Moro RF, Dıez D, Basabe P, Sanz F, et al. (December 2003). "Synthesis of (+)-totarol".
789:
1922:
214:
4678:"Larvicidal potential of Thuja orientalis leaves and fruits extracts against Culex pipiens (Diptera: Culicidae)"
4429:"The application of natural antibacterial coating for the surface modification of dental implants and abutments"
4270:"Preventing Surgical Site Infections Using a Natural, Biodegradable, Antibacterial Coating on Surgical Sutures"
746:
that contain totarol are distributed worldwide but are concentrated in North America, the far-south regions of
670:
4914:
4544:"Design, Hemiysnthesis, crystal structure and anticancer activity of 1, 2, 3-triazoles derivatives of totarol"
1359:
Totarol has been the subject of numerous syntheses. The first total synthesis of totarol (Scheme 3) utilized
532:
4948:
Hoisang, Jitpean, Seesupa, Kamlangchai, Makpunpol, Ngowwatana, Chaimongkol, Khunbutsri, Khlongkhlaeo, Kampa.
2294:
Gibbons S (January 2005). "Plants as a source of bacterial resistance modulators and anti-infective agents".
1492:. The synthesis was completed by a halogenation-dehydrogenation sequence and subsequent bromination to yield
528:
520:
3108:"Fire, meat and totarol: organic matter in the embankments of the Neolithic site Bastuloken (North Sweden)"
202:
5121:
3501:
1273:
Totarol decreases the plasma levels of estrogens and can also effectively reduce pathogenic hepatic cells
772:
738:
665:
3975:
705:. In 1951 Short and Wang became the first to identify the chemical structure of totarol with their paper
164:
3700:"Potentiation of methicillin activity against methicillin-resistant Staphylococcus aureus by diterpenes"
1315:
totarol and the “normal” diterpene ferruginol, also found in Podocarpaceae, were derived by a precursor
1279:. Totarol's anti-cancer activity is hypothesized to be due to the natural product's ability to form an
795:
683:
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464:
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48:
38:
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4268:
Reinbold J, Uhde AK, Müller I, Weindl T, Geis-Gerstorfer J, Schlensak C, et al. (September 2017).
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New Zealand scientist Sir Thomas Hill Easterfield was the first person to discover totarol. Photo 1920.
4873:
4427:
Xu Z, Krajewski S, Weindl T, Han X, Kimmerle-Müller E, Schweizer E, et al. (September 25, 2019).
3519:
Kubo I, Muroi H, Himejima M (October 1992). "Antibacterial activity of totarol and its potentiation".
2346:
Kubo I, Muroi H, Himejima M (October 1992). "Antibacterial activity of totarol and its potentiation".
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Laamari Y, Oubella A, Bimoussa A, El Mansouri AE, Ketatni EM, Mentre O, et al. (October 2021).
635:. Podocarpus totara was investigated for unique molecules due to the tree's increased resistance to
5116:
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that would be dehydrated and have its isopropyl group migrate to produce totarol 1 and ferruginol
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648:
295:
90:
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4740:
4719:"Computational modelling of some phenolic diterpenoid compounds as anti-influenza A virus agents"
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4658:
4458:
4065:"The phenolic diterpene totarol inhibits multidrug efflux pump activity in Staphylococcus aureus"
4045:
3626:
3215:
3172:
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2635:
2461:
2386:"The phenolic diterpene totarol inhibits multidrug efflux pump activity in Staphylococcus aureus"
2319:
2273:
1949:
1532:. A Michael addition with the anion obtained from the reaction of methyl 5-methyl-3-oxohexanoate
1403:
1153:
660:
492:
4321:"A Metabolomic and HPLC-MS/MS Analysis of the Foliar Phenolics, Flavonoids and Coumarins of the
3938:
Chemical modification and pharmacological evaluation of the antimalarial natural product totarol
1872:
Antibacterial effects through antibiofilm and combined interaction against vancomycin-resistant
4586:"PLGA-Based Nanoplatforms in Drug Delivery for Inhibition and Destruction of Microbial Biofilm"
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3763:
3721:
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3618:
3610:
3571:
3536:
3392:
Matsumoto T, Suetsugu A (May 1979). "The Total Synthesis of (+)-Totarol and (+)-Podototarin".
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2014:
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3958:, Gendimenico, Gerard J., "Method for treating skin disorders", issued 2005-04-19
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3829:
3818:"Effects of (+)-totarol, a diterpenoid antibacterial agent, on phospholipid model membranes"
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2717:"Effects of (+)-totarol, a diterpenoid antibacterial agent, on phospholipid model membranes"
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2034:"Studies on the chemistry of the New Zealand flora. Part IV.—The chemistry of the Podocarpi"
2006:
1979:
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4637:"Antimicrobial, toxicity, and anti-inflammatory activities of Buddleja perfoliata Kunth"
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3009: This article incorporates text from this source, which is available under the
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Han X, Sharma N, Xu Z, Krajewski S, Li P, Spintzyk S, et al. (22 February 2024).
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2’ (PBP2’), totarol may inhibit the synthesis of PBP2’. Totarol may inhibit effluxing
5110:
4872:
Haidar S, Amesty Á, Oramas-Royo S, Götz C, El-Awaad E, Kaiser J, et al. (2024).
4842:
4744:
4703:
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4001:
3741:"A Mosquito Larvicidal Diterpenoid Isolated from Podocarpus totara D. Don ex Lambert"
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1950:"(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol"
548:
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2909:"Pōhā, airtight storage containers. Science Learning Hub, Pokapū Akoranga Pūtaiao"
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Smith EC, Kaatz GW, Seo SM, Wareham N, Williamson EM, Gibbons S (December 2007).
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3459:
2869:"Ethnobotany, phytochemistry and pharmacology of Podocarpus sensu latissimo (sl)"
2384:
Smith EC, Kaatz GW, Seo SM, Wareham N, Williamson EM, Gibbons S (December 2007).
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Cuevas-Cianca SI, Leal AC, Hernández LR, Arreola ES, Bach H (October 13, 2022).
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Abdullahi M, Uzairu A, Shallangwa GA, Mamza PA, Ibrahim MT (December 8, 2022).
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1306:
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61:)-4b,8,8-Trimethyl-1-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-ol
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Staphylococcus pseudintermedius and Staphylococcus coagulans in dogs and cats
1140:
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4874:"1,2,3-Triazole-totarol conjugates as potent PIP5K1α lipid kinase inhibitors"
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2018:
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474:
2667:
10.1002/(SICI)1521-3838(199808)17:04<327::AID-QSAR327>3.0.CO;2-O
1244:
776:
751:
618:
5096:
5053:
4934:
4899:
4858:
4827:
4621:
4570:
4413:
4360:
4305:
4254:
4213:
4177:
4133:
4098:
4041:
3921:
3886:
3843:
3802:
3725:
3684:
3305:
3211:
3168:
2853:
2815:
2780:
2742:
2701:
2549:
2505:
2457:
2419:
2269:
2150:
606:
4949:
4926:
4584:
Shariati A, Chegini Z, Ghaznavi-Rad E, Zare EN, Hosseini SM (2022-06-21).
3622:
3606:
3575:
3540:
2631:
2591:
2367:
1335:, which proceeds through a spiro intermediate to form totarol (Scheme 2).
625:. It was first isolated by McDowell and Easterfield from the heartwood of
4445:
4428:
4080:
3405:
3378:
3355:
3160:
2401:
2205:
Bendall JG, Cambie RC (1995). "Totarol: A non-conventional diterpenoid".
2099:
1997:
Bendall JG, Cambie RC (1995). "Totarol: a Non-Conventional Diterpenoid".
1983:
1275:
1217:
780:
3532:
3332:
2359:
1163:
Totarol may also function by disrupting the structural integrity of the
2623:
1240:
1235:
1193:
644:
233:
215:
78:-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol
4494:
4477:
4374:
Shi C, Che M, Zhang X, Liu Z, Meng R, Bu X, et al. (March 2018).
