Triterpenoid saponins from the leaves of Ilex kudincha

Eight new triterpenoid saponins, kudinosides I-P along with three known saponins were isolated from the leaves of Ilex kudincha. The aglycone moiety of kudinosides I-K was determined as a new triterpene (kudinolic acid), a fore-genin for the lactonic triterpene. The structures of all saponins were established on the basis of spectroscopic and chemical evidence. The biogenesis of the triterpene with lactonic moiety was briefly discussed.     

Triterpenoid Saponins from the Leaves of Ilex Kudincha

Abstract

Eight new triterpenoid saponins, kudinosides I-P along with three known saponins were isolated from the leaves of Ilex kudincha. The aglycone moiety of kudinosides I-K was determined as a new triterpene (kudinolic acid), a fore-genin for the lactonic triterpene. The structures of all saponins were established on the basis of spectroscopic and chemical evidence. The biogenesis of the triterpene with lactonic moiety was briefly discussed.     

Two new saponins from the roots of Phytolacca esculenta.

Two triterpenoidal saponins having phytolaccagenin as the aglycone were isolated from the roots of Phytolacca esculenta (Phytolaccaceae). The structures of two new saponins, esculentoside I and esculentoside N, were established to be 3-O-[beta-D-glucopyranosyl-(1----4)-beta-D- glucopyranosyl]-28-O-beta-D-glucopyranosyl-phytolaccagenin and 3-O-[beta-D-glucopyranosyl(1----4)-beta-D-xylopyranosyl(1----4)-beta-D- glucopyranosyl]-28-O-beta-D-glucopyranosylphytolaccagenin, respectively, on the basis of spectroscopic and chemical evidence.     

Structure-function relationship of the saponins from the roots of Platycodon grandiflorum for hemolytic and adjuvant activity

To assess the contribution of the aglycone and sugar chain to the biological activity of saponins from Platycodon grandiflorum, seven structurally consecutive saponins, platycodin D (PD), D2 (PD2), D3 (PD3), platycoside A (PA), E (PE), deapioplatycoside E (DPE), and polygalacin D2 (PGD) were compared for their hemolytic activities and adjuvant potentials on the immune responses to Newcastle disease virus-based recombinant avian influenza vaccine (rL-H5) in mice. Among seven compounds, the order of the hemolytic activity was PGD ≈ PD > PD2 > PA > PD3 > PE > DPE. PD, PD2, PA, and PGD significantly not only promoted concanavalin A (Con A)-, lipopolysaccharide (LPS)- and antigen-induced splenocyte proliferation, but enhanced the NK cell activity in mice immunized with rL-H5. PD and PD2 increased the antigen specific IgG, IgG1, IgG2a, and IgG2b antibody titers, while PA and PGD only induce the IgG and IgG1 antibody responses in the immunized mice. However, the other three saponins were not observed for adjuvant activity. The results suggested that the sugar chains attached to C-3, the glycidic moiety at C-28 of aglycone, as well as aglycone affect their biological activities. Interestingly, their hemolytic and adjuvant activities increased with the retention time by reverse phase HPLC analysis. The retention time may be useful for primary estimation of fundamental adjuvanticity of saponin with the same aglycone.     

Rapid profiling and identification of triterpenoid saponins in crude extracts from Albizia julibrissin Durazz. by ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry

Ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC/ESI-Q-TOF-MS/MS) was applied to separate and identify triterpenoid saponins in crude extract from the stem bark of Albizia julibrissin Durazz. The molecular weights were determined by comparing quasi-molecular ions [M+NH(4)](+) in positive mode and [M-H](-) and [M-2H](2-) ions in negative mode. The MS/MS spectra of the [M-H](-) ions for saponins provided a wealth of structural information related to aglycone skeletons, sugar types and linked sequence. On the basis of the fragmentation behavior of known saponins isolated before, saponins from this plant were identified, even though references were not available. As a result, a total of twenty-eight saponins in the crude extract were identified, which all had a common basic skeleton of the triterpene oleanolic acid and eight of them were new compounds.     

A New Bidesmosidic Triterpenoidal Saponin from the Roots of Symphytum officinale

A new triterpenoidal saponin having hederagenin as the aglycone was isolated from the roots of SYMPHYTUM OFFICINALE L. The structure of this saponin was elucidated by FAB-MS, (1)H-, (13)C-NMR, 2D-NMR analyses and chemical studies as 3- O-[beta- D-glucopyranosyl-(1-->4)-alpha- L-arabinopyranosyl]-hederagenin 28- O-[beta- D-glucopyranosyl-(1-->6)-beta- D-glucopyranosyl] ester.     

