Planta Med 2005; 71(2): 165-170
DOI: 10.1055/s-2005-837785
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Antibacterial Caged-Tetraprenylated Xanthones from the Stem Bark of Garcinia scortechinii

Vatcharin Rukachaisirikul1 , Patima Phainuphong1 , Yaowapa Sukpondma1 , Souwaluk Phongpaichit2 , Walter C. Taylor3
  • 1Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla, Thailand
  • 2Department of Microbiology, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla, Thailand
  • 3School of Chemistry, The University of Sydney, Sydney, Australia
Further Information

Publication History

Received: April 29, 2004

Accepted: August 21, 2004

Publication Date:
24 February 2005 (online)

Abstract

Five new caged-tetraprenylated xanthones, scortechinones L - P (1 - 5), together with six known scortechinones (A, B, D, F, I and J) and one known xanthone, 4,5-dihydro-1,5-dihydroxy-6,6-dimethylpyrano(2,3:6,7)-4,4,5-trimethylfurano(2,3:3,4)- xanthone, were isolated from the crude methanol extract of the stem bark of Garcinia scortechinii. The structures were elucidated by analysis of spectroscopic data and comparison of the NMR data with those reported previously. The antibacterial activity of all caged-polyprenylated xanthones, isolated from the latex and stem bark of G. scortechinii, was evaluated. Scortechinone B (6) exhibited significant antibacterial activity against a methicillin-resistant Staphylococcus aureus strain with an MIC value of 2 μg/mL. From the MIC values, some structure-antibacterial activity relationships were established.

References

  • 1 Thoison O, Fahy J, Dumontet V, Chiaroni A, Riche C, Tri M V, Sevenet T. Cytotoxic prenylxanthones from Garcinia bracteata .  J Nat Prod. 2000;  63 441-6
  • 2 Kosela S, Hu L -H, Rachmatia T, Hanafi M, Sim K-Y. Dulxanthones F - H, three new pyranoxanthones from Garcinia dulcis .  J Nat Prod. 2000;  63 406-7
  • 3 Iinuma M, Tosa H, Tanaka T, Kanamaru S, Asai F, Kobayashi Y, Miyauchi K, Shimano R. Antibacterial activity of some Garcinia benzophenone derivatives against methicillin-resistant Staphylococcus aureus .  Bio Pharm Bull. 1996;  19 311-4
  • 4 Cao S -G, Wu X -H, Sim K -Y, Tan B KH, Pereira J T, Wong W H, Hew N F, Goh S H. Cytotoxic caged tetraprenylated xanthonoids from Garcinia gaudichaudii (Guttiferae).  Tetrahedron Lett. 1998;  39 3353-6
  • 5 Cao S -G, Sng V HL, Wu X -H, Sim K -Y, Tan B KH, Pereira J T, Goh S H. Novel cytotoxic polyprenylated xanthonoids from Garcinia gaudichaudii (Guttiferae).  Tetrahedron. 1998;  54 10 915-24
  • 6 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 .  Organic Letters. 2000;  2 3945-8
  • 7 Leong Y W, Harrison L J, Bennett G J, Tan H T-W. Forbesione, a modified xanthone from Garcinia forbesii .  J Chem Res (Synopsis). 1996;  8 392-3
  • 8 Kartha G, Ramachandra G N, Bhat H B, Nair P M, Raphavan V KV, Venhataraman K. The constitution of morellin.  Tetrahedron Lett. 1963;  7 459-72
  • 9 Karanjgaonkar C G, Nair P M, Venkataraman K. Morellic, isomorellic and gambogic acids. Tetrahedron Lett 1966: 687-91
  • 10 Rukachaisirikul V, Kaewnok W, Koysomboon S, Phongpaichit S, Taylor W C. Caged-tetraprenylated xanthones from Garcinia scortechinii .  Tetrahedron. 2000;  56 8539-43
  • 11 Rukachaisirikul V, Painuphong P, Sukpondma Y, Koysomboon S, Sawangchote P, Taylor W C. Caged-triprenylated and -tetraprenylated xanthones from the latex of Garcinia scortechinii .  J Nat Prod. 2003;  66 933-8
  • 12 Delle Monache G, Botta B, De Mello J F, De Borros Coelho J S, Menichini F. Chemical investigation of the genus Rheedia, VI. Three new xanthones from Rheedia brasiliensis .  J Nat Prod. 1984;  47 620-5
  • 13 Lorian V. Antibiotics in Laboratory Medicine. 4th edition William and Wilkins Baltimore; 1996: pp 28-32
  • 14 National Committee for Clinical Laboratory Standards (NCCLS) 2003. Disk Diffusion. Supplemental Tables. M100-S13 (M2). January 2003

Dr. Vatcharin Rukachaisirikul

Department of Chemistry

Faculty of Science

Prince of Songkla University

Hat Yai

Songkhla

Thailand

Fax: +66-74-212-918

Email: vatcharin.r@ratree.psu.ac.th