Abstract |
Seventeen limonoids (tetranortriterpenoids 1-17) were isolated from the n-hexane extract of Azadirachta indica (neem) seeds. The previously unidentified compound 16 was established by spectroscopy to be 17-defurano-17-oxosalannin. The effects of six compounds, 6 and 11-15, on melanogenesis in B16 melanoma cells was evaluated; 2 compounds, salannin (13) and 3-deacetylsalannin (15), exhibited marked inhibitory effects (70-74% reduction of melanin content at 25 µg/mL) with only minor cytotoxicity (79-85% of cell viability). Eleven compounds, 2, 3, 5, 6, and 9-15, were evaluated for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1.7 nmol/ear) in mice; all exhibited marked anti-inflammatory activity (ID(50) values 0.22-0.57 µmol/ear). In addition, compounds 6 and 11-16 exerted moderate inhibition (IC(50) values of 410-471 mol ratio/32 pmol TPA) of TPA-induced Epstein-Barr virus early antigen ( EBV-EA) activation in Raji cells. The triacylglycerol fraction of the n-hexane extract contained oleic acid (50.2%) as the most predominant fatty acid constituent.
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Authors | Toshihiro Akihisa, Akitomo Takahashi, Takashi Kikuchi, Mio Takagi, Kensuke Watanabe, Makoto Fukatsu, Yukiko Fujita, Norihiro Banno, Harukuni Tokuda, Ken Yasukawa |
Journal | Journal of oleo science
(J Oleo Sci)
Vol. 60
Issue 2
Pg. 53-9
( 2011)
ISSN: 1347-3352 [Electronic] Japan |
PMID | 21263200
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Anti-Inflammatory Agents
- Antigens, Viral
- Epstein-Barr virus early antigen
- Fatty Acids
- Hexanes
- Limonins
- Melanins
- Plant Extracts
- n-hexane
- Tetradecanoylphorbol Acetate
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Topics |
- Animals
- Anti-Inflammatory Agents
(pharmacology)
- Antigens, Viral
(metabolism)
- Azadirachta
(chemistry)
- Cell Death
(drug effects)
- Chemoprevention
- Fatty Acids
(analysis)
- Hexanes
(chemistry)
- Limonins
(chemistry, isolation & purification, pharmacology)
- Magnetic Resonance Spectroscopy
- Melanins
(biosynthesis)
- Melanoma, Experimental
- Mice
- Plant Extracts
(chemistry)
- Seeds
(chemistry)
- Tetradecanoylphorbol Acetate
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