Two new triterpenoid saponins from Ardisia crenata

Two new triterpenoid saponins, ardisicrenoside K (1) and ardisicrenoside L (2), have been isolated from the roots of Ardisia crenata Sims. Their structures have been determined as 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranosyl]-13beta,28-epoxy-16-oxo-30,30-dimethoxyoleanane and 3beta-O-[beta-D-xylopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranosyl]-13beta,28-epoxy-16alpha,20-dihydroxyoleanane by means of chemical evidences and spectral analysis. Their weak anti-fungal activity against the plant pathogenic fungus Pyricularia oryzae was evaluated in vitro.     

HPLC-ELSD法测定朱砂根中岩白菜素和百两金皂苷A的含量

目的建立HPLC-ELSD法同步测定朱砂根活性成分岩白菜素和百两金皂苷A的含量。方法采用Phenomenex Luna C18色谱柱（4.6 mm×250 mm,5μm）,以甲醇-水为流动相梯度洗脱,流速1.0 mL min-1,柱温30℃。ELSD参数：漂移管温度100℃,载气流速2.5 mL min-1。结果岩白菜素和百两金皂苷A分别在0.42～8.40μg和0.51～10.20μg与峰面积呈良好的线性关系,平均回收率分别为101.2%、101.4%,RSD分别为1.6%、2.0%。结论建立的含量测定方法操作简便、结果准确、重现性好,可用于朱砂根药材的质量控制。     

Two new triterpenoid saponins from Sarcandra glabra

Two new triterpenoid saponins, named sarcandroside A and B, have been isolated from Sarcandra glabra (Thunb) Nakai. Their structures have been established as 3β,19α,20β-trihydroxyurs-11,13 (18)-diene-28,20β-lactone-3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranoside (1) and 3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranosyl-pomolic acid 28-O-β-d-glucopyranosyl ester (2) by means of spectral and chemical methods.     

Pro-apoptotic and microtubule-disassembly effects of ardisiacrispin (A+B), triterpenoid saponins from Ardisia crenata on human hepatoma Bel-7402 cells

Ardisiacrispin (A+B) is a mixture of ardisiacrispins A and B, derived from Ardisia crenata with a fixed proportion (2:1). The present study was conducted to investigate its anticancer activity on human cancer cells and its underlying mechanism of action. The (IC₅₀)s of ardisiacrispin (A+B) on proliferation of several human cancer cell lines were in the range of 0.9–6.5 μg/ml by sulphorhodamine B-based colorimetric assay, in which Bel-7402 was the most sensitive cell line. Moreover, ardisiacrispin (A+B) induced dose-dependent apoptosis in Bel-7402 cells at doses of 1–10 μg/ml by flow cytometry, and resulted in the changes of the mitochondrial membrane depolarization, membrane permeability enhancement, and nuclear condensation in a dose-dependent manner through high-content screening analysis. Furthermore, ardisiacrispin (A+B) could disassemble microtubule in Bel-7402 cells; the fluorescence intensity of microtubules decreased at the concentration of 5–20 μg/ml. These findings suggest that ardisiacrispin (A+B) could inhibit the proliferation of Bel-7402 cells by inducing apoptosis and disassembling microtubule.     

A new triterpenoid saponin from Ardisia gigantifolia

A new triterpenoid saponin, named 3-O-β-d-glucopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 2)-[α-l-rhamnopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl-3β,16α,28,30-tetrahydroxy-olean-12-ene (1), along with four known triterpenoids (2–5), was isolated from the rhizomes of Ardisia gigantifolia. Their structures were elucidated by spectroscopic methods. Compounds 1–4 showed cytotoxic activity against Hela, EJ, BCG, and HepG-2 cell lines. The percentage of early apoptotic cells after treatment with 1 was significantly increased compared with control cells (p < 0.05).     

