Prenylated benzophenone derivatives from Hypericum patulum

Naonobu Tanaka; Kanji Niwa; Yuki Yano; Yoshiki Kashiwada

doi:10.1007/s11418-019-01350-3

Prenylated benzophenone derivatives from Hypericum patulum

J Nat Med. 2020 Jan;74(1):264-268. doi: 10.1007/s11418-019-01350-3. Epub 2019 Aug 3.

Authors

Naonobu Tanaka¹, Kanji Niwa², Yuki Yano², Yoshiki Kashiwada³

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima, 770-8505, Japan. ntanak@tokushima-u.ac.jp.
² Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima, 770-8505, Japan.
³ Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima, 770-8505, Japan. kasiwada@tokushima-u.ac.jp.

PMID: 31377922
DOI: 10.1007/s11418-019-01350-3

Abstract

A new prenylated benzophenone, hypatulin C (1), was isolated from the leaves of Hypericum patulum together with a biogenetically related analog, hypelodin B (2). Hypatulin C (1) had a tricyclic [4.3.1.0^3,7]-decane moiety substituted by four prenyl groups. The structure of 1 was elucidated by detailed spectroscopic analyses, while the absolute stereochemistries of 1 and 2 were assigned by comparison of their ECD spectra with TDDFT calculated spectra.

Keywords: Hypatulin C; Hypericaceae; Hypericum patulum; Prenylated benzophenone.

MeSH terms

Benzophenones / chemistry*
Hypericum / chemistry*
Molecular Structure
Phloroglucinol / analogs & derivatives
Plant Leaves / chemistry
Prenylation
Stereoisomerism

Substances

Benzophenones
hypelodin B
Phloroglucinol