Dolabranes from the Chinese Mangrove, Ceriops tagal

Abstract

Six new dolabranes, named tagalsins P-U (1-6), were isolated from stems and twigs of a Chinese mangrove, Ceriops tagal, along with seven known dolabranes, an abietane, and a pimarane. The structures of these compounds were established on the basis of spectroscopic data or comparison with data in the literature. The relative configurations of tagalsins P and Q (1, 2), two new 15,16-dinor-dolabranes, were confirmed by means of single-crystal X-ray diffraction analysis. This is the first report of 16-nordolabranes and 15,16-dinordolabranes from plants of the Ceriops genus. Tagalsins Q (2), R (3), and U (6) showed moderate antifeedant activity against the third-instar larvae of Brontispa longissima at a concentration of 1 mg/mL. However, none of the new dolabranes exhibited significant activity against human cancer cell lines.

Dolabrane-type diterpenes from the mangrove plant Ceriops tagal with antitumor activities

“…In addition, it is reported that the crude extract of the plant possesses the activities to cure for hepatitis and diabetes [10]. Previous chemical investigation revealed that C. tagal not only abounded in tannins and triterpenoids [11,12], but also contained diverse dolabrane-type diterpenes such as tagalsin A-U [13][14][15] and tetraterpens [16,17]. Terpenoids from the root of C. tagal possess antifouling activity, while dolabrane derivatives exerted antifeedant and anticancer activities.…”

Chemical Constituents and Some Biological Activities of Plants from the Genus Ceriops

“…The relative configurations of tagalsins P and Q (9 and 12, resp.) were confirmed by means of single-crystal X-ray diffraction analysis in 2010 [10]. Tagalsins A -G and O (1 -7 and 8, resp.)…”

“…Compounds 12, 14, and 17, obtained from stems and twigs of the Chinese C. tagal, exhibited moderate antifeedant activity against the third-instar larvae of Brontispa longissima at a concentration of 1 mg ml À 1 . However, Compounds 12 -17 showed no significant activities against human melanoma (A2058, G361), prostate (DU145), and breast (MDA-MB-468, MDA-MB-435) cancer cell lines [10].…”

ent-5α,3,15-Dioxodolabr-4(18)-ene-16,18-diol

“…For ring conformations, see: Cremer & Pople (1975). For background to diterpenoids, see, for example: Hu et al (2010); Zhang et al (2005). For related structures, see: Chantrapromma et al (2007); Fun et al (2006).…”