A new biphenyl and other constituents from the wood of Garcinia schomburgkiana

Natural Product Research

Volumn 27, Issue 21, 2013, Pages 1949-1955

  Mungmee, Chutichot ^a   Sitthigool, Supotchana ^a   Buakeaw, Anumart ^a   Suttisri, Rutt ^a  

^a CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

benzophenone; biphenyl; cytotoxicity; Garcinia schomburgkiana; schomburgbiphenyl; xanthone

Indexed keywords

1,3,5,6 TETRAHYDROXYXANTHONE; AUCUPARIN; BENZOPHENONE DERIVATIVE; BIFLAVONOID; BIPHENYL DERIVATIVE; BUCHANAXANTHONE; CYTOTOXIC AGENT; DOXORUBICIN; FUKUGISIDE; GARCIBIPHENYL C; GUTTIFERONE K; ISOJACAREUBIN; MORELLOFLAVONE; NIGROLINEABIPHENYL B; OBLONGIFOLIN C; SCHOMBURGBIPHENYL; UNCLASSIFIED DRUG; VOLKENSIFLAVONE; XANTHONE DERIVATIVE;

ARTICLE; BREAST CANCER; CELL STRAIN HEPG2; CLUSIACEAE; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; GARCINIA SCHOMBURGKIANA; HELA CELL; HUMAN; HUMAN CELL; LIVER CANCER; LUNG CANCER; PROTON NUCLEAR MAGNETIC RESONANCE; STOMACH CANCER; WOOD;

BENZOPHENONES; BIFLAVONOIDS; BIPHENYL COMPOUNDS; CELL LINE; CELL SURVIVAL; GARCINIA; HEP G2 CELLS; HUMANS; MOLECULAR STRUCTURE; PLANT EXTRACTS; STEROIDS; WOOD; XANTHONES;

EID: 84888246372     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2013.796469     Document Type: Article

References (28)

