Bodiniosides S–Y, Seven New Triterpenoid Saponins from Elsholtzia bodinieri and Their Anti-Influenza Activities
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ABSTRACT:
SUBMITTER: Yang L
PROVIDER: S-EPMC8587758 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:Seven new triterpenoid saponins (1?7), together with three known ones (8?10), were isolated from Ilex pubescens. Elucidation of their structures was performed based on high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS), infrared spectra (IR), and nuclear magnetic resonance (NMR) spectroscopic data. The anti-inflammatory activity of the isolates toward lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages was investigated. The results demonstrated that compounds 3, 5, and 6 inhibited the expression of inducible nitric oxide synthase (iNOS) protein in comparison with LPS stimulation in RAW264.7 cells.
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Project description:Background:Panax notoginseng saponin (PNS) is the extraction from the roots and rhizomes of Panax notoginseng (Burk.) F. H. Chen. PNS is the main bioactive component of Xuesaitong, Xueshuantong, and other Chinese patent medicines, which are all bestselling prescriptions in China to treat cardiocerebrovascular diseases. Notoginsenoside R1 and ginsenoside Rg1, Rd, Re, and Rb1 are the principal effective constituents of PNS, but a systematic research on the rare saponin compositions has not been conducted. Objective:The objective of this study was to conduct a systematic chemical study on PNS and establish the HPLC fingerprint of PNS to provide scientific evidence in quality control. In addition, the cytotoxicity of the new compounds was tested. Methods:Pure saponins from PNS were isolated by means of many chromatographic methods, and their structures were determined by extensive analyses of NMR and HR-ESI-MS studies. The fingerprint was established by HPLC-UV method. The cytotoxicity of the compounds was tested by 3-(4,5-dimethylthiazol-2-yl)-2,5 -diphenyltetrazolium bromide assay. Results and Conclusion:Three new triterpenoid saponins (1-3) together with 25 known rare saponins (4-28) were isolated from PNS, except for the five main compounds (notoginsenoside R1 and ginsenoside Rg1, Rd, Re, and Rb1). In addition, the HPLC fingerprint of PNS was established, and the peaks of the isolated compounds were marked. The study of chemical constituents and fingerprint was useful for the quality control of PNS. The study on antitumor activities showed that new Compound 2 exhibited significant inhibitory activity against the tested cell lines.
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Project description:Inflammation is a very common and important pathological process that can cause many diseases. The discovery of anti-inflammatory drugs and the treatment of inflammation are particularly essential. Dammarane-type triterpenoid saponins (PNS) were demonstrated to show anti-inflammatory effects in the leaves of Panax notoginseng. Chromatographies and spectral analysis methods were combined to isolate and identify PNS. Moreover, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. As a result, eleven new dammarane-type triterpenoid saponins, notoginsenosides NL-A1-NL-A4 (1-4), NL-B1-NL-B3 (5-7), NL-C1-NL-C3 (8-10), and NL-D (11) were isolated, and their structures were identified by using various spectrometric techniques and chemical reactions. Among them, compounds 4 and 11 were characterized by the malonyl substitution at 3-position. The 3-malonyl substituted dammarane-type terpennoids were first obtained from natural products. In addition, compounds 1, 2, 5, 6, and 8-10 were found to play an important role in suppressing NO levels at 50 ?M, without cytotoxicity. All inhibitory activities were found to be dose-dependent.
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Project description:Three new 30-noroleanane triterpenoid saponins, akebonoic acid 28-O-β-d-glucopyranosyl-(1''→6')-β-d-glucopyranosyl ester (1), akebonoic acid 28-O-(6''-O-caffeoyl)-β-d-glucopyranosyl-(1''→6')-β-d-glucopyranosyl ester (Holboelliside A, 2) and 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 3-O-(6'-O-caffeoyl)-β-d-glucopyranoside (Holboelliside B, 3) were isolated from the stems of Holboellia coriacea Diels, together with five known compounds, eupteleasaponin VIII (4), 3α-akebonoic acid (5), quinatic acid (6), 3β-hydroxy-30-norhederagenin (7) and quinatoside A (8). The structures of these compounds were determined on the basis of spectral and chemical evidence. Compounds 1-5 were evaluated for their inhibitory activity against three human tumors HepG2, HCT116 and SGC-7901 cell lines in vitro.
