Cytotoxic and New Tetralone Derivatives fromBerchemia floribunda (Wall.)Brongn.

Abstract

Two new a-tetralone ( ¼ 3,4-dihydronaphthalen-1(2H)-one) derivatives, berchemiaside A and B (1 and 2, resp.), and one new flavonoid, quercetin-3-O-(2-acetyl-a-l-arabinofuranoside (3), together with ten known flavonoids compounds, eriodictyol (4), aromadendrin (5), trans-dihydroquercetin (6), cisdihydroquercetin (7), kaempferol (8), kaempferol-3-O-a-l-arabinofuranoside (9), quercetin (10), quercetin-3-O-a-l-arabinofuranoside or avicularin (11), quercetin 3'-methyl ether, 3-O-a-l-arabinofuranoside (12), and maesopsin (13), were isolated from the bark of Berchemia floribunda. Their structures were determined by various NMR techniques and chemical studies. Compounds 3 -13 were tested for their cytotoxic activity against human leukemia cells. Among them, kaempferol (8) and maesopsin (13) showed significant inhibitory activities against human leukemia cells CCRF-CEM and its multidrugresistant sub-line, CEM/ADR5000, with IC 50 values of 14.0, 5.3, 10.2, and 12.3 mm, respectively.Introduction. -Berchemia floribunda (Wall.) Brongn., which is widely distributed in China, was used for treatment of rheumatic arthritis, jaundice and contusions, and strains and dysmenorrhoea [1]. No work has been previously performed on the chemical constituents and biological activity. The AcOEt extract showed activity against human leukemia cells CCRF-CEM. So we undertook the study of bioactive constituents. From the AcOEt fraction of EtOH extracts of B. floribunda, two new atetralone ( ¼ 3,4-dihydronaphthalen-1(2H)-one) derivatives, 1 and 2, and one new flavonoid, 3, together with ten known flavonoid compounds, 4 -13, were obtained. Compounds 3 -13 were examined for their biological activities against human leukemia cells CCRF-CEM and its multidrug-resistant sub-line, CEM/ADR5000. This paper mainly reports the isolation and structure elucidation of the new compounds, and the cytotoxicity of the tested compounds.

Prediction of Broad Spectrum Resistance of Tumors towards Anticancer Drugs

“…The traditional Chinese medicine (TCM) -derived drugs cephalotaxine, homoharringtonine, berberine, and cantharidin were purchased from Sigma-Aldrich and artesunate from Saokim. The other natural products were isolated from their medicinal plants of origin as described (10,11).…”

Willmar Schwabe Award 2006: Antiplasmodial and Antitumor Activity of Artemisinin - From Bench to Bedside

“…dol, berberine, cantharidin, cephalotaxine, curcumin, homoharringtonine, luteolin, isoscopoletin, scopoletin and others [7], [8], [9], [10], [11], [12], [13], [14], [15]. Furthermore, several novel bioactive compounds were described and analyzed in the course of our investigations, i. e., tetracentronsine A, tetracentronside A, B and C, the two novel a-tetralone derivatives berchemiaside A and B as well as the novel flavonoid quercetin-3-O-(2-acetyl-a-L-arabinofuranoside) [16], [17].…”

New Glycosides fromTetracentron sinense and Their Cytotoxic Activity

“…We found that the extract of T. sinense showed significant cytotoxicity to human leukaemia cells in vitro. Recently, we reported the cytotoxic components from Berchemia floribunda [3]. As a part of our ongoing search for new biologically active compounds, we were interested in T. sinense.…”

“…The HMBC spectrum showed the (E)-propenyl group located at C(5), which was confirmed by the correlations at d 6.44 (HÀC(8)) with 7.34 (HÀC(4)), and 6.11 (HÀC(9)) with 6.87 (HÀC(6)) in its ROESY. The relative configuration of HÀC(2) and HÀC(3) was trans as judged from the ROE correlations between HÀC(2) and MeÀC (3), and between HÀC(3) and HÀC(2',6') ( Figure). This was also confirmed by the coupling constant J(2,3) ¼ 7 Hz [4].…”