Four new azaphilones named longirostrerones A-D (1-4) and three known sterols, ergosteryl palmitate, ergosterol, and ergosterol peroxide, have been isolated from ethyl acetate extract of the fungus Chaetomium longirostre. These structures were determined by 1D and 2D NMR, IR, UV, MS, and CD spectroscopy. Compounds 1-4 exhibited strong cytotoxicity against KB cancer cell lines (IC(50) 0.23-6.38 μM), while only 1 showed potent cytotoxicity against MCF7 and NCI-H187 cell lines (IC50 0.24 and 3.08 μM, respectively). In addition, 1-3 showed antimalarial activity against Plasmodium falciparum (IC50 0.62-3.73 μM).
Balanophora fungosa is a parasitic plant growing on the root of various plants and belongs to the family Balanophoraceae. It is known as "Ka-noon-din", "Kok-mag-pasi", "Head-hin", "Wan-dok-din" and "Bua-pud" in Thai. It is monoecious or rarely dioecious, with yellowish brown rhizome and 10-15 cm in height.1) In Thai traditional medicine, B. fungosa is used for ear discharge and as an antiseptic.2) Previous phytochemical investigation of Balanophora species have resulted in the isolation of various types of compounds such as lignans, 3) phenylpropanoids, 3) steroids, 4) triterpene, 5) fatty acid, 5) phenylpropanoide glucosides, galloyl and hexahydroxydiphenoyl esters of phenylpropanoid glucosides, 6) and ellagitannins.7) The present study deals with the isolation and characterization of five new compounds (21-25), together with twenty known compounds (1-20) from B. fungosa which grew on the root of Diospyros mollis. It should be noted that compounds 9, 11 and 14 are the first isolation from Balanophoraceae.
Results and DiscussionThe hexane, EtOAc and MeOH extracts of rhizomes of B. fungosa were fractionated by column chromatography on silica gel PF60, cosmosil (75C 18 -OPN coumaroyl-3-galloyl-4,6-(S)-HHDP-b b-D-glucopyranose (21), 1-O-(E)-coumaroyl-3,4,6-trigalloyl-
Five new galloyl and (S)-hexahydroxydiphenyl (HHDP) esters of phenylpropanoid glucosides; 1-O-(E)-
Two new angular types of azaphilones, isochromophilonol (1) and ochrephilonol (2), together with ten known compounds (3-12), were isolated from Chaetomium cupreum RY202. Their structures were established on the basis of spectroscopic data and the absolute configurations of 1 and 3 were determined by the modified Mosher's method. Compounds 1, 2 and 4 showed moderated cytotoxicity against KB and NCI-H187 cell lines (IC50 9.63-32.42 µg/mL).
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