Chemical constituents of dichloromethane extract from the stem bark of Garcinia fagraeoides
Keywords:Garcinia fagraeoides, polyisoprenylated benzophenone, xanthone
The Garcinia genus belonging to the Clusiaceae family (Guttiferae) has been reported to be a rich source of polyisoprenylated benzophenones, xanthones and biflavonoids with various biological activities. Garcinia fagraeoides A.Chev is an evergreen hardwood tree found only in the north provinces of Viet Nam and Guangxi province of China. Its stem bark and leaves have been used in Vietnamese traditional medicine for treatment of malaria and dermatitis diseases. In our continuing studies on chemical constituents and biological activities from the genus Garcinia, the phytochemical of Garcinia fagraeoides’s stem bark collected from Thua Thien Hue province was investigated. Repeated chromatography steps over silica gel and Sephadex LH-20 of the dichloromethane partition from the methanol extract of Garcinia fagraeoides’s stem bark led to the isolation of five compounds including one polyisoprenylated benzophenone (isogarcinol (1)), two tetraoxygenated xanthones (rubraxanthone (2), a-mangostin (3)), ferulic acid (4), and pyromeconic acid (5). Their structures were elucidated mainly by analysis of their 1D, 2D NMR spectroscopy and ESI-MS data, and by comparison with reported data. The absolute configuration of isogarcinol (1) was determined by comparison of its experimental optical rotation and NMR data with the values of its stereoisomer. This is the first reported isolation of compounds 1-5 from the stem bark of Garcinia fagraeoides.
Gustafson K. R., Blunt J. W., Munro M. H. G, Fuller R. W., McKee T. C., Cardellina J. H., McMahon J. B., Cragg M. C. and Boyd M. R. - HIV inhibitory natural products 8. The guttiferones, HIVinhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusiarosea, Tetrahedron 48 (46) (1992) 10093-10102. https://doi.org/10.1016/S0040-4020(01)89039-6. DOI: https://doi.org/10.1016/S0040-4020(01)89039-6 https://doi.org/10.1016/S0040-4020(01)89039-6.">
Williams R. B., Hoch J., Glass T. E., Evans R., Miller J. S., Wisse J. H., and Kingston D. G. I. - A novel cytotoxic guttiferone analogue from Garcinia macrophylla from the Surinam rainforest, Planta Med. 69 (2003) 864–866. https://doi.org/10.1055/s-2005-864129. DOI: https://doi.org/10.1055/s-2003-43204 https://doi.org/10.1055/s-2005-864129.">
Bennett G. J. and Lee H. H. - Xanthones from Guttiferae, Phytochemistry 28 (1989) 967–998. https://doi.org/10.1016/0031-9422(89)80170-0. DOI: https://doi.org/10.1016/0031-9422(89)80170-0 https://doi.org/10.1016/0031-9422(89)80170-0.">
Krishnamurthy N., Lewis Y. S. and Ravindranath B. - On the structures of garcinol, isogarcinol and camboginol, Tetrahedron Lett. 22 (1981) 793–796. https://doi.org/ 10.1016/0040-4039(81)80154-2. DOI: https://doi.org/10.1016/0040-4039(81)80154-2 https://doi.org/ 10.1016/0040-4039(81)80154-2.">
Marti G., Eparvier V., Moretti C., Susplugas S., Prado S., Grellier P., Retailleau P., Gueritte F. and Litaudon M. - Antiplasmodial benzophenones from the trunk latex of Moronobea coccinea (Clusiaceae), Phytochemistry 70 (2009) 75-85. https://doi.org/ 10.1016/ j.phytochem.2008.10.005. DOI: https://doi.org/10.1016/j.phytochem.2008.10.005 https://doi.org/ 10.1016/ j.phytochem.2008.10.005.">
Lee H. H. and Chan H. K. - 3,6-Trihydroxy-7-methoxy-. 8-(3,7-dimethyl-2,6-octadienyl)xanthone from Garcinia cowa, Phytochem. Lett. 16 (1977) 2038-20401. DOI: https://doi.org/10.1016/0031-9422(77)80129-5
Phitaktim S., Chomnawang M., Sirichaiwetchakoon K., Dunkhunthod B., Hobbs G. and Eumkeb G. - Synergism and the mechanism of action of the combination of α-mangostin isolated from Garcinia mangostana L. and oxacillin against an oxacillin-resistant Staphylococcus saprophyticus, BMC Microbiology 16 (2016) 195. https://doi.org/10.1186/s12866-016-0814-4. DOI: https://doi.org/10.1186/s12866-016-0814-4 https://doi.org/10.1186/s12866-016-0814-4.">
Sajjadi S. E., Shokoohinia Y. and Moayedi, N. S. - Isolation and identification of ferulic acid from aerial parts of Kelussia odoratissima Mozaff. Jundishapur, J. Nat. Pharm. Prod. 7(4) (2012) 159-162. https://doi.org/10.5812/jjnpp.4861. DOI: https://doi.org/10.17795/jjnpp-4861 https://doi.org/10.5812/jjnpp.4861.">
Hashidoko Y. - Pyromeconic acid and its glucosidic derivatives from leaves of Erigeron annuus and the siderophile activity of pyromeconic acid, Bioscience Biotechnology and Biochemistry, 59 (5) (1995), 886-890. https://doi.org/10.1271/bbb.59.886. DOI: https://doi.org/10.1271/bbb.59.886 https://doi.org/10.1271/bbb.59.886.">
How to Cite
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
Vietnam Journal of Sciences and Technology (VJST) is an open access and peer-reviewed journal. All academic publications could be made free to read and downloaded for everyone. In addition, articles are published under term of the Creative Commons Attribution-ShareAlike 4.0 International (CC BY-SA) Licence which permits use, distribution and reproduction in any medium, provided the original work is properly cited & ShareAlike terms followed.
Copyright on any research article published in VJST is retained by the respective author(s), without restrictions. Authors grant VAST Journals System a license to publish the article and identify itself as the original publisher. Upon author(s) by giving permission to VJST either via VJST journal portal or other channel to publish their research work in VJST agrees to all the terms and conditions of https://creativecommons.org/licenses/by-sa/4.0/ License and terms & condition set by VJST.
Authors have the responsibility of to secure all necessary copyright permissions for the use of 3rd-party materials in their manuscript.