Cytotoxic Coumarins from the Bark of Mammea siamensis.
A new geranylated coumarin, (E)-4-(1-hydroxypropyl)-5,7-dihydroxy-6-(3,7-dimethyl-2,6-octadienyl)-8-(3-methyl-1-oxobutyl)coumarin (named surangin D), was isolated from the bark of Mammea siamensis collected in Vietnam, along with four known coumarins, surangins B and C, and theraphins B and C, and seven xanthones, 1,7-dihydroxyxanthone, 7-hydroxy-1-methoxyxanthone, 1,7-dimethoxyxanthone, 1,7-dimethoxy-6-hydroxyxanthone, 1,6,7-trihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,7-dihydroxy-3-methoxyxanthone. Their structures were determined by spectroscopic methods (mainly 1D- and 2D-NMR) and preparation of methylated derivatives. The four coumarins, surangins C and D and theraphins B and C, were tested for inhibition of cell proliferation in DLD-1 (colon cancer), MCF-7 (breast adenocarcinoma), HeLa (human cervical cancer) and NCI-H460 (human lung cancer) cell lines using the sulforhodamine B (SRB) assay. In all four cell lines, theraphin C showed the strongest activity (IC₅₀ in the range of 1.6-5.7 µM). Testing the anti-proliferative effect of the methylated derivatives showed reduced cellular effects of all derivatives, indicating that the number and position of free hydroxyl groups were very important for the anti-proliferative effect.
Ho Chi Minh City University of Science, Ho Chi Minh City, Vietnam.
Ngoc Trang Nhu
NT
Ngo
Vy Thuy
VT
Nguyen
Hoa Van
HV
Vo
Ole
O
Vang
Fritz
F
Duus
Thuy-Duong Huynh
TD
Ho
Hung Dinh
HD
Pham
Lien-Hoa Dieu
LH
Nguyen
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003374:Coumarins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D031252:Mammea / Q000737:chemistry*; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy; D024301:Plant Bark / Q000737:chemistry; D014744:Vietnam
D000972:Antineoplastic Agents, Phytogenic; D003374:Coumarins