Deoxymanoalides from the Nudibranch Chromodoris willani

• Published in: Chemical & Pharmaceutical Bulletin Vol. 57; no. 8; pp. 885 - 887
• Main Authors: Uddin, Mohammad Helal, Otsuka, Masahito, Muroi, Toshinobu, Ono, Atsushi, Hanif, Novriyandi, Matsuda, Seiko, Higa, Tatsuo, Tanaka, Junichi
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.08.2009; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Animals; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Bacillus subtilis; Bacillus subtilis - drug effects; Cell Line; Cell Survival - drug effects; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Chromodoris; Chromodoris willani; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - isolation & purification; Enzyme Inhibitors - pharmacology; Escherichia coli; Escherichia coli - drug effects; Inhibitory Concentration 50; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy - standards; manoalide; Microbial Sensitivity Tests; Molecular Conformation; Mollusca; Mollusca - chemistry; Pharmacology & Pharmacy; phospholipase A2; Phospholipase A2 Inhibitors; Physical Sciences; Rats; Reference Standards; Science & Technology; Sesterterpenes - chemistry; Sesterterpenes - isolation & purification; Sesterterpenes - pharmacology; Snake Venoms - enzymology; Stereoisomerism; Japan, Nansei-shoto, Okinawa; Chromodoris willani; manoalide; ABSOLUTE-CONFIGURATIONS; MARINE; phospholipase A2
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.57.885

Two sesterterpenes, deoxymanoalide (1) and deoxysecomanoalide (2), were isolated from the nudibranch Chromodoris willani collected in Okinawa and their structures determined on the basis of spectroscopic data and chemical conversions. The mollusk feeds on a sponge containing manoalide (3) and secomanoalide (4) and is likely to biotransform them into 1 and 2. Both 1 and 2 showed moderate antimicrobial activity against Escherichia coli and Bacillus subtilis and inhibited snake venom phospholipase A2 at 0.2 to 0.5 μM.