Cytotoxic Xanthones and Biphenyls from the Root of Garcinia linii

Abstract

Three new xanthones, linixanthones A - C, two new biphenyls, garcibiphenyls A and B, and a new benzopyran, garcibenzopyran, together with twelve known xanthones and a known biphenyl have been isolated from the root of Garcinia linii. The structures of these new compounds were determined through spectral analyses. Among the isolates, five compounds exhibited cytotoxicities (ED₅₀ values < 4 μg/mL) against P-388 and HT-29 cell lines in vitro.

Garcinia linii - Guttiferae - root - linixanthones A - C - garcibiphenyls A - B - garcibenzopyran - cytotoxicity

• 1 Robson N KB. Guttiferae in Flora of Taiwan. 2nd edition. Editorial Committee of the Flora of Taiwan Taipei, Taiwan; 1996 Vol. 2: 694-714
• 2 Asano J, Chiba K, Tada M, Yoshii T. Cytotoxic xanthones from Garcinia hanburyi .  Phytochemistry. 1996;  41 815-20
• 3 Xu Y J, Yip S C, Kosela S, Fitri E, Hana M, Goh S H, Sim K Y. Novel cytotoxic, polyprenylated heptacyclic xanthonoids from Indonesian Garcinia gaudichaudii (Guttiferae).  Org Lett. 2000;  2 3945-8
• 4 Xu Y J, Chiang P Y, Lai Y H, Vittal J J, Wu X H, Tan B KH, Imiyabir Z, Goh S H. Cytotoxic prenylated depsidones from Garcinia parvifolia .  J Nat Prod. 2000;  63 1361-3
• 5 Ito C, Itoigawa M, Miyamoto Y, Onoda S, Rao K S, Mukainaka T, Tokuda H, Nishino H, Furukawa H. Polyprenylated benzophenones from Garcinia assigu and their potential cancer chemopreventive activities.  J Nat Prod. 2003;  66 206-9
• 6 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
• 7 Chen J J, Duh C Y, Huang H Y, Chen I S. Furoquinoline alkaloids and cytotoxic constituents from the leaves of Melicope semecarpifolia .  Planta Medica. 2003;  69 542-6
• 8 Gunasekera S P, Selliah S, Sultanbawa M US. Chemical investigation of Ceylonese plants. Part XV. Extractives of Kayea stylosa Thw. (Guttiferae).  J Chem Soc Perkin Trans. 1975;  I 1539-44
• 9 Monache G D, Monache F D, Bettolo G BM, Lima R A. Chemical investigation of the genus Rheedia. II. Prenylated xanthones from Rheedia gardneriana .  J Nat Prod. 1983;  46 655-9
• 10 Nkengfack A E, Mkounga P, Meyer M, Fomum Z T, Bodo B. Globulixanthones C, D and E: three prenylated xanthones with antimicrobial properties from the root bark of Symphonia globulifera .  Phytochemistry. 2002;  61 181-7
• 11 Dall′Acqua S, Innocenti G, Viola G, Piovan A, Caniato R, Cappelletti E M. Cytotoxic compounds from Polygala vulgaris .  Chem Pharm Bull. 2002;  50 1499-1501
• 12 Cardona M L, Fernández I F, Pedro J R, Seoane E, Vidal R. Additional new xanthones and xanthonolignoids from Hypericum canariensis .  J Nat Prod. 1986;  49 95-100
• 13 Rocha L, Marston A, Kaplan M AC, Stoeckli-Evans H, Thull U, Testa B, Hostettmann K. An antifungal γ-pyrone and xanthones with monoamine oxidase inhibitory activity from Hypericum brasiliense .  Phytochemistry. 1994;  36 1381-5
• 14 Iinuma M, Tosa H, Tanaka T, Asai F, Shimano R. Three xanthones from root bark of Garcinia subelliptica .  Phytochemistry. 1995;  38 247-9
• 15 Wolfender J L, Hamburger M, Msonthi J D, Hostettmann K. Xanthones from Chironia krebsii .  Phytochemistry. 1991;  30 3625-9
• 16 Ikeya Y, Sugama K, Okada M, Mitsuhashi H. Two xanthones from Polygala tenuifolia .  Phytochemistry. 1991;  30 2061-5
• 17 Zhang Z, ElSohly H N, Jacob M R, Pasco D S, Walker L A, Clark A M. Natural products inhibiting Candida albicans secreted aspartic proteases from Tovomita krukovii .  Planta Medica. 2002;  68 49-54
• 18 Tosa H, Iinuma M, Murakami K I, Ito T, Tanaka T, Chelladurai V, Riswan S. Three xanthones from Poeciloneuron pauciflorum and Mammea acuminata .  Phytochemistry. 1997;  45 133-6
• 19 Gunatilaka A AL, Jasmin de Silva A MY, Sotheeswaran S. Minor xanthones of Hypericum mysorense .  Phytochemistry. 1982;  21 1751-3
• 20 Borejsza-Wysocki W, Lester C, Attygalle A B, Hrazdina G. Elicited cell suspension cultures of apple (Malus × domestica) cv. Liberty produce biphenyl phytoalexins.  Phytochemistry. 1999;  50 231-5