Three New Steroidal Glycosides from the Roots of Cynanchum auriculatum

Three new C₂₁ steroidal glycosides with a cinnamoyl group at C(12) and a 2‐methylbutanoyl group at C(20), and a straight sugar chain at C(3), namely cyanoauriculosides C–E ( 1 – 3 , resp.), together with three known steroidal derivatives, were isolated from the roots of Cynanchum auriculatum (Asclepiadaceae). Their structures were determined by spectroscopic analyses and chemical methods. The known constituents were identified as wilfoside K1N ( 4 ), cynanauriculoside II ( 5 ), and auriculoside IV ( 6 ).     

New C21 steroidal glycoside from Cynanchum paniculatum

A new C21 steroidal glycoside, neocynapanogenin F 3-O-β-D-thevetoside 1, as well as its known aglycone neocynapanogenin F 2, which have an aberrant 13, 14:14, 15-disecopregnane-type skeleton were isolated from the root of Cynanchum paniculatum.Their structures were elucidated on the basis of spectroscopic data analysis. These compounds showed certain cytotoxic activities invitro.     

A new C21-steroidal glycoside from Cynanchum stauntonii

A new C21-steroidal glycoside with two known compounds were isolated from the root of Cynanchum Stauntonii.Based on thespectral analysis,including MS,1H NMR,13C NMR,DEPT,1H-1H COSY,13C-1H COSY,HMQC and HMBC,their chemicalstructures were determinated as glaucogenin-C 3-O-a-L-cymaropyranosyl-(1→4)-b-D-digitoxopyranosyl-(1→4)-β-D-canaropyranoside(1),stigmasterol(2)and ursolic acid(3).     

Six New C21 Steroidal Glycosides from Cynanchum bungei Decne

Six new C₂₁ steroidal glycosides 1 – 6 were isolated from the stem parts of Cynanchum bungei Decne . The structures of the new glycosides were determined on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR and HR‐ESI‐MS techniques as well as by comparison of their spectral data with those of related compounds.     

Identification of C-21 steroidal glycosides from the roots of Cynanchum chekiangense by high-performance liquid chromatography/tandem mass spectrometry

High-performance liquid chromatography coupled with electrospray tandem mass spectrometry (HPLC/ESI-MS/MS) was used to identify C-21 steroidal glycosides with immunological activities in roots of Cynanchum chekiangense. In the MS/MS spectra, fragmentation reactions of the [M + Na]⁺ were recorded to provide structural information about the glycosyl and aglycone moieties. To further confirm the fragments structures, off-line Fourier transform ion cyclotron resonance tandem mass spectrometry (FT-ICR-MS/MS) was also performed. In the study, four known steroidal glycosides cynascyroside C, chekiangensosides A and B, glaucoside H, and four novel steroidal glycosides chekiangensosides C, D, E and chekiangensoside A isomer were identified based on mass spectral data, NMR spectral data and standards. This is the first report on identifying steroidal glycosides in roots of C. chekiangense by HPLC/ESI-MS/MS directly, which could save time and material consuming efforts in traditional phytochemistry analysis.     

Isolation and Structural Study on Carbohydrates from Cynanchum otophyllum and Cynanchum paniculatum

Three new carbohydrates were isolated from the acidic hydrolysis part of the ethyl acetate extract of Cynanchum otophyllum Schneid (Asclepiadaceae) and one new carbohydrate from the ethyl acetate extract of Cynanchum paniculatum Kitagawa. Their structures were determined as methyl 2,6-dideoxy-3-O-methyl-α-D-arabino-hexopyranosyl-(1 → 4)-2,6-deoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α-D-arabino-hexopyranoside (1), ethyl 2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α-l-lyxo-hexopyranoside (2), met hyl 2,6-dideoxy-3-O-methyl-α-l-ribo-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-β-D-lyxo-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α-D-arabino-hexopyranoside (3), and 2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α-d-arabino-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α -d-arabino-hexopyranose (4), respectively, by spectral methods.     

Optimisation of extraction conditions for total saponins from Cynanchum wallichii using response surface methodology and its anti-tumour effects

Cynanchum wallichii Wight, is a traditional Chinese medicine herb, which is rich in saponins and has varieties of pharmacological activities. In this study, a standardized C. wallichii extract was established and the anti-tumor activity of the total saponins was evaluated by MTT assay. The extraction conditions of the standardized extract was optimized using response surface methodology. The experimental value was in good agreement (the yield 4.28%) with predicted values. The total saponins of the extract showed significant anti-tumor activity against three human tumor cell lines (A549, HepG2 and MCF-7), especially for MCF-7 (IC₅₀. 67.63 μg/mL) cells in vitro.     

