Two New Steroidal Glycosides from Ophiopogon japonicus

Two new C27 steroidal glycosides, named ophiopojaponin A (1) and B (2), were isolated from the tubers of famous traditional Chinese herb(Ophiopogon japonicus. The spectroscopic and chemical evidences revealed their structures to be Pennogenin 3-O-[2’-O-acetyl-(-L-rhamnopyranosyl (1?2)]-(-D-xylopyranosyl (1?3)-(-D-glucopyranoside (1) and 26-O-(-D-glucopyranosyl-(22(, 25R)-3(, 14(, 22(, 26-tetrahydroxyfurost-5-ene 3-O-(-L-rhamnopyranosyl (1?2)-(-D-glucopyranoside (2), respectively.

Two New C21 Steroidal Glycosides from the Roots of Cynanchum paniculatum

Two new C21 steroidal glycosides,paniculatumosides H and I,together with four known ones were isolated from the roots of Cynanchum paniculatum(Bge.)Kitag.Their structures were identifed by spectroscopic methods including extensive 1D and 2D NMR techniques.All compounds were subjected to detect the anti-tobacco mosaic virus(TMV)activities and their cytotoxities against three human tumor cell lines(SMMC-7721,MDA-MB-231 and A549).The results showed that compounds 1 and 5 exhibited potent protective activities against TMV,while 2,4 and 6 had moderate efects on the SMMC7721 cancer cells viability.

Steroidal Saponins from the Genus Smilax and Their Biological Activities

The Smilax species,widely distributed in tropical region of the world and the warm areas of East Asia and North America,are extensively used as folk medicine to treat inflammatory disorders.Chemical investigation on Smilax species showed they are rich sources of steroidal saponins with diversified structure types,including spirostane,isospirostane,furostane,pregnane,and cholestane.This review mainly summarizes the steroidal saponins(1–104)reported from the genus Smilax between 1967 and 2016,and their biological activities.The relationship between structures of steroidal saponins and related biological activities were briefly discussed.

STEROIDAL ALKALOIDS FROM SARCOCOCCA VAGANS

A new steroidal alkaloid, vaganine A (1) was isolated togetherwith a known compound paohysandrine A (2) from Sarcooocca vagans. Theirstructures were determined by spectroscopic evidence.

Antiproliferative and apoptosis-inducing potential of 3β-hydroxy-△5-steroidal congeners purified from the soft coral Dendronephthya putteri

The exploration and identification of antiproliferative phytochemicals have received increased attention in medicinal chemistry. In particular, research focused on the toxicology of marine natural products has increased in recent years. Terpenoids, among many secondary metabolites, have been demonstrated to act as effective anticancer agents. Soft corals, a group of marine invertebrates, produce a variety of terpenoids with biofunctional properties. The current study presents the extraction, purification, and identification of sterol congeners from the soft coral Dendronephthya putteri. The method involves 50% chloroform-methanol extraction, polar column fractionation, and analysis through GC-MSn. Dose-dependent antiproliferative activity was observed within the sterol-rich fraction (DPCMH 2-4), which consisted of 3β-hydroxy-Δ5-steroidal congeners. This fraction inhibited the growth of HL-60 and MCF-7 cells with IC50 values of 25.27±1.43 and 22.81±0.15 μg/mL, respectively. Apoptotic body formation, DNA damage, cell cycle arrest, and apoptotic cell signaling pathway activation were also observed, reinforcing the dose-dependent antiproliferative and apoptosis-inducing activity of 3β-hydroxy-Δ5-steroidal congeners. To our knowledge, this is the first report of anticancer agent identification from the soft coral D. putteri. Based on the observations, these steroidal congeners are promising candidates for the development of anticancer drugs.

SIECHUANSINE,A NEW STEROIDAL ALKALOID FROM FRITILLARIA

From the bulbs of Fritillaria siechuanica S.C.Chen cultivated in Sichuanprovince,a new steroidal alkaloid,siechuansine,was isolated.Spectral methods demonstrated thatit is a 13—epimer of wanpeinine A.

NEW MINOR STEROIDAL SAPONINS FROM SMILAX LEBRUNII

Two new minor steroidal saponins, (25R) spirostan-3β-ol-6-one-3-O-[α-L-arabinopyranosyl(1-4)]-β-D-glucopyranosidc (1) and (25S) spirost-5-en -3β, 17α, 27-triol-3-O-[α-L-arabinopyranosyl(1-6)]-β-D-glucopyranosidc (2) were isolated from the roots of Smilax lebrunii. Theirstructures were established on thc basis of chemical and spectral methods.

