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1.
The saponin fraction from the ethanolic extracts of the root of Ilex pubescens Hook. et Arn. (Ilexaceae) was found to exhibit potent anti-inflammatory effects on carrageenan-induced paw edema in rats. Two novel triterpene saponins, pubescenosides C and D (1 and 2, resp.), together with five known saponins were isolated from this saponin fraction. The structures of 1 and 2 were elucidated as (20beta)-3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa-12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, and (20beta)-3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa- 12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, respectively, on the basis of chemical and spectroscopic data. Five known saponins isolated from the saponin fraction were identified as ilexsaponin B(1), B(2), B(3), A(1), and chikusetsusaponin IV(a).  相似文献   

2.
Three saponins, named minutoside A (1), minutoside B (2), minutoside C (3), and two known sapogenins, alliogenin and neoagigenin, were isolated from the bulbs of Allium minutiflorum Regel. Elucidation of their structure was carried out by comprehensive spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry. The structures of the new compounds were identified as (25R)-furost-2alpha,3beta,6beta,22alpha,26-pentaol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (1), (25S)-spirostan-2alpha,3beta,6beta-triol 3-O-beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranoside (2), and (25R)-furost-2alpha,3beta,5alpha,6beta,22alpha,26-esaol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (3). The isolated compounds were evaluated for their antimicrobial activity. All the novel saponins showed a significant antifungal activity depending on their concentration and with the following rank: minutoside B>minutoside C>minutoside A. No appreciable antibacterial activity was recorded. The possible role of these saponins in plant-microbe interactions is discussed.  相似文献   

3.
Two new steroidal saponins were isolated from the rhizomes of Costus spiralis Rosc. Their structures were established as (3beta,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (1) and (3beta,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->4)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (2). Their structural identifications were performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HETCOR and COLOC) and chemical conversions. The steroidal saponins were evaluated for anti-inflammatory activity.  相似文献   

4.
Further saponins from Meryta lanceolata   总被引:2,自引:0,他引:2  
Five new oleanane-type saponins along with 11 known ones were isolated from the leaves and stems of Meryta lanceolata. The new saponins were characterised by spectroscopic analysis including FAMS, 1 and 2D NMR experiments and the results of hydrolysis as 3-O-[beta-d-glucopyranosyl-(1-->2)-beta-d-glucuronopyranosyl] hederagenin 28-O-[alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl] ester, 3-O-[beta-d-glucopyranosyl-(1-->2)-beta-d-glucuronopyranosyl] oleanolic acid 28-O-[alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl]ester, 3-O-[beta-d-glucopyranosyl-(1-->2)-beta-d-glucuronopyranosyl] oleanolic acid 28-O-[alpha-l-rhamnopyranosyl-(1-->4)-beta-d-6-O-acetyl glucopyranosyl-(1-->6)-beta-d-glucopyranosyl]ester, 3-O-[beta-d-glucopyranosyl-(1-->3)-beta-d-glucopyranosyl-(1-->3)-alpha-l-arabinopyranosyl] oleanolic acid 28-O-[alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl] ester and 3-O-[beta-d-glucopyranosyl-(1-->2)-beta-d-glucuronopyranosyl] hederagenin, respectively.  相似文献   

5.
Two lupin saponins, 3beta,21alpha,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-arabinopyranoside and 3beta,21alpha,22beta,24-tetrahydroxyolean-12-en-3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-rhamnopyranoside, along with eight other saponins and one triterpene previously reported from other legumes, were isolated from the aerial parts of Lupinus oreophilus collected in northern Chile. The structures of the isolated compounds were established with the help of extensive spectroscopic techniques.  相似文献   

6.
Four new oleanane-type saponins and a known one were isolated from the leaves and stems of Meryta lanceolata. The new saponins were characterised by spectroscopic means and chemical hydrolysis as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D- glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-6-O-acetyl glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester and 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester. The NMR assignments were made by means of HOHAHA, 1H-1H COSY, HMQC, HMBC and NOE difference studies.  相似文献   

7.
Isotheasaponins B1-B3 from Camellia sinensis var. sinensis tea leaves   总被引:1,自引:0,他引:1  
Three saponins, isotheasaponins B1-B3, were isolated from the leaves of the tea plant Camellia sinensis var. sinensis, and their structures were determined to be theasapogenol B [beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-gulcopyranosiduronic acid with two acyl groups by spectroscopic analysis.  相似文献   

8.
Five 3-O-glucuronide triterpene saponins (1-5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-betulinic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl]-oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-xylopyranosyl-(1-->6)-beta-d-glucopyranosyl]-oleanolic acid (3), 3-O-[beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl]-oleanolic acid (4), and 3-O-[beta-d-glucopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-d-xylopyranosyl-(1-->6)-beta-D-glucopyranosyl]-oleanolic acid (5).  相似文献   

