Roots Of Cynanchum Stauntonii Research Articles

14,15-Secopregnane-Type Glycosides with 5α:9α-Peroxy and Δ6,8(14)-diene Linkages from the Roots of Cynanchum stauntonii.

Three new 14,15-secopregnane-type glycosides, stauntosides UA, UA1, and UA2, were isolated from the roots of Cynanchum stauntonii. The three compounds share the first reported and same basic structural features of 3β-hydroxy-14:16,15:20,18:20-triepoxy-5α:9α-peroxy-14,15-secopregnane-6,8(14)-diene named as stauntogenin G as the aglycones. The structures of the new compounds were characterized on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR and MS methods and chemical analysis. The isolation and identification of the new compounds graced the structural diversity of pregnane-type steroids from C. stauntonii.

Sugar-free pregnane-type steroids from the roots of Cynanchum stauntonii

Two new sugar-free 14,15-secopregnane-type steroids, 14-O-methyl-3-epi-hirundigenin (1) and 2-deoxyamplexicogenin A (2), along with two known sugar-free pregnane-type steroids, were isolated from the 95% ethanol extract of the roots of Cynanchum stauntonii. The structures of the new compounds were characterized on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR methods, albeit the MS experiments did not display the molecular ion peaks. Compound 2 was the aglycones of stauntosides J and K, etc., previously isolated from C. stauntonii. The isolation and identification of the new compounds graced the structural diversity of pregnane-type steroids from C. stauntonii.

14,15-Secopregnane-type C21-steriosides from the roots of Cynanchum stauntonii

Nine 14,15-secopregnane-type C21-steriosides, stauntosides U, V, V1-V3, W and C1-C3, as well as two known C21-steriosides, were isolated from the roots of Cynanchum stauntonii. Stauntosides U, V and V1-V3 share the same basic structural features of 8α:14α,14:16,15:20,18:20-tetraepoxy-14,15-secopregn-6-ene-3β,5α,9α-triol, with the numbering system following that of C21-pregnanes. The aglycones of stauntosides U, V and V1-V3 are classified into two subcategories, the 5,9-dihydroxy groups and 5α:9α-peroxy bridge, according to the oxidative states of the two hydroxy groups at the C-5 and C-9 positions. The anti-inflammatory activity of the major compounds was assessed in an in vitro inflammatory model of mouse peritoneal macrophages using IC50 values of the inhibition of nitric oxide (NO) production as an indicator. Stauntosides V1 and V3 exhibited target activity with IC50 values of 9.3 μM and 12.4 μM, respectively, compared with dexamethasone, which was used as a positive control.

Steroidal glycosides from the roots of Cynanchum stauntonii and their effects on the expression of iNOS and COX-2

Six new steroidal glycosides, named stauntosides O-T (1–6), along with eight known compounds (7–14), were obtained from the 95% aqueous ethanol extract of the roots of Cynanchum stauntonii. Their chemical structures were elucidated by IR, HR ESI-MS/MS, 1H- and 13C NMR, 1H-1H COSY, HSQC, HSQC-TOCSY, and HMBC spectroscopic analyses, which showed interesting 13,14:14,15-disecopregnane-type or 14,15-secopregnane-type C21 steroidal glycosides. The glycosides’ anti-inflammatory effects were investigated by detecting the inhibitory effects of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) on RAW246.7 murine macrophage cells stimulated by lipopolysaccharide (LPS). Our results showed that compounds 1, 5, 8, 9, 11, and 13 could significantly inhibit iNOS expression, and compounds 5 and 7 could clearly reduce COX-2 expression in RAW246.7 cells stimulated by LPS compared to cells stimulated with LPS and not treated with other compounds. Thus, compounds 1, 5, 7–9, 11, and 13 have the potential to mediate anti-inflammatory effects, with compound 5 having a greater anti-inflammatory effect than the other compounds.

