GAME15, a scaffold protein, orchestrates the biosynthesis of steroidal glycoalkaloids (a class of compounds with known defensive properties) and steroidal saponins (which contribute to plant defense) in Solanaceae pla...GAME15, a scaffold protein, orchestrates the biosynthesis of steroidal glycoalkaloids (a class of compounds with known defensive properties) and steroidal saponins (which contribute to plant defense) in Solanaceae plants, essential for their defense mechanisms. By assembling key enzymes at the endoplasmic reticulum, GAME15 ensures efficient metabolite production, preventing toxic intermediate diffusion. This breakthrough in plant defense biosynthesis opens opportunities for metabolic engineering, enabling the production of valuable metabolites in non-native hosts and offering potential strategies for crop protection, reducing the need for chemical pesticides.展开更多
Unlike most plants, members of the genus Solanum produce cholesterol and use this as a precursor for steroidal glycoalkaloids. The production of the compounds begins as a branch from brassinosteroid biosynthesis, whic...Unlike most plants, members of the genus Solanum produce cholesterol and use this as a precursor for steroidal glycoalkaloids. The production of the compounds begins as a branch from brassinosteroid biosynthesis, which produces cholesterol that is further modified to produce steroidal glycoalkaloids. During the cholesterol biosynthesis pathway, genetic engineering could alter the formation of cholesterol from provitamin D3(7-dehydrocholesterol) and produce vitamin D3. Cholesterol is a precursor for many steroidal glycoalkaloids, including a-tomatine and esculeoside A. Alpha-tomatine is consumed by mammals and it can reduce cholesterol content and improve LDL:HDL ratio. When there is a high a-tomatine content, the fruit will have a bitter flavor, which together with other steroidal glycoalkaloids serving as protective and defensive compounds for tomato against insect, fungal, and bacterial pests. These compounds also affect the rhizosphere bacteria by recruiting beneficial bacteria. One of the steroidal glycoalkaloids, esculeoside A increases while fruit ripening. This review focuses on recent studies that uncovered key reactions of the production of cholesterol and steroidal glycoalkaloids in tomato connecting to human health, fruit flavor, and plant defense and the potential application for tomato crop improvement.展开更多
Highlights●Natural variations in the SGT3 promoter TATA box repeats directly modulate gene expression and SGAs content in tubers,providing a novel molecular marker for low-steroidal glycoalkaloids(SGAs)breeding.●The...Highlights●Natural variations in the SGT3 promoter TATA box repeats directly modulate gene expression and SGAs content in tubers,providing a novel molecular marker for low-steroidal glycoalkaloids(SGAs)breeding.●The SGT3 promoter haplotype with(TA)10exhibits signifcantly higher transcriptional activity,correlating with high SGAs content,while the(TA)13haplotype is linked to low SGAs in natural germplasms.展开更多
The objective of the research is to develop a quantitative method by ultra high-performance liquid chromatography/ quadrupole time-of-flight mass spectrometry （UHPLC/Q-TOF MS） for the analysis of seven major steroid...The objective of the research is to develop a quantitative method by ultra high-performance liquid chromatography/ quadrupole time-of-flight mass spectrometry （UHPLC/Q-TOF MS） for the analysis of seven major steroidal saponins （timosaponin N, timosaponin El, timosaponin BII, timosaponin B, anemarrhenasaponin I, anemarrhenasaponin A2, and timosaponin AIII） in Anemarrhena asphodeloides Bge. The complete separation of these seven steroidal saponins was achieved within 18 min with an ACQUITY UPLC HSS T3 column using an acetonitrile-water （contain 0.1% formic acid） gradient system. The limits of quantitation （LOQ）, 0.18-0.75 ng/pL for seven steroidal saponins, were determined experimentally. The limits of detection （LOD） were found to be 0.05-0.22 ng/μL for these saponins. The correlation coefficients （r2） for calibration curves varied from 0.9902 to 0.9979. This method showed good repeatability for the quantification of these saponins in rhizomes ofA. asphodeloides, with intra-day and inter-day variations of less than 5.0% for seven steroidal saponins. The recoveries of seven steroidal saponins were from 97.13% to 101.98%. The validated method was successfully applied to quantifying seven steroidal saponins in various sources ofA. asphodeloides （different collecting places or processing methods） and Zhimu concentrate-granules （ZMCG）.展开更多