Cytotoxic saponins from Schefflera rotundifolia

Eight new oleanane and lupane saponins (1-8) as well as two new benzyl glycosides (9 and 10) were isolated from the aerial parts of Schefflera rotundifolia (Ten) Frodin (Araliaceae) together with two known benzyl glycosides. Their structures were established using 1D- and 2D-NMR spectroscopy and mass spectrometry. The antiproliferative activity of all compounds was evaluated using three continuous murine and human culture cell lines J774.A1, HEK-293, and WEHI-164. Compounds 7 and 8, having betulinic acid as aglycone, were the most active constituents.     

A novel triterpenoid saponin from Polygala tenuifolia Willd

A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-beta-d-glucopyranosyl presenegenin 28-O-beta-d-xylopyranosyl-(1 --> 3)-beta-d-xylopyranosyl-(1 --> 4)-[beta-D-apiofuranosyl-(1 --> 3)]-alpha-L-rhamnopyranosyl-(1 --> 2)-[4-O-p-methoxycinnamoyl]-[alpha-l-rhamnopyranosyl-(1 --> 3)]-beta-d-fucopyranosyl ester (1). Three known triterpenoid saponins (2-4) were identified on the basis of spectroscopic data.     

A novel triterpenoid saponin from Polygala tenuifolia Willd

A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-beta-d-glucopyranosyl presenegenin 28-O-beta-d-xylopyranosyl-(1 --> 3)-beta-d-xylopyranosyl-(1 --> 4)-[beta-d-apiofuranosyl-(1 --> 3)]-alpha-l-rhamnopyranosyl-(1 --> 2)-[4-O-p-methoxycinnamoyl]-[alpha-l-rhamnopyranosyl-(1 --> 3)]-beta-d-fucopyranosyl ester (1). Three known triterpenoid saponins (2-4) were identified on the basis of spectroscopic data.     

Two new furostanol saponins from Tribulus terrestris L

Two new furostanol saponins, tribufurosides B (1) and C (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D NMR and 2D NMR), the structures of two new furostanol saponins were established as 26-O-beta-d-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-2alpha,3beta,26-triol-3-O-beta-d-galactopyranosyl(1 --> 2)-beta-d-glucopyranosyl(1 --> 2)-beta-d-galactopyranoside (1) and (25S)-5alpha-furost-20(22)-en-12-one-3beta, 26-diol-26-O-beta-d-glucopyranoside (2).     

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.     

Characterization of steroidal saponins in crude extracts from Dioscorea zingiberensis C. H. Wright by ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry

Steroidal saponins are the major bioactive constituents of Dioscorea zingiberensis C. H. Wright (D. zingiberensis). In this work, ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS/MS) was applied to the separation and characterization of steroidal saponins in crude extracts from D. zingiberensis. The results showed that fragment ions from glycosidic and cross-ring cleavages gave a wealth of structural information related to aglycone skeletons, sugar types and the sequence of sugar units. According to the summarized fragmentation patterns, identification of steroidal saponins from D. zingiberensis could be fulfilled, even when reference standards were unavailable. As a result, a total of thirty-one saponins with five aglycone skeletons, including fourteen new trace saponins, were identified or tentatively elucidated in crude extracts from D. zingiberensis based on their retention times, the mass spectrometric fragmentation patterns, and MS and MS/MS data.     

Antinociceptive and anti-inflammatory steroidal saponins from Dracaena ombet

Two new steroidal saponins, namely (25R)-5beta-spirostan-3-beta-ol 3-O-beta-D-galactopyranosyl-(1'-->4')-O-beta-D-galactopyranosyl-(1'-->3')-O-beta-D-glucopyranoside (2), and (25R)-5beta-spirostan-3-beta-ol 3-O-beta-D-galactopyranosyl-(1'-->4')-O-beta-D-glucopyranosyl-(1'-->3')-O-beta-D-glucopyranoside (3), together with six known constituents, have been isolated from the leaves of Dracaena ombet Kotschy & Peyr. (Dracaenaceae). The structures of the two saponins were established by chemical and physicochemical analyses, including FAB- and HR-ESI-MS and 2D NMR. The fraction rich in saponins showed significant analgesic and anti-inflammatory activities (at a high dose of 30 mg/kg b.w.) and non-significant antiulcer activities at the same doses.     

