Laurencia sesquiterpenes

Scheme 1.7 Development of a Prins-pinacol rearrangement strategy for Laurencia sesquiterpenes (50-52).

Ayyad, S. E. N., Jakupovic, J. and Abdel-Mogib, M. 1994. A sesquiterpene ether from Laurencia obtusa. Phytochemistry 36 1077-1078. 

Suzuki, M. and Kurosawa, E. 1978. Two new halogenated sesquiterpenes from the red alga Laurencia majuscula. Tetrahedron Lett. 4805-4808. 

Sims JJ, Lin GHY, Wing RM (1974) Marine natural products. X. Elatol, a halogenated sesquiterpene alcohol from the red alga Laurencia elata. Tetrahedron Lett 39 3487-3490 Singh S, Kate BN, Banerjee UC (2005) Bioactive compounds from cyanobacteria and microalgae an overview. Crit Rev Biotechnol 25 73-95... 

Coll, J. Skelton, B.W. White, A.H. Wright, A.D. (1989) The structure detamination of two novel sesquiterpenes from the red alga Laurencia tenera. Aust. J. Chan., 42, 1695-703. 

Guella, G. Oztun, A. Mancini, I. Pietra, F. (1997A) Stereochemical features of sesquiterpene metabolites as a distinctive trait of red seaweeds in the genus Laurencia. Tetrahedron Lett., 38, 8261-4 Francisco M.E.Y. Turnbull, M.M. Erickson, K.L. Cartilagineoi, the fourth lineage of Laurencia-dsr neA polyhalogenated chamigrene. Ibid., 39, 5289-92. 

An array of new and unusual halogenated terpenes have been isolated and characterized from Laurencia red algae [14], This genus is well known as a source of halogenated sesquiterpenes. New chamigrane-type derivatives were isolated from Laurencia species, some from Laurencia... 

The diversity of ring systems found in Laurencia is shown in Scheme 3.2 (553), although the present organization of marine sesquiterpenes does not follow these categories, but rather continues the previous one (1). 

The new red algal species Laurencia mariannensis from the Great Barrier Reef provides the novel sesquiterpene 297, along with the known pacifenol and deoxy-prepacifenol, which are now fully characterized by NMR for the first time (539). The Philippine Laurencia majuscula has furnished 13 novel halogenated sesquiterpenes 298-310, of which the major components are the majapolenes A (298, 299) (two diastereomers), which are also found in Laurencia caraibica (540). Most of these compounds occur as inseparable diastereomers. A collection of Laurencia majuscula from the South China Sea has yielded the cedrene-type sesquiterpene majusin (311) (541). A new sesquiterpene dichloroimine, stylotellane A (312), was isolated from the sponge Stylotella aurantium (Fig. 3.3) (542). 

An Okinawan collection of Laurencia luzonensis has yielded five new sesquiterpenes, luzonenone (339), luzofuran (340), 3,4-epoxypalisadin B (341), 1,2-dehydro-3,4-epoxypalisadin B (342), and 15-hydroxypalisadin A (343 (558). In addition, the relative stereochemistry of luzonensol (321) (vide supra) (549) was assigned by conversion to the known palisadin B (P) (7). The novel fused bisabo-lene aldingenins A (344), B (345), C (346), and D (347) were isolated from Laurencia aldingensis (559, 560). The interesting chlorotriol 348 was found in a Turkish Laurencia obtusa (561). 

Some 50 marine aromatic halogenated sesquiterpenes were documented in the first survey (1). In the interim a number of new examples have been reported, mainly from Laurencia red algae. 

Erickson KL, Beutler JA, Gray GN, Cardellina II JH, Boyd MR (1995) Majapolene A, a Cytotoxic Peroxide, and Related Sesquiterpenes from the Red Alga Laurencia majuscula. J Nat Prod 58 1848... 

Xu X-H, Zeng L-M, Su J-Y (1997) Tricyclic Sesquiterpene from Laurencia majuscula. Chem Res Chin Univer 13 176... 

Topcu G, Aydogmus Z, Imre S, Goren AC, Pezzuto JM, Clement JA, Kingston DGI (2003) Brominated Sesquiterpenes from the Red Alga Laurencia obtusa. J Nat Prod 66 1505... 

Brito I, Cueto M, Dorta E, Darias J (2002) Bromocyclococanol, a Halogenated Sesquiterpene with a Novel Carbon Skeleton from the Red Alga Laurencia obtusa. Tetrahedron Lett 43 2551... 

Guella G, Skropeta D, Breuils S, Mancini I, Pietra F (2001) Calenzanol, the First Member of a New Class of Sesquiterpene with a Novel Skeleton Isolated from the Red Seaweed Laurencia microcladia from the Bay of Calenzana, Elba Island. Tetrahedron Lett 42 723... 

Guella G, Oztunc A, Mancini I, Pietra F (1997) Stereochemical Features of Sesquiterpene Metabolites as a Distinctive Trait of Red Seaweeds in the Genus Laurencia. Tetrahedron Lett 38 8261... 

Rovirosa J, Soto H, Cueto M, Darias J, Herrera J, San-Martm A (1999) Sesquiterpenes from Laurencia claviformis. Phytochemistry 50 745... 

Davyt D, Fernandez R, Suescun L, Mombru AW, Saldana J, Dominguez L, Coll J, Fujii MT, Manta E (2001) New Sesquiterpene Derivatives from the Red Alga Laurencia scoparia. Isolation, Structure Determination, and Anthelmintic Activity. J Nat Prod 64 1552... 

Brito I, Cueto M, Diaz-Marrero AR, Darias J, San Martin A (2002) Oxachamigrenes, New Halogenated Sesquiterpenes from Laurencia obtusa. J Nat Prod 65 946... 

Iliopoulou D, Roussis V, Pannecouque C, De Clercq E, Vagias C (2002) Halogenated Sesquiterpenes from the Red Alga Laurencia obtusa. Tetrahedron 58 6749... 

Kladi M, Xenaki H, Vagias C, Papazafiri P, Roussis V (2006) New Cytotoxic Sesquiterpenes from the Red Alga Laurencia obtusa and Laurencia microcladia. Tetrahedron 62 182... 

Sun J, HanLJ, Shi DY, FanX, WangSJ, Li S, Yang YC, Shi JG (2005) Sesquiterpenes from Red Alga Laurencia fristicha. Chin Chem Lett 16 1611... 

Kladi M, Vagias C, Fumari G, Moreau D, Roussakis C, Rousis V (2005) Cytotoxic Cuparene Sesquiterpenes from Laurencia microcladia. Tetrahedron Lett 46 5723... 

Mao S-C, Guo Y-W (2005) Cuparene-Derived Sesquiterpenes from the Chinese Red Alga Laurencia okamurai Yamada. Helv Chim Acta 88 1034... 

Ji N-Y, Li X-M, Ding L-P, Wang B-G (2007) Aristolane Sesquiterpenes and Highly Brominated Indoles from the Marine Red Alga Laurencia similis (Rhodomelaceae). Helv Chim Acta 90 385... 

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