A Bornean red algal population of Laurencia simlis Nam et Saito was analyzed for its secondary metabolite composition. Seven compounds were identified: ent -1(10)-aristolen-9β-ol (1), (+)-aristolone (2), axinysone B (3), 9-aristolen-1α-ol (4), 2,3,5,6-tetrabromoindole (5), 1-methyl-2,3,5,6-tetrabromoindole (6), and 1-methyl-2,3,5-tribromoindole (7). Compound 1 was identified as a new optical isomer of 1(10)-aristolen-9β-ol. Compounds 1, 4 and 5 exhibited good antibacterial activity against antibiotic resistant clinical bacteria and cytotoxic effects against selected cancer cell lines.
(a) AbeT., MasudaM., SuzukiT., SuzukiM. (1999) Chemical races in the red alga Laurencia nipponica (Rhomomelaceae, Ceramiales). Phycological Research, 47, 87–95; (b) Walied MA, Al-Lihaibi SS, Abdel-Lateff A, Ayyad SEN. (2010) New antifungal cholestane and aldehyde derivatives from red alga Laurencia papillosa. Natural Products Communications, 6, 1821-1824; (c) Howard BM, Nonomura AM, Fenical W. (1980) Chemotaxonomy in marine algae: secondary metabolites synthesis by Laurencia in unialgal culture. Biochemical Systematics and Ecology, 8, 329-336; (d) Masuda M, Abe T, Suzuki T, Suzuki M. (1996) Morphological and chemotaxanomic studies on Laurencia composita and Laurencia okamurae (Ceramiales, Rhodophyta). Phycologia, 35, 550-562; (e) Suzuki M, Vairappan CS. (2005) Halogenated secondary metabolites from Japanese species of the red algal genus Laurencia (Rhodomelaceae, Ceramiales). Current Topics in Phytochemistry, 5, 1-38; (f) Bruno LA, Beatriz GF, Fujii MT, Teixeira LV. (2008) Sesquiterpenes of the Brazilian marine alga Laurencia filiformis (Rhodophyta, Ceramiales). Natural Product Communications, 3, 1753-1654; (g) Dias DA, White JM, Urban S. (2009) Laurencia filiformis: Phytochemical profiling by conventional and HPLC-NMR approaches. Natural Product Communications, 4, 157-172.
2.
(a) JiN.Y., LiX.M., DingL.P., WangB.G. (2007) Aristolane sesquiterpenes and highly brominated indoles from the marine red algae Laurencia similis (Rhodomelaceae). Helvetica Chimica Acta, 90, 385–391; (b) Nam KW, Saito Y. (1991) Laurencia similis (Ceramiales, Rhodophyta), a new species from Queensland, Australia. British Phycological Journal, 26, 375-382; (c) Masuda M, Kawaguchi S, Takahashi Y, Okamoto K, Suzuki M. (1999) Halogenated secondary metabolites of Laurencia similis (Rhodomelaceae, Rhodophyta). Botanica Marina, 42, 199-202.
3.
(a) SuH., YuanZ.H., LiJ., GuoS.J., DengL.P., HanL.J., ZhuX.B., ShiD.Y. (2009) Two new bromoindoles from red alga Laurencia similis.Chinese Chemical Letters, 20, 456–458; (b) Gin J, Su H, Zhang Y, Gao J, Zhu L, Wu X, Pan H, Li X. (2010) Highly brominated metabolites from marine alga Laurencia similis inhibit protein tyrosine phosphatase 1B. Bioorganic & Medicinal Chemistry Letters, 20, 7152-7154.
4.
VairappanC.S., AngM.Y., OngC.Y., PhangS.M. (2004) Biologically active polybrominated indoles in the red alga Laurencia similis from the coastal waters of Sabah (Rhodomelaceae, Ceramiales). Malaysian Journal of Science, 23, 119–126.
5.
(a) ShideL., OlbrichA., MayerR., RuckerG. (1987) Gansongon, a new aristolane ketone from Nardostachys chinesis and structure revision of an aristolenol. Planta Medica, 53, 556–558; (b) Harrigan GG, Ahmad A, Baj N, Glass TE, Gunatilaka AAL, Kingston DGI. (1993) Bioactive and other sesquiterpenoids from Porella cordeana. Journal of Natural Products, 56, 921-925; (c) Furusawa M, Hashimoto T, Noma Y, Asakawa Y. (2006) Biotransformation of aristolane and 2,3-secoaromadendrane type sesquiterpenoids having a 1,1-dimethylcyclopropane ring by Chlorella fusca var vacuolata, Mucor species, and Aspergillus niger. Chemical & Pharmaceutical Bulletin, 54, 861-868.
6.
(a) VairappanC.S. (2003) Potent antibacterial activity of halogenated metabolites from Malaysian red algae, Laurencia majuscula (Rhodomelaceae, Ceramiales). Biomolecular Engineering, 20, 255–259; (b) Vairappan CS, Suzuki M, Okino T, Ishii T, Abe T, Masuda M. (2008) Antibacterial secondary metabolites from Malaysian Laurencia sp. Phytochemistry, 69, 2490-2494.
7.
SandhyaT., MishraK.P. (2006) Cytotoxic response of breast cancer cell lines, MCF 7 and T47D to triphala and its modification by antioxidants. Cancer Letters, 238, 304–313.
8.
VairappanC.S., KawamotoT., MiwaH., SuzukiM. (2004) Potent antibacterial activity of halogenated compounds against antibiotic resistant bacteria. Planta Medica, 70, 1087–1090.
