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Paper | Special issue | Vol 90, No. 1, 2015, pp.173-185
Published online, 4th March, 2014
DOI: 10.3987/COM-14-S(K)2
Halichonadins M-Q, Sesquiterpenes from an Okinawan Marine Sponge Halichondria sp.

Naonobu Tanaka, Shohei Suto, Miki Asai, Taishi Kusama, Azusa Takahashi-Nakaguchi, Tohru Gonoi, Jane Fromont, and Jun'ichi Kobayashi*

*Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


Four new dimeric sesquiterpenes, halichonadins M–P (14), and one new sesquiterpene, halichonadin Q (5), were isolated from an Okinawan marine sponge Halichondria sp. The sesquiterpenes have eudesmane skeleton in common. Halichonadin M (1) is a symmetrical dimer linked to a nitrilotriacetic acid fragment through amide bonds. Halichonadin N (2) is a structurally unique dimeric sesquiterpene connected via a pyrrolidine unit, while halichonadins O (3) and P (4) have linker moieties consisting of a piperidine unit. Halichonadin Q (5) is a sesquiterpene possessing a pyrrolidine unit. The structures of 15 were elucidated by spectroscopic analysis. Halichonadin O (3) showed antimicrobial activity against Staphylococcus aureus, Micrococcus luteus, and Trichophyton mentagrophytes.