Cytotoxic Acylphloroglucinol Derivatives from the Twigs of Garcinia cowa

Abstract

An unusual polyprenylated acylphloroglucinol derivative unsubstituted at C-2 and C-6, garcicowin A (1), together with three other new (garcicowins B-D, 2-4) and nine known analogues, was isolated and characterized from the twigs of Garcinia cowa. The structures of 1-4 were elucidated by interpretation of their spectroscopic data. The compounds isolated were evaluated for their cytotoxicity against two cancer cell lines (HT-29 and HCT116) and against normal colon cells (CCD-18Co), and the results demonstrated their selective toxicity toward the cancer cells.

Identification and Characterization of Anticancer Compounds Targeting Apoptosis and Autophagy from Chinese Native Garcinia Species

“…These studies suggest that the plant metabolites from Garcinia species have unique chemical structures and potent bioactivities and can be a promising pharmacological target for drug design and development. Previously, we applied bioassay-guided fractionation by using a caspase-3 FRET sensor to identify many novel compounds targeting apoptosis in China native Garcinia species [25][26][27][28][29]. Furthermore, the mechanisms of action of some compounds involve the induction of apoptosis, inhibition of autophagic flux, cell cycle arrest, and modulation of oncogenes, etc.…”

Kaennacowanols A–C, three new xanthones and their cytotoxicity from the roots of Garcinia cowa

“…Garcinia cowa, commonly known as Cha-muang in Thai, is widely distributed throughout Thailand, Malaysia and Myanmar. This plant has been an abundant source of secondary metabolites, especially xanthones [2][3][4][5][6], phloroglucinols [6][7][8][9][10], flavonoids [3,11,12] and terpenoids [12,13]. Xanthones are well recognized as chemotaxonomic markers for plants of the Garcinia species [2][3][4][5][6][14][15][16][17][18] and many of which have interesting pharmacological activities, including antimicrobial [2,6], antiinflammatory [11], antimalarial [19], antioxidant [2,4,11] and cytotoxic activities [5,20].…”

“…Therefore, the roots of this plant were attracted for further investigation. We now report the isolation of twenty-two xanthones, which are comprised of three new xanthones named kaennacowanols A-C (1-3) and nineteen known xanthones (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) (Fig. 1).…”

Qualitative and quantitative analysis of polycyclic polyprenylated acylphloroglucinols from Garcinia species using ultra performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry

“…1, 16 reference compounds, namely garcicowin D (1) [29], garcicowin C (2) [29], 30-epicambogin (3) [30], cambogin (4) [31], oblongifolin F (5) [20], oblongifolin G (6) [20], guttiferone K (7) [32], guttiferone F (8) [30], garciyunnanin B (9) [19], oblongifolin B (10) [33], garciyunnanin A (11) [19], oblongifolin A (12) [33], garcicowin B (13) [29], oblongifolin C (14) [33], guttiferone B (15) [30], and oblongifolin D (16) [33] were isolated from different Garcinia species in our laboratory and were identified by IR, UV, NMR spectroscopic analysis, and the purity of these authentic compounds was verified to be over 95% by HPLC-DAD and UPLC-MS detection. Each accurately weighed standard was dissolved in acetonitrile to give individual stock solutions.…”