Capgermacrenes A and B, Bioactive Secondary Metabolites from a Bornean Soft Coral, Capnella sp.

Abstract

Two new bicyclogermacrenes, capgermacrenes A (1) and B (2), were isolated with two known compounds, palustrol (3) and litseagermacrane (4), from a population of Bornean soft coral Capnella sp. The structures of these metabolites were elucidated based on spectroscopic data. Compound 1 was found to inhibit the accumulation of the LPS-induced pro-inflammatory IL-1β and NO production by down-regulating the expression of iNOS protein in RAW 264.7 macrophages.

Marine natural products

“…808 A series of seventeen sesquiterpenes were reported, comprised of a himachalene-type peroxide 1125 (Litophyton arboretum), 809 cyclopentenones 1126 (Sinularia sandensis) 810 and 1127 and 1128 (Sinularia acuta), 811 eudesmane-type 1129 (Sinularia gaweli), 812 subergane-type 1130 (Subergorgia suberosa), 813 monocyclic and bicyclic germacrenes 1131 (Sarcophyton glaucum) 814 and 1132 and 1133 (Capnella sp. ), 815 caryophyllanes 1134 and 1135 (Rumphella antipathies), 816 and guaiane lactones 1136-1140 (Menella kanisa) 817 and 1141 and 1142 (Menella woodin). 818 Of note was the use of a diverse array of computational techniques, including calculated 13 C NMR chemical shis, optical rotation and ECD to determine the structures and absolute congurations of 1141 and 1142.…”

Capgermacrene C, a New Sesquiterpenoid from a Bornean Soft Coral, Capnella sp.

“…Secondary metabolites isolated from soft corals have been reported to show a variety of biological activities such as anti-tumor, antiviral, antifouling and anti-inflammatory [3]. In our previous chemical investigation of one population of a Bornean soft coral in the genus Capnella, we reported the isolation and structural elucidation of two new bicyclogermacrene-type sesquiterpenoids, capgermacrenes A and B [4]. In this study, we report on yet another population of Capnella sp.…”

Recent Updates on Corals from Nephtheidae

“…Such little inhibition of PGE2 production by capgermacrene A is mediated by suppression of COX-2 expression. [29] Moreover, capgermacrene C (59), a new bicyclogermacrene isolated from the Bornean soft coral Capnella sp. exerted weak antibacterial potential against a panel of antibiotic-resistant bacteria.…”

“…[29] 58 Capgermacrene B C. sp. [29] 59 Capgermacrene C C. sp. [30] 60 Capgermacrene D C. imbricata [31] 61 Capgermacrene E C. imbricata [31] 62 Capgermacrene F C. imbricata [31] 63 Capgermacrene G C. imbricata [31] 64 Flavalin A L. flava [32] 65 Flavalin B L. flava [32] 66 Flavalin C L. flava [32] 67 Flavalin D L. flava [32] 68 Flavalin E L. flava [33] 69 Flavalin F L. flava [33] 70 Flavalin G L. flava [33] 71…”

“…Ethyl 5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]furan-3-carboxylate C. fungiformis [29] 122 Dikelsoenyl ether N. erecta [39] 123 Kelsoenethiol N. erecta [39] 124 Dendrophen D. hemprichi [7] 125 Leucyl-N-methyl-leucyl-leucyl-N-methyl-leucine N. sp. [40] 126 3-methyl-5-(10'-acetoxy-2',6',10'-trimethylundecyl)-2-penten-5-olide S. gracillimum [17] 127 Scleronine S. sp.…”