Skip to main content
Log in

Benzophenone and xanthone derivatives from the inflorescences of Garcinia cowa

  • Research Article
  • Drug Design and Discovery
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

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).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • 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).

    Article  PubMed  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • Likhitwitayawuid, K., Phadungcharoen, T., and Krungkrai, J., Antimalarial xanthones from Garcinia cowa. Planta Med., 64, 70–72 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Mahabusarakam, W., Chairerk, P., and Taylor, W. C., Xanthones from Garcinia cowa Roxb. latex. Phytochemistry, 66, 1148–1153 (2005).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    PubMed  CAS  Google Scholar 

  • Shen, J. and Yang, J., Chemical constituents from fruits of Garcinia cowa. Zhongguo Yaoxue Zazhi, 41, 660–661 (2006).

    CAS  Google Scholar 

  • Sukpondma, Y., Rukachaisirikul, V., and Phongpaichit, S., Antibacterial caged-tetraprenylated xanthones from the fruits of Garcinia hanburyi. Chem. Pharm. Bull., 53, 859–852 (2005)

    Article  Google Scholar 

  • 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).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Thunwadee Ritthiwigrom.

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-012-1004-z

Key words

Navigation