Semisynthesis of mallotus B from rottlerin: evaluation of cytotoxicity and apoptosis-inducing activity.

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 "rottlerone" 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 μM, 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.
AuthorsShreyans K Jain, Anup S Pathania, Samdarshi Meena, Rajni Sharma, Ashok Sharma, Baljinder Singh, Bishan D Gupta, Shashi Bhushan, Sandip B Bharate, Ram A Vishwakarma
JournalJournal of natural products (J Nat Prod) Vol. 76 Issue 9 Pg. 1724-30 (Sep 27 2013) ISSN: 1520-6025 [Electronic] United States
PMID24041234 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Acetophenones
  • Antineoplastic Agents
  • Benzopyrans
  • mallotus B
  • Phloroglucinol
  • rottlerin
  • Acetophenones (chemical synthesis, chemistry, pharmacology)
  • Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
  • Benzopyrans (chemical synthesis, chemistry, pharmacology)
  • Cell Cycle (drug effects)
  • Cell Division (drug effects)
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Hep G2 Cells
  • Humans
  • Mallotus Plant (chemistry)
  • Molecular Structure
  • Phloroglucinol (analogs & derivatives, chemical synthesis, chemistry, pharmacology)

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