Two new C 27 steroidal glycosides, named ophiopojaponin A (1) and B (2), together with two known ones, were isolated from the tubers of the famous traditional Chinese herb Ophiopogon japonicus Ker_Gawl. The spect...Two new C 27 steroidal glycosides, named ophiopojaponin A (1) and B (2), together with two known ones, were isolated from the tubers of the famous traditional Chinese herb Ophiopogon japonicus Ker_Gawl. The spectroscopic and chemical evidence revealed their structures to be pennogenin 3_O_[2′_O_acetyl_α_L_rhamnopyranosyl (1→2)]_β_D_xylopyranosyl (1→3)_β_D_glucopyranoside (1), 26_O_β_D_glucopyranosyl_(22ξ, 25R)_3β, 14α, 22ξ, 26_tetrahydroxyfurost_5_ene 3_O_α_L_rhamnopyranosyl (1→2)_β_D_glucopyranoside (2), diosgenin 3_O_[α_L_rhamnopyranosyl (1→2)]_β_D_xylopyrano_syl (1→3)_β_D_glucopyranoside (3) and ruscogenin 1_O_[α_L_rhamnopyranosyl (1→2)]_β_D_xylopyranosyl (1→3)_β_D_fucopyranoside (4).展开更多
Two previously undescribed steroidal compounds, 16, 23-epoxy-22, 26-epimino-cholest-22(N), 23, 25(26)-trien-3β-ol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(1) and 26-O-β-D-gluc...Two previously undescribed steroidal compounds, 16, 23-epoxy-22, 26-epimino-cholest-22(N), 23, 25(26)-trien-3β-ol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(1) and 26-O-β-D-glucopyranosyl-(25 R)-5α-furost-20(22)-en-3β, 26-diol(2), together with 7 known ones including 26-O-β-D-glucopyranosyl-(25 R)-5, 20(22)-dien-furost-3β, 26-diol(3),(25 R)-5-en-spirost-3β-ol-O-β-D-glucopyranosyl-(1→4)-[α-L-rhmanopyranosyl-(1→2)]-β-D-galactopyranoside(4), funkioside D(5), aspidistrin(6), tigogenin-3-O-β-D-lucotrioside(7), desglucolanatigonin II(8), and degalactotigonin(9), were isolated from Solanum lyratum Thunb. Their cytotoxic activities were tested in two cancer cell lines by MTT method. One of the steroidal glycosides(6) showed significant cytotoxic activity against gastric cancer SGC7901 and liver cancer BEL-7402 cells.展开更多
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...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.展开更多
AIM: To develop and validate a high performance liquid chromatography(HPLC) coupled with diode array and evaporative light scattering detectors(DAD-ELSD) method for the quantitative determination and fingerprint analy...AIM: To develop and validate a high performance liquid chromatography(HPLC) coupled with diode array and evaporative light scattering detectors(DAD-ELSD) method for the quantitative determination and fingerprint analysis of ten active constituents in three chemical classes(namely, xanthone glycosides, steroidal saponins, and alkaloids) in Zhimu-Huangbai herb pair(ZB). METHOD: Chromatographic separation was performed on a Diamonsil C18 column(4.6 mm × 250 mm, 5 μm, Dikma) by gradient elution using acetic acid in acetonitrile solution at a flow rate of 1.0 mL·min–1 at 260 nm. The drift tube temperature of ELSD was set to 60 ℃ and nebulizer gas pressure was 4.0 Bar. Method validation was performed to assure its linearity, limits of detection and quantification, precision, repeatability, stability, and accuracy. RESULTS: The HPLC-DAD-ELSD method allowed the quantification of ten compounds(phellodendrine, jatrorrhizine, palmatine, berberine, neomangiferin, mangiferin, timosaponin E-I, timosaponin B-II, timosaponin B, and timosaponin A-III), and was successfully applied to fingerprint analysis for ten batches of ZB samples. CONCLUSION: This was the first time to apply the combination of DAD and ELSD for the simultaneous determination of ten active ingredients in ZB. The results showed that the combination of quantitative analysis for marker ingredients and chemical fingerprint for the TCM herb pair provides a potentially powerful, widely introduced, and internationally accepted strategy for assessment of complex TCM formulas.展开更多