9.
Eight new steroidal saponins, trillikamtosides K–R (18), along with three known analogues, were isolated from the whole plants of Trillium kamtschaticum. Their structures were unambiguously established by interpretation of spectroscopic data (MS and NMR) and chemical methods. Compound 1 had a rare aglycone featuring a skeleton of 16-oxaandrost-5-en-3-ol-17-one, which was reported for the first time. The isolated saponins were tested for cytotoxicities against HCT116 cells, and trillikamtoside R (8) was found to show the most cytotoxic effect with an IC50 value of 4.92 μM.  相似文献   

10.
Xie BB  Liu HY  Ni W  Chen CX  Lü Y  Wu L  Zheng QT 《化学与生物多样性》2006,3(11):1211-1218
Five new steroids, including the four new steroidal saponins ypsilandroside B (1), ypsilandroside A (2), isoypsilandroside A (4), and isoypsilandroside B (5), as well as the new steroidal sapogenin isoypsilandrogenin (3), were isolated from the whole plant of Ypsilandra thibetica Franch. Their structures were determined on the basis of spectroscopic analyses, including extensive 2D-NMR techniques. The structure and relative configuration of ypsilandroside B (=(3beta,12alpha,25R)-3-[(alpha-L-rhamnopyranosyl-(1-->2)-beta-D-apiofuranosyl)oxy]spirost-5-ene-12,27-diol; 1) was unequivocally determined by single-crystal X-ray diffraction. The antifungal and antibacterial activities of 1-5 towards various types of fungi and bacteria are reported.  相似文献   

11.
Yang SL  Liu XK  Wu H  Wang HB  Qing C 《Steroids》2009,74(1):7-12
Four new steroidal saponins, smilacinoside A (1), B (2), C (3), and D (4), together with three known saponins, funkioside D (5), aspidistrin (6) and 26-O-beta-d-glucopyranosyl-22-methoxyl-(25R)-furost-5-en-3beta,26-diol 3-O-beta-d-glucopyranosyl-(1-->2)-beta-d-glucopyranosyl-(1-->4)-beta-d-galactopyranoside (7) were isolated from the dried tender aerial parts of Smilacina atropurpurea (Franch.) Wang et Tang. The structures of new compounds were elucidated as diosgenin 3-O-alpha-l-rhamnopyranosyl-(1-->2)-O-beta-d-galactopyranoside (1), diosgenin 3-O-alpha-l-rhamnopyranosyl-(1-->3)-[6-O-palmitoxyl]-O-beta-d-galactopyranoside (2), 26-O-beta-d-glucopyranosyl-(25R)-furost-5-en-3beta,22xi,26-triol 3-O-alpha-l-rhamnopyranosyl-(1-->2)}-beta-d-galactopyranoside (3) and 26-O-beta-d-glucopyranosyl-22-methoxyl-(25R)-furost-5-en-3beta,26-diol 3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-galactopyranoside (4) on the basis of chemical methods and detailed spectroscopic analysis, including 1D and 2D NMR techniques and single-crystal X-ray diffraction, respectively. Six of these compounds and MeOH extract were tested for their in vitro cytotoxicity toward K562 human tumor cells by an improved MTT method. Smilacinoside A, funkioside D and aspidistrin exhibited significant in vitro cytotoxicity against K562 with IC(50) values of 1.09, 2.93 and 0.47microg/mL, respectively.  相似文献   

12.
Seven new triterpenoid saponins, randiasaponins I (1), II (2), III (3), IV (4), V (5), VI (6) and VII (7) as well as two known ones, ilexoside XXVII (8) and ilexoside XXXVII (9), were isolated from the methanolic extract of the leaves of Randia formosa. The structures of the new saponins were established as 3-O-alpha-L-arabinopyranosyl-3 beta,19 alpha,23-trihydroxyursa-12,20(30)-dien-28-oic acid 28-beta-D-glucopyranosyl ester (1), 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl rotundic acid (2), 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl pomolic acid 28-beta-D-glucopyranosyl ester (3), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl pomolic acid 28-beta-D-glucopyranosyl ester (4), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl siaresinolic acid 28-beta-D-glucopyranosyl ester (5), 3-O-alpha-L-arabinopyranosyl ilexosapogenin A 28-beta-D-glucopyranosyl ester (6), and 3-O-beta-D-glucopyranosyl ilexosapogenin A 28-beta-D-glucopyranosyl ester (7), based on spectral and chemical evidence. Besides the saponins, two common flavonoids kaempferol 3-O-rutinoside and rutin were also isolated.  相似文献   

13.
Triterpenoid saponins from the fruits and galls of Sapindus mukorossi   总被引:3,自引:0,他引:3  
Huang HC  Wu MD  Tsai WJ  Liao SC  Liaw CC  Hsu LC  Wu YC  Kuo YH 《Phytochemistry》2008,69(7):1609-1616
Six saponins, sapinmusaponin K (1) [hederagenin-3-O-(3-O-acetyl-alpha-L-arabinopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], sapinmusaponin L (2) [hederagenin-3-O-(4-O-acetyl-alpha-L-arabinopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabino-pyranoside], sapinmusaponin M (3) [hederagenin-3-O-(2,3-O-diacetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], sapinmusaponin N (4) [hederagenin-3-O-(2,4-O-diacetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside], sapinmusaponin O (5) [3,7,20(S)-trihydroxydammar-24-ene-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside], and sapinmusaponin P (6) [3,7,20(R)-trihydroxydammar-24-ene-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-d-glucopyranoside], along with seven known saponins (7-13), were isolated from fruits and the galls of Sapindus mukorossi. Their structures were elucidated by 1D and 2D NMR spectroscopic techniques and acid hydrolysis. Biological evaluation indicated that saponins 1-4 and 7-13 showed moderate cytotoxicity against several human tumor cell lines.  相似文献   

