Chemical investigation of a crinoid Himerometra magnipinna has afforded three anthraquinones (1–3), including one new metabolite, (+)-rhodoptilometrin (1). The structures of these compounds were elucidated on the basis of their spectroscopic data and the absolute configuration of 1 was further confirmed by single-crystal X-ray diffraction analysis. In the in vitro anti-inflammatory effects test, compound 2 was found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the LPS-stimulated RAW264.7 macrophage cells.
WrightAD, NielsonJL, TapiolasDM, MottiCA, OvendenSPB, KearnsPS, LiptrotCH. (2009) Detailed NMR, including 1,1-ADEQUATE, and anticancer studies of compounds from the echinoderm Colobometra perspinosa. Marine Drugs, 7, 565–575.
2.
TakahashiD, MaokaT, TsushimaM, FujitaniK, KozukaM, MatsunoT, ShinguT. (2002) New quinone sulfates from the crinoids Tropiometra afra macrodiscus and Oxycomanthus japonicas. Chemical & Pharmaceutical Bulletin, 12, 1609–1612.
3.
LeeNK, KimYH. (1995) New cytotoxic anthraquinones from the crinoid Ptilometra: 1′-Deoxyrhodoptilometrin-6-O-sulfate and rhodoptilometrin-6-O-sulfate. Bulletin of the Korean Chemical Society, 16, 1011–1013.
4.
RideoutTR, SutherlandMD. (1981) Polyketide sulfates from the crinoid Comatula pectinata (Linnaeus). Australian Journal of Chemistry, 34, 2385–2392.
5.
BartolinGL, ErdmanTR, ScheuerPJ. (1973) Anthraquinone pigments from the crinoid Comanthus bennetti. Tetrahedron, 29, 3699–3702.
6.
ErdmanTR, ThomsonRH. (1972) Naturally occurring quinones. Part XXI. Anthraquinones in the crinoids Heterometra savignii (J. Müller) and Lamprometra klunzingeri (Hartlaub). Journal of the Chemical Society, Perkin Transection, 1, 1291–1292.
7.
MatsunoT, FujitaniK, TakedaS, YokotaK, YoshimizuS. (1972) Pigments of sea-lilies. I. Quinonoids of Tropiometra afra macrodiscus (Hara) and Comanthus japonica (Miller). Chemical & Pharmaceutical Bulletin, 20, 1079–1082.
8.
PowellVH, SutherlandMD. (1967) Pigments of marine animals. VI. Anthraquinoid pigments of the crinoids Ptilometra australis Wilton and Tropiometra afra Hartlaub. Australian Journal of Chemistry, 20, 541–543.
9.
Crystallographic data for compound 1 have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC 939051). Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
10.
JeanY-H, ChenW-F, SungC-S, DuhC-Y, HuangS-Y, LinC-S, TaiM-H, TzengS-F, WenZ-H. (2009) Capnellene, a natural marine compound derived from soft coral, attenuates chronic constriction injury-induced neuropathic pain in rats. British Journal of Pharmacology, 158, 713–725.