Two new C21 steroidal glycosides, cynanauriculoside I and cynanauriculoside II, were isolated from the roots of Cynanchum aurichulatum. Their structures were established using spectroscopic methods including one and ...Two new C21 steroidal glycosides, cynanauriculoside I and cynanauriculoside II, were isolated from the roots of Cynanchum aurichulatum. Their structures were established using spectroscopic methods including one and two-dimensional NMR.展开更多
AIM: To investigate the chemical constituents of Dioscorea zingiberensis C. H. Wright. METHODS: The compounds were isolated by various chromatographic techniques, and the structures of the new steroidal saponins were ...AIM: To investigate the chemical constituents of Dioscorea zingiberensis C. H. Wright. METHODS: The compounds were isolated by various chromatographic techniques, and the structures of the new steroidal saponins were elucidated by extensive 1D- and 2D-NMR, MS, and IR spectral analysis. RESULTS: The 70% EtOH extract of the rhizomes of Dioscorea zingiberensis afforded two new steroidal saponins, zingiberenosides A(1) and B(2), along with eight known analogues, 3β, 26-dihydroxy-25(R)-furosta-△5, 20(22)-diene-3-O-α-Lrhamnopyranosyl-(1→2)-O-β-D-glucopyranoside(3), methyl parvifloside(4), deltoside(5), methyl deltoside(6), zingiberensis new saponin(7), deltonin(8), progenin III(9) and diosgenin-diglucoside(10). CONCLUSION: Two new steroidal saponins were isolated from Dioscorea zingiberensis and their structures determined.展开更多
Two new steroidal glycosides named Lm-4 （1） and Lm-5 （2） were isolated from the tubers of Liriope muscari. Their structures were elucidated by 1D and 2D NMR, ESI/MALDIMS techniques, and chemical methods.
Two new steroidal glycosides named cyanoauriculoside A （1） and B （2）, have been isolated from the roots of Cynanchum auriculatum Royle ex Wight. The structure of cyanoauriculoside A （1） was determined to be 20-O...Two new steroidal glycosides named cyanoauriculoside A （1） and B （2）, have been isolated from the roots of Cynanchum auriculatum Royle ex Wight. The structure of cyanoauriculoside A （1） was determined to be 20-O-acetyl-penupogenin-3-O-β-D- glucopyranosyl-（ 1 →4）-β-D-glucopyranosyl-（ 1 →4）-α -L-cymaropyranosyl- （ 1 →4）-β-D-cymaropyranosyl- （ 1 →4）-α-L-diginopyranosyl-（1→4）-β-D-cymaropyranoside. Cyanoauriculoside B （2） was characterized as 20-O-acetylpenupogenin-3-O-β-D-gluco- pyranosyl-（ 1 →4）-α-L-cymaropyranosyl-（ 1 →4）-β-D-cymaropyranosyl-（ 1 →4）-α-L-diginopyranosyl-（ 1 →4）-β-D-cymaropyranoside. The structures of these compounds were elucidated based on the chemical and spectroscopic evidence.展开更多
AIM： To study the chemical constituents of the roots of Asparagus cochinchinensis （Asparagaceae）. METHOD： The compounds were isolated with Diaion HP20, silica gel, and ODS chromatography, and their structures were...AIM： To study the chemical constituents of the roots of Asparagus cochinchinensis （Asparagaceae）. METHOD： The compounds were isolated with Diaion HP20, silica gel, and ODS chromatography, and their structures were de- termined on the basis of chemical methods, HR-ESI-MS, and 1 D- and 2D-NMR techniques. RESULTS： Seven compounds were isolated from the n-butanol fraction of the roots of A. cochinchinensis, and their structures were elucidated as （25S）-26-O-β-D-glucopyranosyl-5β-furostan-3β, 22a, 26-triol-12-one-3-O-β-D-glucopyranoside （1）, （25S）-26- O-β-D-glucopyranosyl-22a-methoxy-5β-furostan-3p, 26-diol-12-one-3-O-β-D-glucopyranoside （2）, （25S）-26-O-β-D-glucopyra- nosyl-5β-furostan-3β, 22a, 26-triol （3）, （25S）-26-O-β-D-glucopyranosyl-5β-furstan-3β, 22a, 26-triol-3-O-β-D-glucopyranoside （4）, （25S）-26-O-β-D-glucopyranosyl-5β-furostan-3β, 22a, 26-triol-3-O-a-L-rhamnopyranosyl-（1, 4）-β-D-glucopyranoside （5）, （25S）- 5β-spirostan-3fl-ol-3-O-a-L-rhamnopyranoside （6）, and （25S）-5β-spirostan-3β-ol-3-O-β-D-glucopyranoside （7）. CONCLUSION： Compounds 1 and 2 were two new furostanol saponins.展开更多
