A New Natural Butenolide, (5R)-3-Tetradecyl-5-methyl-2(5H)-furanone, from Octocoral Cladiella conifera

Abstract

A chemical examination of Cladiella conifera, octocoral collected in the waters of Taiwan, resulted in isolation of a new natural butenolide, (5R)-3tetradecyl-5-methyl-2(5H)-furanone (1). The structure, including the absolute

Marine natural products

“…The structure of butanolide 1183 from Cladiella conifera has been previously reported as a synthetic compound. 482 It exhibited weak ability to inhibit the release of COX-2 from stimulated macrophage cells. A deep-sea collection of the soft coral Duva florida afforded the meroterpene tuaimenal A 1184 .…”

Cladiella Octocorals: Enormous Sources of Secondary Metabolites with Diverse Structural and Biological Properties

“…The first chemical investigation of the octocoral C. conifera collected in the waters of Taiwan yielded a new butanolide, (5 R )‐3‐tetradecyl‐5‐methyl‐2(5 H )‐furanone ( 93 ) [40] . The absolute configuration of 93 was established as R using the CD rule developed by Gawronski et al .…”

“…The first chemical investigation of the octocoral C. conifera collected in the waters of Taiwan yielded a new butanolide, (5R)-3-tetradecyl-5-methyl-2(5H)-furanone (93). [40] The absolute configuration of 93 was established as R using the CD rule developed by Gawronski et al The anti-inflammatory activity bioassay indicated that compound 93 suppressed the release of COX-2 to 84.5 � 2.8 %, compared to the cells stimulated with LPS only at a concentration of 10 μM. The continuing study of this Formosan specimen yielded four new eunicellin-based diterpenoids, namely, coniferains AÀ D (94 -97).…”

“…Sheu et al's continuous study on this soft coral displayed a library of unreported eunicellin-based diterpenes, krempfielins EÀ R (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33), along with a group of known metabolites including 6-methyl ether of litophynol B (34), sclerophytins A (35), B (36) and F (37), litophynin I monoacetate (38), 6-acetoxylitophynin E (39), (1R*,2R*,3R*,6S*,9R*,10R*,14R*)-3-acetoxycladiell-7(16),11( 17)-dien-6-ol (40), litophynin F (41) and cladieunicellin K (42). [24 -27] Compared to the corresponding already known related analogs, the new compounds 20-33 were structurally characterized by either different patterns of oxidation or chain lengths of substitutions.…”