Microbiological hydroxylation in the drimane series

Aranda, G.; Facon, Isabelle; Lallemand, Jean‐Yves; Leclaire, Massoumée; Azerad, Robert; Cortés, Manuel; López, Javier Sánchez; Ramírez, Héctor E.

doi:10.1016/s0040-4039(00)74759-9

Cited by 35 publications

(42 citation statements)

References 10 publications

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“…Compound 1 was obtained as a colorless oil and had a molecular formula C 21 15.0 (q) in 1 indicated an aglycone of sesquiterpene, and these 13 C NMR spectral data were similar to a known drimane sesquiterpene, 3b-hydroxydrimenol [18,19]. The obvious differences were the significant down-fielded shift of C-3 from d C 79.6 to 90.8, as well as the presence of six sugar carbons in compound 1.…”

Section: Resultsmentioning

confidence: 93%

A new drimane sesquiterpenoid glycoside from the seeds of Antiaris toxicaria

Dong

Mei

Zhao

et al. 2011

Journal of Asian Natural Products Research

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A new drimane sesquiterpenoid glycoside, named 7-drimen-3β,11-diol 3-O-β-d-glucopyranoside, was isolated from the 95% EtOH extract of the seeds of Antiaris toxicaria (Pers.) Lesch. The chemical structure was completely elucidated using a combination of 1D and 2D NMR techniques (COSY, HMQC, HMBC, and ROESY) and HR-ESI-MS analysis. The compound showed inhibitory activities toward methicillin-resistant Staphylococcus aureus (MRSA), chronic myelogenous leukemia (K562), and human hepatoma (SMMC-7721) cell lines.

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Section: Resultsmentioning

confidence: 93%

A new drimane sesquiterpenoid glycoside from the seeds of Antiaris toxicaria

Dong

Mei

Zhao

et al. 2011

Journal of Asian Natural Products Research

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“…1). The four known sesquiterpenes were identified as 3b-hydroxydrimenol (3), 11,12-dihydroxydrimene (4), 3b,11,12-trihydroxydrimene (6), 8) 3b-hydroxy-11-acetyldrimene (2), 9) by comparison of their spectroscopic data with literature values. 3b-Hydroxy-11,12-O-isopropylidenedrimene (5) might be not a natural product.…”

Section: Notesmentioning

confidence: 99%

Sesquiterpenes from Cultures of the Basidiomycete Clitocybe conglobata and Their 11.BETA.-Hydroxysteroid Dehydrogenase Inhibitory Activity

Sheng

Zhou

et al. 2009

Chem. Pharm. Bull.

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A new drimane sesquiterpenoid, 3-keto-drimenol (1), were isolated from cultures of the basidiomycete Clitocybe conglobata together with 3b b-hydroxy-11-acetyldrimene (2), 3b b-hydroxydrimenol (3), 11,12-dihydroxydrimene (4), 3b b-hydroxy-11,12-O-isopropyldrimene (5), and 3b b,11,12-trihydroxydrimene (6). Their structures were established from MS and NMR experiments. Compounds 1, 3, and 6 showed inhibitory activities against two isozymes of 11b b-hydroxysteroid dehydrogenases with IC 50 1.7-8.0 m mg/ml (human 11b b-HSD1), 10.7-24.1 m mg/ml (mouse 11b b-HSD1); 177.0-220.0 m mg/ml (human 11b b-HSD2), 250.5-500.2 m mg/ml (mouse 11b b-HSD2), respectively, which catalyze the interconversion of active cortisol and inactive cortisone.

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“…We isolated two new derivatives by microbial transformation using liquid cultures of M. plumbeus. Here, we report a complete assignment of 1 H and 13 C NMR of these two compounds.…”

Section: Introductionmentioning

confidence: 97%

Microbial transformation of the diterpene mulin‐11,13‐dien‐20‐oic acid by Mucor plumbeus

Areche

Loyola

Bórquez

et al. 2008

Magnetic Reson in Chemistry

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Two new mulinane-type derivatives: 16-hydroxy mulin-11,13-dien-20-oic (2) acid and 7alpha,16-dihydroxy mulin-11,13-dien-20-oic (3) acid were obtained by microbial transformation of mulin-11,13-dien-20-oic acid (1), along with tyrosol (4) using liquid cultures of Mucor plumbeus. The latter compound has not been previously identified in the genus Mucor. Structural elucidation of these metabolites was achieved using 1D- and 2D-NMR spectroscopy.

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Microbiological hydroxylation in the drimane series

Cited by 35 publications

References 10 publications

A new drimane sesquiterpenoid glycoside from the seeds of Antiaris toxicaria

A new drimane sesquiterpenoid glycoside from the seeds of Antiaris toxicaria

Sesquiterpenes from Cultures of the Basidiomycete Clitocybe conglobata and Their 11.BETA.-Hydroxysteroid Dehydrogenase Inhibitory Activity

Microbial transformation of the diterpene mulin‐11,13‐dien‐20‐oic acid by Mucor plumbeus

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