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1.
Molecules ; 24(22)2019 Nov 18.
Article in English | MEDLINE | ID: mdl-31752141

ABSTRACT

The tea-like beverage Stevia rebaudiana Bertoni (Stevia) is popular in China because it reduces blood glucose and has a sweet taste. In this work, a comprehensive quality assessment of Stevia led to the discovery of five phenylethanoid glycosides, namely steviophethanoside (1), cuchiloside (2), salidroside (3), icariside D (4), and tyrosol (5). Of them, compound 1 is a novel compound. Mass spectrometry and NMR spectroscopy were employed to confirm the absolute configuration. A hydrolytic step with 4 N TFA at 95 °C for 4 h was used to confirm the monosaccharides. In addition, Discovery Studio 4.0 was used to predict the ADME and toxicity activity of compound 1. The results suggested that compound 1 was biocompatible and had poor toxicity, which was verified by rat INS-1 islet ß cells through an MTT assay. Meanwhile, a significant stimulatory effect on INS-1 cells was observed, which indicated a hypoglycemic effect of compound 1. This is the first report that describes a natural, novel, and hypoglycemic phenylethanoid glycoside in Stevia.


Subject(s)
Glycosides/pharmacology , Insulin Secretion/drug effects , Insulin-Secreting Cells/drug effects , Plant Extracts/pharmacology , Stevia/chemistry , Animals , Cells, Cultured , China , Glycosides/chemistry , Glycosides/isolation & purification , Insulin-Secreting Cells/metabolism , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Rats
2.
J Asian Nat Prod Res ; 20(6): 586-592, 2018 Jun.
Article in English | MEDLINE | ID: mdl-29168389

ABSTRACT

A new furostan type steroidal saponin, kingianoside Z (1), along with four known compounds (2-5), was isolated from the ethanolic extract of Polygonatum sibiricum Delar. ex Redoute. Their structures were determined by spectroscopical method and by comparison with previously reported spectroscopic data. Compounds 3-5 showed significant cytotoxicity against HepG2 cell lines with IC50 values of 14.2, 12.1 and 8.5 µM, respectively.


Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Polygonatum/chemistry , Drug Screening Assays, Antitumor , Hep G2 Cells , Humans , Isoflavones/isolation & purification , Molecular Structure , Rhizome/chemistry , Saponins/chemistry , Saponins/isolation & purification
3.
Arch Pharm Res ; 41(12): 1117-1130, 2018 Dec.
Article in English | MEDLINE | ID: mdl-28895057

ABSTRACT

Four new ursane-type triterpenoid saponins, clinopoursaponins A-D (1-4), six new oleanane-type triterpenoid saponins, clinopodiside VII-XII (5-10), as well as eight known triterpene analogues (11-18), were isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze. The structures of the new compounds were determined based on extensive spectral analyses, including 1D (1H and 13C) and 2D NMR experiments (COSY, NOESY, HSQC, 2D TOCSY, HSQC-TOCSY and HMBC), HR-ESI-MS and chemical methods. Compounds 1-18 were evaluated for their protective effects against anoxia/reoxygenation-induced apoptosis in H9c2 cells and cytotoxicities against murine mammary carcinoma cell line 4T1. Compounds 8, 9 and 18 exhibited significant protective effects, while compound 1 exhibited cytotoxic activity with IC50 value of 7.4 µm compared to 7.6 µm for the positive control 10-hydroxycamptothecin.


Subject(s)
Antineoplastic Agents/pharmacology , Lamiaceae/chemistry , Saponins/pharmacology , Triterpenes/pharmacology , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Apoptosis/drug effects , Cell Line , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Mice , Molecular Structure , Saponins/chemistry , Saponins/isolation & purification , Structure-Activity Relationship , Triterpenes/chemistry , Triterpenes/isolation & purification
4.
Molecules ; 22(10)2017 Oct 17.
Article in English | MEDLINE | ID: mdl-29039768

ABSTRACT

One new cassane diterpene possessing an unusual N bridge between C-19 and C-20 named caesalsappanin R (1), as well as another new diterpene caesalsappanin S (2), were isolated from the seeds of Caesalpinia sappanwith methanol extract. Their structures were determined by spectroscopic analysis and examined alongside existing data from prior studies. Their biological activities were profiled by their antiplasmodial activity.


