Chemical investigation of the secondary metabolites extracted from the marine red alga Laurencia okamurai has resulted in the isolation of one new (lauramurin, 1) and six known (2–7) sesquiterpenes. On the basis of the data obtained by our detailed spectroscopic analysis as well as by comparison with those reported, the structures of these compounds were elucidated as four laurane sesquiterpenes including lauramurin (1), laur-11-en-10-ol (2), aplysinol (3), and debromoaplysinol (4), two cyclolaurane sesquiterpenes laurequinone (5) and laurentristich-4-ol (6), and one cuparane ether sesquiterpene (7). The antibacterial activity against Staphylococcus aureus and brine shrimp (Artemia salina) lethality for the isolated compounds were evaluated. Compounds 2 and 5–7 displayed moderate lethality against brine shrimp.
(a) WangB.G., GloerJ.B., JiN.Y., ZhaoJ.C. (2013) Halogenated organic molecules of Rhodomelaceae origin: Chemistry and biology. Chemical Reviews, 113, 3632–3685; (b) Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR. (2005) Marine Natural Products. Natural Product Reports, 22, 15–61; (c) Erickson KL. (1983) Constituents of Laurencia. In Marine Natural Products, Chemical and Biological Perspectives. Scheuer PJ (Ed). Academic Press, New York, Vol. 5, Chapter 4, 131–257.
2.
(a) MasudaM., AbeT., SuzukiT., SuzukiM. (1996) Morphological and chemotaxonomic studies on Laurencia composite and L. okamurae (Ceramiales, Rhodaphyta). Phycologia, 35, 550–562; (b) Liang Y, Li XM, Cui CM, Li CS, Sun H, Wang BG. (2012) Sesquiterpene and acetogenin derivatives from the marine red alga Laurencia okamurai. Marine Drugs, 10, 2817–2825; (c) Liang Y, Li XM, Cui CM, Li CS, Wang BG. (2009) A new rearranged chamigrane sesquiterpene from Laurencia okamurai. Chinese Chemical Letters, 20, 190–192; (d) Ji NY, Li XM, Wang BG. (2010) Sesquiterpenes and other metabolites from the marine red alga Laurencia composita (Rhodomelaceae). Helvetica Chimica Acta, 93, 2281–2286; (e) Ji NY, Li XM, Xie H, Ding J, Li K, Ding LP, Wang BG. (2008) Highly oxygenated triterpenoids from the marine red alga Laurencia mariannensis (Rhodomelaceae). Helvetica Chimica Acta, 91, 1940–1946.
3.
LiX.D., MiaoF.P., LiK., JiN.Y. (2012) Sesquiterpenes and acetogenins from the marine red alga Laurencia okamurai. Fitoterapia, 83, 518–522.
4.
(a) MaoS.C., GuoY.W. (2005) Cuparene-derived sesquiterpenes from the Chinese red alga Laurencia okamurai Yamada. Helvetica Chimica Acta, 88, 1034–1039; (b) Sun J, Shi D, Ma M, Li S, Wang S, Han L, Yang Y, Fan X, Shi J, He L. (2005) Sesquiterpenes from the red alga Laurencia tristicha. Journal of Natural Products, 68, 915–919; (c) Ji NY, Li XM, Li K, Ding LP, Wang BG. (2008) Laurane-derived sesquiterpenes from the marine red alga Laurencia tristicha (Rhodomelaceae). Natural Product Research, 22, 715–718; (d) Shizuri Y, Yamada A, Yamada K. (1984) Laurequinone, a cyclolaurane sesquiterpene from the red alga Laurencia nidifica. Phytochemistry, 23, 2672–2673.
5.
ChenP., WangJ., LiuK., LiC. (2008) Synthesis and structure revision of (±)-Laurentristich-4-ol. Journal of Organic Chemistry, 73, 339–341.
6.
(a) SuzukiM., KurosawaE. (1979) Halogenated and non-halogenated aromatic sesquiterpenes from the red alga Laurencia okamurai Yamada. Bulletin of the Chemical Society of Japan, 52, 3352–3354; (b) Meyer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nichols DE, McLaughlin JL. (1982) Brine shrimp: a convenient general bioassay for active plant constituents. Planta Medica, 45, 31–34.