RRC ID 71707
Author Kitdamrongtham W, Ishii K, Ebina K, Zhang J, Ukiya M, Koike K, Akazawa H, Manosroi A, Manosroi J, Akihisa T.
Title Limonoids and flavonoids from the flowers of Azadirachta indica var. siamensis, and their melanogenesis-inhibitory and cytotoxic activities.
Journal Chem Biodivers
Abstract A new limonoid, 7-O-acetyl-7-O-debenzoyl-22-hydroxy-21-methoxylimocinin (2), and two new flavonoids, 3'-(3-hydroxy-3-methylbutyl)naringenin (7) and 4'-O-methyllespedezaflavanone C (9), along with nine known compounds, including two limonoids, 1 and 3, and seven flavonoids, 4-6, 8, and 10-12, were isolated from a MeOH extract of the flowers of Azadirachta indica A.Juss. var. siamensis Valeton (Siamese neem tree; Meliaceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. All of these compounds were evaluated for their melanogenesis-inhibitory activities in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH). Compound 2 (16.9% melanin content at 30 μM), 6-deacetylnimbin (3; 49.6% melanin content at 100 μM), and kaempferide (10; 41.7% melanin content at 10 μM) exhibited inhibitory effects with no, or almost no, toxicity to the cells (81.0-111.7% cell viability). In addition, evaluation of their cytotoxic activities against HL60, A549, AZ521, and SK-BR-3 human cancer cell lines, isoazadironolide (1), 4'-O-methyl-8-prenylnaringenin (5), euchrestaflavanone A (8), 9, and 3-methoxy-3'-prenylnaringenin (12) revealed potent cytotoxicities against one or more cell lines with IC50 values in the range of 4.5-9.9 μM.
Volume 11(1)
Pages 73-84
Published 2014-1-1
DOI 10.1002/cbdv.201300266
PMID 24443427
MeSH Animals Antineoplastic Agents, Phytogenic / chemistry Antineoplastic Agents, Phytogenic / isolation & purification Antineoplastic Agents, Phytogenic / pharmacology* Azadirachta / chemistry* Cell Line, Tumor Cell Proliferation / drug effects Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Flavonoids / chemistry Flavonoids / isolation & purification Flavonoids / pharmacology* Flowers / chemistry* HL-60 Cells Humans Inhibitory Concentration 50 Limonins / chemistry Limonins / isolation & purification Limonins / pharmacology* Melanins / biosynthesis* Melanins / metabolism Mice Molecular Conformation Structure-Activity Relationship
IF 2.039
Human and Animal Cells B16 melanoma 4A5(RCB0557) HL60(RCB0041) A549(RCB0098) SK-BR-3(RCB2132)