Antineoplastic Agents. 585. Isolation of Bridelia ferruginea Anticancer Podophyllotoxins and Synthesis of 4-Aza-podophyllotoxin Structural Modifications

George Pettit, Justin D. Searcy, Rui Tan, Gordon M. Cragg, Noeleen Melody, John C. Knight, Jean Chapuis

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Cytotoxic constituents of the terrestrial plant Bridelia ferruginea were isolated using bioactivity-guided fractionation, which revealed the presence of the previously known deoxypodophyllotoxin (1), isopicrodeoxypodophyllotoxin (2), β-peltatin (3), β-peltatin-5-O-β-d-glucopyranoside (3a), and the indole neoechinulin (4). As an extension of previous podophyllotoxin research, SAR studies were undertaken focused on 4-aza-podophyllotoxin structural modifications. A number of such derivatives were synthesized following modifications to the A and E rings. Such structural modifications with alkyl and 4-fluorobenzyl substituents at the 4-aza position provided the most potent cancer cell growth inhibitory activity (GI50 0.1 to

Original languageEnglish (US)
Pages (from-to)507-518
Number of pages12
JournalJournal of Natural Products
Volume79
Issue number3
DOIs
StatePublished - Mar 25 2016

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Podophyllotoxin
Antineoplastic Agents
Cell growth
Fractionation
Growth
Bioactivity
Research
Neoplasms
Derivatives
indole
4-aza-podophyllotoxin
deoxypodophyllotoxin
neoechinulin

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmacology
  • Pharmaceutical Science
  • Analytical Chemistry
  • Organic Chemistry
  • Molecular Medicine
  • Complementary and alternative medicine

Cite this

Antineoplastic Agents. 585. Isolation of Bridelia ferruginea Anticancer Podophyllotoxins and Synthesis of 4-Aza-podophyllotoxin Structural Modifications. / Pettit, George; Searcy, Justin D.; Tan, Rui; Cragg, Gordon M.; Melody, Noeleen; Knight, John C.; Chapuis, Jean.

In: Journal of Natural Products, Vol. 79, No. 3, 25.03.2016, p. 507-518.

Research output: Contribution to journalArticle

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