Two new C-27 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 str...Two new C-27 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-alpha-L-rhamnopyranosyl (1-->2)]-beta-D-xylopyranosyl (1-->3)-beta-D-glucopyranoside (1) and 26-O-beta-D-glucopyranosyl-(22 xi, 25R)-3 beta, 14 alpha, 22 xi, 26-tetrahydroxyfurost-5-ene 3-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranoside (2), respectively.展开更多
The present study was designed to investigate the chemical constituents and bioactivities of the roots of Liriope muscari(Decne.) L.H. Bailey. The compounds were isolated through various chromatography techniques, inc...The present study was designed to investigate the chemical constituents and bioactivities of the roots of Liriope muscari(Decne.) L.H. Bailey. The compounds were isolated through various chromatography techniques, including silica gel, Sephadex LH-20, and semi-preparative HPLC. The structures were elucidated by infrared(IR), mass spectrometric(MS), 1D- and 2D-NMR analyses in comparison with reference data. In addition, the cytotoxicity of these compounds against human breast cancer MDA-MB-435 cells was evaluated by the MTT assay. Two new steroidal glycosides, 25(R, S)-ruscogenin-1-O-[β-D-fucopyranosyl(1→2)]-[ β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(Liriopem I, 1) and 25(R, S)- ruscogenin-1-O-[β-D-fucopyranosyl(1→2)]-[β-D-xylopyranosyl(1→4)]-β-D-fucopyranoside(Liriopem II, 2) and two known compounds LM-S6(3) and DT-13(4) were isolated and identified. Liriopem I(1), liriopem II(2) and DT-13(4) showed remarkable cytotoxicity with IC50 values being(0.58 ± 0.08),(0.05 ± 0.10), and(0.15 ± 0.09) μg·m L-1, respectively. In summary, compounds 1 and 2 identified in the present study exerted cytotoxicity against breast cancer cells, providing a basis for future development of these compounds as novel anticancer agents.展开更多
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 config...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.展开更多
Two new C-22 steroidal lactone glycosides, named dracaenoside A and B were isolated from the methanol extract of the fresh stem of Dracaena cochinchinensis. Their structures were established as (20S)3b,14a,16b-trihyd...Two new C-22 steroidal lactone glycosides, named dracaenoside A and B were isolated from the methanol extract of the fresh stem of Dracaena cochinchinensis. Their structures were established as (20S)3b,14a,16b-trihydroxy pregn-5-ene-22-carboxylic acid (22,16)-lactone 3-O-a- L-rhamnopyranosyl (1→2)[ a-L-rhamnopyranosyl (1→4)]-b-D-glucopyranoside and (20S)3b, 14a, 16b-trihydroxy pregn-5-ene-22-carboxylic acid (22,16)-lactone 3-O-a-L-rhamnopyranosyl (1→2) [b-D-glucopyranosyl(1→3)]-b-D-glucopyranoside by means of 2D NMR spectral and chemical methods. It is the first time that steroidal lactone glycosides were isolated from the genus Dracaena.展开更多
Two new steroidal alkaloids, isoconkuressine and N-formylconessimine, together with 6 known steroidal alkaloids including conkuressine, conessine, isoconessimine, conimine, conarrhimine, and funtudienine, were isolate...Two new steroidal alkaloids, isoconkuressine and N-formylconessimine, together with 6 known steroidal alkaloids including conkuressine, conessine, isoconessimine, conimine, conarrhimine, and funtudienine, were isolated from the seeds of Holarrhena antidysenteriaca Wall.ex A.DC. Their intrinsic antibacterial activities and synergistic effects with penicillin and vancomycin were analyzed in methicillin sensitive staphylococcus aureus(MSSA) and methicillin resistant staphylococcus aureus(MRSA). Two of the steroidal alkaloids including one new compound(N-formylconessimine) showed potential antibacterial activity and possessed synergistic effects with penicillin and vancomycin, respectively.展开更多
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 glycoalka...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.展开更多
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 increas...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.展开更多
基金supported by the National Natural Science Foundation of China(31971314)the Open Fund of State Key Laboratory of Tea Plant Biology and Utilization(SKLTOF20210122).
