Alkenylresorcinols and cytotoxic activity of the constituents isolated from Labisia pumila.
Phytochemical investigation on the leaves of Labisia pumila (Myrsinaceae), an important medicinal herb in Malaysia, has led to the isolation of 1-O-methyl-6-acetoxy-5-(pentadec-10Z-enyl)resorcinol (1), labisiaquinone A (2) and labisiaquinone B (3). Along with these, 16 known compounds including 1-O-methyl-6-acetoxy-5-pentadecylresorcinol (4), 5-(pentadec-10Z-enyl)resorcinol (5), 5-(pentadecyl)resorcinol (6), (-)-loliolide (7), stigmasterol (8), 4-hydroxyphenylethylamine (9), 3,4,5-trihydroxybenzoic acid (10), 3,4-dihydroxybenzoic acid (11), (+)-catechin (12), (-)-epicatechin (13), kaempferol-3-O-α-rhamnopyranosyl-7-O-β-glycopyranoside (14), kaempferol-4'-O-β-glycopyranoside (15), quercetin-3-O-α-rhamnopyranoside (16), kaempferol-3-O-α-rhamnopyranoside (17), (9Z,12Z)-octadeca-9,12-dienoic acid (18) and stigmasterol-3-O-β-glycopyranoside (19) were also isolated. The structures of these compounds were established on the basis of 1D and 2D NMR spectroscopy techniques (¹H, ¹³C, COSY, HSQC, NOESY and HMBC experiments), mass spectrometry and chemical derivatization. Among the constituents tested 1 and 4 exhibited strongest cytotoxic activity against the PC3, HCT116 and MCF-7 cell lines (IC₅₀ values ≤ 10 μM), and they showed selectivity towards the first two-cell lines relative to the last one.
Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Malaysia.
Nabil Ali
NA
Al-Mekhlafi
Khozirah
K
Shaari
Faridah
F
Abas
Ralf
R
Kneer
Ethel Jeyaseela
EJ
Jeyaraj
Johnson
J
Stanslas
Naoshi
N
Yamamoto
Toshio
T
Honda
Nordin H
NH
Lajis
D000970:Antineoplastic Agents / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D029623:Primulaceae / Q000737:chemistry*; D012118:Resorcinols / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D012118:Resorcinols; C031389:resorcinol