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1.
Roots of Gypsophila L. (Caryophyllaceae) have been shown to accumulate bidesmosides of triterpenoid carboxylic acids, also called GOTCAB saponins (Glucuronide Oleanane-type Triterpenoid Carboxylic Acid 3, 28-Bidesmosides). The study aimed at in-depth characterization of GOTCABs from root extracts of cultivated Gypsophila scorzonerifolia Ser., G. acutifolia Stev. ex Spreng., G. altissima L., G. pacifica Kom., G. paniculata L., G. oldhamiana Miq. and G. zhegualensis Krasnova using ultra high-performance liquid chromatography coupled with hybrid quadrupol-Orbitrap high resolution mass spectrometry (UHPLC-HRMS). Based on the accurate mass measurements, elemental composition, isotopic peak profiles, fragmentation pattern in tandem mass spectrometry (MS/MS) and literature data, a total of 53 GOTCABs were tentatively identified. In addition, 29 core structures, forming between 2 and 12 isobaric isomers were described. They possess gypsogenin, quillaic and gypsogenic acid as sapogenin, substituted at C-3 with O-β-d-galactopyranosyl-(1 → 2)-[pentosyl-(1 → 3)]-β-d-glucuronopyranoside (β-chain). According to the C-28 ester-bonded oligosaccharide (α-chain) saponins were classified into four groups: GOTCABs with C-28 tetra- and pentasaccharide (type I), GOTCABs with C-28 oligosaccharide substituted with methoxycinnamoyl group (type II), GOTCABs with mono- and diacetylated C-28 oligosaccharide (type III) and GOTCABs with C-28 oligosaccharide substituted with both acetyl and methoxycinamoyl groups (type IV). The possible fragmentation pathways of saponins were proposed. Eleven core structures forming between 2 and 7 isobars are undescribed in the literature. To examine the differences between the assayed Gypsophila species at the same environmental conditions, the variation of saponins was estimated by hierarchical clustering on isobaric fingerprints of GOTCABs. The clustering of the studied species revealed three well-defined clusters. The first cluster comprises G. scorzonerifolia (G1) and G. altissima (G3), characterized by GOTCABs from type III. G. acutifolia (G2) and G. pacifica (G4) formed the second cluster accumulating saponins from types II and III. The third cluster grouped G. paniculata (G5), G. oldhamiana (G6) and G. zhegualensis (G7) sharing GOTCABs from types IV in addition to II and III. This is the first report on the saponins from G. scorzonerifolia and G. zhegualensis. An in-depth depiction of the GOTCAB saponin composition of seven cultivated Gypsophila species was achieved. Therefore, saponins are worth investigating for better understanding of the potential use of Gypsophila roots for pharmaceutical purposes. 相似文献
2.
Babar Maqbool Yong Wang Xuemei Cui Shanshan He Ran Guan Shenghao Wang Yuemin Wang Songhua Hu 《Microbiology and immunology》2019,63(7):269-279
Pseudorabies, a herpesvirus infection, is mainly controlled by using attenuated live vaccines. In this study, the effect of ginseng stem and leaf saponins (GSLS) in combination with selenium (Se; in the form of sodium selenite) on vaccination against attenuated pseudorabies virus (aPrV) was evaluated. It was found that GSLS and Se have an adjuvant effect and that a combination of GSLS and Se stimulates significantly enhanced immune responses than does GSLS or Se alone. Following oral administration of GSLS, mice immunized with an attenuated PrV vaccine diluted in Se‐containing physiological saline solution (PSS) provoked a significantly stronger gB‐specific serum antibodies response (IgG, IgG1 and IgG2a), enhanced lymphocyte proliferation and cytolytic activity of NK cells, along with higher production of cytokines (IFN‐γ, IL‐12, IL‐5 and IL‐10) by splenocytes. Notably, the combination of GSLS and Se conferred a much higher resistance to fPrV challenge after immunization of the mice with aPrV vaccine. This study offers convincing experimental evidence that an injection of Se with oral GSLS is a promising adjuvant combination that improves the efficacy of vaccination against PrV and deserves further study regarding improvement of responses to other animal vaccines. 相似文献
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Two new oleanane-type triterpene saponins, identified as 16α-hydroxy-22-O-angeloyl-23-formyl-28,31-dihydroxymethylene-olean-12-ene-3β-O-{β-d-galactopyranosyl-(1 → 2)[β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl(1 → 3)]-β-d-glucopyranosiduronic acid} (oleiferasaponin B1, 1) and 22-O-hydrocinnamoyl-23-formyl-28-dihydroxymethylene-olean-12-ene-3β-O-{β-d-glucopyranosyl-(1 → 2)[β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl(1 → 3)]-β-d-glucopyranosiduronic acid} (oleiferasaponin B2, 2), were isolated from the seed cake of Camellia oleifera Abel. Their structures were established by extensive 1D- and 2D-NMR experiments along with TOF-MS analysis and acid hydrolysis. The cytotoxicity of the isolated compounds was evaluated in four human carcinoma cell lines: A 549, SK-OV-3, SK-MEL-2 and HCT15. Both compounds 1 and 2 exhibited significantly cytotoxic activity with IC50 values of 18.5 μM (A549), 11.3 μM (SK-OV-3), 13.9 μM (SK-MEL-2) and 1.6 μM (HCT15) for 1 and IC50 values of 8.4 μM (A549), 6.3 μM (SK-OV-3), 9.2 μM (SK-MEL-2) and 0.8 μM (HCT15) for 2. In addition, compound 2 showed more effective cytotoxic activity than compound 1. 相似文献
5.
