Biotransformation of cycloartane-type triterpenes by the fungus Glomerella fusarioides

Journal of Natural Products
Toshihiro AkihisaYumiko Kimura

Abstract

Biotransformation of three cycloartane-type triterpenes, cycloartenol (1), 24-methylenecycloartanol (2), and cycloartenone (3), by the fungus Glomerella fusarioides was studied. Compound 1 was converted to 3, cycloart-25-ene-3beta,24-diol (4), and cycloartane-3beta,24,25-triol (5). Compound 2 was metabolized to cycloeucalenol (6) and two new compounds, 24-methylcycloartane-3beta,24,24(1)-triol (7) and 24(1)-methoxy-24-methylcycloartane-3beta,24-diol (8). Compound 3 was converted into two new metabolites, 4alpha,4beta,14alpha-trimethyl-9beta,19-cyclopregnane-3,20-dione (9) and 25-hydroxy-24-methoxycycloartan-3-one (14), and four known compounds, viz., cycloartane-3,24-dione (10), 24-hydroxycycloart-25-en-3-one (11), (23E)-25-hydroxycycloart-23-en-3-one (12), and 24,25-dihydroxycycloartan-3-one (13). The structures of four new metabolites, 7, 8, 9, and 14, were established by spectroscopic methods.

References

Nov 1, 1993·Phytochemistry·S B Mahato, I Majumdar
Jul 11, 2000·Journal of Agricultural and Food Chemistry·T AkihisaK Arai
Apr 28, 2001·Journal of Natural Products·M HosnyJ P Rosazza
Nov 17, 2001·Phytochemistry·Hironori OhtsuShunyo Matsunaga
Dec 13, 2002·The Journal of Steroid Biochemistry and Molecular Biology·Sameera Al-AwadiS Oommen
Jul 1, 1964·Journal of Medicinal Chemistry·A I LASKINJ FRIED

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Citations

Oct 11, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Nighat Sultana, Zafar Saeed Saify
Nov 26, 2013·Journal of Asian Natural Products Research·Haq Nawaz Bhatti, Rasheed Ahmad Khera
Oct 17, 2008·Journal of Natural Products·Hsi-Lin ChiuYueh-Hsiung Kuo
Jul 3, 2021·Marine Drugs·Valery M DembitskyVladimir V Poroikov

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