Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells.

Two new triterpene saponins (8 and 9) and seven previously reported triterpene saponins (1-7) based upon oleanolic acid or hederagenin, along with two known lignans, (+)-pinoresinol (10) and beta-peltatin (11), were isolated from a saponin fraction prepared from the MeOH extract of the roots of Pulsatilla chinensis. The structures of the new saponins were determined by spectroscopic analysis, including 2D NMR spectroscopic techniques, and the results of hydrolytic cleavage. The isolated compounds and some derivatives were evaluated for their cytotoxic activity against HL-60 human leukemia cells.     

Triterpene saponins from the roots of Clematis chinensis

A saponin-enriched fraction prepared from the MeOH extract of the roots of Clematis chinensis showed cytotoxic activity against HL-60 promyelocytic leukemia cells, from which five new triterpene saponins based on oleanolic acid, along with three known saponins, were isolated. The structures of the new saponins were determined on the basis of spectroscopic analysis, including extensive 1D and 2D NMR data and hydrolysis followed by chromatographic and spectroscopic analysis. Among the isolated saponins, monodesmosidic saponins exhibited cytotoxic activities against cultured tumor cells.     

Triterpenoid saponins from Ilex kudincha.

Ten new triterpene saponins, ilekudinosides A-J (2, 6-8, 10, 13-17), together with seven known triterpene saponins, ilexoside XLVIII (1); cynarasaponin C (5); latifolosides A (9), C (3), G (12), and H (4); and kudinoside G (11), were isolated from an aqueous extract of the leaves of Ilex kudincha. They possessed oleanane- and ursane-type triterpenoids as the aglycons. The structures were elucidated by 1D and 2D NMR experiments, including ROE difference, HOHAHA difference, 1H-1H COSY, and 1H-13C COSY (HMQC, HMBC) methods and sugar analysis. Compounds 1 and 5 exhibited acyl CoA cholesteryl acyl transferase (ACAT) inhibitory activity.     

Triterpene saponins in the defensive secretion of a chrysomelid beetle, Platyphora ligata

The secretion of the defensive glands of adults of the chrysomelid beetle Platyphora ligata from Panama has been shown to contain, besides chlorogenic acid (1) and a mixture of phosphatidylcholines, two new oleanane triterpene saponins, named ligatosides A and B. Their structures were established as 3-O-beta-D-glucuronopyranosyl-16alpha,23-dihydroxyoleanol ic acid-28-O-2-(3,4-dimethoxybenzoyl)-beta-D-glucopyranoside (2) and 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-16a lpha, 23-dihydroxyoleanolic acid-28-O-2-(3, 4-dimethoxybenzoyl)-beta-D-glucopyranoside (3), respectively, by a combination of extensive 1D and 2D NMR methods (COSY, HMQC, HMBC, and TOCSY) and FABMS. This is the first report of triterpene saponins in the defensive secretion of an insect.     

New bisdesmosidic triterpene saponins from the roots of Pulsatilla chinensis

Further phytochemical analysis aimed at the triterpene saponin constituents of the roots of Pulsatilla chinensis has resulted in the isolation of four new bisdesmosidic triterpene saponins whose aglycons are based on the lupane skeleton (1-4), together with three known saponins (5-7). The structures of the new compounds were determined by spectroscopic analysis and acid-catalyzed hydrolysis.     

Five new triterpene saponins from Pulsatilla patens var. multifida

Five new oleanane-type glycosides (1-5), along with two known triterpene saponins, were isolated from the roots of Pulsatilla patens var. multifida (Ranunculaceae). The structures of the new triterpene saponins were elucidated as 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-galactopyranosyl hederagenin 28-O-beta-D-glucopyranosyl ester (1), hederagenin 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->6)]-beta -D-galactopyranoside (2), 3-O-beta-D-glucopyranosyl bayogenin 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-galactopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (4), and 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->6)]-beta -D-galactopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (5). Structure elucidation was accomplished by 1D and 2D NMR (HMQC, HMBC, and ROESY) methods, FABMS, and hydrolysis.     