| S-EPMC6274467 | biostudies-literature
Project description:Two new bidesmoside triterpenoid saponins which were identifed as 28-O-?-D-xylopyranosyl(1?3)-?-D-xylopyranosyl(1?4)-?-L-rhamnopyranosyl(1?2)-[?-L-rhamno-pyranosyl(1?3)]-?-D-fucopyranosyl gypsogenin 3-O-?-D-glucopyranosyl (1?2)-?-D-glucopyranosiduronic acid (C1) and 28-O-?-D-xylopyranosyl(1?4)-?-L-rhamnopyranosyl (1?2)-[?-L-rhamnopyranosyl(1?3)]-?-D-fucopyranosyl gypsogenin 3-O-?-D-gluco-pyranosyl(1?2)-?-D-glucopyranosiduronic acid (C2) were isolated together with two known compounds from the seeds of Momordica charantia L. Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments and chemical reactions.
| S-EPMC6271465 | biostudies-literature
Project description:Plants of the genus Elsholtzia (Lamiaceae) have a long history of medicinal use in folk. The phytochemical investigations revealed the presence of flavonoids, phenylpropanoids, terpenoids, and other compounds. Abundant volatile components are also identified. Pure compounds, volatile constituents and crude extracts from the genus exhibited a wide spectrum of in vitro and in vivo pharmacological activities. The aims of this review hopefully provide comprehensive information on the distribution, phytochemistry, volatile components, and pharmacological research of Elsholtzia for exploring the potential and advance researches.
| S-EPMC3536681 | biostudies-literature
Project description:Five new triterpenoid saponins, heinsiagenin A 3-O-[?-l-rhamnopyranosyl-(1?2)-?-d-glucopyranosyl-(1?2)]-?-d-glucopyranoside (1), heinsiagenin A 3-O-[?-l-rhamnopyranosyl-(1?2)-?-d-glucopyranosyl-(1?2)]-[?-d-glucopyranosyl-(1?4)]-?-d-glucopyranoside (2), 2?-hydroxyheinsiagenin A 3-O-[?-l-rhamnopyranosyl-(1?2)-?-d-glucopyranosyl-(1?2)]-?-d-glucopyranoside (3), 2?-hydroxyheinsiagenin A 3-O-[?-d-glucopyranosyl-(1?2)]-[?-d-glucopyranosyl-(1?4)]-?-d-glucopyranoside (4) and N-(2S, 3R, 4R-3-methyl-4-pentanolid-2-yl)-18-hydroxylanosta-8 (9), 22E, 24E-trien-27-amide-3-O-[?-l-rhamnopyranosyl-(1?2)-?-d-glucopyranosyl-(1?2)]-[?-d-glucopyranosyl-(1?4)]-?-d-glucopyranoside (5) were isolated from the aerial parts of Mussaenda luteola Delile (Rubiaceae). Structural elucidation was based on the analysis of spectroscopic data (1D and 2D NMR) and HR-ESI-MS. Compound 1 showed potent antitrypanosomal activity with an IC50 value of 8.80?M. Compounds 2-4 showed highly potent antitrypanosomal activity with IC50 values ranging between (2.57-2.84?M) and IC90 values ranging between (3.36-4.35?M), which are 5 fold greater than the positive control DFMO (IC50 and IC90 values of 13.06 and 28.99?M, respectively). Compounds 1 and 2 showed moderate affinity to ?-opioid receptors with Ki values of 9.936?M and 0.872?M, respectively compared to a Ki value of 1.958nM for the positive control, naloxone HCl.
