Cytotoxic flavonoids from the stem bark of Lonchocarpus aff. fluvialis

Abstract

Activity-guided fractionation of a chloroform-soluble extract of Lonchocarpus aff. fluvialis stem bark using a human epidermoid (KB) tumour cell line as a monitor afforded five rotenoids, one pterocarpan, one chalcone, three flavanones, one flavone and one triterpenoid. All of the compounds isolated proved to be of previously known structure. Among them, the rotenoids (-)-sumatrol and (+/-)-villosinol, the dibenzoylmethane derivative (+)-3,4-methylenedioxy-2'-methoxy-[2",3":4',3']-furanodibenzoylmethane, and the flavanones (-)-isoglabrachromene and (-)-candidone have been shown to exhibit significant cytotoxic activity against human cancer cells for the first time. This is the first report of the chemical constituents of this species, and the profile of compounds obtained was in accordance with the established chemosystematic patterns of species in the tribe Tephrosieae (Leguminosae, Papilionoideae).

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“…Flavonoids constitute a large and important class of naturally occurring, low molecular weight benzo-␥-pyrone derivatives which are reported to have a myriad of biological activities including antioxidant [13,14], anticarcinogenic [15], cytotoxic [16,17], and antimicrobial [18] activities. In addition, some flavonoids inhibit phenoloxidase, which is responsible for the molting process in insects [19], and the mitochondrial respiratory chain [20,21].…”

Relationships between Inhibitory Activity against a Cancer Cell Line Panel, Profiles of Plants Collected, and Compound Classes Isolated in an Anticancer Drug Discovery Project

“…as some of the other compound classes. Selected examples of the structural diversity of the active compound classes isolated during this project include cucurbitacin D (1; cucurbitacin type) [36], silvestrol (2; flavagline type) [30], (S)-coriolic acid (3; fatty acid type) [39], pervilleine A (4; tropane alkaloid type) [41], ( AE )-pinoresinol (5; lignan type) [42], nataloe-emodin (6; anthraquinone type) [43], (1S,5S,6R,7R,8R,9S, 10S)-5-(angeloyloxy)-1-hydroxy-2-oxo-8,9-epoxyxantha-3,11-dien-6,12-olide (7; sesquiterpenoid type) [44], exostemin I (8; coumarin type) [37], plumbagin (9; naphthoquinone type) [35], 13-hydroxy-15-oxozoapatlin (10; diterpenoid type) [45], (À)-sumatrol (11; flavonoid type) [46], dichapetalin A (12; triterpenoid type) [47], evolitrine (13; alkaloid type) [48], methylenebis(aspininol) (14; benzenoid type) [49], (E)-15,16-dihydrominquartynoic acid (15; alkyne type) [50], and cratoxyarborenone B (16; xanthone type) [51].…”

Acetylcholinesterase inhibition and cytotoxicity of flavonoids and chalcones from Derris indica

“…The hexane www.scienceasia.org extracts were subjected to repeated column chromatography over silica gel, RP-18, preparative TLC to obtain 11 compounds. All isolated compounds were six flavonoids, desmethoxykanugin (compound 1) 5 , karanjin (compound 2) 5 , kanjone (compound 3) 12 , pongaflavone (compound 4) 13 , (2R,3R)-3-hydroxy-5-methoxy-2 ,2 -dimethylpyrano [7,8:5 ,6 ]-flavanone (compound 5) 14 , and candidone (compound 6) 15 ; and five chalcones, pongamol (compound 7) 16 , obovatachalcone (compound 8) 17 , derrischalcone (compound 9) 18 , tunicatachalcone (compound 10) 19 , and ovalichalcone (compound 11) 20 ( Fig. 1).…”