Diterpenes from the timber of Erythroxylum pictum

Ansell, Steven M.; Pegel, K. H.; Taylor, David A.

doi:10.1016/0031-9422(93)85234-i

Cited by 29 publications

(30 citation statements)

References 11 publications

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“…18-Hydroxy-miltiradiene (9) (4), sclareol (5), manool (6), 3β-hydroxy-manool (11), 19-hydroxy-manool (13), 3β-hydroxy-manoyl oxide (12) and 4-epidehydroabietol were isolated in pure form and identified on the basis of their spectroscopic data and their comparison to literature values (Ansell et al, 1993;Cabrera et al, 1988;Chamy et al, 1987;Dai et al, 2012;Hieda et al, 1982;Lu et al, 1995).…”

Section: Structure Elucidation Of Isolated Compoundsmentioning

confidence: 99%

Reconstructing the chemical diversity of labdane-type diterpene biosynthesis in yeast

Ignea

Iοannou

Georgantea

et al. 2015

Metabolic Engineering

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Terpenes are a large class of natural products, many of which are used in cosmetics, pharmaceuticals, or biofuels. However, terpene's industrial application is frequently hindered by limited availability of natural sources or low yields of chemical synthesis. In this report, we developed a modular platform based on standardized and exchangeable parts to reproduce and potentially expand the diversity of terpene structures in Saccharomyces cerevisiae. By combining different module-specific parts, we exploited the substrate promiscuity of class I diterpene synthases to produce an array of labdane-type scaffolds. These were subsequently modified by a scaffold decoration module consisting of a mutant library of a promiscuous cytochrome P450 to afford a range of hydroxylated diterpenes. Further P450 protein engineering yielded dedicated and efficient catalysts for specific products. Terpenes produced include precursors of pharmacologically important compounds, molecules that are difficult to obtain from natural sources, or new natural products. The approach described here provides a platform on which additional gene mining, combinatorial biosynthesis, and protein engineering efforts can be integrated to sustainably explore the terpene chemical space.

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Section: Structure Elucidation Of Isolated Compoundsmentioning

confidence: 99%

Reconstructing the chemical diversity of labdane-type diterpene biosynthesis in yeast

Ignea

Iοannou

Georgantea

et al. 2015

Metabolic Engineering

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“…This carbon skeletal-pattern, also designated by dolabrane, has been observed for compounds from Erythroxylum species. [10][11][12][13] The junction of the A/B ring is trans, since the 13 C NMR spectra did not show any signal referent to a methyl group at approximately δ 32.0. 14 Finally, the X-ray analysis of a crystal obtained from MeOH confirmed the structure of 1 as 7-(2-hydroxy-acetyl)-10-hydroxy-tetradecahydro-1-methylene-4b,7,10a-trimethylphenantrene.…”

Section: Resultsmentioning

confidence: 99%

“…The BB 13 Table 1. The more downfield character of the carbinolic methylene protons relative to the carbinolic methine Table 1.…”

