Abstract
The purification of the acetone extract from the inflorescences of Garcinia cowa led to the isolation of a new benzophenone derivative, cowanone (1), together with seven known xanthones, α-mangostin (2), β-mangostin (3), cowanin (4), fuscaxanthone A (5), 9-hydroxycalabaxanthone (6), garcinianone A (7) and cowanol (8). The structures of the isolated compounds were elucidated by analysis of their spectroscopic data including 1D and 2D NMR data. All isolated compounds were evaluated for their antibacterial activities against Staphylococcus aureus (SA) and methicillin-resistant S. aureus (MRSA).
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Acuña, U. M., Figueroa, M., Kavalier, A., Jancovski, N., Basile, M. J., and Kennelly E. J., Benzophenones and biflavonoids from Rheedia edulis. J. Nat. Prod., 73, 1775–1779 (2010).
Cheenpracha, S., Phakhodee, W., Ritthiwigrom, T., Prawat, U., and Laphookhieo, S., A new depsidone from the twigs of Garcinia cowa. Heterocycles, 83, 1139–1144 (2011).
Chiang, Y.-M., Kuo, Y.-H., Oota, S., and Fukuyama, Y., Xanthones and benzophenones from the stems of Garcinia multiflora. J. Nat. Prod., 66, 1070–1073 (2003).
CLSI, Method for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved Standard M7-A4. http://isoforlab.com/phocadownload/csli/M7-A7.pdf (2006).
Gao, X.-M., Yu, T., Lai, F. S. F., Zhou, Y., Liu, X., Qiao, C.-F., Song, J.-Z., Chen, S.-L., Luo, K. Q., and Xu, H.-X., Identification and evaluation of apoptotic compounds from Garcinia paucinervis. Bioorg. Med. Chem., 18, 4957–4964 (2010).
Ha, L. D., Hansen, P. E., Vang. O., Duus, F., Pham, H. D., and Nguyen, L.-H. D., Cytotoxic geranylated xanthones and O-alkylated derivatives of β-Mangostin. Chem. Pharm. Bull., 57, 830–834 (2009).
Han, A.-R., Kim, J.-A., Lantvit, D. D., Kardono, L. B. S., Riswan, S., Chai, H., Carcache de Blanco, E. J., Farnworth, N. R., Swanson, S. M., and Kinghorn, A. D., Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (Mangosteen). J. Nat. Prod., 72, 2028–2031 (2009).
Ito, C., Itoigawa, M., Takakura, T., Ruangrungsi, N., Enjo, F., Tokuda, H., Nishino, H., and Furukawa, H., Chemical consituents of Garcinia fusca: Structure elucidation of eight new xanthones and their cancer chemopreventive activity. J. Nat. Prod., 66, 200–205 (2003).
Likhitwitayawuid, K., Phadungcharoen, T., and Krungkrai, J., Antimalarial xanthones from Garcinia cowa. Planta Med., 64, 70–72 (1998).
Mahabusarakam, W., Chairerk, P., and Taylor, W. C., Xanthones from Garcinia cowa Roxb. latex. Phytochemistry, 66, 1148–1153 (2005).
Nguyen, H. D., Trinh, B. T. D., and Nguyen, L.-H. D., Guttiferones Q-S, cytotoxic polyisoprenylated benzophenones from the pericarp of Garcinia cochichinensis. Phytochem. Lett., 4, 129–133 (2011).
Pan, E., Cao, S., Brodie, P. J., Miller, J. S., Rakotodrajaona, R., Ratovoson, F., Birkinshaw, C., Andriantsiferana, R., Rasamison, V. E., and Kingston, D. G. I., An antiproliferative xanthone of Symphonia pauciflora from the Madagascar rainforest. Nat. Prod. Commun., 5, 751–754 (2010).
Pereira, I. O., Marques, M. J., Pavan, A. L. R., Codonho, B. S., Barbiéri, C. L., Beijo, L. A., Doriguetto, A. C., D’Martin, E. C., and Dos Santos, M. H., Leishmanicidal activity of benzophenones and extracts from Garcinia brasiliensis Mart. fruits. Phytomedicine, 17, 339–345 (2010).
Ren, Y., Lantvit, D. D., Carcache de Blanco, E. J., Kardono, L. B. S., Riswan, S., Chai, H., Cottrell, C. E., Farnsworth, N. R., Swanson, S. M., Ding, Y., Li, X.-C., Marais, J. P. J., Ferreira, D., and Kinghorn, A. D., Proteasome-inhibitory and cytotoxic constituents of Garcinia lateriflora: absolute configuration of caged xanthones. Tetrahedron, 66, 5311–5320 (2010).
Rukachaisirikul, V., Painuphong, P., Sukpondma, Y., Koysomboon, S., Sawangchote, P., and Taylor, W. C., Cagedtriprenylated and -tetraprenylated xanthones from the latex of Garcinia scortechinii. J. Nat. Prod., 66, 933–938 (2003).
Ryu, H. W., Curtis-Long, M. J., Jung, S., Jin, Y. M., Cho, J. K., Ryu, Y. B., Lee, W. S., and Park, K. H., with neuraminidase inhibitory activity from seedcases of Garcinia mangostana. Bioorg. Med. Chem., 18, 6258–6264 (2010).
Shen, J., Tian, Z., and Yang, J.-S., The constituents from the stems of Garcinia cowa Roxb. and their cytotoxic activities. Pharmazie, 62, 549–551 (2007).
Shen, J. and Yang, J., Chemical constituents from fruits of Garcinia cowa. Zhongguo Yaoxue Zazhi, 41, 660–661 (2006).
Sukpondma, Y., Rukachaisirikul, V., and Phongpaichit, S., Antibacterial caged-tetraprenylated xanthones from the fruits of Garcinia hanburyi. Chem. Pharm. Bull., 53, 859–852 (2005)
Xiao, Z. Y., Mu, Q., Shiu, W. K. P., Zeng, Y. H., and Gibbons, S., Polyisoprenylated benzoylphloroglucinol derivatives from Hypericum sampsonii. J. Nat. Prod., 70, 1179–1782 (2007).
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Trisuwan, K., Ritthiwigrom, T. Benzophenone and xanthone derivatives from the inflorescences of Garcinia cowa . Arch. Pharm. Res. 35, 1733–1738 (2012). https://doi.org/10.1007/s12272-012-1004-z
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DOI: https://doi.org/10.1007/s12272-012-1004-z