Isolation and Identification of Chemical Constituents from Stahlianthus Involucratus

Le résumé fourni par la source

Zingiberaceae is a large family of the perennial herbaceous plants, members of which have attracted continuous phytochemical interest due to their culinary uses as well as their biological and the pharmaceutical activities. Stahlianthus involucratus is a tropical Zingiberaceae plant and its rhizomes have long been used in traditional medicine to treat inflammation, pain, and fever. In order to clarify the action mechanism of Stahlianthus involucratus and its further development and utilization, systematic study of the chemical composition of Stahlianthus involucratus is of great significance. Previous phytochemical investigations on this species resulted in isolation of cadinane dimers, sesquiterpenoids. In order to further study the chemical constituents of Stahlianthus involucratus, different column chromatographic techniques such as semi-preparative high perfrmance liquid chrmatgraphy and the column chromatography were used to separate and the purify chemical constituents from ethyl acetate fraction and n-hexane fraction of 75% ethanol extract of Stahlianthus involucratus, and the structures of monomer compound were elucidated by mass spectrometry and NMR. Eleven compounds were separated and purified, which were identified as: stigmastern (1), 2–hydroxy–1,2–bis[5–(hydroxymethyl)–2–furanyl]ethenone (2), (Z)–2–acetoxy–5–ethylidene–2–methyl–3–methylenehexanedioic acid (3), hexanedioic acid, 2–(acetyloxy)–5–ethylidene–2,3–dimethyl–, [R–[R*,S*–(Z)]]–(9CI) (4), hexanedioic acid, 5–ethylidene–2–hydroxy–2,3–dimethyl–, [R–[R*,S*–(Z)]]–(9CI) (5), 1,4-dihydroxy–2–methylbenzene (6), 2–ethyl–2–butenoic acid (7), 2–furoic acid (8), (2E)–3–(4–hydroxyphenyl)–2–propenoic acid (9), senecio-nan-11,16-dione (10), Seneciphyllinine (11). Among these compounds, compound 3 was a new natural product and the others were known compounds. Compound 3 was obtained as a white amorphous powder. Its molecular formula was established as C12H16O6 by mass spectrometry at m/z 279.0841 ([M+Na]+). The relationship of C–H can be determined by13C NMR spectrum and HSQC experiments. Combined with the COSY spectrum, the structure of the compound can be inferred. According to chemical shift of the C–2 olefin proton in the1H NMR spectrum data, it can be inferred that the olefin between C–2 and C–3 is ofZ–isomerism. Herein, compound 3 was named as (Z)–2–acetoxy–5–ethylidene–2–methyl–3–methylenehexanedioic acid.

Ce résumé expose les affirmations des auteurs. BNTIC ne l’interprète pas comme une validation indépendante des résultats.