Section: Resultsmentioning

confidence: 99%

Fatty acids and terpenoids from Trigonia fasciculata

Mafezoli

Santos

Gambardela

et al. 2003

J. Braz. Chem. Soc.

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A fração lipídica do extrato hexânico das raízes de Trigonia fasciculata foi analisada por CG/EM sob a forma de seus ésteres metílicos, identificando-se dezessete ácidos graxos, sendo o ácido oléico (38,8%) o principal componente. A análise por CG/EM da fração menos polar da parte insaponificável do extrato hexânico das raízes permitiu identificar quinze sesquiterpenos não oxigenados, sendo o α-santaleno (28,4%) o componente majoritário. Cromatografia em gel de sílica da fração mais polar permitiu o isolamento de dois triterpenos conhecidos, ácido betulínico e friedelina, e o diterpeno inédito 7-(2-hidroxiacetil)-10-hidroxitetradecaidro-1-metileno-4b,7,10a-trimetilfenantreno (6α-hidroxi-15-oxo-allodevadarool). Todas as substâncias isoladas e identificadas são inéditas para a espécie. A determinação estrutural foi realizada por derivatização química, comparação com dados da literatura, análise espectral, incluíndo RMN 2D (COSY, HETCOR e COLOC), e cristalografia de raios X.The fatty portion of the hexane extract from roots of Trigonia fasciculata has been determined by GC/MS analysis of the methyl ester mixture. Seventeen fatty acids were identified and oleic acid (38.8%) was the major component. The GC/MS analysis of the less polar fraction of the nonsaponifiable part of the root hexane extract allowed the identification of fifteen sesquiterpenes and α-santalene (28.4%) was the major component. Chromatography over silica gel of the more polar fraction allowed the isolation of two known compounds: betulinic acid and friedelin, and a novel diterpene 7-(2-hydroxy-acetyl)-10-hydroxy-tetradecahydro-1-methylene-4b,7,10a-trimethylphenantrene (6α-hydroxy-15-oxo-allodevadarool), all unknown for the species. Structure determination was accomplished by chemical derivatization, comparison to literature data and spectral analysis, including 2D NMR (COSY, HETCOR, COLOC) and X-ray crystallography. Keywords Results and DiscussionTFRH, the clear viscous brownish extract obtained after hexane extraction of ground roots of T. fasciculata, yielded a precipitate after standing at room temperature. Silica gel chromatography column of the precipitate allowed the isolation of friedelin and betulinic acid. Coarse chromatography of the mother liquor yielded a non-polar fraction after elution with hexane designated TFRH(1). Hydrolysis with KOH/EtOH 1:1 solution, yielded the free fatty acids mixture (TFRH(1)/FA) and a unsaponifiable 407 Fatty Acids and Terpenoids from Trigonia fasciculata Vol. 14, No. 3, 2003 portion (TFRH(1)/NS) after usual work up. Methylation of an aliquot of TFRH(1)/FA with BF 3 /MeOH 14% solution followed by GC/MS analysis of the methyl ester mixture allowed the identification of the fatty acids listed in the Experimental Section. Silica gel chromatography of TFRH(1)/NS yielded a yellowish fraction by elution with hexane. 1 H and 13 C NMR analysis indicated its terpenoid character. GC/MS analysis of this fraction, followed by comparison of the mass spectra obtained for each compound with a computer library data ban...

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“…Chemically, the genus is characterized by the presence of tropane alkaloids. Also were also isolated flavonoids, terpenes, and tannins (Ansell, et al, 1993;Barreiros, et al, 2002;Brock, et al, 2005;Chávez, et al, 1996;González-Guevara, et al, 2006;Johnson, et al, 1997;Zuanazzi, et al, 2001). Erythroxylum coca Lamk.…”

Section: Introductionmentioning

confidence: 99%

Chemical composition and antioxidant activity of extracts from Erythroxylum suberosum A.St. Hil.leaves

2017

J App Pharma Sci

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Erythroxylum suberosum A. St. Hill. has been used as anti-rheumatism, anesthetic and for indigestion in Brazilian folk medicine.The crude extracts from leaves were obtained by maceration or infusion. The extracts showed no toxicity to brine shrimp lethality assay. The total phenolics and flavonoids contents were more significant in aqueous and ethanol extracts than its fractions (dichloromethane and hydro-methanol). The antioxidant potential of the crude aqueous extract was, approximately, 4.5 times higher than BHT, while the ethanol extract was 5.9 times. On the other hand, a hydro-methanol fraction from crude ethanol extract was 7.6 times more potent than BHT. Also, it was described the isolation and structural identification of isoquercitrin, rutin, quercetin and isomers catechin and epicatechin, from leaves of E. Suberosum.

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Diterpenes from the timber of Erythroxylum pictum

Cited by 29 publications

References 11 publications

Reconstructing the chemical diversity of labdane-type diterpene biosynthesis in yeast

Reconstructing the chemical diversity of labdane-type diterpene biosynthesis in yeast

Fatty acids and terpenoids from Trigonia fasciculata

Chemical composition and antioxidant activity of extracts from Erythroxylum suberosum A.St. Hil.leaves

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