Parviflorals A-F, trinorcadalenes and bis-trinorcadalenes from the roots of Decaschistia parviflora

Phytochemistry. 2013 Nov:95:368-74. doi: 10.1016/j.phytochem.2013.07.017. Epub 2013 Aug 10.

Abstract

Trinorcadalenes, parviflorals A and B (1 and 2), and four bis-trinorcadalenes, parviflorals C-F (3-6), together with the known trinorcadalenes, syriacusins A (7) and C (8), scopoletin (9) and stigmasterol were isolated from roots of Decaschistia parviflora. Their structures were established by spectroscopic techniques. The CD spectra of the bis-trinorcadalenes (3-6) established their absolute configurations at the binaphthyl axis. Further, structure 6 was confirmed by a single-crystal X-ray crystallographic analysis. Compounds 2 and 6 showed antimalarial activity against Plasmodium falciparum with IC50 values of 11.45 and 6.85 μM, respectively. Compounds 1, 5, 7 and 8 also exhibited weak antifungal activity against Candida albicans, with IC50 values in the range of 37.03-197.68 μM. Compounds 1-3 and 5-8 showed weak antimycobacterial activity against Mycobacterium tuberculosis with MIC values in the range of 54.30-192.13 μM. In addition, several of these compounds possessed cytotoxicity towards the cancer cell lines, KB, MCF7 and NCI-H187 with IC50 values in the range of 2.20-90.09 μM.

Keywords: Antimalarial; Binaphthyl; Cytotoxicity; Decaschistia parviflora; Malvaceae; Parvifloral; Trinorcadalenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Antineoplastic Agents, Phytogenic / therapeutic use
  • Candida albicans / drug effects*
  • Humans
  • Inhibitory Concentration 50
  • KB Cells
  • MCF-7 Cells
  • Malvaceae / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Neoplasms / drug therapy*
  • Phytotherapy
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • Plant Extracts / therapeutic use
  • Plant Roots / chemistry*
  • Plasmodium falciparum / drug effects*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antimalarials
  • Antineoplastic Agents, Phytogenic
  • Plant Extracts