Isoprenoid-substituted flavonoids from wood of Artocarpus heterophyllus on B16 melanoma cells: cytotoxicity and structural criteria.
As a result of cytotoxicity-guided fractionation, nine flavonoids, artocarpin (1), cudraflavone C (2), 6-prenylapigenin (3), kuwanon C (4), norartocarpin (5), albanin A (6), cudraflavone B (7), brosimone I (8) and artocarpanone (9) were identified from the methanol extract of the wood of Artocarpus heterophyllus, known commonly as Nangka in Indonesia. A structure-activity investigation of the effect of these isolated compounds (1-9) and structurally related compounds on B16 melanoma cells indicated that isoprenoid moiety substitutions in flavonoids enhance their cytotoxicity, and that the position of attachment and the number of isoprenoid-substituent moieties per molecule influence flavonoid cytotoxicity.
Arung
Enos Tangke
ET
Department of Systematic Forest and Forest Products Sciences, Faculty of Agriculture, Kyushu University, Fukuoka 812-8581, Japan.
Yoshikawa
Keisuke
K
Shimizu
Kuniyoshi
K
Kondo
Ryuichiro
R
D000818:Animals; D031622:Artocarpus / Q000737:chemistry*; D045744:Cell Line, Tumor; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D008546:Melanoma, Experimental / Q000188:drug therapy*; D051379:Mice; D015394:Molecular Structure; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018547:Plant Stems; D012878:Skin Neoplasms / Q000188:drug therapy*; D013329:Structure-Activity Relationship; D013729:Terpenes; D014934:Wood
D005419:Flavonoids; D010936:Plant Extracts; D013729:Terpenes