Two New Steroidal Saponins from Diuranthera inarticulata

Two new steroidal saponins, diuranthosides D and E, were isolated from the whole plant of Diuranthera inarticulata Wang et K. Y. Lang. By means of spectral and chemical analysis, the structure of the new compounds were established as neotigogenin-3-O-(-D-glucopyranosyl (1?3)-(-D-xylopyranosyl-(1?3)-[(-D-glucopyranosyl(1?2)]-(-D-glucopyranosyl(1?4)-(-D-galactopyranoside (1) and neotigogenin-3-O-(-D-glucopyranosyl(1?3)-(-D-glucopyranosyl (1?3)-(-D-xylopyranosyl(1?3)-[(-D-glucopyranosyl(1?2)]-(-D-glucopyranosyl(1?4)-(-D-galactopyranoside (2) respectively.

Effects of structural modification of anti-inflammatory steroidal antedrug on pro-inflammatory mediators and inhibitory cytokines in human alveolar epithelial cells

The anti-inflammatory effects of the new ster-oidal antedrug, 21-acetyloxy-9α-fluoro-11β-hy-droxyl-3, 20-dioxo-1, 4-pregnadieno-[16α, 17α-d] isoxazoline (FP-ISO-21AC), on nitric oxide (NO) and interleukin 8 (IL-8) production, were inves-tigated together with its parent steroid predni-solone (PRED). PRED is one of the anti-in-flammatory steroids but has systemic side ef-fects which limit the use of it. PRED was modi-fied with ‘antedrug concept’ to create safer drugs that attack problems such as inflamma-tion, then quickly become inactive before they can cause systemic side effect. We had a test about the effect of the modified anti-inflamma-tory steroidal antedrug on anti-inflammatory activity. The present study evaluated their ability to inhibit cytokine-induced NO and IL-8 produc-tion in human alveolar epithelial cells. We also investigated their ability to enhance the expres-sion of inhibitory cytokine receptor, interleukin 22 receptor (IL-22R) in human alveolar epithelial cells. Our results showed that FP-ISO-21AC sh- owed higher ability to inhibit the cytokine - in-duced production of NO than PRED. Exogenous IL-22 was added to the media of both human alveolar epithelial cells (A549) and human lung fibroblast (HLF-1). In the presence of the ex-ogenous inhibitory cytokine IL-22, further re-duction of NO production was observed in A549 cells, which express IL-22R, but not in HLF1, which does not express IL-22R. These data suggested that the steroidal antedrugs en-hanced the expression of IL-22R. FP-ISO- 21AC showed higher potency than PRED to restore the expression of IL-22R. FP-ISO-21AC further reduced NO production to 27% and PRED further reduced NO production to 39%. In con-clusion, a synthesized steroidal antedrug FP- ISO-21AC showed higher anti-inflammatory ef-fects than PRED by inhibiting the expression of pro-inflammatory mediator NO and stimulating the expression of IL-22R.

Steroidal saponins with anti-inflammatory activity from Tribulus terrestris L.

Objective:Tribulus terrestris L.(T.terrestris)is a highly valuable traditional Chinese medicine used to treat stroke,inflammation,pulmonary fibrosis,liver cancer,and urolithiasis.To identify the basic substance responsible for the anti-inflammatory effect of TST(total saponins of Tribulus),its chemical composition was systematically studied,and its effect of inhibiting nitric oxide generation and the expression of related inflammatory factors were determined.Methods:To separate chemical constituents from T.terrestris by column chromatography.Spectroscopic methods,including 1D and 2D nuclear magnetic resonance spectroscopy(NMR)and mass spectrometry(MS)techniques,were used to elucidate the isolated compounds.The anti-inflammatory activities of TST and several compounds were evaluated in vitro.Results:Fifteen steroidal saponins,including 9 furostanol steroidal saponins(1,2,3,4,5,6,7,8,and 15)and 6 isospirostanol steroidal saponins(9,10,11,12,13,and 14),were isolated from T.terrestris.TST significantly decreased the expression of tumor necrosis factor-a(TNF-a)and interleukin-6(IL-6)in RAW 264.7 cells stimulated by lipopolysaccharides.Compounds 13 and 15 evidently reduced TNF-a expression.Compounds 6,10,12,13,and 15 markedly reduced IL-6 expression.Conclusions:Compounds 1 was a novel furostanol steroidal saponin,named 26-O-b-D-glucopyranosyl-(25R)-5afurostan-12-carbonyl-20(22)-en-3b,26-diol-3-O-{b-D-xylopyranosyl-(1→2)-[b-D-xylopyranosyl-(1→3)]-b-D-glucopyranosyl-(1→4)-[a-L-rhamnopyranosyl-(1→2)]-b-D-galactopyranoside}.Compounds 2 was isolated from the family Zygophyllaceae for the first time,and 5 and 6 were isolated from the Tribulus genus.TST and compounds 6,10,12,13,and 15 exerts antiinflammatory activity.