1. Cao S, Brodie PJ, Miller JS, Ratovoson F, Birkinshaw C, Randrianasolo S, Rakotobe E, Rasamison VE, Kingston DGI. 2007. Guttiferones K and L, antiproliferative compounds of Rheedia calcicola from the Madagascar rain forest. J Nat Prod. 70:686-688.
2. Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB. 1987. Evaluation of a tetrazolium-based semiautomated colorimetric assay: Assessment of chemosensitivity testing. Cancer Res. 47:936-942.
3. Chen J-J, Chen I-S, Duh C-Y. 2004. Cytotoxic xanthones and biphenyls from the root of Garcinia linii. Planta Med. 70:1195-1200.
4. Chen J-J, Peng C-F, Huang H-Y, Chen I-S. 2006. Benzopyrans, biphenyls and xanthones from the root of Garcinia linii and their activity against Mycobacterium tuberculosis. Planta Med. 72:473-477.
5. Compagnone RS, Suarez AC, Leitao SG, Monache FD. 2008. Flavonoids, benzophenones and a new euphane derivative from Clusia columnaris Engl. Braz J Pharmacognosy. 18:6-10.
6. Cui E-J, Park H-J, Wu Q, Chung I-S, Kim J-Y, Baek N-I. 2010. Sterols from the seed of cowpea (Vigna sinensis K). J Appl Biol Chem. 53:77-81.
7. Feng C, Zhou L-Y, Yu T, Xu G, Tian H-L, Xu J-J, Xu H-X, Luo KQ. 2012. A new anticancer compound, oblongifolin C, inhibits tumor growth and promotes apoptosis in HeLa cells through bax activation. Int J Cancer. 131:1445-1454.
8. Fun HK, Koysomboon S, Chantrapromma K, Chantrapromma S. 2006. A cocrystal of clusiacitran A, clusiacitran B, fluorinated clusiacitran A and fluorinated clusiacitran B (0.45:0.45:0.05:0.05). Acta Crystallogr E. E62: O3228-o3230.
9. Häfner A, Frahm AW. 1993. Biflavanoids from the heartwood of Garcinia schomburgkiana and their structural elucidation as atropisomers. Planta Med. 59:A604-A604.
10. Hamed W, Brajeul S, Mahuteau-Betzer F, Thoison O, Mons S, Delpech B, Van Hung N, Sévenet T, Marazano C. 2006. Oblongifolins A-D, polyprenylated benzoylphloroglucinol derivatives from Garcinia oblongifolia. J Nat Prod. 69:774-777.
11. Han Q-B, Tian H-L, Yang N-Y, Qiao C-F, Song J-Z, Chang DC, Luo KQ, Xu H-X. 2008. Polyprenylated xanthones from Garcinia lancilimba showing apoptotic effects against HeLa-C3 cells. Chem Biodivers. 5:2710-2717.
12. Huang S-X, Feng C, Zhou Y, Xu G, Han Q-B, Qiao C-F, Chang DC, Luo KQ, Xu H-X. 2009. Bioassay-guided isolation of xanthones and polycyclicprenylated acylphloroglucinols from Garcinia oblongifolia. J Nat Prod. 72:130-135.
13. Jackson B, Locksley HD, Moore I, Scheinmann F. 1968. Extractives from Guttiferae. IX. The isolation of buchanaxanthone and two related xanthones from Garcinia buchananii Baker. J Chem Soc C Org. :2579-2583.
14. Jiang D-J, Hu G-Y, Jiang J-L, Xiang H-L, Deng H-W, Li Y-J. 2003. Relationship between protective effect of xanthone on endothelial cells and endogenous nitric oxide synthase inhibitors. Bioorg Med Chem. 11:5171-5177.
15. Kan WLT, Yin C, Xu HX, Xu G, To KKW, Cho CH, Rudd JA, Lin G. 2013. Antitumor effects of novel compound, guttiferone K, on colon cancer by p21Waf1/Cip1-mediated G0/G1cell cycle arrest and apoptosis. Int J Cancer. 132:707-716.
16. Kokubun T, Harborne JB, Eagles J, Waterman PG. 1995. Antifungal biphenyl compounds are the phytoalexins of the sapwood of Sorbus aucuparia. Phytochemistry. 40:57-59.
17. Konoshima M, Ikeshiro Y. 1970. Fukugiside, the first biflavonoid glycoside from Garcinia spicata Hook f Tetrahedron Lett. 20:1717-1720.
18. Koysomboon S. 2006. Isolation and biological activities of the chemical constituents from Derris indica and Garcinia schomburgkiana and seasonal variation in the major metabolites of the brown alga Cystophora moniliformis. [Ph.D. dissertation]. Nakhon Si Thammarat: Walailak University.
19. Li X-C, Joshi AS, Tan B, ElSohly HN, Walker LA, Zjawiony JK, Ferreira D. 2002. Absolute configuration, conformation, and chiral properties of flavanone-(3 ! 800)-flavone biflavonoids from Rheedia acuminata. Tetrahedron. 58:8709-8717.
20. Lim TK. 2012. Edible medicinal and non-medicinal plants vol. 2: Fruits. New York: Springer.
21. Murakami A, Jiwajinda S, Koshimizu K, Ohigashi H. 1995. Screening for in vitro anti-tumor promoting activities of edible plants from Thailand. Cancer Lett. 95:139-146.
22. Rukachaisirikul V, Naklue W, Sukpondma Y, Phongpaichit S. 2005. An antibacterial biphenyl derivative from Garcinia bancana Miq. Chem Pharm Bull. 53:342-343.
23. Rukachaisirikul V, Tadpetch K, Watthanaphanit A, Saengsanae N, Phongpaichit S. 2005. Benzopyran, biphenyl, and tetraoxygenated xanthone derivatives from the twigs of Garcinia nigrolineata. J Nat Prod. 68:1218-1221.
24. Twentyman PR, Luscombe M. 1987. A study of some variables in a tetrazolium dye (MTT) based assay for cell growth and chemosensitivity. Br J Cancer. 56:279-285.
25. Vo HT, Nguyen N-TT, Nguyen HT, Do KQ, Connolly JD, Maas G, Heilmann J, Werz UR, Pham HD, Nguyen L-HD. 2012. Cytotoxic tetraoxygenated xanthones from the bark of Garcinia schomburgkiana. Phytochem Lett. 5:553-557.
26. Wu Q-L, Wang S-P, Du L-J, Yang J-S, Xiao P-G. 1998. Xanthones from Hypericum japonicum and H. henryi. Phytochemistry. 49:1395-1402.
27. Xia Z-X, Zhang D-D, Liang S, Lao Y-Z, Zhang H, Tan H-S, Chen S-L, Wang X-H, Xu H-X. 2012. Bioassay-guided isolation of prenylated xanthones and polycyclic acylphloroglucinols from the leaves of Garcinia nujiangensis. J Nat Prod. 75:1459-1464.
28. Xu G, Feng C, Zhou Y, Han Q-B, Qiao C-F, Huang S-X, Chang DC, Zhao Q-S, Luo KQ, Xu H-X. 2008. Bioassay and ultraperformance liquid chromatography/mass spectrometry guided isolation of apoptosis-inducing benzophenones and xanthone from the pericarp of Garcinia yunnanensis Hu. J Agric Food Chem. 56:11144-11150.