A sterol glycoside from leaves of Clerodendron colebrookianum

Goswami, Pratul; Kotoky, Jibon; Chen, Ze-Nai; Liu, Yang

doi:10.1016/0031-9422(95)00557-9

Cited by 26 publications

(21 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…compounds are steroid glucosides. 11,12 All the other signals are compatible with the structure of 3a and 3b. The steroid 3a has been isolated from Clerodendron colebrookianum (Verbenaceae).…”

Section: Resultsmentioning

confidence: 58%

“…The H-3 multiplet is deshielded by 0.4 ppm suggesting that the mixture is composed by, glycopyranosyl steroids, with β configuration on the anomeric carbon, evidenced by the doublet at δ 5.02 (7.6 Hz). 11 The 13 C NMR ( Table 2) data suggested that the Compounds 3a + 3b were measured in C 5 D 5 N. Assignments with the same symbol ( a,b,c ) in the column are interchangeable. Signals for carbons of the glucosyl moiety in compounds 3a and 3b occurred at δ 103.0 (C-1'), 75.8 (C-2'), 78.6 (C-3'), 72.2 (C-4'), 78.9 (C-5'), 63.3 (C-6').…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Steroids and flavonoids of Porcelia macrocarpa

Chaves¹,

Roque²,

Ayres³

2004

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Três misturas de esteróides (1a+1b, 2a+2b e 3a+3b) e dois flavonóides glicosilados (4 e 5) foram isolados do extrato etanólico dos galhos da Porcelia macrocarpa (Warm.) R. E. Fries (Annonaceae). Os esteróides Estigmasta-4,25-dien-3-ona (2a) e (22E)-Estigmasta-4,22,25-trien-3-ona (2b) são substâncias novas. As estruturas foram determinadas com base na análise de dados espectrais de RMN e de massas e por comparação com dados de substâncias da literatura usadas como modelos.Three mixtures of steroids (1a+1b, 2a+2b and 3a+3b) and two flavonoid glycosides (4 and 5) were isolated from the ethanol extract of branches of Porcelia macrocarpa (Warm.) R. E. Fries (Annonaceae). The steroids Stigmasta-4,25-dien-3-one (2a) and (22E)-Stigmasta-4,22,25-trien-3-one (2b) are news. The structures were elucidated by NMR and MS data and comparison with literature data of model compounds.

show abstract

Section: Resultsmentioning

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Steroids and flavonoids of Porcelia macrocarpa

Chaves¹,

Roque²,

Ayres³

2004

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…All these analyses led this compound to be identified as clerosterol (Fig. 2) previously isolated from the marine green alga Codium iyengarii (Ahmad et al, 1992) and from the leaves of Clerodendron colebrookinaum (Goswami et al, 1996). The hexane extract from the fruits of Cassia fistula showed also triglycerides and fatty acids that did not show antileishmanial activity.…”

Section: Resultsmentioning

confidence: 94%

Isolation of antileishmanial sterol from the fruits of Cassia fistula using bioguided fractionation

Sartorelli

Andrade

Melhem

et al. 2007

Phytotherapy Research

View full text Add to dashboard Cite

Natural products represent a rich source of new chemical entities for the development of drugs for neglected diseases. Leishmaniasis still afflicts the poorest populations in the world, with 12 million cases worldwide. This work analysed crude extracts and fractions from the fruits of Cassia fistula against the most dramatic and fatal disease form of leishmaniasis, the visceral form (VL). Hexane extract from the fruits showed significant antileishmanial activity against the promastigote form of Leishmania L. chagasi. The bioguided fractionation resulted in the isolation of a sterol, clerosterol, which was further analysed in different models. Promastigotes presented an inhibitory concentration 50% (IC50) of 10.03 microg/mL and intracellular amastigotes demonstrated high susceptibility, with an IC50 of 18.10 microg/mL. Mammalian cytotoxicity was evaluated and it was demonstrated that clerosterol was 3.6-fold less toxic than the standard drug pentamidine. No antifungal activity of the isolated clerosterol was found. Future studies of the extracted compounds of Cassia fistula could be a useful tool for the development of new therapeutic agents for VL.

show abstract

“…The downfield shift in H-3 signal allowed us to assign α-orientation to H-3. [20] The 1 H NMR spectrum also depicted doublets for three methyls at δ H 1.03 (J = 6.21 Hz, CH 3 -21), 0.85 (J = 6.41 Hz, CH 3 -26), 0.79 (J = 6.51 Hz, CH 3 -27) and a triplet of three protons at δ H 0.81 (J = 7.24 Hz, CH 3 -29). The three proton triplet at δ H 0.81 suggested an ethyl moiety in the side chain at C-24 on biogenetic grounds.…”

Section: Resultsmentioning

confidence: 97%