Inheritance of steroidal glycoalkaloids in potato tuber flesh

Potato (Solanum tuberosum L.) is the third most important food crop worldwide after wheat and rice in terms of human consumption. A critical domestication trait for potato was the decrease of toxic steroidal glycoalkaloids (SGAs) in tuber flesh. Here, we used a diploid F2 segregating population derived from a cross between S. tuberosum and the wild potato species Solanum chacoense to map the quantitative trait loci (QTLs) associated with the regulation of SGAs content in tuber flesh. In a three-year study, we identified two QTLs on chromosomes 2 and 8 affecting SGAs content in tuber flesh. The QTL on chromosome 8 harbors 38 genes that are co-expressed with the GLYCOALKALOID METABOLISM genes. These findings lay the foundation for exploiting the genes controlling SGAs content in tuber flesh and they provide a theoretical basis for the use of wild germplasm in potato breeding.

A NEW STEROIDAL SAPONIN FROM SMILAX LEBRUNH

A New steroidal saponin was isolated from the rhizomes of Smilax lebrunii. On the basis of spectral and chemical methods, its structure was elucidated as:(25S)spirost-5-en-3β, 17α, 27-triol-3-0-[β-D-glucopyranosyl(1-4)][α-L-arabinopyranosyl(1-6)]-β-D-glucopyranoside.

STUDIES ON STEROID PLANT-GROWTH REGULATOR 27.ENHANCED PRODUCT DIASTEREOMERIC EXCESSES IN ASYMMETRIC DIHYDROXYLATION OF THE(22E,24R)-AND THE(22E,24S)-24-ALKYL STEROIDAL UNSATURATED SIOECHAIN BY USING THE SHARPLESS IMPROVED CHIRAL LIGAND

The osmium tetroxide catalyzed asymmetric dihydroxylation of the(22E)-steroidal sidechain is described and an unexpected 8:1 ratio of(22R,23R)and(22S,23S)was obtained from the(22E,24S)-24-ethyl substituted sidechain.

A NEW METHOD FOR AROMATIZAT ION OF Δ^(5(10))-STEROIDAL C_3-DIMETHYL KETALS

A new method for aromatization of Δ5（10）-steroidal C3-dimethyl ketalswith pyridinium hydrobromide perbromide （PHP.Py·HBr·Br2） to aromatic Aring steroids in high yield （90-95%） is described.

NEW METHODS FOR AROMATIZATION OF STEROIDAL 2,5(10)-DIENES

New methods for dehydrogenation of steroidal 2,5（10）-dienes with2,3-dichloro-5,6-dicyano-1,4-benzoquinone （DDQ） or pyridinium hydrobromideperbromide（PHP,Py·HBr·Br2） to aromatic A ring steroid in quantitative yield inshort time are described.

Steroidal alkaloids ameliorate cell proliferation,oxidative stress,inflammation and histology outcome in vitro and in vivo

Objective: To investigate the effects of steroidal alkaloids and sarcovagine D isolated from Sarcococca hookeriana var. digyna on cell-proliferation and secretion of inflammatory cytokines in TNF-a-induced human RA-FLS MH7 A in vitro, and against complete Freund's adjuvant(CFA)-induced arthritis rats in vivo. Methods: CCK-8 assay was utilized to evaluate the anti-proliferation activity in vitro. In in-vivo study, rats were randomly divided into control group, model group(CFA), steroidal alkaloids(STA) groups(5.0, 2.5 and 1.25 g/kg BW),and sarcovagine D(SD) groups(50, 100 and 200 mg/kg BW), 10 rats for each group. To evaluate the anti-inflammation effect, the histology, biochemical parameters and expression of inflammatory cytokines were detected. Results: Steroidal alkaloids and sarcovagine D showed strong anti-proliferative activity during MH7 A cell culture proliferation and downregulated NO levels, and inflammatory cytokines(IL-1β, IL-6 and PGE_2) in vitro. The rats treated with CFA induced ankle inflammation and lymphocyte infiltration, upregulated IL-1β, TNF-α,IL-6, PGE_2, MDA and NO levels, and downregulated IL-10 and SOD. On the contrary,steroidal alkaloids ameliorated all the changes induced by CFA in rats, suggesting the antiinflammatory effect of steroidal alkaloids and sarcovagine D. Conclusions: The results suggest that Sarcococca hookeriana var. digyna has anti-inflammatory effect. Steroidal alkaloids and sarcovagine D has the potential to cure RA.

