Three new steroidal saponins from Fritillaria pallidiflora

Three new steroidal saponins, pallidiflosides A (1), B (2), and C (3), have been isolated from the dry bulbs of Fritillaria pallidiflora Schrenk. Their structures were elucidated as 26-O-β-d-glucopyranosyl-(25R)-furost-5,20(22)-dien-3β,26-diol-3-O-β-d-xylopyranosyl(1?→?4)-[α-l-rhamnopyranosyl(1?→?2)]-β-d-glucopyranoside (1); 26-O-β-d-glucopyranosyl-3β,26-dihydroxyl-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-α-l-rhamnopyranosyl(1?→?2)-β-d-glucopyranoside (2); and (25R)-spirost-5-ene-3β,17α-diol-3-O-β-d-glucopyranosyl(1?→?4)-β-d-galactopyranoside (3) by spectroscopic techniques and chemical means.     

伊犁贝母的生药学鉴定

目的：研究伊犁贝母的生药学鉴别特征。方法：利用性状、显微、薄层色谱与紫外光谱鉴别法为该药材进行初步鉴定研究,并确立其鉴别特征。结果：确定了伊犁贝母的性状、显微、薄层色谱与紫外光谱鉴别特征。结论：本研究可为伊犁贝母的鉴别、开发利用与质量控制提供依据。     

Two new steroidal saponins from Tribulus terrestris

Two new steroidal saponins and two known flavonoid glycosides were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic analysis and chemical reaction as 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-12-one-3β,22α,26-triol-3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (1), 26-O-β-d-glucopyranosyl-(25S)-5α-furostan-22-methoxy-2α,3β,26-triol-3-O-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl(1 → 4)-β-d-galactopyranoside (2), kaempferol-3-gentiobioside (3), and isorhamnetin-3-gentiobioside (4).     

Two new steroidal saponins from Tribulus terrestris L.

Two new steroidal saponins were isolated from the fruits of Tribulus terrestris L. Their structures were elucidated by spectroscopic and chemical analysis as (23S,24R,25R)-5α-spirostane-3β,23,24-triol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (1) and (23S,24R,25S)-5α-spirostane-3β,23,24-triol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (2).     

伊贝母的HPLC指纹图谱研究

目的 建立伊贝母的HPLC-ELSD指纹图谱.方法 采用HPLC-ELSD法对伊贝母样品进行测定,并用SPSS 22.0软件对不同批次的样品进行主成分分析和聚类分析.结果 筛选出特征峰累计贡献率达81.436％的4个主成分,并对原始数据进行系统聚类分析,建立了伊贝母的特征指纹图谱.结论 聚类分析的结果与其植物学分类的一致,表明该法可用于伊贝母的质量控制.     

伊犁贝母中西贝素和西贝素苷的高效液相色谱-蒸发光散射检测法

目的建立伊犁贝母中无紫外吸收的活性异甾体生物碱西贝素和西贝素苷的HPLC测定方法。方法HPLC-蒸发光散射检测器法。结果西贝素苷和西贝素的线性范围分别为48.72-194.88μg·mL^-1和60.72-161.92μg·mL^-1;RSD日内0.7%和0.9%,日间1.0%和1.5%;低、中、高浓度回收率分别为95.8%,96.9%,96.0%和97.1%,96.7%,96.8%;最低检测限分别为1.53和2.43μg·mL^-1。结论本法快速、简便、灵敏和分离度好,适用于伊贝母中活性生物碱的测定。     

穿龙薯蓣中甾体皂苷的分离与鉴定

目的 研究穿龙薯蓣Dioscorea ni pponica Makin根茎的化学成分.方法 采用硅胶柱色谱、ODS柱色谱以及制备HPLC等手段进行分离纯化,通过理化性质和波谱学技术进行结构鉴定.结果 从正丁醇层中分离得到5个甾体皂苷类化合物,分别鉴定为纤细皂苷(1)、薯蓣皂苷(2)、伪原薯蓣皂苷(3)、甲基原纤细皂苷(4)、原薯蓣皂苷(5).结论 其中化合物4为首次从穿龙薯蓣中分离得到.     

化学合成具有抗肿瘤活性甾体皂苷的研究进展

甾体皂苷是天然产物中～类重要的生物活性物质，人们已经发现了许多具有抗肿瘤活性的甾体皂苷化合物，对该类化合物的合成、结构改造及药理活性的研究也取得了一些进展，并初步总结出一些构效关系的规律。对进一步开发抗癌新药具有指导作用。该文对近10年来，化学合成的具有抗肿瘤活性的甾体皂苷的研究情况进行综述。     

Two new steroidal saponins from the roots of Cynanchum limprichtii

Abstract

As a part of our continuing research for bioactive constituents from Cynanchum limprichtii Schltr., two new C₂₁ steroidal glycosides limproside A (1) and limproside B (2) were isolated from the roots of Cynanchum limprichtii. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. The cytotoxicity of two compounds against two selected human cancer cell lines was assayed.     

