Crystal structure and antibacterial evaluation of epifriedelinol isolated from Vitex peduncularis Wall. ex Schauer

Abstract

Epifriedelinol, an antibacterial pentacyclic triterpene was isolated from the methanol extract of Vitex peduncularis by bio-assay guided separation and the structure of the compound was elucidated by various spectroscopic methods such as 1 H NMR, 13 C NMR and single crystal X-ray Diffraction. The antibacterial activity of epifriedelinol was examined against five species of Gram positive and seven strains of Gram negative bacteria. The presence of epifriedelinol in V. peduncularis and its antibacterial activity were reported for the first time. ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

In Vitro Cytotoxic Study of Euphorbia grantii Oliv. Aerial Parts against MCF-7 and MCF-7ADR Breast Cancer Cell Lines: A Bioactivity-Guided Isolation

“…The isolated compounds were identified as friedelin ( 1 ), 3-β- friedelinol ( 2 ), epifriedelanol ( 3 ), euphol ( 4 ), cycloartenyl acetate ( 5 ), cycloartenol ( 6 ), epifriedelinyl acetate ( 7 ), and euphylbenzoate ( 8 ) using 1 H and 13 C NMR (see the Supporting Information). The structures of the isolated compounds were elucidated by comparison of their physical and spectral data ( 1 H and 13 C NMR) with those mentioned in the literature. − …”

Phytochemical Characterization of Cannabis sativa L. Roots from Northeastern Brazil

“…The 13 C‐NMR spectrum ( Figure 8) of the compounds 1 and 2 showed 32 carbon signals ( Table 2). The main chemical shifts referring to the presence of the compound 1 were: the signal at δ C 72.8 ppm (C‐3), indicative of the presence of carbinolic carbon; the signal at δ C 49.2 ppm, attributed to the methine carbon (C‐4); and the signal at δ C 11.6 ppm, which corresponds to the methyl group (C‐23) bonded to C‐4 [18] . The 1 H‐NMR spectrum ( Figure 9) for compound 1 showed a broad singlet at δ H 3.73 ppm, corresponding to hydrogen (H‐3) bonded to the carbinolic carbon, which is unshielded due to the electron‐withdrawing inductive effect exerted by oxygen atom.…”

“…Studies performed with the pentacyclic triterpene epifriedelanol showed that the compound possesses antibacterial activity [18] . Friedelan‐3‐one exhibits antiproliferative, antioxidant, anti‐inflammatory, analgesic and antipyretic activities [31] .…”

Protective effects of epifriedelinol in a rat model of traumatic brain injury assessed with histological and hematological markers

“…However, the secondary injury induced by TBI cannot be managed with existing drugs. Epifriedelinol (EFD), isolated from the roots of Aster tataricus [ 12 ], has strong anti-inflammatory, antibacterial, antioxidant, and anti-cancer effects [ 13 , 14 ]. This study evaluated the protective effects of EFD in TBI.…”