4125:
2997:
2693:
2218:
2010:
470:
2449:
2261:
1450:
A more recent organic synthesis of totarol was achieved by utilizing
1372:
1299:
Totarol is a precursor to the formation of nagilactones that possess
1247:
site in Northern Sweden. Scientists have suggested that totarol from
1185:
647:
properties. Consequently, totarol is a candidate for a new source of
155:
556:
Except where otherwise noted, data are given for materials in their
3816:
Micol V, Mateo CR, Shapiro S, Aranda FJ, Villalaín J (April 2001).
3055:. Bedford Park - Australian Association for the Study of Religions.
2867:
Abdillahi HS, Stafford GI, Finnie JF, Van Staden J (January 2010).
2715:
Micol V, Mateo CR, Shapiro S, Aranda FJ, Villalaín J (April 2001).
806:
Table 1. Antibacterial activity of totarol against microorganisms
25:
1503:
1469:
yielded a diol that was acylated in pyridine and oxidized to give
1459:
1441:
1414:
1350:
1337:
1305:
1234:(territory). In Māori tradition totara is the first born child of
1209:
1189:
1181:
605:
597:
135:
123:
113:
3976:"The use of totarol to treat acne in an adolescent: A case study"
1446:
Scheme 5. The total synthesis of (+) totarol from zamoranic acid.
4950:"Evaluation of Totarol for Promoting Open Wound Healing in Dogs"
1327:
undergoes typical diterpene cyclization to form (−)-abietadiene
1231:
723:, totarol has also been identified in numerous other species of
544:
4000:
Yamaji K, Mori S, Akiyama M, Kato A, Nakashima T (2007-12-05).
1883:
Evaluation of totarol for promoting open wound healing in dogs
1496:
and ring aromatization with elimination via a lithium complex.
1473:. The key step in the synthesis was the cyclization of ring C:
1419:
Scheme 4. The first total enantioselective synthesis of totarol
1310:
Scheme 1. The initially proposed biosynthetic route of totarol.
1287:. Totarol also prevents cells from undergoing oxidative stress
4376:"Antibacterial activity and mode of action of totarol against
3087:"Fire protection of New Zealand's traditional Maori buildings"
1342:
Scheme 2. The currently accepted biosynthetic route of totarol
1516:
undergoes lipase-assisted resolution to yield chiral alcohol
283:
4988:
3591:"Antioxidative Action of Diterpenoids from Podocarpus nagi"
1728:
Ultrasound treatment on whey protein-totarol nanoparticles
412:
128 to 132 °C (262 to 270 °F; 401 to 405 K)
3502:"Chemistry of the podocarpaceae—XI: Reductions of totarol"
2038:
Transactions and Proceedings of the New Zealand Institute
2236:(2nd ed.). Kew: Royal Botanic Gardens. p. 212.
659:
Totarol was discovered in 1910 by New Zealand scientist
4325:
Species Resistant and Susceptible to Emerald Ash Borer"
1974:
Short WF, Stromberg H (1937). "116. Totarol. Part I.".
1544:
which is brominated and debrominated to yield totarol.
574:
1848:
3D printed PEEK implants with natural totarol coating
3989:(4): 253–255 – via Essentially New Zealand Ltd.
4517:
Velathanthiri N, Balmer T, Grinberg A (March 2020).
3027:
Carved Histories: Rotorua Ngati Tarawhai Woodcarving
4319:Qazi SS, Lombardo DA, Abou-Zaid MM (October 2018).
3822:Biochimica et Biophysica Acta (BBA) - Biomembranes
3346:Short WF, Wang H (1951). "662. Totarol. Part II".
2761:Biochimica et Biophysica Acta (BBA) - Biomembranes
2721:Biochimica et Biophysica Acta (BBA) - Biomembranes
1508:Scheme 6. The chemoenzymatic synthesis of totarol.
1355:Scheme 3. The first total synthesis of (±)-totarol
1920:Totarol has been found on the posterior tibia of
1616:Anti methicillin-resistant Staphylococcus aureus
1584:Anti methicillin-resistant Staphylococcus aureus
1536:with NaOMe gives a 2:1 diastereomeric mixture of
639:. Recent studies have confirmed totarol's unique
4590:Frontiers in Cellular and Infection Microbiology
3944:(Master Thesis thesis). University of Cape Town.
1402:. The synthesis was finalized by treatment with
245:
701:Stromberg continued investigations, publishing
99:
3698:Nicolson K, Evans G, O'Toole PW (1999-10-01).
3589:Haraguchi H, Ishikawa H, Kubo I (1997-06-01).
799:; and anacardic acid and erythromycin against
2655:Quantitative Structure-Activity Relationships
2431:
2429:
651:and has been the goal of numerous syntheses.
42:14-(Propan-2-yl)podocarpa-8,11,13-trien-13-ol
8:
4973:: CS1 maint: multiple names: authors list (
4476:Hou Y, Zhang X, Wang C, Guo M (2020-04-24).
2605:
2603:
2601:
2234:World Checklist and Bibliography of Conifers
1969:
1967:
1965:
1398:and another ketone that were inseparable by
4227:Ma S, Shi C, Wang C, Guo M (October 2017).
3106:Kaal J, Linderholm J, Martínez Cortizas A.
1927:, a species of stingless bees from Brazil.
3500:CR Bennett, RC Cambie (21 February 1966).
3321:Journal of Agricultural and Food Chemistry
2523:
2521:
2519:
2517:
2515:
2289:
2287:
298:
205:
183:
17:
4889:
4817:
4760:Monatshefte für Chemie - Chemical Monthly
4734:
4693:
4682:Journal of King Saud University - Science
4652:
4611:
4601:
4493:
4444:
4403:
4350:
4340:
4295:
4285:
4244:
4088:
3833:
3715:
3394:Bulletin of the Chemical Society of Japan
3371:Journal of the Chemical Society (Resumed)
3348:Journal of the Chemical Society (Resumed)
3295:
3277:
2996:
2986:
2884:
2827:
2825:
2732:
2479:
2477:
2475:
2409:
2200:
2198:
2196:
2092:Journal of the Chemical Society (Resumed)
2069:Transactions of the New Zealand Institute
1976:Journal of the Chemical Society (Resumed)
1800:Drug delivery destroys microbial biofilm
1371:which was converted to the corresponding
265:
3739:Lee SE, Park EK, Kim JG (October 2000).
2754:
2752:
2565:
2563:
2561:
2559:
2379:
2377:
1576:Bacteria killer and antibiotic enhancer
1551:
1176:The use of Podocarpus totara extract in
808:
663:. While investigating the properties of
4954:Veterinary Sciences, Volume 11, Issue 9
4847:Japanese Journal of Veterinary Research
2341:
2339:
2337:
2335:
2333:
1941:
1331:, which is oxidized to form ferruginol
731:, with the majority found in the genus
717:Although totarol was first isolated in
351:
319:
294:
4966:
4384:Journal of Food Science and Technology
2956:Totara: A Natural and Cultural History
196:
4069:Antimicrobial Agents and Chemotherapy
3101:
3099:
2390:Antimicrobial Agents and Chemotherapy
1864:Prostate and breast cancer inhibitor
1131:Mechanism of antimicrobial inhibition
163:
143:
7:
4878:Bioorganic & Medicinal Chemistry
4841:Tsunoi M, Iyori K, Harada K (2024).
3974:Nixon D, Hobbs D (August 15, 2006).
3902:Bioorganic & Medicinal Chemistry
3665:Bioorganic & Medicinal Chemistry
2834:Bioorganic & Medicinal Chemistry
2486:Bioorganic & Medicinal Chemistry
2055:Easterfield TH, Mcdowell JC (1915).
354:CC(C)C1=C(C=CC2=C1CC32(CCCC3(C)C)C)O
4150:Toxicology and Applied Pharmacology
3650:(Thesis thesis). Massey University.