文摘GAME15, a scaffold protein, orchestrates the biosynthesis of steroidal glycoalkaloids (a class of compounds with known defensive properties) and steroidal saponins (which contribute to plant defense) in Solanaceae plants, essential for their defense mechanisms. By assembling key enzymes at the endoplasmic reticulum, GAME15 ensures efficient metabolite production, preventing toxic intermediate diffusion. This breakthrough in plant defense biosynthesis opens opportunities for metabolic engineering, enabling the production of valuable metabolites in non-native hosts and offering potential strategies for crop protection, reducing the need for chemical pesticides.
文摘Unlike most plants, members of the genus Solanum produce cholesterol and use this as a precursor for steroidal glycoalkaloids. The production of the compounds begins as a branch from brassinosteroid biosynthesis, which produces cholesterol that is further modified to produce steroidal glycoalkaloids. During the cholesterol biosynthesis pathway, genetic engineering could alter the formation of cholesterol from provitamin D3(7-dehydrocholesterol) and produce vitamin D3. Cholesterol is a precursor for many steroidal glycoalkaloids, including a-tomatine and esculeoside A. Alpha-tomatine is consumed by mammals and it can reduce cholesterol content and improve LDL:HDL ratio. When there is a high a-tomatine content, the fruit will have a bitter flavor, which together with other steroidal glycoalkaloids serving as protective and defensive compounds for tomato against insect, fungal, and bacterial pests. These compounds also affect the rhizosphere bacteria by recruiting beneficial bacteria. One of the steroidal glycoalkaloids, esculeoside A increases while fruit ripening. This review focuses on recent studies that uncovered key reactions of the production of cholesterol and steroidal glycoalkaloids in tomato connecting to human health, fruit flavor, and plant defense and the potential application for tomato crop improvement.
基金financially supported by the Guangdong Major Project of Basic and Applied Basic Research,China(2021B0301030004)the National Natural Science Foundation of China(32360757,U2202206 and 32361143517)the Yunnan Fundamental Research Projects,China(202201AT070037,202501AS070012)。
文摘Highlights●Natural variations in the SGT3 promoter TATA box repeats directly modulate gene expression and SGAs content in tubers,providing a novel molecular marker for low-steroidal glycoalkaloids(SGAs)breeding.●The SGT3 promoter haplotype with(TA)10exhibits signifcantly higher transcriptional activity,correlating with high SGAs content,while the(TA)13haplotype is linked to low SGAs in natural germplasms.
基金Major National Science and Technology Projects (Grant No. 2009ZX09102-106, 2011ZX09102-002-09)National Natural Science Foundation of China (Grant No. 81274053)
文摘The objective of the research is to develop a quantitative method by ultra high-performance liquid chromatography/ quadrupole time-of-flight mass spectrometry （UHPLC/Q-TOF MS） for the analysis of seven major steroidal saponins （timosaponin N, timosaponin El, timosaponin BII, timosaponin B, anemarrhenasaponin I, anemarrhenasaponin A2, and timosaponin AIII） in Anemarrhena asphodeloides Bge. The complete separation of these seven steroidal saponins was achieved within 18 min with an ACQUITY UPLC HSS T3 column using an acetonitrile-water （contain 0.1% formic acid） gradient system. The limits of quantitation （LOQ）, 0.18-0.75 ng/pL for seven steroidal saponins, were determined experimentally. The limits of detection （LOD） were found to be 0.05-0.22 ng/μL for these saponins. The correlation coefficients （r2） for calibration curves varied from 0.9902 to 0.9979. This method showed good repeatability for the quantification of these saponins in rhizomes ofA. asphodeloides, with intra-day and inter-day variations of less than 5.0% for seven steroidal saponins. The recoveries of seven steroidal saponins were from 97.13% to 101.98%. The validated method was successfully applied to quantifying seven steroidal saponins in various sources ofA. asphodeloides （different collecting places or processing methods） and Zhimu concentrate-granules （ZMCG）.
