Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata

Abstract

Two new nitrogen-containing verticillene diterpenoids, cespilamides A and B (1 and 2), three new nitrogen-containing sesquiterpenoids, cespilamides C–E (3–5), and five new norverticillene and verticillene diterpenoids, cespitaenins A–E (6–10), were isolated from the Taiwanese soft coral Cespitularia taeniata. Compound 1 possesses an unusual oxazo ring system at C-10 while compound 2 displays an unprecedented C–C bond cleavage between C-10 and C-11 with an N-ethylphenyl group at C-10. Biogenetic pathways of 1 and 2 are proposed. The absolute configuration of 1 was confirmed by Mosher’s method and molecular mechanics calculations (MM2). The cytotoxicities of compounds 1–10 were evaluated against a small panel of human cancer cell lines.

Marine natural products

“…833 A series of nitrogenous diterpenoids and sesquiterpenoids 1178-1187 were reported from Cespitularia taeniatathe absolute conguration of cespilamide A 1178 was established by a combination of MM2 modeling and Mosher's analysis. 834 Rare examples of cembranoid 7,8-diols 1188 and 1189 were isolated from Sinularia gaweli. 812 The structure assigned 1188 is the (À)-enantiomer of the known cembranoid leptodiol acetate (Leptogorgia sp.…”

Natural Nitrogenous Sesquiterpenoids and Their Bioactivity: A Review

“…One eudesmane-type sesquiterpene, phaeusmane I (267) (Figure 5), was isolatedfrom the rhizomes of Curcumaphaeocaulis [63]. Three new nitrogen-containing sesquiterpenoids, the cespilamides C-E (268-270, Figure 5) were purified from the Taiwanese soft coral Cespitulariataeniata, and 270 exhibited cytotoxicity against human breast adenocarcinoma (MCF-7), medulloblastoma (Daoy), and cervical epitheloid carcinoma (Hela) cancer cells with IC50 of 17.5, 22.3, and 24.7 μM, respectively [64]. Acanthine B (271), acanthine C (272), 11isocyano-7βH-eudesm-5-ene (273), 11-isothiocyano-7βH-eudesm-5-ene (274), and 11-formamido-7βH-eudesm-5-ene (275) (Figure 5), were isolated from the Thai sponge Halichondriasp [65].…”

Alcyonacea: A Potential Source for Production of Nitrogen-Containing Metabolites

“…Cespilamide E ( 15 ) exhibited cytotoxicity against Hela, Daoy, WiDr and MCF-7 cells with IC 50 of 24.7, 22.3, 34.1 and 17.5 μM, respectively. Cespilamide E ( 13 ) exhibited cytotoxicity against Hela, Daoy, WiDr and MCF-7 cells with IC 50 of 30.9, 34.8, 49.5 and 30.6 μM, respectively, while cespilamide D ( 14 ) was inactive (>40 μM) [31,33].…”