Laurencia venusta

Sakemi, S. Higa, T. Jeffwd, C.W. Banardinelli, G. (1986) Venustatriol. A new, anti-viral, triterpene tetracyclic etha- from Laurencia venusta. Tetrahedrrai Lett., 27,4287-90. 

In 1986, venustatriol (2) was isolated from the red algae Laurencia venusta [5]. This compound was shown to possess many of the same structural features as thyrsiferol (1), with the exception of the stereocenters at Cig and C19 as indicated in Fig. (1). At the time of its isolation, venustatriol (2) was reported to display anti-viral activity against vesicular stomatitis virus (VSV) and herpes simplex virus type 1 (HSV-1). The absolute configuration of venustatriol (2) was verified by x-ray crystallography, an experiment that facilitated the assignment of the absolute stereochemistry of thyrsiferol (1). 

Sakemi, S. Higa, T. Jefford, C.W. Bernardinelli, G. Venustatriol A New Antiviral Triterpene Tetracyclic Ether from Laurencia venusta. Tetrahedron Lett. 1986,27, 4287- 4290. 

Several metabolites isolated from the red alga Laurencia venusta Yamada, which contain a pentenyne side chain, have been isolated <83CL779>. The structure of (3Z)-epoxyvenustin (19), m.p. 72-73 °C, [ ]d — 44.1° (c 1.00, chloroform) has been determined by x-ray diffraction methods. 

Venustatriol, isolated from the Japanese species Laurencia venusta, is a diastereoisomer of thyrsiferol in Cis/Cig. the study of which has allowed the determination of the absolute configuration of (+)-thyrsiferol (Blunt et al., 1978 Sakemi et al., 1986). 

Suzuki, M Kurosawa, E., Furuzaki, A., and Matsumoto, T. (1983) Constituents of marine plants. 55. The stmcture of (32)-epoxyvenustin, (32)-venustrn, and (3Z)-venustinene, new halogenated Ci5-nonterpenoids from the red alga Laurencia venusta Yamada. Chem. Lett., 12,779-782. 

Suzuki, M., Kurosawa, E., and Ktuata, K. (1988) Venustanol, a brominated labdane diterpene from the red alga Laurencia venusta. Phytochemistry, 27,1209-1210. 

---