超高压液相/电喷雾-LTQ-Orbitrap质谱联用技术分析三七根中皂苷类成分

建立三七药材的UPLC-ESI-HRMS定性分析方法。采用Kinetics色谱柱,梯度洗脱,经DAD检测器后采用ESI-LTQ-Orbitrap质谱负离子模式采集,三七成分的一级全扫描离子在离子阱内进行CID多级质谱,FT检测高分辨质谱数据进行分析。结果表明三七皂苷成分分离良好,根据多级质谱碎片信息和精确相对分子质量信息,结合文献,从三七中鉴定分析了43个成分,并首次从三七中检测到新型的三七皂苷母核和乙酰取代皂苷成分。本方法分离度良好、灵敏度高,可用于三七药材的定性分析,并有助于对三七进行进一步的活性成分研究和质量控制。     

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.     

Triterpenoid saponins from the rhizomes of Anemone flaccida and their inhibitory activities on LPS-induced NO production in macrophage RAW264.7 cells

A new ursane-type triterpenoid saponin, flaccidoside IV (1), and three new oleanane-type triterpenoid saponins, flaccidosides V–VII (2–4), along with 17 known saponins (5–21), were isolated from the rhizomes of Anemone flaccida. The structures of the new triterpenoid saponins were determined based on spectroscopic analyses and chemical methods. All the isolated saponins were tested for their inhibitory activities on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages, and several bisdesmosidic oleanane-type triterpenoid saponins (2, 7, and 10) showed significant inhibitory activities, which indicated they had potential anti-inflammatory activities under their noncytotoxic concentrations in vitro.     

积雪草皂苷微生物转化研究#br#

目的 从微生物菌库中筛选对积雪草皂苷化学结构修饰的阳性菌株，并对其转化进行研究。方法 在含积雪草皂苷提取物的转化培养基中接种红曲霉(Monascus purpureus Went)、毛霉菌(Mucor sp.)、酱油曲霉(Aspergillus sojae)、醋酸菌(Cusuanjun)等微生物。先用薄层色谱法(TLC)初步筛选出转化积雪草皂苷的微生物，然后通过高效液相色谱法(HPLC)检测转化液的成分。结果 薄层色谱法测出毛霉菌能对积雪草苷进行转化，高效液相色谱法测出转化液中含有新的未知转化产物及其皂苷苷元，且苷元转化率高达83.12%。结论 利用筛选出的毛霉菌对积雪草皂苷转化，其条件简单，转化率高。为中药积雪草的二次开发利用提供了新的方法。     

Minor Saponins from the Leaves of Panax ginseng C.A. Meyer

<正> Five minor compounds isolated from the leaves of Panax ginseng C. A. Meyer were characterized as 20(R)-protopanaxatriol (1), daucosterin (2), 3β, 12β-dihydroxy-dammar-20 (22), 24-diene-3-O-β-D-glucopyranoside (3), 20 (R)-protopanaxadiol-3-O-β-D-glucopyranoside (4) and ginsenoside-Rh_2 (5), respectively, on the basis of spectral analyses and chemical evidence. The two new saponins, 3 and 4, were named as ginsenoside-Rh_3 and 20(R)-ginsenoside-Rh_2.Nine other major saponins obtained simultaneously were identical with ginsenoside-Rh_1(6),-Rg_3 (7), -Rg_2 (8), -Rg_1 (9),-Re(10),-Rd (11), -Rc (12), -Rb_2(13) and Rb_1 (14), respectively.     

Cytotoxic triterpenoid saponins from the rhizomes of Anemone taipaiensis

Two new oleanane-type triterpenoid saponins, 1 and 2, and a new natural product, 3, together with five known saponins, 4- 8, were isolated from the rhizomes of ANEMONE TAIPAIENSIS. Their structures were elucidated by extensive spectroscopic analysis and chemical evidences. Six saponins, 1, 2, 4- 7, which possessed a free carboxylic group at C-28, exhibited significant cytotoxicity against human leukemia HL-60 cells and human hepatocellular carcinoma Hep-G2 cells with IC (50) values in the range of 1.31-10.12?μM.     

Cycloartane triterpenoids from Cassia occidentalis

A phytochemical investigation of the whole plants of Cassia occidentalis led to the isolation of two new cycloartane triterpenoids, cycloccidentalic acids A and B (1 and 2), and five new related saponins, cycloccidentalisides I-V (3-7), together with sixteen known compounds. The structures of the isolated compounds were elucidated through detailed spectroscopic analyses, including 1D and 2D NMR techniques, and chemical methods. Compounds 2 and 5 showed modest anti-HIV-1 activities with EC?? values of 2.23 μM and 4.36 μM, respectively, in comparison to the positive control.