Masahide Nonaka 《Phytochemistry》1985,25(1):73-75
Eight saponins were isolated from alfalfa roots (Medicago sativa). The sensitivity of Trichoderma viride to the saponin varied with the individual saponin isolate. Seven isolates appeared to contain the aglycone, medicagenic acid, and while the other did not, it inhibited the growth of the fungus at higher concentrations than the other isolates. One pair and a triplet of saponins with divergent Rfs evoked near identical biological responses suggesting structural similarity toxic to T. viride. 相似文献
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7.
室内条件下研究了夹竹桃皂甙对福寿螺的杀灭效果及其对水稻幼苗的影响。结果表明,福寿螺的致死率随着皂甙浓度的增加和处理时间的延长而显著上升,其中50mg/L 浓度皂甙处理48h的致死率达100%,与0.156g/L氯硝柳胺水溶液的灭螺效果相当。皂甙对福寿螺的杀灭效果与福寿螺的大小有关。皂甙对壳高h<10 mm的福寿螺的杀螺效果最好, 而对20≤h<30 mm的杀螺效果最差。水稻幼苗的存活率随着皂甙浓度的增加而显著增加,且低浓度皂甙处理24h也具有较高的值。此外,采用水培方法研究了皂甙对水稻幼苗鲜重的影响。高浓度(≥40 mg/L)的皂甙处理7d显著地抑制了水稻幼苗根部和地上部分的鲜重,其中对根部的影响大于地上部分。当处理时间延长到14d时,皂甙对水稻幼苗鲜重的抑制作用逐渐减弱,仅50mg/L 皂甙处理对根部鲜重有显著地抑制。而在氯硝柳胺水溶液处理下,水稻幼苗停止生长。综合结果表明夹竹桃皂甙是一种环境友好且能高效防治福寿螺的灭螺剂。 相似文献
8.
空心莲子草营养器官结构与三萜皂苷动态积累的关系 总被引:1,自引:0,他引:1
王桂芹;徐如松;王锐 《植物研究》2011,31(6):686-691
采用组织化学定位、显微制片技术和三萜皂苷定量分析方法对空心莲子草营养器官结构与三萜皂苷类物质积累关系进行了研究。结果表明:空心莲子草宿根、根状茎、茎和叶中均有三萜皂苷物质的积累,叶和根状茎内含量十分丰富。在相同采收期内含量依次为:叶>根状茎>根>茎,叶中主要积累于栅栏组织细胞内。空心莲子草的根和根状茎横切面均属于异常结构,具有成同心环状排列的三生维管束。在宿根和根状茎的次生韧皮部、栓内层、三生韧皮部和结合组织内均有三萜皂苷的分布,三生结构在宿根和根状茎中占有主要地位,是三萜皂苷积累的主要场所。在不同采收期内叶、根状茎和根中三萜皂苷的积累趋势基本一致,均随生长期的增加而递增。空心莲子草茎的横切面由表皮、皮层、维管束和髓腔组成,仅部分皮层细胞和初生韧皮部内有三萜皂苷分布。 相似文献
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10.
Alberto Sánchez-Medina Solomon Habtemariam Olivia Corcoran Nigel C. Veitch 《Phytochemistry》2009,70(6):765-2704
Evaluation of the cytotoxicity of an ethanolic root extract of Sideroxylonfoetidissimum subsp. gaumeri (Sapotaceae) revealed activity against the murine macrophage-like cell line RAW 264.7. Systematic bioassay-guided fractionation of this extract gave an active saponin-containing fraction from which four saponins were isolated. Use of 1D (1H, 13C, DEPT135) and 2D (COSY, TOCSY, HSQC, and HMBC) NMR, mass spectrometry and sugar analysis gave their structures as 3-O-(β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, 3-O-β-d-glucopyranosyl-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, 3-O-(β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)[β-d-apiofuranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, and the known compound, 3-O-β-d-glucopyranosyl-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-protobassic acid. Two further saponins were obtained from the same fraction, but as a 5:4 mixture comprising 3-O-(β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)[β-d-apiofuranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid and 3-O-(β-d-apiofuranosyl-(1 → 3)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, respectively. This showed greater cytotoxicity (IC50 = 11.9 ± 1.5 μg/ml) towards RAW 264.7 cells than the original extract (IC50 = 39.5 ± 4.1 μg/ml), and the saponin-containing fraction derived from it (IC50 = 33.7 ± 6.2 μg/ml). 相似文献