Stereochemistry of hydrogen peroxide - acetic acid oxidation of ursolic acid and related compounds.

Ткачев, А. В.; Denisov, A. Yu.; Gatilov, Yuri V.; Bagryanskaya, I. Yu.; Shevtsov, S. A.; Rybalova, Т. V.

doi:10.1016/s0040-4020(01)89285-1

Cited by 48 publications

(48 citation statements)

References 42 publications

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“…Compound 1 was characterized as ursolic acid 5,6 and compound 2 turned out to be acetylursolic acid. 5,7 The 2D NMR experiments H 1 -H 1 COSY, HMQC and HMBC brought detailed information allowing to complete the signal assignments reported in the literature (Tables 1 and 2).…”

Section: Resultsmentioning

confidence: 99%

Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté)

Taketa¹,

Breitmaier²,

Schenkel³

2004

J. Braz. Chem. Soc.

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Dos frutos deIlex paraguariensis foram isolados um novo glicosídeo triterpenóide, o ácido rotúndico 3β-O-α-L-arabinopiranosídeo, denominado matesídeo (4), os triterpenos ácido ursólico (1), ácido acetilursólico (2), ácido 23-hidroxi-ursólico (3) e as saponinas ziyu-glicosídeo I (5) e ilexosídeo II (6). As estruturas foram estabelecidas com base em métodos espectroscópicos, principalmente RMN mono-e bidimensional. Os valores de amargor foram determinados para matesídeo e ilexosídeo II e comparados com os valores obtidos para as saponinas de I. paraguariensis e outras espécies de Ilex. O elevado amargor encontrado para o ilexosídeo II, uma das saponinas majoritárias presentes nos frutos e não encontrada nas folhas de I. paraguariensis, sugere que o uso dos frutos alteraria de maneira significativa o sabor do produto erva-mate e também poderia produzir efeitos fisiológicos ainda não conhecidos.A new triterpenoid glycoside, 3β-O-α-L-arabinopyranosyl rotundic acid, named here mateside (4), and the known triterpenes ursolic acid (1), acetylursolic acid (2), 23-hydroxyursolic acid (3), the saponins ziyu-glycoside I (5) and ilexoside II (6), were isolated from fruits of Ilex paraguariensis. Their structures were established on the basis of 1D and 2D NMR spectroscopic methods. The threshold bitterness values for mateside and ilexoside II were also determined and compared with saponins obtained from leaves of I. paraguariensis and other Ilex species. The high bitterness of Ilexoside II, one of the main saponins found the fruits, but not in the leaves of I. paraguariensis, suggests that the utilization of the fruits in the Maté production can produce a strong taste variation and unknown physiological effects.

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Section: Resultsmentioning

confidence: 99%

Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté)

Taketa¹,

Breitmaier²,

Schenkel³

2004

J. Braz. Chem. Soc.

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“…Our finding revealed that the 1 H-and 13 C-NMR data of 5 were similar to those reported for the corresponding synthetic product. 8) Compound 4, documented as a synthetic product by oxidation of 5 using CrO 3 , 8) was obtained for the first time from a natural source in this study. We herein report the structural elucidation of compounds 1-3.…”

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confidence: 90%

“…4) Chromatographic separation of the hexane and CH 2 Cl 2 extracts led to the isolation of two new acetylenic fatty acids (1, 2), a new triglyceride (3), as well as, 11 known compounds, including 3b-hydroxy-11-oxours-12-en-28-oic acid 5) (isolated as its acetate derivative), 3b-hydroxy-27-p-(Z)-coumaroyloxyolean-12-en-28-oic acid, 6,7) 3-oxo-11a,12a-epoxyurs-13b,28-olide (4), 8) 3b-hydroxy11a,12a-epoxyurs-13b,28-olide (5), 8,9) 3b-hydroxyurs-11-en-13(28)-lactone (6), 8,[10][11][12] oleanolic acid (7), 13,14) b-sitosterol, 15) uncarinic acid E (3b-hydroxy-27-(E)-p-coumaroyloxyolean-12-en-28-oic acid, 8), 6,7) ursolic acid (9), 13,14) ursonic acid (10), and 3b-(formyloxy)-urs-12-en-28-oic acid (11). 16) Compound 5 was reported to be isolated from Thevetia neriifolia, 9) but the reported NMR chemical shifts were not consistent with the proposed structure.…”

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confidence: 99%

Acetylenic Fatty Acids, Triglyceride and Triterpenes from the Leaves of Hymenodictyon excelsum

Nareeboon

Komkhunthot

Lekcharoen

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Ursolic acid structure was elucidated by comparison of its spectral data (DIP MS, 1 H NMR, 13 C NMR, DEPT, 1 H-1 H COSY, HMQC, HMBC) with previously published data (The Aldrich Library, 1993;Tkachev et al, 1994).…”

Section: Extraction and Isolationmentioning

confidence: 99%

Anti-inflammatory activity of extract and fractions from Nepeta sibthorpii Bentham

Miceli

Taviano

Giuffrida

et al. 2005

Journal of Ethnopharmacology

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Stereochemistry of hydrogen peroxide - acetic acid oxidation of ursolic acid and related compounds.

Cited by 48 publications

References 42 publications

Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté)

Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté)

Acetylenic Fatty Acids, Triglyceride and Triterpenes from the Leaves of Hymenodictyon excelsum

Anti-inflammatory activity of extract and fractions from Nepeta sibthorpii Bentham

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