Bioactive 30-Noroleanane Triterpenes from the Pericarps of Akebia trifoliata

Abstract

Abstract:Two new 30-noroleanane triterpenes, 2α,3β,20α-trihydroxy-30-norolean-12-en-28-oic acid (1), 2α,3β-dihydroxy-23-oxo-30-norolean-12,20(29)-dien-28-oic acid (2), were isolated from the pericarps of Akebia trifoliata, together with four known ones, 3β-akebonoic acid (3), 2α,3β-dihydroxy-30-noroleana-12,20(29)-dien-28-oic acid (4), 3α-akebonoic acid (5) and quinatic acid (6). Their structures were established on the basis of detailed spectroscopic analysis, and they were all isolated from the pericarps of A. trifoliata for the first time. Compounds 3−6 showed in vitro bacteriostatic activity against four assayed Gram-positive bacterial strains. In particular 3 showed antibacterial activity toward MRSA with a MIC value 25 μg/mL, which was more potent than kanamycin (MIC 125 μg/mL). No compounds showed antibacterial activity toward the three Gram-negative bacteria tested. Compounds 4 and 5 showed interesting in vitro growth inhibitory activity against human tumor A549 and HeLa cell lines, with IC 50 values ranging from 8.8 and 5.6 μM, respectively. Compounds 1, 2, 5 and 6 were further revealed to show significant in vitro α-glucosidase inhibitory activity with IC 50 values from 0.035 to 0.367 mM, which were more potent than the reference compound acarbose (IC 50 0.409 mM).

New 30-Noroleanane Triterpenoid Saponins from Holboellia coriacea Diels

“…Only compound 5 showed interesting cytotoxicity against HCT-116, HepG2 and SGC-7901 cell lines, with IC 50 values of 9.1, 15.2 and 41.0 µM, respectively. Previous cytotoxicity studies on this type of nortriterpenoids suggested that the exocyclic double bond at C-20(29) might be an important active center to "maintain" their potential cytotoxicity [5], while the present result suggested that the saccharide unit attached at C-28 could greatly reduce the in vitro cytotoxicity. …”

“…Recently, a phytochemical study revealed six triterpenoid saponins, including two noroleanane-type ones from a methanol extract of root of H. coriacea [2]. Noroleanane triterpenoids are recognized as characteristic constituents of the family Lardizabalaceae, some of which were revealed to show significant bioactivities [3][4][5]. Our interest in the chemistry of noroleanane triterpenoids prompted us to continue the phytochemical study of H. coriacea, whereby three new 30-noroleanane triterpenoid saponins (1-3) and five known ones (4)(5)(6)(7)(8) were obtained from the stem of the plant.…”

A four‐step filtering strategy based on ultra‐high‐performance liquid chromatography coupled to quadrupole‐time‐of‐flight tandem mass spectrometry for comprehensive profiling the major chemical constituents of Akebiae Fructus

“…In terms of chemical composition, published literature about AF has mainly focused on the separation and extraction of chemical components. Versatile botanical secondary metabolites of AF, including triterpenoids, triterpenoid saponins, phenylethanoid glycosides, coumarins, iridoids and essential oils, have been isolated by phytochemical approaches . Currently, few reports are focused on the systematic characterization of the chemical constituents from AF, and only a few compounds have been identified .…”

“…Versatile botanical secondary metabolites of AF, including triterpenoids, triterpenoid saponins, phenylethanoid glycosides, coumarins, iridoids and essential oils, have been isolated by phytochemical approaches. [22][23][24][25][26] Currently, few reports are focused on the systematic characterization of the chemical constituents from AF, and only a few compounds have been identified. 27,28 In addition, as a TCM, AF has been widely used in the Herein, we propose a UPLC/QTOF-MS E analysis coupled with a four-step strategy for comprehensive profiling of the main compounds of AF.…”

Validated UHPLC–MS/MS method for simultaneous determination of four triterpene saponins from Akebia trifoliata extract in rat plasma and its application to a pharmacokinetic study

“…Phytochemical investigation has found that A. trifoliata contains many constituents including triterpenes (Wang et al, ; Wang et al, ), triterpenoid saponins (Gao & Wang, ; Gao & Wang, ; Matsuzaki, Murano, Endo, & Kitanaka, ; Mimaki et al, ; Wang, Lu, & Lin, ; Xu et al, ), lignan glycosides (Guan et al, ), phenylpropanoids (Wang, Zhou, Xu, & Tan, ) and caffeoylquinic acid derivatives (Wang, Xu, Zhou, & Tan, ). Among them, the triterpenoid saponins are the main bioactive constituents which contribute to the diuretic pharmacological activity of A. trifoliata .…”