3556:The Journal of Applied Bacteriology
3266:Natural Products and Bioprospecting
2572:The Journal of Applied Bacteriology
2123:Biochemical Systematics and Ecology
1776:Whey protein based tissue adhesive
333:Key: ZRVDANDJSTYELM-FXAWDEMLBD
236:
3717:10.1111/j.1574-6968.1999.tb08733.x
3568:10.1111/j.1365-2672.1996.tb03233.x
2584:10.1111/j.1365-2672.1996.tb03233.x
1929:Frieseomelitta silvestrii languida
1768:Antibacterial for dental implants
1696:Staphyloccocus auereus inhibition
14:
4785:Belahcene S (February 14, 2024).
3132:Belahcene S (February 14, 2024).
3053:An Introduction to Māori Religion
2923:"Pōhā Tītī - Te Papa New Zealand"
4919:Canadian Journal of Microbiology
4913:Hyeon G, Eom Y (July 29, 2024).
3748:Journal of Entomological Science
3004:
2187:10.1016/j.orggeochem.2008.02.020
1411:Total enantioselective synthesis
1079:Staphylococcus aureus ATCC 11632
1062:Staphylococcus aureus ATCC 33591
1045:Staphylococcus aureus ATCC 12598
994:Mycobacterium tuberculosis H37Rv
564:
440:
381:
24:
4433:Clinical Oral Implants Research
2958:. University of Auckland Press.
2873:South African Journal of Botany
2796:Chemistry and Physics of Lipids
2207:Australian Journal of Chemistry
1999:Australian Journal of Chemistry
560:(at 25 °C , 100 kPa).
3192:Archives of Pharmacal Research
1524:with 10% HCl and p-TsOH gives
1500:Total chemoenzymatic synthesis
1427:via a Wittig reaction between
1394:was subsequently converted to
387:
375:
1:
5089:10.1016/s0022-1910(01)00170-6
4676:Bosly HA (November 3, 2022).
3914:10.1016/S0968-0896(03)00491-7
3879:10.1016/S0022-1910(01)00170-6
3835:10.1016/S0005-2736(01)00284-X
3677:10.1016/S0968-0896(99)00162-5
3433:10.1016/S0040-4020(01)82004-4
3247:10.1016/S0040-4020(02)00496-9
3066:Gilchrist S (July 24, 2017).
3030:. Auckland University Press.
2846:10.1016/s0968-0896(00)00096-1
2808:10.1016/s0009-3084(02)00050-6
2773:10.1016/s0005-2736(00)00291-1
2734:10.1016/s0005-2736(01)00284-x
2498:10.1016/s0968-0896(99)00162-5
2143:10.1016/s0305-1978(00)00047-8
1760:Historical food preservative
1720:Bacillus subtilis alteration
1656:Antiplasmodial and cytotoxic
1540:which is hydrolyzed to yield
5069:Journal of Insect Physiology
4819:10.1016/j.dental.2024.02.011
4654:10.1016/j.phyplu.2022.100357
4563:10.1016/j.bioorg.2021.105165
4246:10.4315/0362-028X.JFP-17-078
3859:Journal of Insect Physiology
3783:Journal of Ethnopharmacology
3487:10.1016/j.tetasy.2007.11.024
3460:10.1016/j.tetlet.2003.09.193
3115:Analytical Pyrolysis Letters
2530:Journal of Ethnopharmacology
1407:(±)-totarol, it is notable.
4736:10.1016/j.sciaf.2022.e01462
4695:10.1016/j.jksus.2022.102396
4529:10.13140/RG.2.2.29327.33449
4206:10.1016/j.jprot.2014.10.025
4006:Journal of Chemical Ecology
3760:10.18474/0749-8004-35.4.474
3521:Journal of Natural Products
2348:Journal of Natural Products
1230:(land) and their ancestral
1180:medicines for treatment of
661:Sir Thomas Hill Easterfield
5148:
4772:10.1007/s00706-023-03102-2
4233:Journal of Food Protection
4170:10.1016/j.taap.2015.10.001
3279:10.1007/s13659-020-00268-8
2886:10.1016/j.sajb.2009.09.002
1488:-TsOH in benzene to yield
1145:penicillin binding protein
790:Mycobacterium tuberculosis
631:, a conifer tree found in
5046:10.1016/j.aca.2008.09.005
4891:10.1016/j.bmc.2024.117727
4603:10.3389/fcimb.2022.926363
4396:10.1007/s13197-017-3000-2
4342:10.3390/molecules23112734
4287:10.3390/molecules22091570
4026:10.1007/s10886-007-9390-2
3795:10.1016/j.jep.2009.09.007
3704:FEMS Microbiology Letters
3204:10.1007/s12272-001-1239-9
2542:10.1016/j.jep.2009.09.007
2316:10.1007/s11101-005-2494-9
2086:Short WF, Wang H (1951).
1923:Frieseomelitta silvestrii
554:
421:
416:
362:
342:
310:
83:
67:
47:
37:
32:
23:
3085:Duncan CR (2004-01-01).
2988:10.3390/genealogy5020029
1736:Surgical site infection
1113:Streptococcus pneumoniae
1028:Proprionibacterium acnes
617:is a naturally produced
487:Precautionary statements
5007:"Products with Totarol"
4523:. Antimicrobials 2020.
3260:Bailly C (2020-12-01).
2088:"662. Totarol. Part II"
2032:Easterfield TH (1910).
1712:Neurological disorders
1200:, chest complaints and
977:Mycobacterium smegmatis
943:Mycobacterium fortuitum
5026:Analytica Chimica Acta
4859:10.57494/jjvr.71.4_117
3475:Tetrahedron: Asymmetry
2296:Phytochemistry Reviews
1568:Reductions of totarol
1509:
1447:
1420:
1356:
1343:
1311:
1269:Biochemical properties
1223:Māori creation stories
875:Caenorhabditis elegans
841:Bacterium ammoniagenes
773:gram-positive bacteria
767:Antimicrobial activity
739:Rosmarinus officinalis
611:
603:
4927:10.1139/cjm-2024-0014
4378:Staphylococcus aureus
4194:Journal of Proteomics
3607:10.1055/s-2006-957655
2438:Phytotherapy Research
2250:Phytotherapy Research
1874:Enterococcus faecalis
1624:Mosquito insecticide
1507:
1445:
1418:
1354:
1341:
1309:
1149:Staphylococcus aureus
1139:strains resistant to
1137:Staphylococcus aureus
909:Klebsiella pneumoniae
892:Enterococcus faecalis
801:Staphylococcus aureus
796:Staphylococcus aureus
621:that is bioactive as
609:
601:
49:Systematic IUPAC name
4551:Bioorganic Chemistry
4446:10.1111/clr.90_13509
4081:10.1128/AAC.00216-07
3406:10.1246/bcsj.52.1450
3379:10.1039/JR9580002566
3356:10.1039/JR9510002979
3161:10.1055/s-2002-33787
2402:10.1128/AAC.00216-07
2167:Organic Geochemistry
2100:10.1039/jr9510002979
1984:10.1039/JR9370000516
1528:-unsaturated ketone
1165:phospholipid bilayer
1096:Streptococcus mutans
785:parasitic protozoans
5132:Isopropyl compounds
5081:2002JInsP..48..249P
5038:2008AcAC..628..222V
4989:"Bioactive Totarol"
4162:2015ToxAP.289..142G
4018:2007JCEco..33.2254Y
3871:2002JInsP..48..249P
3644:Nicolson K (1998).
3533:10.1021/np50088a008
3448:Tetrahedron Letters
3333:10.1021/jf00036a045
2937:"Podocarpus Totara"
2360:10.1021/np50088a008
2308:2005PChRv...4...63G
2179:2008OrGeo..39..658L
2135:2001BioSE..29..215S
2063:Podocarpus spicatus
1553:
1388:polyphosphoric acid
1208:(canoes), fencing,
1154:anaerobic organisms
1011:Leishmania donovani
960:Mycobacterium phlei
926:Mycobacterium aurum
762:Biological activity
402: g·mol
20:
4723:Scientific African
4641:Phytomedicine Plus
3068:"Children of Tane"
2954:Simpson P (2017).
