np400433g_si_001.pdf (1.77 MB)
Semisynthesis of Mallotus B from Rottlerin: Evaluation of Cytotoxicity and Apoptosis-Inducing Activity
journal contribution
posted on 2013-09-27, 00:00 authored by Shreyans
K. Jain, Anup S. Pathania, Samdarshi Meena, Rajni Sharma, Ashok Sharma, Baljinder Singh, Bishan
D. Gupta, Shashi Bhushan, Sandip B. Bharate, Ram A. VishwakarmaMallotus 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.