紫金牛属植物中三萜皂苷类成分核磁共振波谱学特征

目的对紫金牛属植物近 2 0年的三萜皂苷类成分的结构及波谱学研究内容进行综述。方法查阅国内外研究文献 ,对紫金牛属植物中分离得到的皂苷结构及波谱特征进行归纳、总结。结果目前已从紫金牛属植物中分离鉴定了 32个皂苷 ,通过分析其核磁数据 ,应用烯碳数据和羰基碳的数据可推测基本结构类型 ,根据含氧碳及相邻碳的化学位移值可确定羟基的取代位置。同时也总结了该属植物皂苷中糖的种类和连接位置。结论通过总结紫金牛属三萜皂苷波谱特征规律 ,对进一步鉴定该类化合物结构以及进行波谱数据的归属都起着重要的作用     

Two new triterpenoid saponins from Symplocos Chinensis

Two new triterpenoid saponins, symplocososides X (1) and Y (2) have been isolated from the roots of Symplocos chinensis, and their structures elucidated as 21β-O- cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (1) and 21β-O-cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-(3-O-acetyl)-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (2) by spectral and chemical methods. Their antitumor activities have also been tested.     

Cytotoxic triterpenoid saponins from the roots of Ardisia crenata

Ardisiacrenoside I (1), a new triterpenoid pentasaccharide with an unusual glycosyl glycerol side chain, was isolated from Ardisia crenata together with five closely related triterpenoid saponins. Their structures were elucidated by a combination of mass spectrometry, IR, 1D, and 2D NMR spectroscopy. Their cytotoxic activities were evaluated against several different human tumor cell lines by the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide (MTT) method.     

正交试验优选朱砂根中朱砂根皂苷提取工艺

目的:优选朱砂根中朱砂根皂苷的提取工艺。方法:用反相高效液相色谱法测定朱砂根皂苷的含量;以朱砂根皂苷提取质量分数为评价指标,以乙醇体积分数、提取温度、提取时间和提取次数为考察因素,通过正交试验选取最佳提取工艺。结果:最佳提取工艺:80%乙醇为溶剂、提取温度80℃、提取时间20min、提取次数3次;朱砂根皂苷的提取质量分数为6.04%。结论:所选工艺可行、重现性好,可为大批量提取朱砂根皂苷提供理论依据。     

A new triterpenoid saponin from Ardisia crenata.

A new triterpenoid saponin, ardicrenin (1), isolated from the roots of Ardisia crenata Sims was established as cyclamiretin A-3-O-[alpha-L-rhamnopyranosyl-(1----4)-beta-D-glucopyranosyl-(1----4)][ beta-D-glucopyranosyl-(1----2)]-alpha-L-arabinopyranoside. A partially hydrolyzed saponin (3) was characterized as cyclamiretin A-3-O-beta-D-glucopyranosyl-(1----2)-alpha-L-arabinopyranoside .     

黄连花中两个新的三萜皂苷黄连花中两个新的三萜皂苷

目的对黄连花(Lysimachia davurica Ledeb.)全草的三萜皂苷成分进行分离和结构鉴定。方法通过大孔树脂纯化,硅胶和反相硅胶色谱分离正丁醇萃取物物中的三萜皂苷;利用多种波谱技术并结合酸水解方法鉴定其化学结构。结果分离鉴定了2个三萜皂苷,其结构分别为3β,16α,29-三羟基-13,28-环氧-齐墩果烷-3-O-β-D-吡喃葡糖基-(1→2)-β-D-吡喃葡糖酸甲酯苷(I),3β,16α,28-三羟基-齐墩果-12-烯-3-O-｛β-D-吡喃葡糖基(1→2)-β-D-吡喃葡糖醛酸｝-28-O-β-D-吡喃葡糖苷(II)。结论化合物I和II为新的三萜皂苷,分别命名为黄连花皂苷D和J。     

细梗香草中的两个新三萜皂苷

目的对细梗香草(Lysimachia capillipes Hemsl.)全草的三萜皂苷成分进行分离和结构鉴定。方法通过大孔树脂纯化，硅胶和反相硅胶色谱分离正丁醇萃取物中的三萜皂苷；利用多种波谱技术并结合酸水解方法鉴定其化学结构。结果分离鉴定了2个三萜皂苷，其结构分别为3β，22α-二羟基-16α-当归酰氧基-28→13-内酯-齐墩果烷-3-O-［β-D-吡喃葡糖基-(1→2)-α-L-吡喃阿拉伯糖基］-22-O-(6-乙酰基)-β-D-吡喃葡糖苷(I),3β,13β,22α-三羟基-16α-乙酰氧基-齐墩果烷-28羧酸钠-3-O-［β-D-吡喃葡糖基-(1→2)-α-L-吡喃阿拉伯糖基］-22-O-β-D-吡喃葡糖苷(II)。结论化合物I和II为新的三萜皂苷，分别命名为细梗香草皂苷I和细梗香草皂苷J。     

