Premium
New Eremophilane Sesquiterpenes from a Rhizome Extract of Petasites hybridus
Author(s) -
Bodensieck Antje,
Kunert Olaf,
Haslinger Ernst,
Bauer Rudolf
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790014
Subject(s) - chemistry , rhizome , sesquiterpene , stereochemistry , terpene , organic chemistry , traditional medicine , medicine
A total of 21 natural products, 1 – 21 , were isolated from a supercritical CO 2 extract of the rhizomes of Petasites hybridus. Thereby, seven new eremophilane (= (1 S ,4a R ,7 R ,8a R )‐decahydro‐1,8a‐dimethyl‐7‐(1‐methylethyl)naphthalene) sesquiterpenes, compounds 4, 5, 9, 11, 12, 15 , and 17 , were identified. The new constituent 9‐hydroxyisobakkenolide ( 15 ) is the first representative of a group of compounds closely related to the well‐known, but rare, bakkenolides. Tsoongianolide B ( 18 ) and its degradation product ligularenolide ( 19 ) were found as new Petasites constituents as well. The known eremophilanolide 2 was isolated from a plant source for the first time and the oxofuranopetasin 16 was isolated for the first time from the rhizomes of P. hybridus , together with eight other known compounds. The C(8)‐epimeric 2‐[(tigloyl)oxy]eremophilanolides 3 and 8 could clearly be differentiated. All structures were established by extensive 1D‐ and 2D‐NMR experiments ( Tables 1–3 ), and confirmed by in‐depth GC/MS and HPLC/MS experiments.