Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest

J Nat Prod. 2015 Jul 24;78(7):1543-7. doi: 10.1021/np501020m. Epub 2015 Jun 19.

Abstract

The two new lignans 3α-O-(β-D-glucopyranosyl)desoxypodophyllotoxin (1) and 4-O-(β-D-glucopyranosyl)dehydropodophyllotoxin (2) were isolated from Cleistanthus boivinianus, together with the known lignans deoxypicropodophyllotoxin (3), (±)-β-apopicropodophyllin (4), (-)-desoxypodophyllotoxin (5), (-)-yatein (6), and β-peltatin-5-O-β-D-glucopyranoside (7). The structures of all compounds were characterized by spectroscopic techniques. Compounds 1, 4, and 5 showed potent antiproliferative activities against the A2780 ovarian cancer cell line, with IC50 values of 33.0 ± 3.6, 63.1 ± 6.7, and 230 ± 1 nM, respectively. Compounds 2 and 7 showed only modest A2780 activities, with IC50 values of 2.1 ± 0.3 and 4.9 ± 0.1 μM, respectively, while compounds 3 and 6 had IC50 values of >10 μM. Compound 1 also had potent antiproliferative activity against the HCT-116 human colon carcinoma cell line, with an IC50 value of 20.5 nM, and compound 4 exhibited modest antiproliferative activity against the A2058 human caucasian metastatic melanoma and MES-SA human uterine sarcoma cell lines, with IC50 values of 4.6 and 4.0 μM, respectively.

Publication types

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

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / chemistry
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Proliferation / drug effects
  • Dioxoles / chemistry
  • Drug Screening Assays, Antitumor
  • Forests
  • HCT116 Cells
  • Humans
  • Inhibitory Concentration 50
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology*
  • Madagascar
  • Malpighiaceae / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plasmodium falciparum / drug effects
  • Stereoisomerism

Substances

  • 3alpha-O-(beta-D-glucopyranosyl)desoxypodophyllotoxin
  • 4-O-(beta-D-glucopyranosyl)dehydropodophyllotoxin
  • Antineoplastic Agents, Phytogenic
  • Dioxoles
  • Lignans
  • yatein
  • 4-Butyrolactone