| S-EPMC4883117 | biostudies-literature
Project description:BackgroundPanax stipuleanatus represents a folk medicine for treatment of inflammation. However, lack of experimental data does not confirm its function. This article aims to investigate the analgesic and anti-inflammatory activities of triterpenoid saponins isolated from P. stipuleanatus.MethodsThe chemical characterization of P. stipuleanatus allowed the identification and quantitation of two major compounds. Analgesic effects of triterpenoid saponins were evaluated in two models of thermal- and chemical-stimulated acute pain. Anti-inflammatory effects of triterpenoid saponins were also evaluated using four models of acetic acid-induced vascular permeability, xylene-induced ear edema, carrageenan-induced paw edema, and cotton pellet-induced granuloma in mice.ResultsTwo triterpenoid saponins of stipuleanosides R1 (SP-R1) and R2 (SP-R2) were isolated and identified from P. stipuleanatus. The results showed that SP-R1 and SP-R2 significantly increased the latency time to thermal pain in the hot plate test and reduced the writhing response in the acetic acid-induced writhing test. SP-R1 and SP-R2 caused a significant decrease in vascular permeability, ear edema, paw edema, and granuloma formation in inflammatory models. Further studies showed that the levels of inflammatory mediators, nitric oxide, malondialdehyde, tumor necrosis factor-α, and interleukin 6 in paw tissues were downregulated by SP-R1 and SP-R2. In addition, the rational harvest of three- to five-year-old P. stipuleanatus was preferable to obtain a higher level of triterpenoid saponins. SP-R2 showed the highest content in P. stipuleanatus, which had potential as a chemical marker for quality control of P. stipuleanatus.ConclusionThis study provides important basic information about utilization of P. stipuleanatus resources for production of active triterpenoid saponins.
| S-EPMC8020355 | biostudies-literature
Project description:PurposeDiabetes is a common disease caused by a combination of genetic and environmental factors, which was the top three diseases threatening human health. Therefore, it is necessary to seek more efficient hypoglycemic drugs. The main objective of this study was to investigate the potential hypoglycemic effects of compounds from Polygonum capitatum.Materials and methodsOur experiments were divided into three steps: (1) α-amylase test and oral starch tolerance test (OSTT) for screening the biological extract part of P. capitatum; (2) chemical isolation and identification using various separation techniques, and spectrum methods; and (3) evaluation of α-amylase inhibitory activity of isolates and in silico analysis for mechanism investigation.ResultsThe n-butanol fractioned part of P. capitatum was confirmed to be the biological part according to α-amylase test. Then, two new triterpenoid saponins were isolated from the n-butanol part, which were also the first isolated triterpenoid saponins from P. capitatum. The activities of compounds 1 and 2 against α-amylase were 51.9±2.8% and 38.1±2.2%, respectively, which was consistent with the molecular docking analysis. In which, 1 and 2 showed the binding affinity energy for α-amylase was -9.4 kcal/mol and -7.8 kcal/mol, respectively.ConclusionTwo new triterpenoid saponins were firstly isolated from P. capitatum, and displays potency as a hypoglycemic agent through blocking α-amylase.
| S-EPMC8689516 | biostudies-literature
Project description:Recently the number of studies investigating triterpenoid saponins has drastically increased due to their diverse and potentially attractive biological activities. Currently the literature contains chemical structures of few hundreds of triterpenoid saponins of plant and animal origin. Triterpenoid saponins consist of a triterpene aglycone with one or more sugar moieties attached to it. However, due to similar physico-chemical properties, isolation and identification of a large diversity of triterpenoid saponins remain challenging. This study demonstrates a methodology to screen saponins using hyphenated analytical platforms, GC-MS, LC-MS/MS, and LC-SPE-NMR/MS, in the example of two different phenotypes of the model plant Barbarea vulgaris (winter cress), glabrous (G) and pubescent (P) type that are known to differ by their insect resistance. The proposed methodology allows for detailed comparison of saponin profiles from intact plant extracts as well as saponin aglycone profiles from hydrolysed samples. Continuously measured 1D proton NMR data during LC separation along with mass spectrometry data revealed significant differences, including contents of saponins, types of aglycones and numbers of sugar moieties attached to the aglycone. A total of 49 peaks were tentatively identified as saponins from both plants; they are derived from eight types of aglycones and with 2-5 sugar moieties. Identification of two previously known insect-deterrent saponins, hederagenin cellobioside and oleanolic acid cellobioside, demonstrated the applicability of the methodology for relatively rapid screening of bioactive compounds.
| S-EPMC6273444 | biostudies-other