Five new saponins, including three steroid saponins, paristenoids A-C (1-3), and two triterpenoid saponins, paristenoids D-E (4-5), along with four known ones (6-9) were isolated from the rhizomes of Paris polyphylla var. stenophylla. The structures of the isolated compounds were identified mainly by detailed spectroscopic analysis, including extensive 1D and 2D NMR, MS, as well as chemical methods. Compound 3 is a new cyclocholestanol-type steroidal saponin with a rare 6/6/6/5/5 fused-rings cholestanol skeleton, and this skeleton has been first found from the genus Paris. The cytotoxicities of the isolated compounds against three human three glioma cell lines (U87MG, U251MG and SHG44) were evaluated, and compound 7 displayed certain inhibitory effect with IC₅₀ values of 15.22 ± 1.73, 18.87 ± 1.81 and 17.64 ± 1.69 μmol·L^-1, respectively.
Humans ; Rhizome/chemistry* ; Steroids/chemistry* ; Liliaceae/chemistry* ; Saponins/chemistry* ; Triterpenes/analysis*

Thirteen steroids(1-13) were isolated from the non-alkaloid constituents of Uncaria rhynchophylla by column chromatography on silica gel, ODS, Sephadex LH-20, and preparative HPLC chromatography, and their structures were elucidated by analyses of the MS and NMR spectral data. All the compounds were isolated from the genus Uncaria for the first time, and 1 was a new compound. The ~1H-NMR and ~(13)C-NMR data of two compounds(12 and 13) in deuteron-chloroform were completely assigned. This study enriched the steroid constituents of U. rhynchophylla and provided scientific references for the elucidation of active constituents and further development and utilization of U. rhynchophylla.
Chromatography, High Pressure Liquid ; Steroids ; Uncaria/chemistry*

Two previously undescribed steroidal alkaloids, compounds 1-2, along with two known ones(3-4), were isolated from the 80% ethanol extract of ripe berries of Solanum nigrum by chromatographic methods, including silica gel, ODS, and HPLC. Based on spectroscopic and chemical evidence, including IR, NMR, and HR-ESI-MS data, the structures of the isolated compounds were identified as 12β,27-dihydroxy solasodine-3-O-β-D-glucopyranoside(1), 27-hydroxy solasodine-3-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside(2), solalyraine A(3), and 12β,27-dihydroxy solasodine(4). Compounds 1-2 were tested for their potential effects against the proliferation of A549 cells, which revealed that compounds 1-2 had weak cytotoxic activity.
Alkaloids/analysis* ; Ethanol ; Fruit/chemistry* ; Molecular Structure ; Plant Extracts/chemistry* ; Saponins/analysis* ; Silica Gel/analysis* ; Solanum/chemistry* ; Solanum nigrum/chemistry* ; Steroids/pharmacology*

Steroid saponins are secondary metabolites with multiple medicinal values that are found in large quantities in natural medicines, especially Vernonia amygdalina, a famous nature medicine for the treatment of tonsillitis, diabetes, pneumonia. The current study was designed to combine molecular networking (MN) with diagnostic ions for rapid identification of Δ^7,9(11) stigmastane-type saponins which were the α-glucosidase inhibitory active substances in V. amygdalina. First, the α-glucosidase inhibitory activities of five Δ^7,9(11) stigmastane-type steroid saponins that were previously isolated were screened, which indicated that the Δ^7,9(11) stigmastane-type steroid saponin was one of the active constituents responsible for ameliorating diabetes. Furthermore, a strategy was proposed to identify stigmastane-type steroid saponins and verify the plausibility of derived fragmentation pathways by applying MN, MolNetEnhancer and unsupervised substructure annotation (MS2LDA). Based on this strategy, other seven Δ^7,9(11) stigmastane-type steroid saponins were identified from this plant. Our research provide scientific evidence for the antidiabetic potential of the steroid saponin-rich extract of V. amygdalina leaf.
alpha-Glucosidases/metabolism* ; Vernonia/chemistry* ; Plant Extracts/chemistry* ; Plant Leaves/chemistry* ; Saponins/chemistry* ; Steroids/chemistry* ; Diabetes Mellitus

To date, 205 compounds have been identified from different medicinal parts of Eucommia ulmoides, including lignans, iridoid terpenoids, phenols, flavonoids, terpenoids and steroids, polysaccharides and others. Their pharmacological effects include blood pressure-lowering, blood sugar-lowering, blood lipids-regulating, prevention of osteoporosis, anti-inflammation, liver protection, anti-cancer and so on. Their efficacy and mechanism from different parts are slightly different. In this paper, the chemical composition, pharmacological action and mechanism of different parts of E. ulmoides were systematically summarized, as well as its quality control and processing research, to provide theoretical basis for further rational development and utilization of E. ulmoides.
Eucommiaceae/chemistry* ; Flavonoids ; Iridoids ; Lignans ; Phenols ; Phytochemicals/pharmacology* ; Plants, Medicinal/chemistry* ; Polysaccharides ; Steroids ; Terpenes

The steroidal saponins are one of the saponin types that exist in an unbound state and have various pharmacological activities, such as anticancer, anti-inflammatory, antiviral, antibacterial and nerves-calming properties. Cancer is a growing health problem worldwide. Significant progress has been made to understand the antitumor effects of steroidal saponins in recent years. According to reported findings, steroidal saponins exert various antitumor activities, such as inhibiting proliferation, inducing apoptosis and autophagy, and regulating the tumor microenvironment, through multiple related signaling pathways. This article focuses on the advances in domestic and foreign studies on the antitumor activity and mechanism of actions of steroidal saponins in the last five years to provide a scientific basis and research ideas for further development and clinical application of steroidal saponins.
Animals ; Antineoplastic Agents, Phytogenic ; chemistry ; pharmacology ; Apoptosis ; drug effects ; Cell Proliferation ; drug effects ; Humans ; Neoplasms ; drug therapy ; physiopathology ; Plant Extracts ; chemistry ; pharmacology ; Saponins ; chemistry ; pharmacology ; Steroids ; chemistry ; pharmacology