Rapid structural determination of modified pregnane glycosides from Cynanchum forrestii by liquid chromatography-diode-array detection/electrospray ionization multi-stage tandem mass spectrometry

The fragmentation behaviors of the two types of modified pregnane glycosides from Cynanchum forrestii were investigated by positive ion electrospray ionization multi-stage tandem mass spectrometry equipped with an ion trap analyzer. The spectral data further illuminated the predominance of ESI-MSⁿ technique on the identification of pregnane glycosides, especially of two sorts of modified pregnane glycosides with aglycone skeletons of 13,14:14,15-disecopregnane-type and 14,15-secopregnane-type, which differed in the presence of the characteristic [M−46+Na]⁺ ion. For sugar residues, the fragment ions were analyzed and some possible fragmentation pathways were proposed, especially for 3-demethyl-2-deoxythevetose, the glycosidic cleavage reaction was easier to occur than those of other sugar units in its moiety. The natures and differences of the pregnane cores, and the types and linked sequences of sugar residues were illustrated. According to these conclusions, eight new pregnane glycosides in the fraction of Cynanchum forrestii were structurally elucidated by HPLC/HRMS and HPLC-DAD/ESI-MSⁿ techniques. Results of the present studies can benefit the rapid identification and structural determination of analogous constituents in crude plant extracts.     

Two new 14, 15-secopregnane-type steroidal glycosides from the roots of Cynanchum limprichtii

Two new steroidal glycosides 1 and 2, along with three known ones (3–5), were isolated from the 95% ethanol extract of the roots of Cynanchum limprichtii Schltr. The structure of the new compounds was elucidated as 3-O-α-L-diginopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-thevetopyranosyl-14, 16:15, 20:18, 20-triepoxy-14, 15-secopregn-4, 6, 8 (14)-triene (1) and 3-O-α-L-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl- (1→4)-β-D-3-demethyl-2-deoxythevetopyranosyl-14, 16: 15, 20: 8, 20-triepoxy-14, 15-secopregn-5, 8 (14)-diene (2) on the basis of spectroscopic analysis together with acidic hydrolysis. All compounds showed cytotoxic activity against the human cancer cell line HL60, with IC₅₀ values of 55.36, 65.41, 17.88, 17.68 and 33.5 μM, respectively. While, only compound 3 showed cytotoxicity against the Caco-2 cell line, with an IC₅₀ value of 67.47 μM.     

A novel dimeric flavonol glycoside from Cynanchum acutum subsp. sibiricum

A novel dimeric flavonol glycoside, Cynanflavoside A (1), together with six analogues, kaempferol-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (2), quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3), kaempferol-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (4), quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (5), kaempferol-3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (6), and quercetin-3-O-galactoside (7) were isolated from the n-butyl alcohol extract of Cynanchum acutum subsp. sibiricum. Their structures were determined spectroscopically and compared with previously reported spectral data. All compounds were evaluated for their anti-complementary activity in vitro, and only compound 5 exhibited anti-complement effects with CH₅₀ value of 0.33 mM.     

C21 Steroidal Glycosides from Cynanchum wilfordii

Eight new C₂₁ steroidal glycosides, named wilfosides A–H ( 1 – 8 , resp.), along with one known compound wilfoside KIN ( 9 ), were isolated from the roots of Cynanchum wilfordii. The structures of the new glycosides were determined on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR, and ESI‐MS techniques, as well as by comparison of the spectral data with those of related compounds.     

The Constituents of Cynanchum Taiwanianum

The isolation and identification of eleven crystalline components from the aerial part of Cynanchum taiwanianum Yamazaki (Asclepiadaceae) are described. Their structures were determined on the basis of spectral evidence and chemical transformation. Besides caffeic acid, β-amyrin, and methyl phaeophorbide a, the isolated flavonoid components are classified into two groups, i.e. kaempferol derivatives (kaempferol, astragalin, afzelin, trifolin) and quercetin derivatives (quercetin, isoquercitrin, quercitrin, hyperin).     