2624:10.1007/BF01969731
2057:"The chemistry of
1840:Anti-inflammatory
1808:Anti-inflammatory
1752:Food preservative
1672:Anti-inflammatory
1552:
1510:
1448:
1421:
1404:N-Bromosuccinimide
1357:
1344:
1312:
612:
604:
587:Infobox references
18:
4495:10.3390/pr8040496
4239:(10): 1657–1665.
4126:10.1021/bi602573e
4120:(14): 4211–4220.
4075:(12): 4480–4483.
4012:(12): 2254–2265.
3908:(20): 4417–4422.
3527:(10): 1436–1440.
3481:(24): 2915–2922.
3454:(49): 8831–8835.
3427:(41): 9101–9110.
3327:(12): 2447–2450.
3241:(27): 5367–5406.
3072:Otago Daily Times
3037:978-1-86940-257-0
2969:Connor H (2021).
2941:Landcare Research
2694:10.1021/bi602573e
2444:(12): 1570–1576.
2232:Farjon A (2001).
2219:10.1071/CH9950883
2059:Podocarpus totara
2011:10.1071/ch9950883
1887:
1886:
1648:Insect repellant
1477:was treated with
1283:-quinone methide
1262:anti-inflammatory
1128:
1127:
858:Bacillus subtilis
720:Podocarpus totara
696:Podocarpus totara
628:Podocarpus totara
595:Chemical compound
593:
592:
465:Hazard statements
279:CompTox Dashboard
125:Interactive image
5139:
5101:
5100:
5064:
5058:
5057:
5021:
5015:
5014:
5003:
4997:
4996:
4995:. July 23, 2023.
4985:
4979:
4978:
4972:
4964:
4962:
4960:
4945:
4939:
4938:
4910:
4904:
4903:
4893:
4869:
4863:
4862:
4838:
4832:
4831:
4821:
4806:Dental Materials
4797:
4791:
4790:
4782:
4776:
4775:
4755:
4749:
4748:
4738:
4714:
4708:
4707:
4697:
4673:
4667:
4666:
4656:
4632:
4626:
4625:
4615:
4605:
4581:
4575:
4574:
4548:
4539:
4533:
4532:
4514:
4508:
4507:
4497:
4473:
4467:
4466:
4448:
4424:
4418:
4417:
4407:
4380:in carrot juice"
4371:
4365:
4364:
4354:
4344:
4316:
4310:
4309:
4299:
4289:
4265:
4259:
4258:
4248:
4224:
4218:
4217:
4188:
4182:
4181:
4144:
4138:
4137:
4109:
4103:
4102:
4092:
4060:
4054:
4053:
3997:
3991:
3990:
3980:
3971:
3965:
3964:
3963:
3959:
3952:
3946:
3945:
3943:
3935:Tacon C (2004).
3932:
3926:
3925:
3897:
3891:
3890:
3854:
3848:
3847:
3837:
3813:
3807:
3806:
3778:
3772:
3771:
3745:
3736:
3730:
3729:
3719:
3695:
3689:
3688:
3671:(9): 1953–1964.
3660:
3654:
3651:
3641:
3635:
3634:
3586:
3580:
3579:
3551:
3545:
3544:
3516:
3510:
3509:
3497:
3491:
3490:
3470:
3464:
3463:
3443:
3437:
3436:
3416:
3410:
3409:
3400:(5): 1450–1453.
3389:
3383:
3382:
3366:
3360:
3359:
3343:
3337:
3336:
3316:
3310:
3309:
3299:
3281:
3257:
3251:
3250:
3230:
3224:
3223:
3187:
3181:
3180:
3144:
3138:
3137:
3129:
3123:
3122:
3112:
3103:
3094:
3093:
3091:
3082:
3076:
3075:
3063:
3057:
3056:
3051:Irwin J (1984).
3048:
3042:
3041:
3024:Neich R (2001).
3021:
3015:
3008:
3002:
3000:
2990:
2966:
2960:
2959:
2951:
2945:
2944:
2933:
2927:
2926:
2919:
2913:
2912:
2905:
2899:
2898:
2888:
2864:
2858:
2857:
2829:
2820:
2819:
2791:
2785:
2784:
2767:(1–2): 167–175.
2756:
2747:
2746:
2736:
2712:
2706:
2705:
2677:
2671:
2670:
2650:
2644:
2643:
2607:
2596:
2595:
2567:
2554:
2553:
2525:
2510:
2509:
2492:(9): 1953–1964.
2481:
2470:
2469:
2450:10.1002/ptr.2460
2433:
2424:
2423:
2413:
2381:
2372:
2371:
2343:
2328:
2327:
2291:
2282:
2281:
2262:10.1002/ptr.1420
2244:
2238:
2237:
2229:
2223:
2222:
2202:
2191:
2190:
2161:
2155:
2154:
2118:
2112:
2111:
2083:
2077:
2076:
2052:
2046:
2045:
2029:
2023:
2022:
1994:
1988:
1987:
1971:
1960:
1959:
1946:
1554:
1202:venereal disease
1143:via creation of
809:
742:(rosemary). The
577:
571:
568:
567:
550:
546:
542:
538:
534:
530:
526:
522:
518:
514:
510:
506:
502:
498:
494:
480:
476:
472:
444:
401:
389:
383:
377:
370:Chemical formula
303:
302:
287:
285:
269:
249:
238:
217:
209:
198:
187:
167:
147:
127:
103:
28:
21:
5147:
5146:
5142:
5141:
5140:
5138:
5137:
5136:
5107:
5106:
5105:
5104:
5066:
5065:
5061:
5023:
5022:
5018:
5005:
5004:
5000:
4987:
4986:
4982:
4965:
4958:
4956:
4947:
4946:
4942:
4912:
4911:
4907:
4871:
4870:
4866:
4840:
4839:
4835:
4799:
4798:
4794:
4784:
4783:
4779:
4757:
4756:
4752:
4716:
4715:
4711:
4675:
4674:
4670:
4634:
4633:
4629:
4583:
4582:
4578:
4546:
4541:
4540:
4536:
4516:
4515:
4511:
4475:
4474:
4470:
4426:
4425:
4421:
4373:
4372:
4368:
4318:
4317:
4313:
4267:
4266:
4262:
4226:
4225:
4221:
4190:
4189:
4185:
4146:
4145:
4141:
4111:
4110:
4106:
4062:
4061:
4057:
3999:
3998:
3994:
3978:
3973:
3972:
3968:
3961:
3954:
3953:
3949:
3941:
3934:
3933:
3929:
3899:
3898:
3894:
3856:
3855:
3851:
3815:
3814:
3810:
3780:
3779:
3775:
3743:
3738:
3737:
3733:
3697:
3696:
3692:
3662:
3661:
3657:
3643:
3642:
3638:
3588:
3587:
3583:
3553:
3552:
3548:
3518:
3517:
3513:
3499:
3498:
3494:
3472:
3471:
3467:
3445:
3444:
3440:
3418:
3417:
3413:
3391:
3390:
3386:
3368:
3367:
3363:
3345:
3344:
3340:
3318:
3317:
3313:
3259:
3258:
3254:
3232:
3231:
3227:
3189:
3188:
3184:
3146:
3145:
3141:
3131:
3130:
3126:
3110:
3105:
3104:
3097:
3089:
3084:
3083:
3079:
3065:
3064:
3060:
3050:
3049:
3045:
3038:
3023:
3022:
3018:
2968:
2967:
2963:
2953:
2952:
2948:
2943:. July 1, 2020.
