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The melanogenesis-inhibitory, anti-inflammatory, and chemopreventive effects of limonoids in n-hexane extract of Azadirachta indica A. Juss. (neem) seeds.

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.
AuthorsToshihiro Akihisa, Akitomo Takahashi, Takashi Kikuchi, Mio Takagi, Kensuke Watanabe, Makoto Fukatsu, Yukiko Fujita, Norihiro Banno, Harukuni Tokuda, Ken Yasukawa
JournalJournal of oleo science (J Oleo Sci) Vol. 60 Issue 2 Pg. 53-9 ( 2011) ISSN: 1347-3352 [Electronic] Japan
PMID21263200 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Anti-Inflammatory Agents
  • Antigens, Viral
  • Epstein-Barr virus early antigen
  • Fatty Acids
  • Hexanes
  • Limonins
  • Melanins
  • Plant Extracts
  • n-hexane
  • Tetradecanoylphorbol Acetate
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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