A new lupane-type triterpenoid fatty acid ester and other isolates from Ophiorrhiza shendurunii

• Published in: Natural product research Vol. 30; no. 19; pp. 2197 - 2203
• Main Authors: Rajan, Renjith, Venkataraman, Ramaswamy, Baby, Sabulal
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 01.10.2016
• Subjects: antifungal activity; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; Candida albicans; Drug Evaluation, Preclinical - methods; Fatty Acids - chemistry; Fusarium oxysporum; Gas Chromatography-Mass Spectrometry; Hexanes - chemistry; Hydrolysis; India; lupan-20-ol-3(β)-yl hexadecanoate; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Structure; Ophiorrhiza shendurunii; pentacyclic triterpenoid fatty acid ester; Plant Extracts - chemistry; Plant Extracts - pharmacology; Rubiaceae - chemistry; Spectrometry, Mass, Electrospray Ionization; Spectroscopy, Fourier Transform Infrared; Triterpenes - chemistry; Triterpenes - isolation & purification; Triterpenes - pharmacology; lupan-20-ol-3(β)-yl hexadecanoate; Ophiorrhiza shendurunii; antifungal activity; pentacyclic triterpenoid fatty acid ester
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2016.1160232

A new pentacyclic triterpenoid fatty acid ester, lupan-20-ol-3(β)-yl hexadecanoate (1), together with lupan-20-ol-3(β)-yl acetate (2), olean-18-en-3(β)-yl hexadecanoate (3), dotriacontanoic acid (4), stigmasterol (5), rubiadin (6), nonadecanoic acid (7), palmitic acid (8) and camptothecin (9) were isolated from the hexane and chloroform extracts of Ophiorrhiza shendurunii from South India. Structures of the isolates were determined by 1 H, 13 C, 13 C DEPT, 1 H- 1 H COSY, HMBC, HSQC, NOESY NMR, FT-IR, DART-MS, ESI-MS, alkaline hydrolysis, derivatisation, GC-MS and HPTLC analyses. O. shendurunii hexane and chloroform extracts showed significant activities against Candida albicans and Fusarium oxysporum. Compounds 1 to 3 showed only moderate antiyeast/antifungal activities.