2935:
2934:
2930:
2921:
2920:
2916:
2907:
2906:
2902:
2866:
2865:
2861:
2831:
2830:
2823:
2793:
2792:
2788:
2758:
2757:
2750:
2714:
2713:
2709:
2688:(14): 4211–20.
2679:
2678:
2674:
2652:
2651:
2647:
2609:
2608:
2599:
2569:
2568:
2557:
2527:
2526:
2513:
2483:
2482:
2473:
2435:
2434:
2427:
2383:
2382:
2375:
2354:(10): 1436–40.
2345:
2344:
2331:
2293:
2292:
2285:
2246:
2245:
2241:
2231:
2230:
2226:
2204:
2203:
2194:
2163:
2162:
2158:
2120:
2119:
2115:
2085:
2084:
2080:
2054:
2053:
2049:
2031:
2030:
2026:
1996:
1995:
1991:
1973:
1972:
1963:
1948:
1947:
1943:
1938:
1910:
1901:
1892:
1550:
1520:. Treatment of
1502:
1482:
1467:
1463:
1413:
1363:and the alkyne
1349:
1297:
1271:
1258:Myrtus Communis
1174:
1172:Traditional use
1133:
1124:
1119:
1107:
1102:
1090:
1085:
1073:
1068:
1056:
1051:
1039:
1034:
1022:
1017:
1005:
1000:
988:
983:
971:
966:
954:
949:
937:
932:
920:
915:
903:
898:
886:
881:
869:
864:
852:
847:
835:
830:
769:
764:
715:
657:
596:
589:
584:
583:
582: ?)
573:
569:
565:
561:
489:
467:
453:
437:
399:
386:
380:
372:
358:
355:
350:
349:
338:
335:
334:
331:
325:
324:
318:
317:
306:
288:
281:
272:
252:
239:
227:
190:
170:
150:
130:
117:
106:
93:
79:
63:
62:
43:
12:
11:
5:
5145:
5143:
5135:
5134:
5129:
5124:
5119:
5109:
5108:
5103:
5102:
5075:(2): 249–254.
5059:
5016:
4998:
4980:
4940:
4905:
4864:
4833:
4812:(4): 674–688.
4792:
4777:
4766:(8): 915–923.
4750:
4709:
4668:
4627:
4576:
4534:
4509:
4468:
4419:
4390:(3): 924–934.
4366:
4311:
4260:
4219:
4183:
4156:(2): 142–154.
4139:
4104:
4055:
3992:
3966:
3947:
3927:
3892:
3865:(2): 249–254.
3849:
3828:(2): 281–290.
3808:
3789:(3): 500–505.
3773:
3754:(4): 474–477.
3731:
3710:(2): 233–239.
3690:
3655:
3636:
3601:(3): 213–215.
3581:
3562:(4): 387–394.
3546:
3511:
3506:Science Direct
3492:
3465:
3438:
3411:
3384:
3361:
3338:
3311:
3272:(6): 367–375.
3252:
3225:
3182:
3139:
3124:
3095:
3077:
3058:
3043:
3036:
3016:
2961:
2946:
2928:
2914:
2900:
2859:
2840:(7): 1663–75.
2821:
2786:
2748:
2707:
2672:
2661:(4): 327–337.
2645:
2597:
2555:
2511:
2471:
2425:
2396:(12): 4480–3.
2373:
2329:
2283:
2239:
2224:
2213:(5): 883–917.
2192:
2173:(6): 658–675.
2156:
2129:(2): 215–217.
2113:
2078:
2047:
2024:
1989:
1961:
1940:
1939:
1937:
1934:
1909:
1906:
1900:
1897:
1891:
1888:
1885:
1884:
1881:
1877:
1876:
1870:
1866:
1865:
1862:
1858:
1857:
1854:
1850:
1849:
1846:
1842:
1841:
1838:
1834:
1833:
1830:
1826:
1825:
1822:
1818:
1817:
1814:
1810:
1809:
1806:
1802:
1801:
1798:
1794:
1793:
1790:
1786:
1785:
1782:
1778:
1777:
1774:
1770:
1769:
1766:
1762:
1761:
1758:
1754:
1753:
1750:
1746:
1745:
1744:Plant defense
1742:
1738:
1737:
1734:
1730:
1729:
1726:
1722:
1721:
1718:
1714:
1713:
1710:
1706:
1705:
1702:
1698:
1697:
1694:
1690:
1689:
1686:
1682:
1681:
1678:
1674:
1673:
1670:
1666:
1665:
1662:
1658:
1657:
1654:
1650:
1649:
1646:
1642:
1641:
1638:
1634:
1633:
1630:
1626:
1625:
1622:
1618:
1617:
1614:
1610:
1609:
1608:Antibacterial
1606:
1602:
1601:
1598:
1594:
1593:
1590:
1586:
1585:
1582:
1578:
1577:
1574:
1570:
1569:
1566:
1562:
1561:
1558:
1549:
1546:
1501:
1498:
1480:
1465:
1461:
1412:
1409:
1400:chromatography
1348:
1345:
1296:
1293:
1270:
1267:
1254:ethnomedicinal
1173:
1170:
1132:
1129:
1126:
1125:
1122:
1120:
1117:
1115:
1109:
1108:
1105:
1103:
1100:
1098:
1092:
1091:
1088:
1086:
1083:
1081:
1075:
1074:
1071:
1069:
1066:
1064:
1058:
1057:
1054:
1052:
1049:
1047:
1041:
1040:
1037:
1035:
1032:
1030:
1024:
1023:
1020:
1018:
1015:
1013:
1007:
1006:
1003:
1001:
998:
996:
990:
989:
986:
984:
981:
979:
973:
972:
969:
967:
964:
962:
956:
955:
952:
950:
947:
945:
939:
938:
935:
933:
930:
928:
922:
921:
918:
916:
913:
911:
905:
904:
901:
899:
896:
894:
888:
887:
884:
882:
879:
877:
871:
870:
867:
865:
862:
860:
854:
853:
850:
848:
845:
843:
837:
836:
833:
831:
828:
826:
824:Artemia salina
820:
819:
816:
813:
812:Microorganism
768:
765:
763:
760:
714:
711:
707:Totarol Part 2
703:Totarol Part 1
656:
653:
610:Totarol powder
594:
591:
590:
585:
563:
562:
558:standard state
555:
552:
551:
517:P305+P351+P338
490:
485:
482:
481:
468:
463:
460:
459:
454:
449:
446:
445:
438:
433:
430:
429:
419:
418:
414:
413:
410:
404:
403:
397:
391:
390:
384:
378:
373:
368:
365:
364:
360:
359:
357:
356:
353:
345:
344:
343:
340:
339:
337:
336:
332:
329:
328:
326:
322:
321:
313:
312:
311:
308:
307:
305:
304:
291:
289:
277:
274:
273:
271:
270:
262:
260:
254:
253:
251:
250:
242:
240:
232:
229:
228:
226:
225:
221:
219:
211:
210:
200:
192:
191:
189:
188:
180:
178:
172:
171:
169:
168:
160:
158:
152:
151:
149:
148:
140:
138:
132:
131:
129:
128:
120:
118:
111:
108:
107:
105:
104:
96:
94:
89:
86:
85:
81:
80:
69:
65:
64:
52:
51:
45:
44:
41:
35:
34:
30:
29:
13:
10:
9:
6:
4:
3:
2:
5144:
5133:
5130:
5128:
5125:
5123:
5122:Phenanthrenes
5120:
5118:
5115:
5114:
5112:
5098:
5094:
5090:
5086:
5082:
5078:
5074:
5070:
5063:
5060:
5055:
5051:
5047:
5043:
5039:
5035:
5031:
5027:
5020:
5017:
5012:
5008:
5002:
4999:
4994:
4990:
4984:
4981:
4976:
4970:
4959:September 17,
4955:
4951:
4944:
4941:
4936:
4932:
4928:
4924:
4920:
4916:
4909:
4906:
4901:
4897:
4892:
4887:
4883:
4879:
4875:
4868:
4865:
4860:
4856:
4852:
4848:
4844:
4837:
4834:
4829:
4825:
4820:
4815:
4811:
4807:
4803:
4796:
4793:
4788:
4781:
4778:
4773:
4769:
4765:
4761:
4754:
4751:
4746:
4742:
4737:
4732:
4728:
4724:
4720:
4713:
4710:
4705:
4701:
4696:
4691:
4688:(1): 102396.