文摘Two new C 27 steroidal glycosides, named ophiopojaponin A (1) and B (2), together with two known ones, were isolated from the tubers of the famous traditional Chinese herb Ophiopogon japonicus Ker_Gawl. The spectroscopic and chemical evidence revealed their structures to be pennogenin 3_O_[2′_O_acetyl_α_L_rhamnopyranosyl (1→2)]_β_D_xylopyranosyl (1→3)_β_D_glucopyranoside (1), 26_O_β_D_glucopyranosyl_(22ξ, 25R)_3β, 14α, 22ξ, 26_tetrahydroxyfurost_5_ene 3_O_α_L_rhamnopyranosyl (1→2)_β_D_glucopyranoside (2), diosgenin 3_O_[α_L_rhamnopyranosyl (1→2)]_β_D_xylopyrano_syl (1→3)_β_D_glucopyranoside (3) and ruscogenin 1_O_[α_L_rhamnopyranosyl (1→2)]_β_D_xylopyranosyl (1→3)_β_D_fucopyranoside (4).
基金supported by the Science and Technology Department Plan of Jilin Province(Nos.20160101341JC and 20160622010JC)
文摘Two previously undescribed steroidal compounds, 16, 23-epoxy-22, 26-epimino-cholest-22(N), 23, 25(26)-trien-3β-ol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(1) and 26-O-β-D-glucopyranosyl-(25 R)-5α-furost-20(22)-en-3β, 26-diol(2), together with 7 known ones including 26-O-β-D-glucopyranosyl-(25 R)-5, 20(22)-dien-furost-3β, 26-diol(3),(25 R)-5-en-spirost-3β-ol-O-β-D-glucopyranosyl-(1→4)-[α-L-rhmanopyranosyl-(1→2)]-β-D-galactopyranoside(4), funkioside D(5), aspidistrin(6), tigogenin-3-O-β-D-lucotrioside(7), desglucolanatigonin II(8), and degalactotigonin(9), were isolated from Solanum lyratum Thunb. Their cytotoxic activities were tested in two cancer cell lines by MTT method. One of the steroidal glycosides(6) showed significant cytotoxic activity against gastric cancer SGC7901 and liver cancer BEL-7402 cells.
基金supported by the National Natural Science Foundation of China(No.81503295)2011 Program for Excellent Scientific and Technological Innovation Team of Jiangsu Higher Education+1 种基金Funded by the Priority Academic Program Development of Jiangsu Higher Education InstitutionsJiangsu Province 2011 Plan for Collaborative Innovation
文摘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.
基金supported by the Natural Science Foundation of Shanghai City,China(No.10411969800)the National Nature Science Foundation of China(Nos.81202866 and 81302856)
文摘AIM: To develop and validate a high performance liquid chromatography(HPLC) coupled with diode array and evaporative light scattering detectors(DAD-ELSD) method for the quantitative determination and fingerprint analysis of ten active constituents in three chemical classes(namely, xanthone glycosides, steroidal saponins, and alkaloids) in Zhimu-Huangbai herb pair(ZB). METHOD: Chromatographic separation was performed on a Diamonsil C18 column(4.6 mm × 250 mm, 5 μm, Dikma) by gradient elution using acetic acid in acetonitrile solution at a flow rate of 1.0 mL·min–1 at 260 nm. The drift tube temperature of ELSD was set to 60 ℃ and nebulizer gas pressure was 4.0 Bar. Method validation was performed to assure its linearity, limits of detection and quantification, precision, repeatability, stability, and accuracy. RESULTS: The HPLC-DAD-ELSD method allowed the quantification of ten compounds(phellodendrine, jatrorrhizine, palmatine, berberine, neomangiferin, mangiferin, timosaponin E-I, timosaponin B-II, timosaponin B, and timosaponin A-III), and was successfully applied to fingerprint analysis for ten batches of ZB samples. CONCLUSION: This was the first time to apply the combination of DAD and ELSD for the simultaneous determination of ten active ingredients in ZB. The results showed that the combination of quantitative analysis for marker ingredients and chemical fingerprint for the TCM herb pair provides a potentially powerful, widely introduced, and internationally accepted strategy for assessment of complex TCM formulas.
文摘Two new C21 steroidal glycosides, cynanauriculoside I and cynanauriculoside II, were isolated from the roots of Cynanchum aurichulatum. Their structures were established using spectroscopic methods including one and two-dimensional NMR.