Subject(s)
Antimalarials/chemistry , Antimalarials/pharmacology , Caesalpinia/chemistry , Diterpenes/chemistry , Diterpenes/pharmacology , Antimalarials/isolation & purification , Diterpenes/isolation & purification , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , Parasitic Sensitivity Tests , Plant Extracts/chemistry , Plant Extracts/pharmacology
5.
Zhongguo Zhong Yao Za Zhi ; 42(13): 2510-2517, 2017 Jul.
Article in Chinese | MEDLINE | ID: mdl-28840692

ABSTRACT

Twenty-eight compounds were isolated and purified from Clinopodium chinense by Sephedax LH-20, ODS, MCI and preparative HPLC. Their structures were identified as apigenin (1), apigenin-7-O-ß-D-glucopyranoside (2), apigenin-7-O-ß-D-glucuronopyranoside (3), thellungianol (4), apigenin-7-O-ß-D-rutinoside (5), luteolin (6), luteolin-4'-O-ß-D-glucopyranoside (7), apigenin-7-O-ß-D-pyranglycuronate butyl ester (8), luteolin-7-O-ß-D-rutinoside (9), luteolin-7-O-ß-D-noehesperidoside (10), acacetin (11), acacetin-7-O-ß-D-glucuronopyranoside (12), buddleoside (13), naringenin (14), pruning (15), nairutin (16), isosakuranetin (17), isosakuranin (18), didymin (19), hesperidin (20), kaempferol (21), quercetin (22), kaempferol-3-O-α-L-rahmnoside (23), p-hydroxycinnamic acid (24), caffeic acid (25), cis-3-[2-[1-(3,4-dihydroxy-phenyl)-1 -hydroxymethyl]-1,3-ben-zodioxol-5-yl]-(E)-2-propenoic acid (26), mesaconic acid (27), gentisic acid 5-O-ß-D-(6'-salicylyl)-glucopyranoside (28). Among them, compounds 7, 9-10, 12, 23, 26-28 were isolated from the Clinopodium for the first time. The protective effects of compounds 1-6, 8-17 and 19 against H2O2-induced H9c2 cardiomyocyte injury were tested, compounds 15 exhibited significantly protective effects. Compared with the cell viability of (62.12±6.18)% in the model, pruning exhibited viabilities of (84.25±7.36)% at 25.0 mg•L⁻¹, respectively, using quercetin as a positive control [cell viability of (84.55±8.26)%, 20 mg•L⁻¹].


Subject(s)
Lamiaceae/chemistry , Phytochemicals/isolation & purification , Animals , Apigenin/isolation & purification , Cell Line , Cell Survival , Myocytes, Cardiac/drug effects , Rats
7.
Nat Prod Res ; 30(9): 1075-80, 2016.
Article in English | MEDLINE | ID: mdl-26551245

ABSTRACT

Two new abietane diterpenoid glycosides, named clinopoditerpenes B (1) and C (2), were isolated from Clinopodium chinese. The structures of the new compounds were determined on the basis of extensive spectral analysis. Compound 1 exhibited cardioprotective effect against H2O2-induced apoptosis in H9c2 cells.


Subject(s)
Abietanes/pharmacology , Cardiotonic Agents/pharmacology , Glycosides/chemistry , Glycosides/isolation & purification , Hydrogen Peroxide/toxicity , Lamiaceae/chemistry , Abietanes/chemistry , Apoptosis/drug effects , Cardiotonic Agents/chemistry , Cell Line , Drugs, Chinese Herbal/chemistry , Humans , Plant Extracts/analysis , Spectrometry, Mass, Electrospray Ionization
8.
Fitoterapia ; 105: 61-5, 2015 Sep.
Article in English | MEDLINE | ID: mdl-26073946

ABSTRACT

Four new phenolic acids, clerodens A-D (1-4) possessing an unusual bicycle [2.2.2] octane moiety were isolated from the whole plants of Clerodendranthus spicatus. Their structures were elucidated by extensive spectroscopic methods, including NMR, MS, and ECD data. All isolates were evaluated for their anti-inflammatory activities on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7, and compound 4 showed significant inhibitory activities with IC50 value of 6.8 µM.


Subject(s)
Anti-Inflammatory Agents/chemistry , Hydroxybenzoates/chemistry , Lamiaceae/chemistry , Octanes/chemistry , Animals , Anti-Inflammatory Agents/isolation & purification , Hydroxybenzoates/isolation & purification , Inhibitory Concentration 50 , Mice , Molecular Structure , Nitric Oxide/metabolism , Octanes/isolation & purification , RAW 264.7 Cells
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