Biologically Active Xenicane Diterpenoids from the Gorgonian Acalycigorgia Sp.

A new xenicane norditerpene from the Indian marine gorgonianAcanthogorgia turgida

“…These fractions were submitted to subsequent chromatographic steps by both silica-gel column chromatography and reverse-phase HPLC to give pure xenicanes 1 (3.0 mg), 2 (9.0 mg), 3 (12.0 mg), 4 (13.0 mg), 5 (11.0 mg) and 6 (6.0 mg). The known compounds 2-6 were identified by comparison of spectral data with those reported in the literature (Fusetani et al, 1987;Hokama et al, 1988;Rho et al, 2000;Ochi et al, 1994), whereas the structure of isoacalycixeniolide-A (1) was determined as follows.…”

“…With the exception of diterpene 2, all compounds isolated were norditerpenes. The known xenicane acalycigorgin-E (2) (Ochi, Kataoka, Tatsukawa, Kotsuki, & Shibata, 1994) and 19-norxenicanes acalycixeniolide-B (3) (Fusetani, Asano, Matsunaga, & Hashimoto, 1987), acalycixeniolide-G (4) (Rho, Lee, Seo, Cho, & Shin, 2000), acalycixeniolide-D (5) (Rho, Lee, Seo, Cho, & Shin, 2000), and ginamallene (6) (Hokama et al, 1988) (Figure 1) have been previously reported from gorgonians of genus Acalycigorgia.…”

Xenicane Natural Products: Biological Activity and Total Synthesis

“…Acalycixeniolide C (29) was obtained from Acanthogorgia sp. [84][85][86] and showed biological activities ranging from moderate cytotoxicity against mouse P388 leukemia cells, to very poor, but detectable activity in a sea urchin (Hemicentrotus pulcherrimus) egg assay, to antifungal activity against Mortierella ramannianus and Penicillium chrysogenum [84]. The highly oxidized and structurally unusual xeniolide I (30) was extracted from Xenia novaebrittanniae and showed moderate antibacterial activity against Escherichia coli and Bacillus subtilis [87].…”

“…Acalycixeniolide G (39), the epoxide of 36, was co-isolated with 24 and 31 and was reported to be moderately cytotoxic towards K562 leukemia cells [78,79]. Acalycixeniolide B' (40) is the α-epimer of 36 and was isolated together with 29 [84][85][86]. A range of biological tests revealed moderate cytotoxicity against P388 leukemia cells (IC50 < 2.5 µg/mL), and very low activity in a sea urchin egg assay; the compound also showed antifungal activity against Mortierella ramannianus and Penicillium chrysogenum [84].…”

Asterolaurins G – J, New Xenicane Diterpenoids from the Taiwanese Soft Coral Asterospicularia laurae

“…The similarity in polyp structure is a striking feature among species of the genera Asterospicularia, Xenia, and Sympodium, and several members of these soft corals have been the subject of phytochemical investigation that resulted in the isolation of a number of natural products with interesting antitumor and cytotoxic activities [2] [3]. Literature surveys also revealed a few reports concerning the isolation and characterization of marine natural products with the xenicane-diterpenoid skeleton from the soft coral genera Xenia [4 -11], Anthelia [12] [13], Alcyonium [13], and Capnella [14], from the blue coral Heliopora coerulea [15], and also from gorgonians [16]. Among these, only three reports were on the chemistry of the genus Asterospicularia, including the isolation of 24-methyl-5a-cholestane-3b,5,6b,22R,24-pentol 6-acetate from A. randalli [17], the isolation of 13-epi-9-deacetoxyxenicin, 13-epi-9-deacetylxenicin, and gorgosterol from A. laurae [18], and recently we reported the isolation of six new xenicane-type diterpenoids, asterolaurins A -F, from A. laurae [19].…”