Cytotoxic triterpenoid saponins acylated with monoterpenic acid from Pithecellobium lucidum

Three new oleanane-type triterpene saponins, named pithelucosides A-C (1-3), together with two known saponins (4, 5) were isolated from the roots of Pithecellobium lucidum. The structures of the new saponins were established on the basis of extensive 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. Compounds 1-5 and 7 (pro-sapogenin obtained from the mild alkaline hydrolysate of 1) were evaluated for cytotoxic activity on five human tumoral cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) and for hemolytic property against rabbit erythrocytes. Compounds 2-5 showed significant cytotoxic activities with IC50 values of 0.61-7.56 microM. All tested compounds did not exhibit any hemolytic activity in the concentration range 0.01-100 microM.     

Bioactive triterpene saponins from the roots of Phytolacca americana

Five new triterpene saponins named phytolaccasaponins N-1 (1), N-2 (2), N-3 (3) N-4 (4), and N-5 (5) were isolated from the roots of Phytolacca americana together with seven known triterpene saponins (6-12). The structures of the five new saponins were established as shown in structures 1-5 on the basis of their spectroscopic data. The MDR-reversal activity of 1-12 was evaluated on the basis of the amount of calcein accumulated in MDR human ovarian cancer 2780 AD cells in the presence of each compound. The most effective compound was 8 (155% of control at 25 microg/mL).     

Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda

Three new oleanane-type triterpene saponins (1-3), named grandibracteosides A-C, were isolated from the methanolic extract of leaves of Albizia grandibracteata, a species consumed by primates in the Kibale National Park, Uganda. The structures of the saponins were established using 1D and 2D NMR experiments and mass spectrometry and confirmed by acid and alkaline hydrolysis. The crude extract and the pure compounds showed significant inhibitory activity against KB and MCF7 tumoral cell lines in vitro. The compounds are glycosides of acacic acid acylated by an o-aminobenzoyl unit. This is the first report of such ester saponins in dicotyledonous plants. Studies of the primate diet may provide a useful method for finding naturally occurring compounds of medicinal significance.     

Structures of new dammarane-type Triterpene Saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal Ginseng Saponins

The saponin fraction from the flower buds of Panax notoginseng exhibited protective effect on liver injury induced by d-galactosamine and lipopolysaccharide. From the saponin fraction with hepatoprotective effect, five new dammarane-type triterpene saponins, notoginsenosides-O (1), -P (2), -Q (3), -S (4), and -T (5), were isolated together with nine known protopanaxadiol oligoglycosides. The structures of the new saponins were elucidated on the basis of chemical and physicochemical evidence. The principal dammarane-type triterpene saponins from the roots and flower buds of Panax notoginseng were found to show potent hepatoprotective effects.     

Characterization of new sweet triterpene saponins from Albizia myriophylla

Five new oleanane-type triterpene saponins, albiziasaponins A-E (1-5), were isolated from the stems of Albizia myriophylla collected in Thailand, together with two known triterpene saponins, licorice-saponin F3 and yunganoside B(1). The structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. In addition, when sensory tests were performed on sweetness, albiziasaponin B (2), with a carbonyl group at the C-30 position, was found to show a potent sweetness intensity relative to sucrose (600 times).     

Triterpene saponins from the leaves of Ilex kudingcha

Nine new triterpene saponins, ilekudinosides K-S (1-9), and eight known triterpene saponins were isolated from the 70% ethanol extract of the leaves of Ilex kudingcha. The new saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (1), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-beta-kudinlactone (2), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-gamma-kudinlactone (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (4), 3-O-beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranosyl-alpha-kudinlactone (5), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-alpha-kudinlactone (6), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-beta-kudinlactone (7), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-beta-kudinlactone (8), and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-gamma-kudinlactone (9), respectively. The structures and stereochemistry of compounds 1-9 were elucidated by spectroscopic data interpretation and chemical degradation.     

