Dihydroosajaxanthone: A New Natural Xanthone from the Branches of Garcinia Schomburgkian a Pierre

Imron Meechai, Worrapong Phupong, Warangkana Chunglok, Puttinan Meepowpan, Imron Meechai, Worrapong Phupong, Warangkana Chunglok, Puttinan Meepowpan

Abstract

Garcinia schomburgkiana, locally known in Thailand as an edible fruit "Ma-dan", is a plant species of the Clusiaceae family which has been reported as sources of a variety of compounds with biological activities. In the phytochemical studies of Ma-dan, four xanthones were, for the very first time, isolated from the branch acetone extract of G. schomburgkiana. Their structures were determined through the analysis of spectroscopic data (1H, 13C-NMR, IR and MS) and the comparison with those previously reported. Dihydroosajaxanthone (1), an original synthetic xanthone, is reported herein for the first time as a naturally occurring xanthone, together with three known xanthones: xanthochymone A (2), 1,3,7-trihydroxy-2-(3-hydroxy-3-methylbutyl) xanthone (3) and 1,3,5,6-tetrahydroxyxanthone (4). These compounds, especially dihydroosajaxanthone (1), might be considered as chemotaxonomic markers of the Garcinia genus.

Keywords: Clusiaceae; Dihydroosajaxanthone; Garcinia schomburgkiana; Phytochemical; Xanthone.

Figures

Figure 1
Figure 1
The structure of compound 1-4

References

    1. Lim TK. Edible Medicinal And Non-Medicinal Plants. Volume 2. Dordrecht : Springer Netherlands; 2012. pp. 123–4.
    1. Ritthiwigrom T, Laphookhieo S, Pyne SG. Chemical constituents and biological activities of Garcinia cowa Roxb. Maejo Int. J. Sci. Technol. 2013;7:212–31.
    1. Bennett GJ, Lee HH. Xanthones from guttiferae. Phytochemistry . 1989;28:967–98.
    1. Fun HK, Koysomboon S, Chantrapromma K, Chantrapromma S. fluorinated clusiacitran A and fluorinatedclusiacitran B (0.45:0.45:0.05:0.05) Acta Crystallogr. Sect. E Struct. Rep. Online. 2006;62:o3228–o3230.
    1. Häfner A, Frahm AW. Biflavanoids from the heartwood of Garcinia schomburgkiana and their structural elucidation as atropisomers. Planta Med. 1993;59:A604.
    1. Mungmee C, Sitthigool S, Buakeaw A, Suttisri R. A new biphenyl and other constituents from the wood of Garcinia schomburgkiana. Nat. Prod. Res. 2013;27:1949–55.
    1. Vo HT, Nguyen NTT, Nguyen HT, Do KQ, Connolly JD, Maas G, Heilmann J, Werz UR, Pham HD, Nguyen LHD. Cytotoxic tetraoxygenated xanthones from the bark of Garcinia schomburgkiana. Phytochem. Lett. 2012;5:553–7.
    1. Castanheiro RA, Pinto MM, Silva AM, Cravo SM, Gales L, Damas AM, Nazareth N, Nascimento MS, Eaton G. Dihydroxyxanthones prenylated derivatives: Synthesis, structure elucidation, and growth inhibitory activity on human tumor cell lines with improvement of selectivity for MCF-7. Bioorg. Med. Chem. 2007;15:6080–8.
    1. Ahluwalia VK, Jolly RS, Tehim AK. A convenient synthesis of dihydropyranoxanthones. J. Chem. Soc. Perkin Trans. 1983;1:1229–33.
    1. Wolfrom ML, Komitsky F, Looker JH. Osage orange pigments. XV. Structure of osajaxanthone. Synthesis of dihydroosajaxanthone monomethyl ether. J. Org. Chem. 1965;30:144–9.
    1. Wolfrom ML, Koos EW, Bhat HB. Osage orange pigments XVIII Synthesis of osajaxanthone. J. Org. Chem. 1967;32:1058–60.
    1. Trisuwan K, Boonyketgoson S, Rukachaisirikul V, Phongpaichit S. Oxygenated xanthones and biflavanoids from the twigs of Garcinia xanthochymus. Tetrahedron Lett. 2014;55:3600–2.
    1. Garcia Cortez DA, Young MCM, Marston A, Wolfender JL, Hostettmann K. Xanthones, triterpenes and a biphenyl from Kielmeyera coriacea. Phytochem. 1998;47:1367–74.
    1. Li W, Ding Y, Quang TH, Ngan NTT, Sun YN, Yan XT, Yang SY, Choi CW, Lee EJ, Peak KY, Kim YH. NF-κB inhibition and PPAR activation by phenolic compounds from Hypericum perforatum L adventitious root. Bull. Korean Chem. Soc. 2013;34:1407–13.

Source: PubMed

Sponsorer och medarbetare

Medicinska tillstånd

Läkemedelsinterventioner

3
Prenumerera