Biscembranes from the Soft Coral Sarcophyton glaucum

Abstract

Four novel biscembranes have been isolated from the soft coral Sarcophyton glaucum, collected at Amami Oshima, two of which showed weak activity against proliferation of human promyelocytic leukemia cells (HL-60). Their absolute structures were determined on the basis of the CD spectra.

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

“…The chemical shift of δ C 24.9 (compared with δ C 18.6 in 14 ) indicated the Z geometry at the carbon-carbon double bond between C-4 and C-5 in the biscembranoid 15 . This was also in accordance with the reported value by Iwagawa et al [18] for bisglaucumlide C ( 25 ). The stereochemistry of the biscembranoid 15 in the eastern part of the molecule is suggested to be the same as that found in compound 14 due to the similar ROE experimental results.…”

“…Besides methyl sarcoate, only methyl tetrahydrosarcoate and isosarcophytonolide D are reported to act as dienophile (western part) in over 60 described biscembranoids [49]. The western parts in the bisglaucumlides [18,41] and isobisglaucumlides isolated in this study ( 14 and 15 ) correspond with the structure of methyl sarcoate. To our best knowledge, there are no literature reports on biscembranoids having 6,13-bisdesoxomethyl sarcoate ( 5 ) or pavidolide A as building blocks.…”

“…Compounds 1 and 5 are new chemical structures. The same applies to the biscembranoids 14 and 15 , which however show close resemblance to bisglaucumlides B and C [18], but differ in their stereochemistry from the latter. Since no studies regarding the stereochemical features of the cembranoid bisepoxide 12 were published to date, we propose here its relative configuration.…”

Lobophytones H-N, Biscembranoids from the Chinese Soft Coral Lobophytum pauciflorum

“…The plausible biogenetic pathway of biscembrane analogues was assumed to be derived by a Diels-Alder cycloaddition of two "mono" cembranoids, representing cembranoid-diene and cembranoid-dienophile. [1][2][3][4][5][6][7][8] This depiction was late on supported by the natural occurring monomeric cembranoids, such as dienophiles methyl sarcoate 3) and methyl tetrahydrosarcoate 7) (methyl tortuosoate), 6) which were regarded to be the precursors to form left part of biscembranoids. Biscembranoids were mainly obtained from the coral genus of Sarcophyton (S. tortuosum, S. glaucum, S. latum, and S. elegans), with the exception of isobiscembranoids 9) recently to be isolated from a soft coral Lobophytum pauciflorum which was previously reported to contain steroids 10,11) and diterpenoids.…”

Isolation et caractérisation de composés bioactifs de la résine de sapin baumier (Abies balsamea (L.) Mill) /

“…Il est intéressant de souligner que ce type de composé a été identifié seulement dans une autre espèce végétale que le genre Abies, soit l'espèce de palétuvier asiatique Ceriops tagal qui contient les tagalsines I et J (Zhang, Lu et al 2005). Quelques autres tétraterpènes non caroténoïdiques ont été isolés de différents animaux marins, principalement de Sarcophyton spp., un genre de corail mou (Kusumi et al 1990;Feller et al 2004;Iwagawa et al 2006;Bishara et al 2007;Lan et al 2009). …”