Four New Steroidal Alkaloids from the Roots of Sarcococca Vagans

Four new steroidal alkaloids, named sarcovagine A-D, were isolated from the roots of Sarcococca vagans. Their structures were determined as 20α -dimethylamino-2β,4β-dihydroxy-3β-tigloylamino-5α-pregnane (sarcovagine A, 1), 20α-dimethylamino-2α-hydroxy-4β-acetoxy-3β-tigloylamino-5α-pregnane (sarcovagine B, 2 ), 20α-dimethyltamino-4β-acetoxy-3β-tigloylamino-5α-pregnane(sarcovagine C, 3), 20α-dimethylamino-3-tigloylamin-5α-pregn-2(3)-en-4-one (sarcoagine D. 4),

Chemistry and bioactivities of natural steroidal alkaloids

Steroidal alkaloids possess the basic steroidal skeleton with a nitrogen atom in rings or side chains incorporated as an integral part of the molecule.They have demonstrated a wide range of biological activities,and some of them have even been developed as therapeutic drugs,such as abiraterone acetate(Zytiga®),a blockbuster drug,which has been used for the treatment of prostate cancer.Structurally diverse natural steroidal alkaloids present a wide spectrum of biological activities,which are attractive for natural product chemistry and medicinal chemistry communities.This review comprehensively covers the structural classification,isolation and various biological activities of 697 natural steroidal alkaloids discovered from 1926 to October 2021,with 363 references being cited.

Limonoid and Steroidal Saponin from Azadirachta indica

A new limonoid,17-(5-methoxy-2-oxofuran-3-yl)-28-deoxonimbolide(1),and a new C21 steroidal saponin,2a,4a-dihydroxy-pregn-5-en-16-one-3a-O-D-glucopyranoside(2),together with 11 known compounds were isolated from the methanol extract of the leaves of Azadirachta indica.The structures were elucidated by means of spectroscopic analysis and putative biosynthetic origins.All the compounds were evaluated for their antibacterial activities against six bacterial strains.

Induction of Tolerance to Non Steroidal Anti Inflammatory Drugs Might Be an Alternative Therapeutic in the Painful Crisis of Sickle Cell Disease

Background and Aims: In Ivoirian’s school, the management of vaso-occlusive painful crisis in sickle cell disease requires non steroidal anti inflammatory drugs (NSAIDs). Although their effectiveness, these drugs may be accompanied by intolerance reactions. When these occur, no codified alternative therapeutic seems to be used to our knowledge. Authors aimed to evaluate the induction of tolerance to NSAIDs as an effective alternative therapeutic. Methods: 22 patients (15 men and 7 women aged from 12 to 39 years with mean age: 22.41 ± 7.88) suffering from vaso-occlusive painful crisis were enrolled. They were known to have a history of sickle cell disease and at least one episode of adverse reactions following the Ibuprofen or Diclofenac intake. A rapid protocol of oral challenge was used in patients to induce tolerance to NSAIDs. The first day, initial doses (8.82 mg for Ibuprofen and 2.20 mg for Diclofenac) were given and gradually increased at intervals of 1 hour over a total period of 6 hours. On the second and third days, the therapeutic dose has been orally administrated with an interval of 6 hours over a period of 12 hours. Results: Despite of some cases of failure that might be related to the severity of symptoms or possible patho-physiological mechanism, more than 80% of patients have successfully tolerated Diclofenac and Ibuprofen. Conclusion: This experience appears to be the first in our context. It might be used as a solution in the lack of alternative therapeutic in the management of vaso-occlusive painful crisis of sickle cell disease as well as in other diseases such as HIV infection where patients often develop intolerance to none alternative antibiotics.