Rearranged Benzophenones and Prenylated Xanthones from Garcinia propinqua Twigs

Abstract

The first phytochemical investigation of Garcinia propinqua has led to the isolation and identification of three new compounds, including two rearranged benzophenones, doitunggarcinones A (1) and B (2), and a xanthone, doitunggarcinone C (3), together with seven known compounds (4-10). The structures of 1-3 were elucidated on the basis of spectroscopic methods, including UV, IR, NMR, and MS. The antibacterial activity of the 10 isolates was evaluated against Escherichia coli TISTR 780, Salmonella typhimurium TISTR 292, Staphylococcus aureus TISTR 1466, and methicillin-resistant Staphylococcus aureus (MRSA) SK1.

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

“…Branches no [78] Dihydroxyprenyl xanthone acetylated Oenothera biennis Roots no [79] Doitunggarcinone C Garcinia propinqua Twigs no [80] Dulcisxanthone H Garcinia dulcis Branches no [81] Dulcisxanthone I Garcinia dulcis Branches no [81] Dulcisxanthone J Garcinia dulcis Stem barks no [82] Dulcisxanthone K Garcinia dulcis Stem barks no [82] Dulcisxanthone L Garcinia dulcis Stem barks no [82] Epiisobractatin Garcinia bracteata Leaves yes [38] Esculentin A Garcinia esculenta Twigs no [83] Fuscaxanthone I Garcinia fusca Roots yes [84] Fuscaxanthone J Garcinia fusca Roots no [85] Fuscaxanthone K Garcinia fusca Roots no [85] Garcibractatin A Garcinia bracteata Leaves yes [86] Garcibracteatone Garcinia bracteata Leaves yes [38] Garcibractone A Garcinia bracteata Leaves yes [86] Garcibractone B Garcinia bracteata Leaves yes [86] Garcicowanone A Garcinia cowa Fruits no [87] Garcicowanone B Garcinia cowa Fruits no [87] Garciesculenxanthone A Garcinia esculenta Twigs yes [88] Garcihombronone A Garcinia hombroniana Twigs no…”

Recent Advances on anti-MRSA Natural Products Derived from Plants

“…[31] Phytochemical investigation of the other genus Garcinia propinqua led to the isolation and identification of compounds 10-O-methylmacluraxanthone (56) and macluraxanthone (57), which showed good activity against MRSA SK1 and S. aureus TISTR 1466, with MIC values in the range 2-4 μg/mL. [32] Tala et al found 1,5-dihydroxy-2-methoxyxynthone (58) showed activity against MRSA with IC50 value of 18.5 μg/mL ( Figure 6). [7] Figure 6 The structures of compounds 54-58.…”

Synthesis of toxyloxanthone B

“…The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried (MgSO 4 ), and concentrated under reduced pressure. The residue was purified by flash column chromatography (2:3 ethyl acetate/light petroleum) to give the title compound as a pale yellow solid (5 3.10. 7-(2,2-Dimethylbut-3-ynyl)-1,3,6-tribenzyloxy-9H-xanthen-9-one 13…”

“…Plants and trees of the Garcinia genus are a particularly rich source of bioactive xanthones, and recently isolated examples possess activity against platelet aggregation, 2 a-glucosidases, 3 cancer, 4 and MRSA. 5,6 In higher plants, xanthones are of mixed polyketide and shikimic acid biosynthetic origin, with many examples also possessing isoprenederived side chains. 3e5 Indeed it was prenylated xanthones such as a-mangostin 1, rubraxanthone 2, and toxyloxanthone B 3a ( Fig.…”