Brominated 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... 

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... 

These terpenes are involved in chemical defense. Red algae contain brominated diterpenes of several established skeletal types. 

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. 

Schmitz, F.J., D.P. Michaud, and P.G. Schmidt Marine Natural Products Par-guerol, Deoxyparguerol, and Isoparguerol. New Brominated Diterpenes with Modified Pimarane Skeletons from the Sea Hare Aplysia dactylomela. J. Am. Chem. Soc. 104, 6415 (1982). Erratum J. Am. Chem. Soc. 106, 3385 (1984). 

For general biogenetic pathways to all series of brominated diterpenes from Sphaerococcus coronopifolius, see Smyrniotopoulos, Vagias, and Roussis, 2009 Smyrniotopoulos et al, 2010a, 2010b. 

Interestingly, viridiols A and B are probably the only two non-brominated diterpenes isolated from a species... 

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). 

Awad, N. (2004) Bioactive brominated diterpenes from the marine red alga Jania rubens (L). Phytother. Res., 18,275-279. 

Iliopoulou, D., Mihopoulos, N., Vagias, C., Papazafiri, P., and Roussis, V. (2003b) Novel cytotoxic brominated diterpenes from the red alga Laurencia obtusa. J. Org. Chem., 68, 7667—7674. 

Ojika, M., Yoshida, Y, Okumura, M., leda, S., and Yamada, K. (1990) Aplysiadiol, a new brominated diterpene from the marine mollusc Aplysia kurodai. J. Nat. Prod., 53, 1619-1622. 

Rochfort, S.J. and Capon, R.J. (1996) Parguerenes revisited new brominated diterpenes from the Southern Australian marine red alga Laurenciafiliformis. Aust.j. Chem., 49, 19—26. 

Schmitz, F.J., Michaud, D.P., and Schmidt, P.G. (1982) Marine natural products parguerol, deoxy-parguerol and isoparguerol. New brominated diterpenes with modified pimarane skeletons from the sea hare Aplyda dactylomda. J. Am. Chem. Soc., 104, 6415-6423. 

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. 

The food chain between the Japanese species Aplysia kurodai and Laurencia concinna (Ceramiales) and Laurencia perforata yielded three closely related brominated diter-penes aplysin-20 was found only in the sea hare (Matsuda et al, 1967) isoaplysin-20 was identified in the mollusk and in Laurencia perforata and concinndiol was isolated only from Laurencia concinna. These three structures and their biosynthetic patterns are presented in Chapter 13. More recently, the food chain between the species Aplysia parvula and the red alga Laurencia filiformis, harvested in Tasmania, has led to similar comments (Jongaramruong et al, 2002). Other examples of brominated diterpenes found in Aplysia and Laurencia are presented in Chapter 13 (see also Komprobst and Al Easa, 2003). 

A brominated diterpene, concinndiol, an isomer of aplysin-20, has been recently described from the alga Laurencia concinna (171). Some simple bromophenols also occur in algae (160, p. 88) and a highly brominated phenolic pyrrole has been found in a marine bacterium (111, 132). 

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