Two new glycosides and one new neolignan from the roots of Cynanchum stauntonii

Three new compounds including one C21-steroidal glycoside, one methylglycoside, and one neolignan, named as Deoxyamplexicogenin A-3-O-yl-4-O-(4-O-α-l-cymaropyranosoyl-β-d-digitoxopyranosoyl)-β-d-canaropyranoside (1), Methyl-O-α-l-cymaropyranosoyl-(1→4)-β-D-digitoxopyranoside (2), and (+)-(7S, 8R, 7′E)-5-hydroxy-3, 5′-dimethoxy-4′, 7-epoxy-8, 3′-neolign-7′-ene-9, 9′-diol 9′-ethyl ether (3), respectively, were isolated from the roots of Cynanchum stauntonii. The structure elucidations were achieved by in-depth spectroscopic examination, mainly including the experiments and analyses of multiple 1D- and 2D-NMR and HRESIMS and CD analysis and qualitative chemical tests. Cytotoxicity activities of compounds 1–3 were evaluated against five tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) in cell based assays where they were found to be inactive.

Steroids and Related Compounds: Basic and Clinical Aspects

The steroid hormones generate myriad effects through several well-known mechanisms of action. Beyond the physiological function of steroid hormones, the steroid-like effects of some natural and synthetic compounds have led to the promising field of alternative therapies. However, to these new compounds, the molecular, subcellular, and cellular signal transductions need to be elucidated. Although new questions about the relevance of multiple targets of action for exogenous compounds are deeply in discussion, the original contributions that depict novel insights into basic and clinical aspects with perspectives on medical application are welcome. This special issue compiles papers from renowned research groups in the world that cover the frontiers of the latest findings on steroids and related compounds effect, mechanism of action and its relevance on carcinogenesis, immune suppression, and osteoporosis, as well as novel steroidal glycosides characterization. The papers on sex steroids hormones review the role of progesterone (precursor for androgens and estrogens produced by the gonadal and adrenal cortical tissues) and related progestins compounds in hepatocellular carcinoma. The authors highlight that the higher incidence of hepatocellular carcinoma in men than women might have resulted from the stimulatory effects of androgen and the protective effects of estrogen and also eventually suggest a new insight into the associations of progesterone and related compounds with hepatocellular carcinoma development and treatment. Also, the sex steroid hormones in the modulation of bacterial-host interactions were revised since the dimorphic sex difference (low immune responses presented in males as compared to females) is mainly due to the differential modulation of the immune system by sex steroid hormones through the control of proinflammatory and anti-inflammatory cytokines expression, as well as Toll-like receptors expression and antibody production. Some interesting studiesonhumans addressed the effect of chronic glucocorticoid therapy on osteoporosis in children with 21-hydroxylase deficiency as much to replace congenital deficits in cortisol synthesis as to reduce androgen secretion by adrenal cortex. As consequence, a secondary osteoporosis is formed. It results in an early, transient increase in bone resorption accompanied by decrease in bone formation, maintained for the duration of glucocorticoid therapy. Based on conflicting results from the literature about the bone status on glucocorticoid-treated patients with 21-hydroxylase deficiency, the authors point that the monitoring of the bone status of these patients, checking bone mineral density and bone turnover markers, and studying the expression of regulators of bone resorption should be useful in order to avoid glucocorticoid-induced osteoporosis in adulthood. Also, based on many epidemiological studies concerning the inverse relationship between isoflavone intake and bone loss and fracture rate, some substances on serum levels after food intake indicated for patients with osteopenia/osteoporosis were analyzed. Concerning genistein bioavailability, it was deeply discussed that, beyond the intestinal bacteria, solubility and permeability, glucosidase activity, viscosity induced by food additives, and a multitude of transporters on luminal intestinal cells for absorption, several factors from the diet composition influence the net absorption of single entity and also the effectiveness of the bone build. So, with these data in mind, the bioavailability of genistein depends on specific ingredients and excipients in each formulation which can interfere with absorption and could have clinical implications on efficacy. The ongoing investigations of some groups in the world have characterized new steroidal compounds from plants with medicinal interest. Three new steroidal glycosides, named as stauntosides L, M, and N, along with one known C21 steroidal glycoside, anhydrohirundigenin monothevetoside, were isolated from the roots of Cynanchum stauntonii (Decne.) and extensively evaluated by spectroscopic analyses, mainly 1D and 2D NMR, HRESI-MS and chemical methods. It is known that C21 steroids and their glycosides are of considerable bioactivities, such as hypolipidemic and antitumor activity. So the enriched information about C. stauntonii as a significant source of steroidal glycosides deserves careful phytochemistry investigation as well as the classification of bioactive compounds to be proposed as nutraceutical agents interesting both to academy and industry and also to specific therapy option.