Laurencia diterpenes

Rochfort SJ, Capon RJ (1996) Parguerenes Revisited New Brominated Diterpenes from the Southern Australian Marine Red Alga Laurencia filiformis. Aust J Chem 49 19... 

Kuniyoshi M, Marma MS, Higa T, Bemardinelli G, Jefford CW (2000) 3-Bromobarek-oxide, an Unusual Diterpene from Laurencia luzonensis. Chem Commun 1155... 

Iliopoulou D, Mihopoulos N, Roussis V, Vaglas C (2003) New Brominated Labdane Diterpenes from the Red Alga Laurencia obtusa. J Nat Prod 66 1225... 

Mihopoulos N, Vagias C, Mikros E, Scoullos M, Roussis V (2001) Prevezols A and B New Brominated Diterpenes from the Red Alga Laurencia obtusa. Tetrahedron Lett 42 3749... 

Two labdane-type brominated diterpenes (1 and 2) containing unprecedented seven- and eight-membered ether rings were isolated from the red alga Laurencia ohtusa, collected in Mitikas Bay, Greece. 

Sims, J.J., Lin, G.H.Y., Wing, R.M. and Fenical, W., 1973. Marine natural products. Concinndiol, a bromo-diterpene alcohol from the red alga Laurencia concinna. J. Chem. Soc., Chem. Common., 1973 470—471. 

Bioactive sesquiterpenes isolated from red algae species Laurencin rigida Laurencia luzonesis )delded deschloroelatol, elatol, luzonenone, luzofuran, 3,4-epoxypalisadin, l,2-dehydro-3,4-epoxypalisadin B, and 15-hydroxy-palisadin and a new diterpene former has shown antibacterial action on Bacillus megaterium and also possess antifungal action (Konig et al, 2000 Kuniyoshi et al., 2005). 

Cuparene (Enzell and Erdtman, 1958) has been found in fossil resins and today is among the hydrocarbons (terpene, sesquiterpene, diterpenes, etc.) present in cedarwood oil (from, e.g.. Juniperes virginiana L.). Interestingly, halogenated relatives are also found in red algae (Laurencia spp.). A few biosynthetic studies have been undertaken, and it is clear that a pattern of cyclization processes, such as that shown in Scheme 11.60, obtains. 

Mohammed, K.A. et al. (2004) Laurenditerpenol, a new diterpene from the tropical marine alga Laurencia intricata that potently inhibits HIF-1 mediated hypoxic signaling in breast tumor cells. J. Nat. Prod. 67, 2002-2007... 

These iodine-containing diterpenes are not, however, explicitly produced by a Laurencia because the authors say they were isolated from a combination of a cyanobacterium and an rmdetermined red alga. The similarity of the carbon skeleton with those of tasihahdes A and B, nevertheless su ests that the red alga could be a Giga-rtinale or a Ceramiale (Wesley et al., 2003). 

Nearly as widespread as the diterpenes of the parguer-ane series, the derivatives of irieane are also isolated from species of Laurencia and Aplysia. Discovered in 1975 in an undetermined species of Laurencia from the Gulf of California (Mexico), irieol A and iriediol are the first terms of this series, which cxurently numbers about 20. 

Many representatives of these skeletons have been isolated from terrestrial plants, and the only major difference from their marine analogs lies in the stereochemistry of the junction of cycles, which is generally ent for the diterpenes extracted from Laurencia or Aplysia. 

Two related brominated diterpenes belonging to dac-tylomelane (diprenylpyronane) series, luzodiol and laurendecumtriol, have been identified in Laurencia luzonensis (Okinawa, Japan) and I. decumbens (South China Sea), respectively. Both are brominated on C-10, as displayed in Figure 13.15. Luzodiol is accompanied by a dozen brominated sesquiterpenes all with the carbon skeleton of snyderane (Kuniyoshi et al., 2005). 

Caccamese, S., Toscano, R.M., Cerrini, S., and Gavuzzo, E. (1982) Laurendanol, a new halogenated diterpene from the marine alga Laurencia obtusa. Tetrahedron Lett., 23, 3415-3418. 

Iliopoulou, D., Mihopoulos, N., Roussis, V., and Vagias, C. (2003a) New brominated labdane diterpenes from the red alga Laurencia obtusa. J. Nat. Prod., 66,1225-1228. 

Mihopoulos, N Vagias, C Mikros, E Scouflos, M., and Roussis, V. (2001) Prevezols A and B new brominated diterpenes from the red alga Laurencia obtusa. Tetrahedron Lett., 42, 3749-3752. 

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

Suzuki, T., Takeda, S., Hayama, N., Tanaka, I., and Komiyama, K. (1989b) The structure of brominated diterpene from the marine red alga Laurencia obtusa (Hudson) Lamouroux. Chem, Lett, 18,969-970. 

Vairappan, C.S., Ishii, T, Lee, T.K., Suzuki, M., and Zhaoqi, Z. (2010) Antibacterial activities of a new brominated diterpene from Bomeon Laurencia spp.. Marine Drugs. 8,1743-1749. 

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