基金supported by the Science and Technology Achievement Transformation Project of Jiangsu Province(No.BA2010144)the scientific and technological major special project for "Significant Creation of New Drugs"(No.2012ZX09101231)
文摘AIM: To investigate the chemical constituents of Dioscorea zingiberensis C. H. Wright. METHODS: The compounds were isolated by various chromatographic techniques, and the structures of the new steroidal saponins were elucidated by extensive 1D- and 2D-NMR, MS, and IR spectral analysis. RESULTS: The 70% EtOH extract of the rhizomes of Dioscorea zingiberensis afforded two new steroidal saponins, zingiberenosides A(1) and B(2), along with eight known analogues, 3β, 26-dihydroxy-25(R)-furosta-△5, 20(22)-diene-3-O-α-Lrhamnopyranosyl-(1→2)-O-β-D-glucopyranoside(3), methyl parvifloside(4), deltoside(5), methyl deltoside(6), zingiberensis new saponin(7), deltonin(8), progenin III(9) and diosgenin-diglucoside(10). CONCLUSION: Two new steroidal saponins were isolated from Dioscorea zingiberensis and their structures determined.
文摘Two new steroidal glycosides named Lm-4 （1） and Lm-5 （2） were isolated from the tubers of Liriope muscari. Their structures were elucidated by 1D and 2D NMR, ESI/MALDIMS techniques, and chemical methods.
基金financial support of this work by the National Key Technology R&D Program in the 11th Five Year Plan of China(No.2007BAI48B08)
文摘Two new steroidal glycosides named cyanoauriculoside A （1） and B （2）, have been isolated from the roots of Cynanchum auriculatum Royle ex Wight. The structure of cyanoauriculoside A （1） was determined to be 20-O-acetyl-penupogenin-3-O-β-D- glucopyranosyl-（ 1 →4）-β-D-glucopyranosyl-（ 1 →4）-α -L-cymaropyranosyl- （ 1 →4）-β-D-cymaropyranosyl- （ 1 →4）-α-L-diginopyranosyl-（1→4）-β-D-cymaropyranoside. Cyanoauriculoside B （2） was characterized as 20-O-acetylpenupogenin-3-O-β-D-gluco- pyranosyl-（ 1 →4）-α-L-cymaropyranosyl-（ 1 →4）-β-D-cymaropyranosyl-（ 1 →4）-α-L-diginopyranosyl-（ 1 →4）-β-D-cymaropyranoside. The structures of these compounds were elucidated based on the chemical and spectroscopic evidence.
基金supported by the National Natural Science foundation of China(No.20962013)
文摘AIM： To study the chemical constituents of the roots of Asparagus cochinchinensis （Asparagaceae）. METHOD： The compounds were isolated with Diaion HP20, silica gel, and ODS chromatography, and their structures were de- termined on the basis of chemical methods, HR-ESI-MS, and 1 D- and 2D-NMR techniques. RESULTS： Seven compounds were isolated from the n-butanol fraction of the roots of A. cochinchinensis, and their structures were elucidated as （25S）-26-O-β-D-glucopyranosyl-5β-furostan-3β, 22a, 26-triol-12-one-3-O-β-D-glucopyranoside （1）, （25S）-26- O-β-D-glucopyranosyl-22a-methoxy-5β-furostan-3p, 26-diol-12-one-3-O-β-D-glucopyranoside （2）, （25S）-26-O-β-D-glucopyra- nosyl-5β-furostan-3β, 22a, 26-triol （3）, （25S）-26-O-β-D-glucopyranosyl-5β-furstan-3β, 22a, 26-triol-3-O-β-D-glucopyranoside （4）, （25S）-26-O-β-D-glucopyranosyl-5β-furostan-3β, 22a, 26-triol-3-O-a-L-rhamnopyranosyl-（1, 4）-β-D-glucopyranoside （5）, （25S）- 5β-spirostan-3fl-ol-3-O-a-L-rhamnopyranoside （6）, and （25S）-5β-spirostan-3β-ol-3-O-β-D-glucopyranoside （7）. CONCLUSION： Compounds 1 and 2 were two new furostanol saponins.
基金a key project of Chinese Academy of sciences. We are grateful to the members of Instrument Group of Phytochemistry Laboratory, K
文摘Two new C-27 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-alpha-L-rhamnopyranosyl (1-->2)]-beta-D-xylopyranosyl (1-->3)-beta-D-glucopyranoside (1) and 26-O-beta-D-glucopyranosyl-(22 xi, 25R)-3 beta, 14 alpha, 22 xi, 26-tetrahydroxyfurost-5-ene 3-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranoside (2), respectively.
