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New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba.

Al-Mekhlafi, Nabil Ali Naji and Shaari, Khozirah and Abas, Faridah and Jeyaraj, Ethel Jeyaseela and Stanslas, Johnson and Khalivulla, Shaik Ibrahim and Lajis, Md Nordin (2013) New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. Natural Product Communications, 8 (4). pp. 447-451. ISSN 1934-578X; ESSN: 1555-9475

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Abstract

In the present study phytochemical investigation of the methanol extract of the stem bark of Horsfieldia superba led to the isolation of twenty compounds (1-20), of which three (1-3) were new. However, compounds 2 and 3 were previously reported as synthetic alpha,beta-lactones. The compounds were characterized as (-)-3,4',7-trihydroxy-3'-methoxyflavan (1), (-)-5,6-dihydro-6-undecyl-2H-pyran-2-one (2), and (-)-5,6-dihydro-6-tridecyl-2H-pyran-2-one (3). Seventeen other known compounds were also isolated and identified as (-)-viridiflorol (4), hexacosanoic acid (5), beta-sitosterol (6), methyl 2,4-dihydroxy-6-methylbenzoate (methylorsellinate) (7), methyl 2,4-dihydroxy-3,6-dimethylbenzoate (8), (-)-4'-hydroxy-7-methoxyflavan (9), (-)-4',7-dihydroxyflavan (10), (-)-4',7-dihydroxy-3'-methoxyflavan (11), (+)-3,4',7-trihydroxyflavan (12), (-)-catechin (13), (-)-epicatechin (14), (-)-7-hydroxy-3',4'-methylenedioxyflavan (15), 2',3,4-trihydroxy-4'-methoxydihydrochalcone (16), 3',4',7-trihydroxyflavone (17), (+)-4'-hydroxy-7-methoxyflavanone (18), hexadecanoic acid (palmitic acid) (19) and 3,4-dihydroxybenzoic acid (20). The structures of the compounds were fully characterized by various physical methods (melting point, optical rotation), spectral (UV, IR, ID and 2D NMR) and mass spectrometric techniques. In vitro assay of compounds 2 and 3 demonstrated moderate cytotoxic activities against human prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cells, while the chloroform and ethyl acetate fractions of H. superba were found to exhibit moderate AChE inhibitory activity (IC50 72 and 60 microg/mL).

Item Type:Article
Keyword:Horsfieldia superba; Myristicaceae; Flavan; Alkyl alpha; Beta-lactones; Cytotoxicity; Acetylcholinesterase inhibitor
Faculty or Institute:Faculty of Food Science and Technology
Publisher:Natural Product Communications
ID Code:30491
Deposited By: Khairil Ridzuan Khahirullah
Deposited On:03 Dec 2014 13:05
Last Modified:17 Sep 2015 11:51

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