Plants of the Genus Zingiber: A Review of Their Ethnomedicine,Phytochemistry and Pharmacology

Plant of the genus Zingiber (Zingiberaceae) have primarily distributed in subtropical and tropical Asia, South America and Africa. The species of this genus have been widely used as food and in folk with a long history for treating various diseases. Reports related to the phytochemistry and phytochemistry of Zingiber species are numerous, but articles on the summary of the genus Zingiber remain scarce. This review aims at presenting comprehensive information about the genus Zingiber and providing a reference for the future application by systematically reviewing the literature from 1981 to 2020. Currently, a total of 447 phytochemical constituents have been isolated and identified from this genus, in which volatile oils, diarylheptanoids, gingerols, flavonoids and terpenoids are the major components. Gingerols, which are the main functional components, are the spicy and aromatic ingredients in the Zingiber species. Extracts and single compounds from Zingiber plants have been discovered to possess numerous biological functions, such as anti-inflammatory, anticancer, antimicrobial, larvicidal, antioxidant and hypoglycemic activities. This review provides new insights into the ethnomedicine, phytochemistry and pharmacology of the genus Zingiber and brings to the forefront key findings on the functional components of this genus in food and pharmaceutical industries.     

Phytoconstituents and pharmacological activities of cyanobacterium Fischerella ambigua

Cyanobacteria, also known as blue-green algae, are known to be a rich source of secondary metabolites with diverse chemical structures and biological activities. Over 1100 natural constituents of cyanobacterial origin have been reported in the literature. These include various natural biologically active constituents with antimicrobial, antiviral, immunosuppressive, and anticancer activities. Terrestrial cyanobacteria of genus Fischerella (Family Fischerellaceae), belonging to order Stigonematales have recently received enormous attention from the researchers due to the presence of vast array bioactive compounds. Fischerella species are filamentous cyanobacteria with creeping thallus and sheath in filaments. Several species within the genus are known to produce interesting bioactive constituents. Perhaps the best characterized are F. ambigua and F. muscicola, which have been reported to produce antibacterial, antifungal and antialgal isonitrile containing indole alkaloids, such as hapalindoles, ambiguine isonitriles, fischerindoles, and wetwitindolinones. Keeping in mind these resources, a detailed literature survey on a cultured, fresh water and terrestrial cyanobacterium Fischerella ambigua (N?g.) Gom. has been carried out. The current review describes the chemical constituents isolated from different extracts of Fischerella ambigua, as well as their biological activities.     

Bergenia Genus: Traditional Uses,Phytochemistry and Pharmacology

Bergenia (Saxifragaceae) genus is native to central Asia and encompasses 32 known species. Among these, nine are of pharmacological relevance. In the Indian system of traditional medicine (Ayurveda), “Pashanabheda” (stone breaker) is an elite drug formulation obtained from the rhizomes of B. ligulata. Bergenia species also possess several other biological activities like diuretic, antidiabetic, antitussive, insecticidal, anti-inflammatory, antipyretic, anti-bradykinin, antiviral, antibacterial, antimalarial, hepatoprotective, antiulcer, anticancer, antioxidant, antiobesity, and adaptogenic. This review provides explicit information on the traditional uses, phytochemistry, and pharmacological significance of the genus Bergenia. The extant literature concerned was systematically collected from various databases, weblinks, blogs, books, and theses to select 174 references for detailed analysis. To date, 152 chemical constituents have been identified and characterized from the genus Bergenia that belong to the chemical classes of polyphenols, phenolic-glycosides, lactones, quinones, sterols, tannins, terpenes, and others. B. crassifolia alone possesses 104 bioactive compounds. Meticulous pharmacological and phytochemical studies on Bergenia species and its conservation could yield more reliable compounds and products of pharmacological significance for better healthcare.     

Potential hypoglycemic effect of acetophenones from the root bark of Cynanchum wilfordii

Three new acetophenones, named cynwilforones A–C (1–3), together with cynandione A (4) were isolated from the root bark of Cynanchum wilfordii (Maxim.) Hemsl. Their structures were deduced based on spectroscopic analysis and chemical methods. Compounds 1 and 4 exhibited potential hypoglycemic effects through inhibition of hepatic gluconeogenesis by down-regulating the expression of phosphoenolpyruvate carboxykinase and glucose-6-phosphatase. This is the first report that acetophenones from the root bark of C. wilfordii possesses potential hypoglycemic activity in vitro.     

