Petiolins A-C, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum

Naonobu Tanaka; Takaaki Kubota; Haruaki Ishiyama; Atsushi Araki; Yoshiki Kashiwada; Yoshihisa Takaishi; Yuzuru Mikami; Jun'ichi Kobayashi

doi:10.1016/j.bmc.2008.03.076

Petiolins A-C, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum

Bioorg Med Chem. 2008 May 15;16(10):5619-23. doi: 10.1016/j.bmc.2008.03.076. Epub 2008 Apr 6.

Authors

Naonobu Tanaka¹, Takaaki Kubota, Haruaki Ishiyama, Atsushi Araki, Yoshiki Kashiwada, Yoshihisa Takaishi, Yuzuru Mikami, Jun'ichi Kobayashi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

PMID: 18430575
DOI: 10.1016/j.bmc.2008.03.076

Abstract

Two new phloroglucinol derivatives possessing chromane skeleton, petiolins A (1) and B (2), and a new phloroglucinol derivative containing a dihydrofuran ring, petiolin C (3), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The gross structures of 1-3 were elucidated by spectroscopic data, and the relative stereochemistry of 3 was elucidated by NOESY data. Petiolins A-C (1-3) showed modest cytotoxicity, while petiolin C (3) exhibited antifungal activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antifungal Agents / chemistry*
Antifungal Agents / isolation & purification
Antifungal Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Drug Screening Assays, Antitumor
Humans
Hypericum / chemistry*
Leukemia L1210 / drug therapy*
Leukemia L1210 / pathology
Magnetic Resonance Spectroscopy / methods
Mice
Microbial Sensitivity Tests
Models, Molecular
Molecular Structure
Phloroglucinol / analogs & derivatives*
Phloroglucinol / chemistry*
Phloroglucinol / isolation & purification
Phloroglucinol / pharmacology*
Stereoisomerism
Trichophyton / drug effects*

Substances

Antifungal Agents
petiolin A
petiolin B
petiolin C
Phloroglucinol