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Nitrogenous sesquiterpenes from the Thai marine sponge Halichondria sp.
- Prawat, Hunsa, Mahidol, Chulabhorn, Wittayalai, Sawangjitt, Intachote, Pakamas, Kanchanapoom, Tripetch, Ruchirawat, Somsak
- Tetrahedron 2011 v.67 no.31 pp. 5651-5655
- Porifera, chemical reactions, chemical structure, cytotoxicity, ergosterol, human cell lines, inhibitory concentration 50, metabolites, sesquiterpenoids, spectroscopy
- Five nitrogenous sesquiterpenes having an isonitrile [(−)-axisonitrile-3], a formamide [(+)-axamide-3, axamide-2 and (3S*,5R*,6R*,9R*)-3-formamido-1(10)-cadinene], and an amine [(−)-halichamine] functionality were isolated from the Thai marine sponge Halichondria sp., together with two steroids, ergosterol and ergosterol peroxide. (−)-Axisonitrile-3 was isolated from the natural source for the first time, while (+)-axamide-3 and (−)-halichamine were new metabolites. The structures of these compounds were elucidated on the basis of their spectroscopic data and by chemical transformations. All sesquiterpenes were tested for their cytotoxic activity against six cancer cell lines (HeLa, HuCCA-1, A549, MOLT-3, HepG2, MDA-MB231). Only (−)-axisonitrile-3 showed strong activity to the HepG2 cell line with an IC₅₀ value of 1.3 μM.