Semisynthesis of Mallotus B from Rottlerin: Evaluation of Cytotoxicity and Apoptosis-Inducing Activity

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• 作者：Shreyans K. Jain ; Anup S. Pathania ; Samdarshi Meena ; Rajni Sharma ; Ashok Sharma ; Baljinder Singh ; Bishan D. Gupta ; Shashi Bhushan ; Sandip B. Bharate ; Ram A. Vishwakarma
• 刊名：Journal of Natural Products
• 出版年：2013
• 出版时间：September 27, 2013
• 年：2013
• 卷：76
• 期：9
• 页码：1724-1730
• 全文大小：529K
• 年卷期：v.76,no.9(September 27, 2013)
• ISSN：1520-6025

文摘

Mallotus B (2d) is a prenylated dimeric phloroglucinol compound isolated from Mallotus philippensis. There have been no reports on the synthesis or biological activity of this compound. In the present paper, a semisynthetic preparation of mallotus B is reported via base-mediated intramolecular rearrangement of rottlerin (1), which is one of the major constituents of M. philippensis. The homodimer 鈥渞ottlerone鈥?was also formed as one of the products of this base-mediated intramolecular reaction. Rottlerin (1), along with rottlerone (2c) and mallotus B (2d), was evaluated for cytotoxicity against a panel of cancer cell lines including HEPG2, Colo205, MIAPaCa-2, PC-3, and HL-60 cells. Mallotus B (2d) displayed cytotoxicity for MIAPaCa-2 and HL-60 cells with IC₅₀ values of 9 and 16 渭M, respectively. Microscopic studies in HL-60 cells indicated that mallotus B (2d) induces cell cycle arrest at the G1 phase and causes defective cell division. It also induces apoptosis, as evidenced by distinct changes in cell morphology.