A New Friedelane Type Triterpene from Euonymus hederaceus

Abstract

Euonymus hederaceus is distributed widely in the south of China; its stems and leaves have been used as folk medicines to treat many diseases such as renal deficiency and chronic diarrhea, traumatic injury, and abnormal menstruation. Chemical investigation of the leaves and stems of Euonymus hederaceus resulted in the isolation for the first time and characterization of a new friedelane type triterpene with a molecular mass of 472 and molecular formula of C30H48O4 by high resolution mass spectrometry. The 1H-NMR 13C-NMR and DEPT1350 spectra matched the characteristic data of the proposed triterpene skeleton. The compound was finally identified as 28-hydroxyfriedelan-3-one-29-oic acid on the basis of spectroscopic evidence, including two dimensional nuclear magnetic resonance as well as its IR spectrum.

Secondary metabolites from Triclisia gilletii (De Wild) Staner (Menispermaceae) with antimycobacterial activity against Mycobacterium tuberculosis

“…However, no correlation was reportedly observed with H-24, H-25 and H-26 from H-28 and H-30. Therefore, it was speculated that D and E-rings of compound 1 adopted boat-boat conformation due to the lack of correlations between H-28 and H-30 ( Figure S1), confirming the difference of stereochemistry of C-17 and other analogues (Chiozem et al 2009;Sun et al 2009;Sousa et al 2012). These additional data have not been reported previously in the literature.…”

“…Consequently, the published values for drypemolundein B could not be accurate. Even though the 3 ppm gap between compounds analysed in the same solvent is considered acceptable (Garson et al 2017), a re-evaluation of the 13 C-NMR shift values suggested that the signals at 31.7 and 34.2 ppm, previously assigned to C-29 and C-30, respectively, were rather associated to C-30 and C-29 (Chiozem et al 2009;Sun et al 2009;Sousa et al 2012 and from this study). Furthermore, NOESY correlations corroborated these revised chemical shift assignments in compound 1, for example key NOESY correlations were observed between H-27 ( H 1.02) and methine at H 1.41 and not 2.38 (H-8) as previously ascribed.…”

Genus Euonymus: Chemical and Pharmacological Perception

“…Twigs of E.alata are used as traditional medicine for stomach ache and as a vermicide in Japan [25]. Euonymus hederaceus is distributed widely in the south of China, its stem and leaves have been used as folk medicines to treat many diseases such as renal deficiency and chronic diarrhea, traumatic injury and abnormal mensuration [63]. An aerial part of E.hamiltonianus is used as diuretic, carminative and stimulant [3,27].…”

“…12-oleanene-3,11-dione (135), 28-hydroxyolean-12-ene-3,11dione (136), 28-hydroxyfriedelan-3-one-29-oic acid (137) [62,63]. …”

3-Oxo-11β-Hydroxyfriedelane from the Roots of Celastrus Monospermus

“…1 Friedelin (3-oxo-friedelane) triterpenes are a very important class. Their sesquiterpene and triterpene constituents possess antibacterial, anti-tumour, insect antifeedant and cytotoxic activities.…”