Sesquiterpene Xylosides from Iphiona mucronata

Journal of Natural Products
1990.0

Abstract

Six sesquiterpene xylosides have been isolated from the polar extract of the aerial parts of Zphiona mucronata, including a previously unreported one. The structures were elucidated by spectroscopic methods and correlated with known compounds. Earlier investigations of the flavonoids of two species of the small genus Iphiona Cass. (Family Compositae, Tribe Inuleae) have been studied. Iphiona scabra and Iphiona mucronata (Forssk.) Asch. et Schweinf. (1,2) revealed that polysulfated flavonoids were the major constituents and seem to be characteristic for the genus. Aerial parts of I. scabra afforded a complex mixture of sesquiterpene xylosides (3,4). Nothing is known in the literature concerning the terpenoids of I. mucronata with the exception of the report of thymol derivatives (5,6). We therefore studied I. mucronata for its terpenoids. The polar extract of the aerial parts of I. mucronata afforded six sesquiterpene xylosides, 1-6, which could be separated in pure state without prior acetylation. The ¹H nmr of the acetylated products of 1-6 were identical to those which have been reported from I. scabra (3). The ¹H-nmr data of 1 differed from those of 2 by the absence of the acetate methyl signal at δ 1.99 and the upfield shift of the double doublet at δ 4.62 in 2 to δ 3.30 in 1. This suggested that 1 contained no acetyl group. Furthermore, the chemical shifts as well as the coupling constants of the sugar protons indicated clearly that a xylopyranoside was present (H-1' at δ 4.53 d, H-2' at δ 3.30 dd, H-3' at δ 3.47 dd, H-4' at δ 3.57 ddd, H-5' at δ 3.95 dd and 3.25 dd). The signals for the sesquiterpene skeleton, including a sharp three-proton singlet, showed that we were dealing with β-eudesmol. The Δ³ bond was indicated by the broadened signal at δ 5.26, while the olefinic methyl appeared as a broad singlet at δ 1.55. The chemical shift of the isopropyl methyl signals at δ 1.19 and 1.18 showed that the sugar moiety could be at C-11. Similarly, the coupling constant and the chemical shift of H-5 as well as the chemical shift of H-14 confirmed the 5,10 trans skeleton. The ¹H nmr, ms, and ir of the acetylated products of 1 and 2 were completely identical with the previous report (3). Compounds 2 and 3 have been reported in mixture (3). We isolated both compounds in the pure state, and 1 has not been previously reported. In conclusion, it seems that sesquiterpene xylosides as well as polysulfated flavonoids are typical for the genus Iphiona and may be of chemotaxonomic value.

Knowledge Graph

Similar Paper