New Eremophilane Sesquiterpenes from a Rhizome Extract of Petasites hybridus

✍ Scribed by Antje Bodensieck; Olaf Kunert; Ernst Haslinger; Rudolf Bauer

• Book ID: 102254768
• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: German
• Weight: 136 KB
• Volume: 90
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200790014

✦ Synopsis

Abstract

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.