小根蒜甾体皂苷类成分的分离鉴定及抗癌活性

目的对小根蒜中甾体皂苷类成分进行分离和结构鉴定,并对得到的化合物进行体外抗癌活性评价.方法使用大孔吸附树脂、硅胶、ODS柱色谱及制备高效液相色谱等方法,通过化合物的理化性质及各种光谱技术鉴定化合物的结构.采用MTT法测定化合物体外抗癌活性.结果从小根蒜60%(φ)乙醇提取物中分离得到8个甾体皂苷类化合物,分别鉴定为薤白皂苷B(1)、薤白皂苷C(2)、薤白皂苷E(3)、(22S)-胆甾-5-烯-1β,3β,16β,22-羟基-1-氧-α-L-鼠李吡喃糖基-16-氧-β-D-葡萄吡喃糖苷(4)、(25R)-26-氧-β-D-葡萄吡喃糖基-22-羟基-呋甾-5(6)-烯-3β,26-二醇-3-氧-β-D-葡萄吡喃糖基(1→2)[β-D-葡萄吡喃糖基(1→3)]-β-D-葡萄吡喃糖基(1→4)-β-D-半乳吡喃糖苷(5)、薤白皂苷F(6)、薤白皂苷G(7)、(25R)-26-氧-β-D-葡萄吡喃糖基-22-羟基-5β-呋甾-3β,26-二醇-3-氧-β-D-葡萄吡喃糖基(1→2)-β-D-半乳吡喃糖苷(8).化合物2、5、8在25μg·mL-1的质量浓度下可以明显地抑制SF-268和NCI-H460肿瘤细胞的生长.结论化合物8为从本属植物中首次分离得到,化合物4、5为首次从中药小根蒜中分离得到,化合物2、5、8有明显的体外抗癌作用.     

New steroidal glycosides from Hosta plantaginea (Lam.) Aschers

Four new furostanol glycosides were isolated from the flowers of Hosta plantaginea (Lam.) Aschers. On the basis of spectroscopic methods including 1D and 2D NMR experiments, their structures were elucidated as 26-O-β-d-glucopyranosyl-(25R)-22-O-methyl-5α-furostan-2α,3β,22ξ,26-tetrol 3-O-α-l-rhamnopyranosyl-(1 → 4)-O-β-d-xylopyranosyl-(1 → 3)-[O-β-d-glucopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (hostaplantagineoside A, 1), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-20(22)-ene-2α,3β,26-triol-3-O-β-d-glucopyranosyl-(1 → 2)-[O-β-d-xylopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (hostaplantagineoside B, 2), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-22(23)-ene-2α,3β,20α,26-tetraol-3-O-β-d-glucopyranosyl-(1 → 2)-[O-β-d-xylopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-galactopyranoside (hostaplantagineoside C, 3), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-20(22)-ene-2α,3β,26-triol-3-O-α-l-rhamnopyranosyl-(1 → 4)-O-β-d-xylopyranosyl-(1 → 3)-[O-β-d-glucopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (hostaplantagineoside D, 4).     

Two new triterpenoid saponins from rhizome of Anemone amurensis

Two new triterpenoid saponins were isolated from the 70% ethanol extract of the rhizome of Anemone amurensis, they are oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1) and 23,27-dihydroxy oleanolic acid 3-O-α-l-arabinopyranoside (2). The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D and 2D NMR data and HR-ESI-MS. Compounds 1 and 2 were tested for cytotoxicities against three human cancer cell lines (A549, Hep-G2, and MCF-7). Compound 1 showed potent cytotoxicity with IC₅₀ values of 34.76, 41.17, and 28.92 μM, respectively, while compound 2 with IC₅₀>100 μM.     

Two new steroidal saponins from the biotransformation product of the rhizomes of Dioscorea nipponica

Two new steroidal saponins, dioscins E (1) and F (2), along with nine known steroidal saponins, were isolated from the biotransformation product of the rhizomes of Dioscorea nipponica using Aspergillus oryzae. The structures of new compounds were established as 25(R)-spirost-5-en-21β-methyl-3β-ol-3-O-α- l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (1) and (25R)-spirost-5-en-3β-ol-7-one 3-O-α- l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (2) by detailed spectroscopic analyses including 1D and 2D NMR spectral data (¹H–¹H COSY, HSQC, and HMBC) and MS spectrometry.     

