Biological activity of Anthraquinones and Triterpenoids from Prismatomeris fragrans.
A new 1,3-dihydroxy-2-methyl-5,6-dimethoxyanthraquinone (1); six known anthraquinones, nordamnacanthal (2), damnacanthal (3), rubiadin (4), rubiadin-1-methyl ether (5), lucidin-omega-methyl ether (6), and 1-hydroxy-2-hydroxymethyl-3-methoxyanthraquinone (7); a beta-sitosterol (8); together with two known triterpenoids, beta-acetylolean-12-en-28-olic acid (9), and 3beta-O-acetyl-11alpha,12alpha-epoxyolean-28,13-olide (10) were isolated from the roots and stems of Prismatomeris fragrans. Their structures were established on the basis of spectral data. This is the first isolation of compounds 2, 6, 7, 9 and 10 from Prismatomeris genus. The isolated compounds were evaluated in antiplasmodial, antituberculosis, antifungal and anticancer cell lines tests. The bioactivity assays showed that only 9 exhibited moderate antimalarial activity, 2 and 3 exhibited antifungal activity while 2, 3, 4, 7 and 9 showed antituberculosis activity. In addition, compounds 2, 3 and 7 exhibited cytotoxicity to BC cell line while 1, 1a (the methyl ether derivative of 1), 2, 3, 4, 5, and 9 exhibited cytotoxicity to NCI-H187 cell line.
Kanokmedhakul
Kwanjai
K
Department of Chemistry, Applied Taxonomic Research Center, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand. kwanjai@kku.ac.th
Kanokmedhakul
Somdej
S
Phatchana
Ruchanee
R
D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D018517:Plant Roots / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects; D019666:Rubiaceae / Q000737:chemistry*; D012997:Solvents; D021241:Spectrometry, Mass, Electrospray Ionization; D013785:Thailand; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology*
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000962:Antimalarials; D000972:Antineoplastic Agents, Phytogenic; D012997:Solvents; D014315:Triterpenes