基金supported by the Major National Science and Technology Project of China for Significant New Drugs Development(No.2012ZX09102201-015)the National Natural Science Foundation of China(No.81274004)+2 种基金the Priority Academic Program Development of Jiangsu Higher Education Institutionsthe 2011’Program for Excellent Scientific and Technological Innovation Team of Jiangsu Higher Educationthe Major Project Program of State Key Laboratory of Natural Medicines,China Pharmaceutical University(No.SKLNMZZ201203)
文摘The present study was designed to investigate the chemical constituents and bioactivities of the roots of Liriope muscari(Decne.) L.H. Bailey. The compounds were isolated through various chromatography techniques, including silica gel, Sephadex LH-20, and semi-preparative HPLC. The structures were elucidated by infrared(IR), mass spectrometric(MS), 1D- and 2D-NMR analyses in comparison with reference data. In addition, the cytotoxicity of these compounds against human breast cancer MDA-MB-435 cells was evaluated by the MTT assay. Two new steroidal glycosides, 25(R, S)-ruscogenin-1-O-[β-D-fucopyranosyl(1→2)]-[ β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(Liriopem I, 1) and 25(R, S)- ruscogenin-1-O-[β-D-fucopyranosyl(1→2)]-[β-D-xylopyranosyl(1→4)]-β-D-fucopyranoside(Liriopem II, 2) and two known compounds LM-S6(3) and DT-13(4) were isolated and identified. Liriopem I(1), liriopem II(2) and DT-13(4) showed remarkable cytotoxicity with IC50 values being(0.58 ± 0.08),(0.05 ± 0.10), and(0.15 ± 0.09) μg·m L-1, respectively. In summary, compounds 1 and 2 identified in the present study exerted cytotoxicity against breast cancer cells, providing a basis for future development of these compounds as novel anticancer agents.
基金supported by the National Natural Science Foundation of China(No.81573560)the National Training Programs of Innovation and Entrepreneurship for Undergraduates(No.G12123)
文摘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.
文摘Two new C-22 steroidal lactone glycosides, named dracaenoside A and B were isolated from the methanol extract of the fresh stem of Dracaena cochinchinensis. Their structures were established as (20S)3b,14a,16b-trihydroxy pregn-5-ene-22-carboxylic acid (22,16)-lactone 3-O-a- L-rhamnopyranosyl (1→2)[ a-L-rhamnopyranosyl (1→4)]-b-D-glucopyranoside and (20S)3b, 14a, 16b-trihydroxy pregn-5-ene-22-carboxylic acid (22,16)-lactone 3-O-a-L-rhamnopyranosyl (1→2) [b-D-glucopyranosyl(1→3)]-b-D-glucopyranoside by means of 2D NMR spectral and chemical methods. It is the first time that steroidal lactone glycosides were isolated from the genus Dracaena.
基金supported by the Natural Science Foundation of Liaoning Province(No.201602208)
文摘Two new steroidal alkaloids, isoconkuressine and N-formylconessimine, together with 6 known steroidal alkaloids including conkuressine, conessine, isoconessimine, conimine, conarrhimine, and funtudienine, were isolated from the seeds of Holarrhena antidysenteriaca Wall.ex A.DC. Their intrinsic antibacterial activities and synergistic effects with penicillin and vancomycin were analyzed in methicillin sensitive staphylococcus aureus(MSSA) and methicillin resistant staphylococcus aureus(MRSA). Two of the steroidal alkaloids including one new compound(N-formylconessimine) showed potential antibacterial activity and possessed synergistic effects with penicillin and vancomycin, respectively.
基金supported by the Agricultural Science and Technology Innovation Program from the Chinese Academy of Agricultural Sciences(ASTIP-CAAS)the Agricultural Science and Technology Innovation Program Cooperation and Innovation Mission,CAAS(CAAS-XTCX2016)+3 种基金the Advanced Technology Talents in Yunnan Province,China 2013HA025)the PhD Scholar Newcomer Award in Yunnan Province,China(01701205020516025)the Graduate Research and Innovation Fund Project,China(yjs201679)supported by the Ministry of Agriculture and Rural Affairs of China,the Shenzhen Municipal and Dapeng District Governments,China
文摘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.
基金Supported by the "Regional Specialized Industry Development Program",Ministry of Trade,Industry,and Energy(MOTIE),Koreasupervised by the Korea Institute for Advancement of Technology(KIAT)
文摘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.