14.
Six triterpene saponins, including two new compounds, were isolated from the fruits of Hedera helix L. (Araliaceae). The structures of the new compounds, named helixosides A and B, were established as 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl hederagenin 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, and 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, respectively, on the basis of chemical and spectral data.  相似文献   

15.
Four new triterpenoid saponins were isolated from the leaves and stem of branches of Dizygotheca kerchoveana along with seven known ones. The new saponins were respectively characterized as 3-O-[beta-D-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid, 3-O-[beta-D-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-3-O-trans-p-coumaroyl-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester and 3-O-[beta-d-3-O-cis-p-coumaroyl-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester. Their structures were elucidated by 1D and 2D NMR experiments, FAB-MS as well as chemical means.  相似文献   

16.
Ying Ye  Yuan Qu  Ruiqi Tang  Shining Cao  Wei Yang  Lan Xiang  Jianhua Qi 《Steroids》2013,78(12-13):1171-1176
Three new steroidal saponins (13) and a known saponin (4) were isolated from Ophiopogon japonicus (Thunb.) Ker-Gawl. Their structures were determined by spectroscopic analyses and chemical derivatization. The isolated compounds (14) were potent inducers of neuritogenesis on PC12 cells. Compound 1 showed the highest neuritogenic activity of 46% at 1 μM. The study of structure–activity relationships suggests that aglycone is important for the neuritogenic activity of the compounds. Specific inhibitor experiments and Western blot analysis suggest that 1-induced neuritogenic activity depends on the activation of mitogen-activated protein kinase kinase (MEK)/extracellular signal regulated kinase (ERK) signaling pathway on PC12 cells.  相似文献   

17.
Zhang T  Kang LP  Yu HS  Liu YX  Zhao Y  Xiong CQ  Zhang J  Zou P  Song XB  Liu C  Ma BP 《Steroids》2012,77(12):1298-1305
Eight novel steroidal saponins, ophiopogonins H-O (1-8), along with seven known steroidal saponins (9-15) were isolated from the tubers of Ophiopogon japonicus. The structures of these new compounds were determined by detailed spectroscopic analysis, including extensive 1D and 2D NMR data, and the analysis of hydrolytic reaction products. For the first time, rare furostanol saponins with disaccharide moiety linked at position C-26 of the aglycone were reported to be isolated from a natural source.  相似文献   

18.
Four new triterpenoid saponins, clematochinenoside H–K (14), and five known structures (59), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. All isolates were evaluated for inhibitory effects against nitric oxide (NO) production in LPS-induced RAW 246.7 macrophages. Monodesmosidic saponins (13, 5, and 6) with a free carboxylic acid function at C-28 exhibited potent inhibitory activities with IC50 values in the range of 12.9–32.3 μM, where as bisdesmosidic saponin (4, and 7–9) showed modest inhibitory effects with the inhibition ratios (%) from 39.9 to 59.0 at 50 μM. In addition, the hydroxyl group at C-21 showed negative effect on the NO production inhibitory activity.  相似文献   

19.
Bioactive flavonoids and saponins from Climacoptera obtusifolia   总被引:1,自引:0,他引:1  
Two bidesmosidic saponins were isolated from Climacoptera obtusifolia (Chenopodiaceae) and their structures were determined as gypsogenin 3-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside]-28-O-{beta-D-glucopyranosyl} ester (1) and hederagenin 3-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-glucopyranoside]-28-O-[beta-D-glucopyranosyl} ester (2), by spectroscopic methods. Two known compounds, isorhamnetin 3-O-beta-D-glucopyranoside (3), and isorhamnetin 3-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (4) were also isolated for the first time from this plant. Compounds 1-4 were tested in various immunomodulatory assays. Compound 2 suppressed (92%) the reactive oxygen species (ROS) production on mononuclear cells in luminol-based chemiluminescence (CL) assay at a higher concentration (50 microg/mL). Compounds 3 and 4 demonstrated a strong inhibition on ROS production in the oxidative burst activity of whole blood, neutrophils, and mononuclear cells. Additionally compounds 3 and 4 also suppressed PHA T-cell proliferation with no cytotoxic effects.  相似文献   

20.
Two new triterpene saponins, namely, ilexpublesnin S (1) and T (2), and six known saponins were isolated from the roots of Ilex pubescens. The structures of the new compounds were elucidated through extensive spectroscopic methods (IR, HR-ESI-MS, 1D and 2D NMR). Sugar residues obtained after acid hydrolysis were identified through TLC and HPLC. Compound 1 contains a 24-aldehyde group, which is rare for triterpene saponins from Ilex.  相似文献   

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