Antitumor evaluation and multiple analysis on different extracted fractions of the root of Cynanchum auriculatum Royle ex Wight

The root of Cynanchum auriculatum (C. auriculatum ) Royle ex Wight has been shown to possess various pharmacological effects and has recently attracted much attention with respect to its potential role in antitumor activity. The C‐21 steroidal glycosides are commonly accepted as the major active ingredients of C. auriculatum . In this study, the antitumor abilities of different extracted fractions of the root bark and the root tuber of C. auriculatum were investigated by using a 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay in human cancer cell lines HepG2 and SMMC‐7721. The results showed that the chloroform and ethyl acetate fractions of the root tuber suppressed tumor cell growth strongly. To identify and characterize the chemical constituents of different active fractions, an ultra high performance liquid chromatography with triple‐quadrupole tandem mass spectrometry method was developed for the simultaneous quantitation of eight C‐21 steroidal glycosides. The analysis revealed that the C‐21 steroidal glycosides were concentrated in the chloroform and ethyl acetate fractions, and the total contents of different fractions in the root tuber were significantly higher than those of corresponding ones in the root bark. Furthermore, the C‐21 steroidal glycosides based on different types of aglucones were prone in different medicinal parts of C. auriculatum .     

Botanical,Phytochemical and Pharmacological Properties of Hedychium (Zingiberaceae) – A Review

Zingiberaceae is one of the most widely distributed plants in tropic and subtropic area, about 19 genus and 375 species weredistributed in Indonesia. Based on empirical data, some of the plants were used traditionally to treat various diseases. Nowadays, Zingiberaceae plants are extensively studied for their phytochemistry and pharmacological properties included genus Hedychium. The various bioactive compounds were isolated from these plants and they were known to have the pharmacological effect. This review showed that Hedychium plants were prospective as a natural product medicine.     

Thuja occidentalis L. (Cupressaceae): Ethnobotany,Phytochemistry and Biological Activity

Thuja occidentalis L. (Cupressaceae) has its origins in Eastern North America and is cultivated in Europe and Brazil as an ornamental tree, being known as the “tree of life” or “white cedar”. In traditional medicine, it is commonly used to treat liver diseases, bullous bronchitis, psoriasis, enuresis, amenorrhea, cystitis, uterine carcinomas, diarrhea, and rheumatism. The chemical constituents of T. occidentalis have been of research interest for decades, due to their contents of essential oil, coumarins, flavonoids, tannins, and proanthocyanidines. Pharmacology includes antioxidant, anti-inflammatory, antibacterial, antifungal, anticancer, antiviral, protective activity of the gastrointestinal tract, radioprotection, antipyretic, and lipid metabolism regulatory activity. Therefore, the present review represents the synthesis of all the relevant information for T. occidentalis, its ethnobotany, phytochemistry, and a thorough analysis of their pharmacological activities, in order to promote all the biological activities shown so far, rather than the antitumor activity that has promoted it as a medicinal species.     

Quantitative analysis of two adulterants in Cynanchum stauntonii by near-infrared spectroscopy combined with multi-variate calibrations

Authentication of traditional Chinese medicines (TCMs) has become important because they can be adulterated with relatively cheap herbal medicines similar in appearance. Detection of such adulterated samples is needed because their presence is likely to reduce the pharmacological potency of the original TCM and, in the worst cases, the samples may be harmful. The aim of this study was to develop a rapid near-infrared spectroscopy (NIRS) analytical method which was supported by multi-variate calibration, e.g. partial least squares regression (PLSR) and radial basis function artificial neural networks (RBF-ANN), in order to quantify the TCM and the adulterants. In this work, Cynanchum stauntonii (CS), a commonly used TCM, in mixtures with one or two adulterants ?? two morphological types of TCM, Cynanchum atrati (CA) and Cynanchum paniculati (CP), were determined using NIR reflectance spectroscopy. The three sample sets, CS adulterated with CA or CP, and CS with both CA and CP, were measured in the range of 800?C2500 nm. Both PLSR and RBF-ANN calibration models provided satisfactory results, even at an adulteration level of 5 mass %, but the RBF-ANN models with better root mean square error of prediction (RMSEP) values for CS, CA, and CP arguably performed better. Consequently, this work demonstrates that the NIR method of sampling complex mixtures of similar substances such as CS adulterated by CA and/or CP is capable of producing data suitable for the quantitative analysis of mixtures consisting of the original TCM adulterated by one or two similar substances, provided the spectral data are interrogated by multi-variate methods of data analysis such as PLS or RBF-ANN.