4687:
4683:
4679:
4672:
4669:
4664:
4660:
4655:
4650:
4647:(4): 100357.
4646:
4642:
4638:
4631:
4628:
4623:
4619:
4614:
4609:
4604:
4599:
4595:
4591:
4587:
4580:
4577:
4572:
4568:
4564:
4560:
4556:
4552:
4545:
4538:
4535:
4530:
4526:
4522:
4521:
4513:
4510:
4505:
4501:
4496:
4491:
4487:
4483:
4479:
4472:
4469:
4464:
4460:
4456:
4452:
4447:
4442:
4438:
4434:
4430:
4423:
4420:
4415:
4411:
4406:
4401:
4397:
4393:
4389:
4385:
4381:
4379:
4370:
4367:
4362:
4358:
4353:
4348:
4343:
4338:
4334:
4330:
4326:
4324:
4315:
4312:
4307:
4303:
4298:
4293:
4288:
4283:
4279:
4275:
4271:
4264:
4261:
4256:
4252:
4247:
4242:
4238:
4234:
4230:
4223:
4220:
4215:
4211:
4207:
4203:
4199:
4195:
4187:
4184:
4179:
4175:
4171:
4167:
4163:
4159:
4155:
4151:
4143:
4140:
4135:
4131:
4127:
4123:
4119:
4115:
4108:
4105:
4100:
4096:
4091:
4086:
4082:
4078:
4074:
4070:
4066:
4059:
4056:
4051:
4047:
4043:
4039:
4035:
4031:
4027:
4023:
4019:
4015:
4011:
4007:
4003:
3996:
3993:
3988:
3984:
3977:
3970:
3967:
3957:
3951:
3948:
3940:
3939:
3931:
3928:
3923:
3919:
3915:
3911:
3907:
3903:
3896:
3893:
3888:
3884:
3880:
3876:
3872:
3868:
3864:
3860:
3853:
3850:
3845:
3841:
3836:
3831:
3827:
3823:
3819:
3812:
3809:
3804:
3800:
3796:
3792:
3788:
3784:
3777:
3774:
3769:
3765:
3761:
3757:
3753:
3749:
3742:
3735:
3732:
3727:
3723:
3718:
3713:
3709:
3705:
3701:
3694:
3691:
3686:
3682:
3678:
3674:
3670:
3666:
3659:
3656:
3653:
3649:
3648:
3640:
3637:
3632:
3628:
3624:
3620:
3616:
3612:
3608:
3604:
3600:
3596:
3595:Planta Medica
3592:
3585:
3582:
3577:
3573:
3569:
3565:
3561:
3557:
3550:
3547:
3542:
3538:
3534:
3530:
3526:
3522:
3515:
3512:
3507:
3503:
3496:
3493:
3488:
3484:
3480:
3476:
3469:
3466:
3461:
3457:
3453:
3449:
3442:
3439:
3434:
3430:
3426:
3422:
3415:
3412:
3407:
3403:
3399:
3395:
3388:
3385:
3380:
3376:
3373:: 2566–2572.
3372:
3365:
3362:
3357:
3353:
3350:: 2979–2987.
3349:
3342:
3339:
3334:
3330:
3326:
3322:
3315:
3312:
3307:
3303:
3298:
3293:
3289:
3285:
3280:
3275:
3271:
3267:
3263:
3256:
3253:
3248:
3244:
3240:
3236:
3229:
3226:
3221:
3217:
3213:
3209:
3205:
3201:
3198:(7): 866–71.
3197:
3193:
3186:
3183:
3178:
3174:
3170:
3166:
3162:
3158:
3154:
3150:
3149:Planta Medica
3143:
3140:
3135:
3128:
3125:
3120:
3116:
3109:
3102:
3100:
3096:
3088:
3081:
3078:
3073:
3069:
3062:
3059:
3054:
3047:
3044:
3039:
3033:
3029:
3028:
3020:
3017:
3014:
3012:
3007:
2999:
2994:
2989:
2984:
2980:
2976:
2972:
2965:
2962:
2957:
2950:
2947:
2942:
2938:
2932:
2929:
2924:
2918:
2915:
2910:
2904:
2901:
2896:
2892:
2887:
2882:
2878:
2874:
2870:
2863:
2860:
2855:
2851:
2847:
2843:
2839:
2835:
2828:
2826:
2822:
2817:
2813:
2809:
2805:
2802:(1–2): 33–9.
2801:
2797:
2790:
2787:
2782:
2778:
2774:
2770:
2766:
2762:
2755:
2753:
2749:
2744:
2740:
2735:
2730:
2727:(2): 281–90.
2726:
2722:
2718:
2711:
2708:
2703:
2699:
2695:
2691:
2687:
2683:
2676:
2673:
2668:
2664:
2660:
2656:
2649:
2646:
2641:
2637:
2633:
2629:
2625:
2621:
2617:
2613:
2606:
2604:
2602:
2598:
2593:
2589:
2585:
2581:
2578:(4): 387–94.
2577:
2573:
2566:
2564:
2562:
2560:
2556:
2551:
2547:
2543:
2539:
2535:
2531:
2524:
2522:
2520:
2518:
2516:
2512:
2507:
2503:
2499:
2495:
2491:
2487:
2480:
2478:
2476:
2472:
2467:
2463:
2459:
2455:
2451:
2447:
2443:
2439:
2432:
2430:
2426:
2421:
2417:
2412:
2407:
2403:
2399:
2395:
2391:
2387:
2380:
2378:
2374:
2369:
2365:
2361:
2357:
2353:
2349:
2342:
2340:
2338:
2336:
2334:
2330:
2325:
2321:
2317:
2313:
2309:
2305:
2301:
2297:
2290:
2288:
2284:
2279:
2275:
2271:
2267:
2263:
2259:
2256:(11): 934–7.
2255:
2251:
2243:
2240:
2235:
2228:
2225:
2220:
2216:
2212:
2208:
2201:
2199:
2197:
2193:
2188:
2184:
2180:
2176:
2172:
2168:
2160:
2157:
2152:
2148:
2144:
2140:
2136:
2132:
2128:
2124:
2117:
2114:
2109:
2105:
2101:
2097:
2094:: 2979–2987.