重楼总皂苷的纯化工艺研究

目的：优选重楼总皂苷的纯化工艺。方法：综合运用醇溶液调节pH、醇提和大孔吸附树脂技术,以总皂苷含量、总皂苷收率为指标,优选重楼总皂苷的纯化工艺。结果：优化后的重楼总皂苷的纯化工艺条件为：70％乙醇提取液调节pH值至9,抽滤,将滤液调pH值至中性,浓缩至0．5g生药／mL,调pH值至8,离心（4000r／min,30min）,上清液部分上D101大孔树脂柱纯化（上样量为70％饱和吸附量,径高比为1：5,上样流速为4．5BV／h,纯化溶剂为20％乙醇,用量为6BV,洗脱溶剂为70％乙醇,用量为8BV,流速为7BV／h）。采用本工艺制备的中间体中总皂苷含量达71．6％,总皂苷收率为85．71％。结论：验证试验结果表明,优选出的工艺稳定、合理、可行。     

Steroidal saponins from the rhizome of Polygonatum sibiricum

Four new steroidal saponins, 3-O-β-D-glucopyranosyl(1→4)-β-D-fucopyranosyl -(25R)-spirost-5-en-3β,17α-diol (1), 3-O-β-D-glucopyranosyl(1→4)-β-D- fucopyranosyl-(25S)-spirost-5-en-3β,17α-diol (2), 3-O-β-D-glucopyranosyl(1→2) -β-D-glucopyranosyl(1→4)-β-D-fucopyranosyl-(25R)-spirost-5-en-3β,17α-diol (3), 3-O-β-D-glucopyranosyl(1→4)-β-D-fucopyranosyl-(25R/S)-spirost-5-en-3β,12β-diol (4), together with five known steroidal saponins were isolated from the ethanolic extract of the rhizome of Polygonatum sibiricum. Chemical structures of these compounds were elucidated by spectroscopic techniques. Anti-inflammatory activities of these new compounds were evaluated.     

Three new steroidal saponins from Aspidistra letreae plants and their cytotoxic activities

Three new steroidal saponins, aspiletreins A–C (1–3), together with 2H-chromen-2-one (4), and α-tocopherol (5), were isolated from whole Aspidistra letreae plants collected in Vietnam. Their structures were elucidated by a combination of spectroscopic analyses, including 1D- and 2D-NMR, IR, and HRESIMS, and by comparison with the reported data in the literature. Compounds 1–3 exhibited moderate cytotoxicities against the LU-1, HeLa, MDA-MB-231, HepG2, and MKN-7 human cancer cell lines, with IC₅₀ values ranging from 7.69?±?0.40 to 20.46?±?3.11 µM.

     

New steroidal glycosides from the rhizome of Anemarrhena asphodeloides

Two new steroidal saponins, timosaponin X (1) and timosaponin Y (2), and one new pregnane glycoside, timopregnane B (3), were isolated from the rhizomes of Anemarrhena asphodeloides, as well as three known compounds 25S-timosaponin BII (4), protodesgalactotigonin (5), and timosaponin BII-a (6) isolated from this plant for the first time. By the detailed analysis of 1D, 2D NMR, MS spectra, and chemical evidences, the structures of new compounds were elucidated as 26-O-β-d-glucopyranosyl-(25S)-5β-22-methoxy-furost-3β,26-diol 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside (1), 5β-pseudo-spirost-3β,15α,23α-triol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (2), (5β,17α)-Δ¹⁶⁽¹⁷⁾-20-one-pregn-2β,3β-diol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (3).     

A new steroidal saponin from Dioscorea panthaica

A new steroidal saponin and three known saponins were isolated from the rhizomes of Dioscorea panthaica. Their structures were elucidated as 3-O-[α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl]-26-O-β-d-glucopyranosyl-20,22-seco-25(R)-furosta-5-ene-20,22-dione-3β,26-diol (1), pregnadienolone-3-O-β-chacotriside (2), pseudoprotodioscin (3), and dioscoreside D (4) mainly by NMR techniques and chemical methods. The inhibitory activities of the saponins against α-glucosidase were investigated, and compound 2 was found to exhibit potent activity with IC₅₀ values of 0.04 ± 0.01 mM.     

Two new steroidal glycosides from Cynanchum wallichii

Two new C21 steroidal glycosides were isolated from Cynanchum wallichii Wight. Their structures were elucidated as caudatin-3-O-β-d-glucopyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (1) and caudatin-3-O-β-d-glucopyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (2) by spectroscopic methods including 1D and 2D NMR experiments.