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Mar. Drugs 2012, 10(8), 1619-1630; doi:10.3390/md10081619

A Great Barrier Reef Sinularia sp. Yields Two New Cytotoxic Diterpenes

Australian Institute of Marine Science, PMB no. 3, Townsville MC, Townsville, QLD 4810, Australia Present address: College of Pharmacy, University of Hawaii, 34 Rainbow Drive, Hilo, HI 96720, USA. Present address: ACD Labs UK, Building A, Trinity Court, Wokingham Road, Bracknell, Berkshire RG42 1PL, UK. § Present address: Advanced Analytical Centre, James Cook University, Townsville, QLD 4811, Australia.
* Author to whom correspondence should be addressed.
Received: 4 June 2012 / Revised: 25 June 2012 / Accepted: 23 July 2012 / Published: 31 July 2012
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The methanol extract of a Sinularia sp., collected from Bowden Reef, Queensland, Australia, yielded ten natural products. These included the new nitrogenous diterpene (4R*,5R*,9S*,10R*,11Z)-4-methoxy-9-((dimethylamino)-methyl)-12,15-epoxy-11(13)-en-decahydronaphthalen-16-ol (1), and the new lobane, (1R*,2R*,4S*,15E)-loba-8,10,13(14),15(16)-tetraen-17,18-diol-17-acetate (2). Also isolated were two known cembranes, sarcophytol-B and (1E,3E,7E)-11,12-epoxycembratrien-15-ol, and six known lobanes, loba-8,10,13(15)-triene-16,17,18-triol, 14,18-epoxyloba-8,10,13(15)-trien-17-ol, lobatrientriol, lobatrienolide, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate and (17R)-loba-8,10,13(15)-trien-17,18-diol. Structures of the new compounds were elucidated through interpretation of spectra obtained after extensive NMR and MS investigations and comparison with literature values. The tumour cell growth inhibition potential of 1 and 2 along with loba-8,10,13(15)-triene-16,17,18-triol, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate, lobatrienolide, (1E,3E,7E)-11,12-epoxycembratrien-15-ol and sarcophytol-B were assessed against three human tumour cell lines (SF-268, MCF-7 and H460). The lobanes and cembranes tested demonstrated 50% growth inhibition in the range 6.8–18.5 µM, with no selectivity, whilst 1 was less active (GI50 70–175 µM).
Keywords: Sinularia; Alcyoniidae; anticancer activity; lobane; cembrane; diterpene Sinularia; Alcyoniidae; anticancer activity; lobane; cembrane; diterpene
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Wright, A.D.; Nielson, J.L.; Tapiolas, D.M.; Liptrot, C.H.; Motti, C.A. A Great Barrier Reef Sinularia sp. Yields Two New Cytotoxic Diterpenes. Mar. Drugs 2012, 10, 1619-1630.

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