Cytotoxic triterpenoid saponins from Vaccaria segetalis

By the guidance of bioassay, one new cytotoxic triterpenoid saponin, 3-O-[β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl] quillaic acid 28-O-β-d-glucopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-fucopyranosyl-(1 → 4)]-β-d-fucopyranoside (1), and five known cytotoxic triterpenoid saponins, vaccaroside E (2), vaccaroside G (3), vaccaroside B (4), segetoside H (5) and segetoside I (6), were isolated from Vaccaria segetalis. Their structures were established on the basis of ESI-MS, IR, extensive NMR (¹H NMR, ¹³C NMR, TOCSY, ¹H–¹H COSY, DEPT, HMQC, HMBC and ROESY) analyses, chemical degradation, and by comparing with previously reported data. Compounds 1–6 showed moderate cytotoxic activities against LNcap, P-388 and A-549 cell lines with IC₅₀ values in the range 0.1–12.9 μM.     

Four new triterpenoid saponins from Ilex godajam

Four new triterpenoid saponins, godosides A - D ( 1 - 4 ), along with eight known saponins, have been isolated from the fresh aerial parts of Ilex godajam . Structure elucidation of 1 - 4 was based on NMR, MS, IR and chemical analyses.     

Four new triterpenoid saponins from Ilex Godajam

Four new triterpenoid saponins, godosides A - D ( 1 - 4 ), along with eight known saponins, have been isolated from the fresh aerial parts of Ilex godajam . Structure elucidation of 1 - 4 was based on NMR, MS, IR and chemical analyses.     

Two new furostanol saponins from Tribulus terrestris

Two new furostanol saponins were isolated from the fruits of Tribulus terrestris L. Their structures were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-20(22)-en-3β,26-diol-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-(25S)-5α-furost-20(22)-en-12-one-3β,26-diol-3-O-β-d-galactopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (2) on the basis of spectroscopic data as well as chemical evidence.     

九子参中一个新三萜皂苷

运用硅胶、SephadexLH-20、0DD以及高效液相色谱法,从九子参的根中分离得到一个新三萜皂苷和一个已知三萜皂苷。通过质谱以及一维二维核磁确定了化合物的结构。化合物1和2均为首次从该属植物中分离得到。     

Two new triterpenoid saponins from ginseng medicinal fungal substance

Two new dammarane-type triterpenoid saponins, namely ginsenosides Rb₄ (1) and Rb₅ (2), were isolated from ginseng medicinal fungal substance. The structures of 1 and 2 were established as 3β,12β,20(S)-trihydroxydammar-24(25)-ene-3-O-[α-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl]-20-O-β-d-glucopyranoside and 3β,12β,20(S)-trihydroxydammar-24(25)-ene-3-O-[α-d-glucopyranosyl-(1→4)-α-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl]-20-O-β-d-glucopyranoside on the basis of spectroscopic analysis and chemical analysis, respectively.     

Biotransformation on the triterpenoid saponin of Ardisia gigantifolia by Aspergillus avenaceus AS 3.4454

Compound 1, a triterpenoid saponin from Ardisia gigantifolia Stapf. showing potential anti-tumor activity, was transformed into three derivatives (2–4) by Aspergillus avenaceus 3.4454. Among them, compounds 2 and 3 are new compounds. Their structures were elucidated on the basis of 1D NMR, 2D NMR, HR-ESI-MS, and optical rotation data. Compounds 1–3 were evaluated for their cytotoxicity against human hepatocellular carcinoma and normal liver cells by cell counting kit 8 colorimetric assay. Compound 3 displayed better cytotoxicity against Bel-7402 and HepG2 cell lines and much weaker cytotoxicity against normal liver L02 cell than that of positive control (epirubicin hydrochloride).     

Cytotoxic triterpenoid saponins from Ardisia gigantifolia

Three new triterpenoid saponins, 1- 3, together with two known saponins, 4 and 5, were isolated from the rhizome of Ardisia gigantifolia. Their structures were elucidated by 1D and 2D NMR spectroscopic studies. Saponins 1, 2, 4, and 5 exhibited significant cytotoxicity against four human cancer cell lines, namely, Hela human cervical carcinoma cells, EJ human bladder tumor cells, HepG-2 human hepatoma cells, and BCG human gastric carcinoma cells with IC (50) values in the range of 1.9-4.8 μM.