Melanogenesis Inhibitory, Anti-Inflammatory, and Chemopreventive Effects of Limonoids from the Seeds of Azadirachta indicia A. Juss. (Neem)

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概要

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• Thirty-one nortriterpenoids, including 28 limonoids (1-28) and 3 degraded limonoids (29-31), and one diterpenoid (32), were isolated from the seed extract of Azadirachta indica (neem). Among these, six were new compounds and their structures were established to be 15-hydroxyazadiradione (3), 7-benzoyl-17-hydroxynimbocinol (5), 23-deoxyazadironolide (12), limocin E (13), 23-epilimocin E (14), and 7α-acetoxy-3-oxoisocopala-1,13-dien-15-oic acid (32). Upon evaluation of compounds 1-32 on the melanogenesis in the B16 melanoma cells, five compounds, 20, 26, 27, 29, and 31, exhibited marked inhibitory effect (74-91% reduction of melanin content at 25 μg/mL) with no or almost no toxicity to the cells. Seven compounds, 1, 6, 9, 10, 18, 20, and 26, on evaluation for their inhibitory effect against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 μg/ear) in mice, exhibited, except for compound 26, marked anti-inflammatory activity (ID50 values 0.09-0.26 mg/ear). In addition, all of the 32 compounds exhibited moderate or potent inhibitory effects (IC50 values of 230-501 mol ratio/32 pmol TPA) against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA. Furthermore, on evaluation of azadirachtin B (21) for its anti-tumor-initiating activity on the two-stage carcinogenesis of mouse skin tumor induced by peroxynitrite (ONOO-; PN) as an initiator and TPA as a promoter, this exhibited marked inhibitory activity.

• 日本油化学会の論文

著者

• Suzuki Takashi

  College of Pharmacy, Nihon University

• Akihisa Toshihiro

  College of Science and Technology, Nihon University

• TOKUDA Harukuni

  Department of Molecular Biochemistry, Kyoto Prefectural University of Medicine

• KOIKE Kazuo

  School of Pharmaceutical Sciences, Toho University

• Takahashi Akitomo

  College of Science and Technology, Nihon University

• Fujita Yukiko

  Ichimaru Pharcos Company Ltd.

• Banno Norihiro

  Ichimaru Pharcos Company Ltd.

• Kimura Yumiko

  College Of Pharmacy Nihon University

• Koike Kazuo

  School Of Pharmaceutical Sciences Toho University

• YASUKAWA Ken

  College of Pharmacy, Nihon University

• Banno Norihiro

  Ichimaru Pharcos Co. Ltd.

• Yasukawa Ken

  College Of Pharmacy Nihon University

• Akihisa T

  College Of Pharmacy Nihon University

• Akihisa Toshihiro

  日本大学 理工学部

• Akihisa Toshihiro

  College Of Science And Technology Nihon University

• Tokuda Harukuni

  Department Of Biochemistry And Molecular Biology Kyoto Prefectural University Of Medicine

• Noto Taisuke

  College of Science and Technology, Nihon University

• KOIKE KAZUO

  School of Pharmaceutical Science, Toho University

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