Perennisosides I-VII, acylated triterpene saponins with antihyperlipidemic activities from the flowers of Bellis perennis

The methanolic extract and its saponin fraction (methanol-eluted fraction) of the flowers of Bellis perennis were found to suppress serum triglyceride elevation in olive oil-treated mice. From the saponin fraction, seven new triterpene saponins, perennisosides I (1), II (2), III (3), IV (4), V (5), VI (6), and VII (7), were isolated together with four known saponins, bellidioside A (8), asterbatanoside D (9), bernardioside B 2 (10), and bellissaponin BS6 (11). The stereostructures of 1- 7 were elucidated on the basis of chemical and spectroscopic evidence. Among these saponins, perennisosides I (1) and II (2) showed inhibitory effects on serum triglyceride elevation at doses of 25-50 mg/kg, po.     

Triterpene saponins from Vietnamese ginseng (Panax vietnamensis) and their hepatocytoprotective activity

The methanol extract of Vietnamese ginseng (Panax vietnamensis) was found to possess hepatocytoprotective effects on D-galactosamine (D-GalN)/tumor necrosis factor-alpha (TNF-alpha)-induced cell death in primary cultured mouse hepatocytes. Further chemical investigation of the extract afforded two new dammarane-type triterpene saponins, ginsenoside Rh(5) (1) and vina-ginsenoside R(25) (2), as well as eight known dammarane-type triterpene saponins, majonoside R(2) (3), pseudo-ginsenoside RT(4) (4), vina-ginsenosides R(1) (5), R(2) (6), and R(10) (7), ginsenosides Rg(1) (8), Rh(1) (9), and Rh(4) (10), and a known sapogenin protopanaxatriol oxide II (11). Their structures were elucidated on the basis of spectral analysis. In addition, by the using LC-electrospray ionization (ESI)-MS method, five known saponins, ginsenosides Rb(1), Rb(2), Rc, Rd, and Re (12--16), were also identified in the extract. Among the compounds isolated, majonoside R(2) (3), the main saponin in Vietnamese ginseng, showed strong protective activity against D-GalN/TNF-alpha-induced cell death in primary cultured mouse hepatocytes. This demonstrates that the hepatocytoprotective effect of Vietnamese ginseng is due to dammarane-type triterpene saponins that have an ocotillol-type side chain, a characteristic constituent of Vietnamese ginseng.     

Triterpene saponins from clematis mandshurica

Four new triterpene saponins, clematomandshurica saponins A-D (1-4), together with three known saponins (5-7) have been isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of their spectroscopic evidence and hydrolysis. Clematomandshurica saponins A and B showed significant inhibitory activity on cyclooxygenase-2 (IC50 = 2.66 and 2.58 microM, respectively).     

升麻三萜皂苷对破骨细胞形成分化的影响及机制研究

目的 探究升麻三萜皂苷（Cimicifuga triterpene saponins）对破骨细胞形成分化和骨吸收功能的影响,并基于网络药理学探讨其作用机制。方法 采用CCK-8法测定升麻三萜皂苷阿克特素、升麻环氧醇苷、升麻醇对骨髓巨噬细胞（bone marrow macrophages,BMMs）增殖活性的影响;抗酒石酸酸性磷酸酶（tartrateresistant acid phosphatase,TRAP）染色测定破骨细胞数目;磷酸苯二钠法测定破骨细胞的TRAP活性;鬼笔环肽染色观察破骨细胞F-actin环的形成;甲苯胺蓝染色检测破骨细胞在牛皮质骨骨片上形成的骨吸收陷窝;Western blotting分析破骨细胞标志基因和蛋白的表达。采用GeneCards和DisGeNET数据库获取破骨细胞功能的靶点,应用Cytoscape 3.7.1软件,采用蛋白互作的方式,筛选升麻三萜皂苷调控破骨细胞功能的核心靶点,并采用DAVID 6.8对核心靶点进行基因本体（gene ontology,GO）功能及京都基因与基因组百科全书（Kyoto encyclopedia of genes and genomes,KEGG）通路富集分析。结果 升麻三萜皂苷对BMMs增殖无显著影响,升麻三萜皂苷阿克特素、升麻环氧醇苷、升麻醇均可减少破骨细胞的数目,抑制破骨细胞TRAP活性和F-actin环的形成,显著抑制破骨细胞活化T细胞核因子1（nuclear factor of activated T cells 1,NFATc1）、原癌蛋白Fos（oncogene Fos,c-Fos）、基质金属蛋白酶9（matrix metalloproteinase 9,MMP9）和组织蛋白酶（cathepsin K,CTSK）的表达（P＜0.05、0.01）,减少破骨细胞在骨片上形成的骨吸收陷窝的面积（P＜0.01）。网络药理学分析表明升麻三萜皂苷主要通过丝裂原活化蛋白激酶（mitogen-activated protein kinase,MAPK）通路调控破骨细胞的骨吸收功能。结论 升麻三萜皂苷通过MAPK通路抑制BMMs诱导的破骨细胞的形成分化和骨吸收,可为抗骨质疏松新药的研发提供先导化合物。     

