Antimicrobially Active Hederagenin Glycosides from Cephalaria elmaliensis

Abstract

A phytochemical investigation of the aerial parts of Cephalaria elmaliensis resulted in the isolation of ten hederagenin-type triterpene saponins (1-10) including three new ones, elmalienoside A (1), elmalienoside B (2), elmalienoside C (3), and two known flavonoid glycosides (11-12). Their structures were identified by extensive spectroscopic techniques (1D and 2D NMR, HR ESIMS) and chemical evidence. The antimicrobial activity of the extracts and the pure compounds was evaluated by the MIC method. According to the results, all pure compounds including the new ones were found to be very active against both gram-positive and gram-negative bacteria.

Genome-Wide Transcriptional Excavation of Dipsacus asperoides Unmasked both Cryptic Asperosaponin Biosynthetic Genes and SSR Markers

“…Since Dipsacus saponin VI is the primary active ingredient in D. asperoides , there must exist glycosylases catalyzing glycosylations (Shi et al, 2011 ) substituted hydroxyl groups of hederagenin by one of four compounds: glucose from UDP-D-glucose, arabinose from UDP-L-arabinose, rhamonose from UDP-L-rhamonose, and xylose from UDP-D-xylose. Obviously, it is rather hederagenin-type (Sarikahya and Kirmizigül, 2012 ) substrates than oleanane-type (Zhang et al, 2015 ) triterpenoid substrates which are bonded hydroxyl groups on the kind of carbon skeleton precursors (Liu et al, 2011 ). We screened the RNA-Seq dataset, and found new genes participating in glycosylation of hederagenin.…”

Identification of novel compounds, oleanane- and ursane-type triterpene glycosides, from Trevesia palmata: their biocontrol activity against phytopathogenic fungi

“…Macranthoside A and α -hederin have previously been isolated from a variety of plants, such as Japanese angelica tree ( Aralia elata ) and ivy plants ( Hedera spp. ), and these compounds exhibited antimicrobial, antitumor, and cytoprotective activities 24 – 29 . Ilekudinoside D was first isolated from the leaves of Ilex kudincha in the course of screening for acyl CoA cholesteryl acyl transferase inhibitors, but its biological activity was not further characterized 23 .…”

Phytochemical and Biological Investigations on Cephalaria anatolica

“…This wide range of usages has led to investigations on different Cephalaria species. Many chemical identification studies have been reported that this genus contains triterpenoid saponins, flavonoids, alkaloids, furofuranic lignans and iridoids [5][6][7][8][9][10][11][12][13]. According to these literatures, it is also known that these compounds have different activities including antimicrobial, hemolytic, hypolipidemic, immunomodulating and cytotoxic [7-8, 11-12, 14].…”

“…The structures of the new triterpene glycosides were determined as 3-O-β-D-glucopyranosyl- (2). The known compounds were identified as davisianoside A (3), davisianoside B (4) [15], elmalienoside A (5), elmalienoside B (6) [8], macranthoside A (7) [16], macranthodin A (8), macranthodin B (9) [17], akebia saponin D (10), dipsacoside B (11) [18], 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranosyl hederagenin 28-O-β-D-glycopyranosyl ester (12) [19] and aristatoside A (13) [10]. The structures of these compounds were identified by chemical methods including acidic and alkaline hydrolysis, silylation and extensive spectroscopic analysis, along with 1D, 2D NMR and HRESIMS data.…”