2093:
2089:
2082:
2079:
2074:
2070:
2066:
2064:
2060:
2051:
2048:
2043:
2039:
2035:
2028:
2025:
2020:
2016:
2012:
2008:
2004:
2000:
1993:
1990:
1985:
1981:
1977:
1970:
1968:
1966:
1962:
1957:
1956:
1955:Sigma-Aldrich
1951:
1945:
1942:
1935:
1933:
1930:
1926:
1924:
1918:
1915:
1907:
1905:
1898:
1896:
1889:
1882:
1879:
1878:
1875:
1871:
1868:
1867:
1863:
1860:
1859:
1855:
1852:
1851:
1847:
1844:
1843:
1839:
1836:
1835:
1831:
1828:
1827:
1823:
1820:
1819:
1815:
1812:
1811:
1807:
1804:
1803:
1799:
1796:
1795:
1791:
1788:
1787:
1783:
1780:
1779:
1775:
1772:
1771:
1767:
1764:
1763:
1759:
1756:
1755:
1751:
1748:
1747:
1743:
1740:
1739:
1735:
1732:
1731:
1727:
1724:
1723:
1719:
1716:
1715:
1711:
1708:
1707:
1704:Tuberculosis
1703:
1700:
1699:
1695:
1692:
1691:
1687:
1684:
1683:
1679:
1676:
1675:
1671:
1668:
1667:
1664:Antimalarial
1663:
1660:
1659:
1655:
1652:
1651:
1647:
1644:
1643:
1639:
1636:
1635:
1632:Tuberculosis
1631:
1628:
1627:
1623:
1620:
1619:
1615:
1612:
1611:
1607:
1604:
1603:
1599:
1596:
1595:
1591:
1588:
1587:
1583:
1580:
1579:
1575:
1572:
1571:
1567:
1564:
1563:
1559:
1556:
1555:
1547:
1545:
1543:
1539:
1535:
1531:
1527:
1523:
1519:
1515:
1506:
1499:
1497:
1495:
1491:
1487:
1483:
1476:
1472:
1468:
1457:
1453:
1444:
1440:
1438:
1434:
1430:
1426:
1417:
1410:
1408:
1405:
1401:
1397:
1393:
1389:
1385:
1381:
1380:hydrogenation
1377:
1374:
1370:
1366:
1362:
1353:
1346:
1340:
1336:
1334:
1330:
1326:
1322:
1318:
1308:
1304:
1302:
1294:
1292:
1290:
1286:
1282:
1278:
1277:
1268:
1266:
1263:
1259:
1255:
1250:
1246:
1242:
1237:
1233:
1229:
1224:
1219:
1218:Carved totara
1215:
1211:
1207:
1203:
1199:
1195:
1191:
1187:
1183:
1179:
1171:
1169:
1166:
1161:
1159:
1155:
1150:
1146:
1142:
1138:
1130:
1121:
1116:
1114:
1111:
1110:
1104:
1099:
1097:
1094:
1093:
1087:
1082:
1080:
1077:
1076:
1070:
1065:
1063:
1060:
1059:
1053:
1048:
1046:
1043:
1042:
1036:
1031:
1029:
1026:
1025:
1019:
1014:
1012:
1009:
1008:
1002:
997:
995:
992:
991:
985:
980:
978:
975:
974:
968:
963:
961:
958:
957:
951:
946:
944:
941:
940:
934:
929:
927:
924:
923:
917:
912:
910:
907:
906:
900:
895:
893:
890:
889:
883:
878:
876:
873:
872:
866:
861:
859:
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855:
849:
844:
842:
839:
838:
832:
827:
825:
822:
821:
817:
814:
811:
810:
807:
804:
802:
798:
797:
792:
791:
786:
782:
778:
774:
766:
761:
759:
757:
753:
749:
748:South America
745:
741:
740:
734:
730:
726:
725:Podocarpaceae
722:
721:
712:
710:
708:
704:
699:
697:
692:
691:
686:
685:
680:
679:
674:
673:
668:
667:
662:
654:
652:
650:
646:
642:
641:antimicrobial
638:
634:
630:
629:
624:
620:
616:
608:
600:
588:
581:
576:
559:
553:
491:
488:
484:
483:
469:
466:
462:
461:
458:
455:
452:
448:
447:
443:
439:
436:
432:
431:
427:
425:
420:
415:
411:
409:
408:Melting point
406:
405:
398:
396:
393:
392:
374:
371:
367:
366:
361:
352:
348:
341:
327:
320:
316:
309:
301:
297:
296:DTXSID9047752
293:
292:
290:
280:
276:
275:
268:
264:
263:
261:
259:
256:
255:
248:
244:
243:
241:
235:
231:
230:
223:
222:
220:
218:
213:
212:
208:
204:
201:
199:
197:ECHA InfoCard
194:
193:
186:
182:
181:
179:
177:
174:
173:
166:
162:
161:
159:
157:
154:
153:
146:
142:
141:
139:
137:
134:
133:
126:
122:
121:
119:
115:
110:
109:
102:
98:
97:
95:
92:
88:
87:
82:
77:
73:
66:
60:
56:
50:
46:
40:
36:
31:
27:
22:
16:
5072:
5068:
5062:
5032:(2): 222–9.
5029:
5025:
5019:
5010:
5001:
4992:
4983:
4957:. Retrieved
4953:
4943:
4918:
4908:
4881:
4877:
4867:
4850:
4846:
4836:
4809:
4805:
4795:
4780:
4763:
4759:
4753:
4726:
4722:
4712:
4685:
4681:
4671:
4644:
4640:
4630:
4593:
4589:
4579:
4554:
4550:
4537:
4519:
4512:
4485:
4481:
4471:
4439:(S19): 132.
4436:
4432:
4422:
4387:
4383:
4377:
4369:
4335:(11): 2734.
4332:
4328:
4322:
4314:
4277:
4273:
4263:
4236:
4232:
4222:
4197:
4193:
4186:
4153:
4149:
4142:
4117:
4114:Biochemistry
4113:
4107:
4072:
4068:
4058:
4009:
4005:
3995:
3986:
3982:
3969:
3950:
3937:
3930:
3905:
3901:
3895:
3862:
3858:
3852:
3825:
3821:
3811:
3786:
3782:
3776:
3751:
3747:
3734:
3707:
3703:
3693:
3668:
3664:
3658:
3646:
3639:
3598:
3594:
3584:
3559:
3555:
3549:
3524:
3520:
3514:
3505:
3495:
3478:
3474:
3468:
3451:
3447:
3441:
3424:
3420:
3414:
3397:
3393:
3387:
3370:
3364:
3347:
3341:
3324:
3320:
3314:
3269:
3265:
3255:
3238:
3234:
3228:
3195:
3191:
3185:
3155:(8): 742–5.
3152:
3148:
3142:
3127:
3118:
3114:
3080:
3071:
3061:
3052:
3046:
3026:
3019:
3003:
2978:
2974:
2964:
2955:
2949:
2940:
2931:
2917:
2903:
2876:
2872:
2862:
2837:
2833:
2799:
2795:
2789:
2764:
2760:
2724:
2720:
2710:
2685:
2682:Biochemistry
2681:
2675:
2658:
2654:
2648:
2618:(6): 573–6.
2615:
2611:
2575:
2571:
2536:(3): 500–5.
2533:
2529:
2489:
2485:
2441:
2437:
2393:
2389:
2351:
2347:
2302:(1): 63–78.
2299:
2295:
2253:
2249:
2242:
2233:
2227:
2210:
2206:
2170:
2166:
2159:
2126:
2122:
2116:
2091:
2081:
2072:
2068:
2062:
2058:
2050:
2041:
2037:
2027:
2002:
1998:
1992:
1975:
1953:
1944:
1928:
1921:
1919:
1914:diterpenoids
1911:
1902:
1893:
1873:
1824:Influenza A
1816:Insecticide
1640:Cell change
1592:Antioxidant
1541:
1537:
1533:
1529:
1525:
1521:
1517:
1513:
1511:
1493:
1489:
1485:
1474:
1470:
1455:
1451:
1449:
1436:
1432:
1428:
1424:
1422:
1395:
1391:
1382:followed by
1375:
1368:
1364:
1360:
1358:
1332:
1328:
1324:
1320:
1316:
1313:
1298:
1295:Biosynthesis
1288:
1284:
1280:
1274:
1272:
1249:Cupressaceae
1175:
1162:
1148:
1136:
1134:
1112:
1095:
1078:
1061:
1044:
1027:
1010:
993:
976:
959:
942:
925:
908:
891:
874:
857:
840:
823:
818:IC50(μg/ml)
815:MIC (μg/ml)
805:
800:
794:
788:
770:
737:
732:
729:Cupressaceae
718:
716:
706:
702:
694:
689:
682:
677:
671:
664:
658:
626:
622:
614:
613:
456:
423:
165:ChEMBL487602
84:Identifiers
75:
71:
68:Other names
58:
54:
15:
5011:INCIDecoder
4993:Totarol.com
4280:(9): 1570.
4200:: 247–262.
3956:US6881756B2
3421:Tetrahedron
3235:Tetrahedron
2879:(1): 1–24.
2612:Experientia
1978:: 516–520.
