A New Cadinane Sesquiterpene from the Marine Brown Alga Dictyopteris divaricata

Abstract

A sample of the marine brown alga D. divaricata collected off the coast of Yantai (P.R. China) was dried, powdered, and extracted with the mixture of CHCl3 and MeOH (1:1, v/v). By a combination of silica gel and Sephadex LH-20 column chromatography and preparative TLC, a new cadinane sesquiterpene 1,4-epoxymuurolan-5β-ol (1) was isolated from this species. Its structure was established by detailed MS and NMR spectroscopic analysis, as well as comparison with literature data.

Marine natural products

“…347 In another large survey, 342 species of marine alga were screened against the bacterium Propionibacterium acnes, and the bacteriostatic compound sargafuran 303 was isolated from Sargassum macrocarpum (Japan). 350,351 Hydroperoxides have rarely been found in algae: two examples, dictyohydroperoxide, 308 and hydroperoxyacetoxycrenulide 309, were isolated from Dictyota dichotoma (Troitsa Bay, Sea of Japan, Russia) along with 15 other known diterpenoid and steroidal secondary metabolites. 348 Two brominated selinane sesquiterpenoids 304 and 305 and five known sesquiterpenes were isolated from Dictyopteris divaricata (Yantan, Shandong Province, China).…”

A New Epoxy-cadinane Sesquiterpene from the Marine Brown Alga Dictyopteris divaricata

“…Marine brown algae of the genus Dictyopteris (Dictyotales, Dictyotaceae) have been found to be a rich source of structurally unique sesquiterpenes, including cadinane, selinane, germacrane, and other rearranged skeleton types [ 1 – 9 ]. Continuing chemical investigation of the secondary metabolites of D. divaricata collected off the coast of Yantai has led to the isolation of one new cadinane sesquiterpene, 4 β ,5 β -epoxycadinan-1 β -ol ( 1 ), and six known cadinane sesquiterpenes: cadinan-1,4,5-triol ( 2 ) [ 5 ], 4 α ,5 β -dihydroxycubenol ( 3 ) [ 6 ], cubenol ( 4 ) [ 6 ], cadinan-3-ene-1,5-diol ( 5 ) [ 5 ], cubenol-3-one ( 6 ) [ 6 ], and torreyol ( 7 ) [ 6 ].…”

Marine natural products: chemical and biological potential of seaweeds and their endophytic fungi

“…New diterpenes featuring the 2,6-cyclo-xenicane skeleton (31) were isolated from Dilophus fasciola (Roth) J. V. Lamouroux and Dilophus spiralis (Montagne) G. Hamel (Ioannou et al, 2009). New brominated selinane (32) and cadinane (33) sesquiterpenes were reported from the genus Dictyopteris Lamouroux Qiao et al, 2009;Wen et al, 2009). The cytotoxic activity of new bisprenylated quinols (34), accumulated in Sporochnus comosus C Agradh, were reported by Oveden et al (2011).…”