Spirocyclic acylphloroglucinol derivatives from Hypericum beanii

Chem Pharm Bull (Tokyo). 2011;59(10):1250-3. doi: 10.1248/cpb.59.1250.

Abstract

Four new acylphloroglucinols with an unusual 6/6/5 spirocyclic skeleton, hyperbeanols A-D (1-4), were isolated from the methanol extract of Hypericum beanii along with 16 known compounds. Their structures were established on the basis of spectroscopic and X-ray diffraction analysis. Hyperbeanols A-C were three stereoisomers different only at the relative configuration of C-4 and C-13, which were distinguished by the nuclear Overhauser effect spectroscopy (NOESY) spectroscopic data in combination with the single X-ray analysis of hyperbeanol A (1). The cytotoxic activity of hyperbeanols A-D against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 was also evaluated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Drug Evaluation, Preclinical
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Hypericum / chemistry*
  • Molecular Structure
  • Phloroglucinol / analogs & derivatives*
  • Phloroglucinol / chemistry
  • Phloroglucinol / metabolism
  • Phytotherapy*
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Stereoisomerism

Substances

  • Antineoplastic Agents, Phytogenic
  • Plant Extracts
  • Phloroglucinol