1832:Antifungal
1792:Anticancer
1688:Antifungal
1384:cyclization
1236:Tāne-Mahuta
1158:cytokinesis
756:East Africa
744:gymnosperms
645:therapeutic
633:New Zealand
451:Signal word
363:Properties
203:100.151.658
145:CHEBI:69241
5117:Diterpenes
5111:Categories
4729:: e01462.
4596:: 926363.
4557:: 105165.
4488:(4): 496.
2998:2292/54952
2075:: 518–520.
2005:(5): 883.
1936:References
1908:Other uses
1890:Extraction
1680:Anti acne
1600:Diterpene
1301:antifungal
1141:penicillin
779:bacteria,
733:Podocarpus
713:Occurrence
435:Pictograms
395:Molar mass
267:67NH2854WW
176:ChemSpider
112:3D model (
91:CAS Number
39:IUPAC name
4745:253944227
4704:253198996
4663:252728375
4504:2227-9717
4482:Processes
4463:204052249
4455:0905-7161
4329:Molecules
4274:Molecules
4034:0098-0331
3768:0749-8004
3631:260248488
3615:0032-0943
3288:2192-2195
3011:CC BY 4.0
2981:(2): 29.
2975:Genealogy
2108:0368-1769
2019:0004-9425
1784:Mastitis
1367:to yield
1347:Synthesis
1245:neolithic
1198:distemper
781:nematodes
777:acid-fast
752:East Asia
672:Kahikatea
655:Discovery
619:diterpene
541:P403+P233
533:P337+P313
529:P332+P313
513:P304+P340
509:P302+P352
426:labelling
224:622-932-2
216:EC Number
5097:12770125
5054:18929011
4969:cite web
4935:39058360
4900:38669736
4828:38388252
4622:35800390
4571:34298240
4414:29487434
4361:30360500
4323:Fraxinus
4306:28925959
4255:28876131
4214:25464363
4178:26440581
4134:17348691
4099:17664318
4050:20883003
4042:18026796
3922:13129578
3887:12770125
3844:11286971
3803:19755141
3726:10518721
3685:10530944
3306:33034879
3220:22860187
3212:18704328
3177:26017116
3169:12221600
3013:license.
2895:85271055
2854:10976514
2816:12270671
2781:11118528
2743:11286971
2702:17348691
2640:31273106
2550:19755141
2506:10530944
2466:10379153
2458:19067375
2420:17664318
2324:24225316
2278:33772478
2270:15597311
2151:11106853
2044:: 53–55.
1925:languida
1899:Products
1560:Subject
1548:Research
1289:in vitro
1276:in vitro
417:Hazards
101:511-15-9
19:Totarol
5127:Phenols
5077:Bibcode
5034:Bibcode
4613:9253276
4405:5821648
4352:6278661
4297:6151728
4158:Bibcode
4090:2168009
4014:Bibcode
3867:Bibcode
3623:9225601
3576:8849640
3541:1453180
3297:7648843
3121:: 1–16.
2632:8698092
2592:8849640
2411:2168009
2368:1453180
2304:Bibcode
2175:Bibcode
2131:Bibcode
1285:in vivo
1241:karakia
1194:cholera
637:rotting
623:totarol
615:Totarol
580:what is
578: (
457:Warning
400:286.459
234:PubChem
5095:
5052:
4933:
4898:
4826:
4743:
4702:
4661:
4620:
4610:
4569:
4502:
4461:
4453:
4412:
4402:
4359:
4349:
4304:
4294:
4253:
4212:
4176:
4132:
4097:
4087:
4048:
4040:
4032:
3962:
3920:
3885:
3842:
3801:
3766:
3724:
3683:
3629:
3621:
3613:
3574:
3539:
3304:
3294:
3286:
3218:
3210:
3175:
3167:
3034:
2893:
2852:
2814:
2779:
2741:
2700:
2638:
2630:
2590:
2548:
2504:
2464:
2456:
2418:
2408:
2366:
2322:
2276:
2268:
2149:
2106:
2017:
1373:ketone
1256:shrub
1228:whenua
1190:coughs
1186:asthma
1182:fevers
914:>32
690:Totara
575:verify
572:
347:SMILES
156:ChEMBL
33:Names
4741:S2CID
4700:S2CID
4659:S2CID
4547:(PDF)
4459:S2CID
4046:S2CID
3979:(PDF)
3942:(PDF)
3744:(PDF)
3627:S2CID
3216:S2CID
3173:S2CID
3111:(PDF)
3090:(PDF)
2891:S2CID
2636:S2CID
2462:S2CID
2320:S2CID
2274:S2CID
1880:2024
1869:2024
1861:2024
1853:2024
1845:2024
1837:2024
1829:2023
1821:2023
1813:2023
1805:2022
1797:2022
1789:2021
1781:2020
1773:2020
1765:2019
1757:2019
1749:2018
1741:2018
1733:2017
1725:2017
1717:2015
1709:2015
1701:2007
1693:2007
1685:2007
1677:2006
1669:2005
1661:2004
1653:2003
1645:2002
1637:2001
1629:2001
1621:2000
1613:1999
1605:1999
1597:1998
1589:1997
1581:1996
1573:1992
1565:1966
1557:Year
1386:with
1178:Māori
684:Matai
649:drugs
315:InChI
247:92783
185:83757
136:ChEBI
114:JSmol
76:trans
5093:PMID
5050:PMID
4975:link
4961:2024
4931:PMID
4896:PMID
4824:PMID
4618:PMID
4567:PMID
4500:ISSN
4451:ISSN
4410:PMID
4357:PMID
4302:PMID
4251:PMID
4210:PMID
4174:PMID
4130:PMID
4095:PMID
4038:PMID
4030:ISSN
3983:NZFP
3918:PMID
3883:PMID
3840:PMID
3826:1511
3799:PMID
3764:ISSN
3722:PMID
3681:PMID
3619:PMID
3611:ISSN
3572:PMID
3537:PMID
3302:PMID
3284:ISSN
3208:PMID
3165:PMID
3032:ISBN
2850:PMID
2812:PMID
2777:PMID
2765:1509
2739:PMID
2725:1511
2698:PMID
2628:PMID
2588:PMID
2546:PMID
2502:PMID
2454:PMID
2416:PMID
2364:PMID
2266:PMID
2147:PMID
2104:ISSN
2061:and
2015:ISSN
1431:and
1378:via
1232:rohe
1214:pōhā
1206:waka
1101:0.78
1084:0.78
1067:0.78
1050:1.56
999:21.1
863:1.56
846:0.78
793:and
754:and
727:and
687:and
678:Rimu
666:Miro
643:and
549:P501
545:P405
537:P362
525:P321
521:P312
505:P280
501:P271
497:P264
493:P261
479:H335
475:H319
471:H315
258:UNII
5085:doi
5042:doi
5030:628
4923:doi
4886:doi
4882:105
4855:doi
4814:doi
4768:doi
4764:154
4731:doi
4690:doi
4649:doi
4608:PMC
4598:doi
4559:doi
4555:115
4525:doi
4490:doi
4441:doi
4400:PMC
4392:doi
4347:PMC
4337:doi
4292:PMC
4282:doi
4241:doi
4202:doi
4198:114
4166:doi
4154:289
4122:doi
4085:PMC
4077:doi
4022:doi
3910:doi
3875:doi
3830:doi
3791:doi
3787:126
3756:doi
3712:doi
3708:179
3673:doi
3603:doi
3564:doi
3529:doi
3483:doi
3456:doi
3429:doi
3402:doi
3375:doi
3352:doi
3329:doi
3292:PMC
3274:doi
3243:doi
3200:doi
3157:doi
2993:hdl
2983:doi
2881:doi
2842:doi
2804:doi
2800:119
2769:doi
2729:doi
2690:doi
2663:doi
2620:doi
2580:doi
2538:doi
2534:126
2494:doi
2446:doi
2406:PMC
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