Cytotoxic alkaloids from the whole plants of Zephyranthes candida

J Nat Prod. 2012 Dec 28;75(12):2113-20. doi: 10.1021/np3005425. Epub 2012 Nov 28.

Abstract

Seven new alkaloids, N-methylhemeanthidine chloride (1), N-methyl-5,6-dihydroplicane (5), O-methylnerinine (6), N-ethoxycarbonylethylcrinasiadine (7), N-ethoxycarbonylpropylcrinasiadine (8), N-phenethylcrinasiadine (9), and N-isopentylcrinasiadine (10), together with eight known alkaloids, hemeanthamin (2), 3-epimacronine (3), (+)-tazettine (4), N-methylcrinasiadine (11), trisphaeridine (12), 5,6-dihydrobicolorine (13), lycorine (14), and nigragillin (15), were isolated from the whole plants of Zephyranthes candida. The structures of the new compounds were established by spectroscopic data interpretation, with single-crystal X-ray diffraction analysis performed on 1. The absolute configuration of 3-epimacronine (3) was determined by single-crystal X-ray diffraction analysis with Cu Kα irradiation. Compounds 1-15 were evaluated for their in vitro cytotoxicity against five human cancer cell lines and the Beas-2B immortalized (noncancerous) human bronchial epithelial cell line. Compounds 1, 2, 9, and 14 exhibited cytotoxicity with IC(50) values ranging from 0.81 to 13 μM with selectivity indices as high as 10 when compared to the Beas-2B cell line.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amaryllidaceae Alkaloids / chemistry
  • Amaryllidaceae Alkaloids / isolation & purification*
  • Amaryllidaceae Alkaloids / pharmacology*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Crystallography, X-Ray
  • Dioxoles / chemistry
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Humans
  • Liliaceae / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phenanthridines / chemistry

Substances

  • Amaryllidaceae Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Dioxoles
  • Drugs, Chinese Herbal
  • Phenanthridines
  • trispheridine
  • tazettine
  • lycorine