The present study was designed to further investigate the C steroidal glycosides in Cynanchum plants. Two new steroidal glycosides based on a 13, 14:14, 15-disecopregnane-type aglycone, komaroside P (1) and komaroside Q (2), together with three known compounds (3-5) were isolated from the whole herbs of Cynanchum komarovii. The aglycones of compounds 1 and 2 were two new disecopregnane. Their structures were elucidated on the basis of 1D, 2D NMR spectroscopic data and acid hydrolysis. All the compounds (1-5) showed potent inhibitory activities against human leukemia cell lines (HL-60) with IC values ranging from 16.6 to 26.3 μmol·L, compared to the positive control 5-fluorouracil (6.4 μmol·L).
Cell Survival ; drug effects ; Cynanchum ; chemistry ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; pharmacology ; Glycosides ; chemistry ; isolation & purification ; pharmacology ; HL-60 Cells ; Humans ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Steroids ; chemistry ; isolation & purification ; pharmacology

Two new steroidal saponins, named timosaponin P (1) and timosaponin Q (2), were isolated from the rhizome parts of Anemarrhena asphodeloides Bunge using various chromatographic methods. Their structures and absolute configurations were elucidated by a combination of spectroscopic and spectrometric data, including 1D, 2D NMR, HR-ESI-MS and ECD calculations, and this is the first time the absolute configuration of C-23 of steroidal saponin was confirmed by ECD calculations.
Anemarrhena ; chemistry ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Molecular Structure ; Saponins ; chemistry ; isolation & purification ; Steroids ; chemistry ; isolation & purification

In the present study, a new ceramide, namely 2S, 3R-4E, 8E-2-(heptadecanoylamino)-heptadeca-4, 8-diene-1, 3-diol (1), along with four known steroids, including 24-methylcholesta-5, 24(28)-diene-3β-ol (2), 24-methylcholesta-5, 24(28)-diene-3β-acetate (3), 4-methyl-24-methylcholesta-22-ene-3-ol (4), and cholesterol, was isolated and characterized from CHCl/MeOH extract of Cespitularia stolonifera. A new acetate derivative of compound 1, termed 2S, 3R-4E, 8E-2-(heptadecanoylamino)-heptadeca-4, 8-diene-1, 3-diacetate (1a), was also prepared in the present study. All the structures were established on the basis of modern spectroscopic techniques, including FT-IR, 1D, 2D-NMR, HRESI-MS, and GC-MS, in addition of chemical methods. (-)-Alloaromadendren, ledane, (1)-alloaromadendren oxide, isoaromadendrene epoxide and (-)-caryophellen oxide were identified from the n-hexane fraction using GC-MS. The extract and the two ceramides (1) and (1a) exhibited significant cytotoxic activity against lung cancer A549 cells, while the extract and the two steroids (2) and (3) exhibited significant cytotoxic activity against breast cancer MCF-7 cells. The CHCl/MeOH extract exhibited significant antiulcer activity in both ethanol and acetic acid induced ulcer models in rats, as evidenced by histopathological, histochemical, and biochemical examinations.
A549 Cells ; Acetic Acid ; Animals ; Anthozoa ; chemistry ; Anti-Ulcer Agents ; chemistry ; isolation & purification ; pharmacology ; therapeutic use ; Antineoplastic Agents ; chemistry ; isolation & purification ; pharmacology ; therapeutic use ; Biological Products ; chemistry ; isolation & purification ; pharmacology ; therapeutic use ; Breast Neoplasms ; drug therapy ; Ceramides ; chemistry ; isolation & purification ; pharmacology ; therapeutic use ; Disease Models, Animal ; Ethanol ; Female ; Humans ; Lung Neoplasms ; drug therapy ; MCF-7 Cells ; Magnetic Resonance Spectroscopy ; methods ; Rats ; Spectroscopy, Fourier Transform Infrared ; methods ; Steroids ; chemistry ; isolation & purification ; pharmacology ; therapeutic use ; Ulcer ; chemically induced ; drug therapy

Cynanchum is one of the most important genera in Asclepiadaceae family, which has long been known for its therapeutic effects. In this genus, 16 species are of high medicinal value. The extracts of the root and/or rhizome parts have been applied in traditional Chinese medicines (TCM) for the prevention and treatment of various illnesses for centuries. C21 steroids, as the typical constituents of Cynanchum species, possess a variety of structures and pharmacological activities. This review summarizes the comprehensive information on phytochemistry and pharmacology of C21 steroid constituents from Cynanchum plants, based on reports published between 2007 and 2015. Our aim is to provide a rationale for their therapeutic application, and to discuss the future trends in research and development of these compounds. A total of 172 newly identified compounds are reviewed according to their structural classifications. Their in vitro and in vivo pharmacological studies are also reviewed and discussed, focusing on antitumor, antidepressant, antifungal, antitaging, Na(+)/K(+)-ATPase inhibitory, appetite suppressing and antiviral activities. Future research efforts should concentrate on in vitro and in vivo biological studies and structure activity relationship of various C21 steroid constituents.
Animals ; Cynanchum ; chemistry ; Humans ; Molecular Structure ; Plant Extracts ; chemistry ; pharmacology ; Steroids ; chemistry ; pharmacology