New acylated triterpene saponins from Silene fortunei that modulate lymphocyte proliferation

Three new acylated triterpene saponins 1-3, with a quillaic acid as aglycon, were isolated from the roots of Silene fortunei together with a known phytoecdysteroid (20-hydroxyecdysone). The compounds were characterized mainly by a combination of 2D NMR techniques, mass spectrometry, and chemical methods. Saponins 1-3, jenisseensosides C and D (4, 5), and 6 (deacylated form of 2/3 and 4/5) were found to stimulate the proliferation of the Jurkat tumor cell lines at low concentration. At high concentration, 2/3 and 4/5 inhibited the proliferation of the cells and suggested the induction of apoptosis.     

Triterpene saponins, quaternary ammonium compounds, phosphatidyl cholines, and amino acids in the pronotal and elytral secretions of Platyphora opima and Desmogramma subtropica

Secretions of the pronotal and elytral glands of adults of the chrysomelid beetle Platyphora opima from Panama have been shown to contain two oleanane triterpene saponins: the known 3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl-oleano lic acid-28-O-beta-D-glucopyranoside and compound 1, whose structure was established as 3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl-29- hydrox yoleanolic acid-28-O-beta-D-glucopyranoside by a combination of 1D and 2D NMR methods (COSY, HMQC, HMBC, and TOCSY) and FABMS. The secretions also contained N,N,N-trimethylcadaverine and its 1, 2-dehydro derivative 3, as well as the nicotinamide derivative 4. Secretions of Desmogramma subtropica, also from Panama, contained as sole triterpene derivative 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-24- hydrox yoleanolic acid (2), together with glutamic acid, glutamine, pyroglutamic acid, and arginine. A mixture of phosphatidylcholines was also present in the secretions of both species.     

Transgenic Panax ginseng inhibits the production of TNF-alpha, IL-6, and IL-8 as well as COX-2 expression in human mast cells

The most well-known medicinal plant, Panax ginseng (P. ginseng), contains various phytosterols and bioactive triterpene saponins (ginsenosides). Squalene synthase is a key regulatory enzyme for triterpene biosynthesis and overexpression of the squalene synthase confers the hyper-production of triterpene saponins to form transgenic ginseng. In this study, we have investigated whether and how transgenic P. ginseng modulates an inflammatory reaction in a stimulated human mast cell line, HMC-1. It was found that transgenic P. ginseng inhibited the production of tumor necrosis factor (TNF)-alpha, interleukin (IL)-6, IL-8, and the expression of cyclooxygenase-2 in phorbol 12-myristate 13-acetate (PMA) plus calcium ionophore A23187 (PMACI)-stimulated HMC-1. Additionally, we have shown that transgenic P. ginseng suppressed the intracellular calcium level induced by PMACI. These results provide new insights into the pharmacological actions of transgenic P. ginseng as a potential molecule for use in therapy in mast cell-mediated inflammatory diseases.     

Pursaethosides A-E, triterpene saponins from Entada pursaetha

Five new triterpenoid saponins, pursaethosides A-E (1-5), were isolated from the n-BuOH extract of the seed kernels of Entada pursaetha along with the known phaseoloidin. The structures of 1-5 were elucidated mainly by spectroscopic data interpretation and chemical degradation. Pursaethosides C-E (3-5) possess as a common structural feature entagenic acid as aglycon, which is rare among triterpene saponins. Compounds 2-4 and phaesolidin were found to be not cytotoxic when tested against HCT 116 and HT-29 human colon cancer cells.