Biologically active secondary metabolites from Asphodelus microcarpus.
Bioassay guided fractionation of the ethanolic extract of Asphodelus microcarpus Salzm.et Vivi (Asphodelaceae) resulted in the isolation of one new metabolite, 1,6-dimethoxy-3-methyl-2-naphthoic acid (1) as well as nine known compounds: asphodelin (2), chrysophanol (3), 8-methoxychrysophanol (4), emodin (5), 2-acetyl-1,8-dimethoxy-3-methylnaphthalene (6), 10-(chrysophanol-7'-yl)-10-hydroxychrysophanol-9-anthrone (7), aloesaponol-III-8-methyl ether (8), ramosin (9) and aestivin (10). The compounds were identified by 1D and 2D NMR and HRESIMS. Compounds 3, 6 and 10 were isolated for the first time from this species. Compounds 3 and 4 showed moderate to weak antileishmanial activity with IC50 values of 14.3 and 35.1 microg/mL, respectively. Compound 4 exhibited moderate antifungal activity against Cryptococcus neoformans with an IC50 value of 15.0 microg/mL, while compounds 5, 7 and 10 showed good to potent activity against methicillin resistant Staphylococcus aureus (MRSA) with IC50 values of 6.6, 9.4 microg/mL and 1.4 microg/mL respectively. Compounds 5, 8 and 9 displayed good activity against S. aureus with IC50 values of 3.2, 7.3 and 8.5 microg/mL, respectively. Compounds 7 and 9 exhibited a potent cytotoxic activity against leukemia LH60 and K562 cell lines. Compound 10 showed potent antimalarial activities against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum with IC50 values in the range of 0.8-0.7 microg/mL without showing any cytotoxicity to mammalian cells.
National Center for Natural Products Research School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
Mohammed M
MM
Ghoneim
Guoyi
G
Ma
Atef A
AA
El-Hela
Abd-Elsalam I
AE
Mohammad
Saeid
S
Kottob
Sayed
S
El-Ghaly
Stephen J
SJ
Cutler
Samir A
SA
Ross
D000890:Anti-Infective Agents / Q000302:isolation & purification*; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification*; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D020014:K562 Cells; D019668:Liliaceae / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D009281:Naphthalenes / Q000302:isolation & purification*; D010946:Plants, Medicinal / Q000737:chemistry
C584637:1,6-dimethoxy-3-methyl-2-naphthoic acid; D000890:Anti-Infective Agents; D000972:Antineoplastic Agents, Phytogenic; D009281:Naphthalenes