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1.
Six cycloartane-type triterpene glycosides were isolated from Astragalus icmadophilus along with two known cycloartane-type glycosides, five known oleanane-type triterpene glycosides and one known flavonol glycoside. The structures of the six compounds were established as 3-O-[α-L-arabinopyranosyl-(1  2)-O-3-acetoxy-α-L-arabinopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane, 3-O-[α-L-rhamnopyranosyl-(1  2)-O-α-L-arabinopyranosyl-(1  2)-O-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxy cycloartane, 3-O-[α-L-arabinopyranosyl-(1  2)-O-3,4-diacetoxy-α-L-arabinopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane, 3-O-[α-L-arabinopyranosyl-(1  2)-O-3-acetoxy-α-L-arabinopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),24(S)-epoxycycloartane, 3-O-[α-L-arabinopyranosyl-(1  2)-O-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24α-tetrahydroxy-20(R),25-epoxycycloartane, 3-O-[α-L-rhamnopyranosyl-(1  2)-O-α-L-arabinopyranosyl-(1  2)-O-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24α-tetrahydroxy-20(R),25-epoxycycloartane by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis.The first four compounds are cyclocanthogenin and cycloastragenol glycosides, whereas the last two are based on cyclocephalogenin as aglycone, more unusual in the plant kingdom, so far reported only from Astragalus spp.  相似文献   

2.
Four new oleanane-type triterpenoid saponins, schefflesides I–L (14), were isolated from the aerial parts of Schefflera kwangsiensis. Their structures were established as oleanolic acid 3-O-β-d-glucopyranosyl (1  2) [α-l-arabinopyranosyl (1  4)]-β-d-(6-O-methyl) glucuronopyranoside (1), 22α-hydroxyoleanolic acid 3-O-α-l-arabinopyranosyl (1  4)-β-d-glucuronopyranoside (2), hederagenin 3-O-α-l-arabinopyranosyl (1  4)-β-d-glucuronopyranoside (3) and oleanolic acid 28-O-β-d-glucopyranosyl (1  2)-β-d-glucuronopyranosyl ester (4) by spectroscopic analyses (HRESIMS, 1D and 2D NMR) and chemical methods.  相似文献   

3.
A new dihydrochalcone, 2‘,4‘-dihydroxy-3‘-methoxy-3,4-methylenedioxy-8-hydroxymethylene dihydrochalcone 1 and two new steroidal saponins, (25S)-ruscogenin-1-O-α-l-rhamnopyranosyl-(1  2)-β-d-glucopyranoside 2, (25S)-ruscogenin-3-O-α-l-rhamnopyranosyl-(1  4)-β-d-glucopyranoside 3, together with three known steroidal saponins (25S)-ruscogenin-3-O-β-d-glucopyranoside 4, (25S)-ruscogenin-1-O-α-l-rhamnopyranosyl-(1  2)-[β-d-xylopyranosyl-(1  3)]-α-l-arabinopyranoside 5 and (25R)-26-O-β-d-glucopyranosyl-furost-5-ene-1β,3β,22α,26-tetrol-1-O-α-L-rhamnopyranosyl-(1  2)-[β-d-xylopyranosyl-(1  3)]-α-l-arabinopyranoside 6 were isolated from the aerial parts of Sansevieria cylindrica. The structures of the new compounds were established by UV, IR, EI-MS, HR-ESI–MS as well as 1D (1H,13C and DEPT-135) and 2D (HSQC, HMBC and TOCSY) NMR spectral analysis. The isolated compounds 1-6 were assayed for in vitro cytotoxicities against the three human tumor cell lines HT116, MCF7 and HepG2. Compound 1 showed a moderate cytotoxicity against MCF7. Compounds 2, 3 and 6 exhibited moderate cytotoxicities against the three used cell lines and compound 5 showed marked cytotoxicities against all used cell lines.  相似文献   

4.
Two new penterpenoid saponins, hemsloside-Ma4 (1) hemsloside-Ma5 (2), and a new diterpenoid glycoside, hemsloside-Ma6 (3), were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra and chemical methods, the structures of new compounds were determined to be 3-O-β-l-arabinopyranosyl-(1  3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-glucopyranosyl-(1  6)-O-β-d-glucopyranoside (1), 3-O-β-l-arabinopyranosyl-(1  3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-xylopyranosyl-(1  6)-O-β-d-glucopy-ranoside (2), and 13ϵ-hydroxylabda-8(17), 14-dien-18-oic acid-18-O-α-l-rhamnopyranosyl-(1  2)-O-β-d-glucopyranosyl-(1  4)-O-α-l-rhamnopyranoside (3). Diterpenoid-type compound (3) was isolated from Hemsleya genus for the first time.  相似文献   

5.
Three new oleanane-type saponins, leptocarposide B-D (13), were isolated from the whole plant of Ludwigia leptocarpa (Nutt.) Hara, together with ten known compounds 4–13.The structures of these compounds were determined by interpretation of their spectral data, mainly HR-TOFESIMS, 1D-NMR (1H, 13C) and 2D-NMR (1H–1H COSY, HSQC, HMBC, and NOESY), and by comparison with the literature data. The structures of the new compounds were established as 28-O-β-d-xylopyranosyl-(1  4)-α-l-rhamnopyranosyl-(1  2)-[α-l-arabinopyranosyl-(1  3)]-4-O-(3′-hydroxybutanoyloxy-3-hydroxybutanoyloxy)-β-d-fucopyranosyl zanhic acid (1); 3-O-β-d-glucopyranosyl-28-O-β-d-xylopyranosyl-(1  4)-α-l-rhamnopyranosyl-(1  2)-4-O-(3′-hydroxybutanoyloxy-3-hydroxybutanoyloxy)-β-d-fucopyranosyl medicagenic acid (2); 3-O-β-d-glucopyranosyl-(1  4)-β-d-glucopyranosyl-28-O-β-d-xylopyranosyl-(1  4)-α-l-rhamnopyranosyl-(1  2)-[α-l- arabinopyranosyl-(1  3)]-4-O-(3′-hydroxybutanoyloxy-3-hydroxybutanoyloxy)-β-d-fucopyranosyl zanhic acid (3).  相似文献   

6.
Two triterpenoid saponins have been isolated from the seed kernels of Entada rheedii. Their structures have been established using 1D- and 2D-NMR and mass spectrometry as 3-O-β-d-xylopyranosyl-(1  3)-O-α-l-arabinopyranosyl-(1  6)-2-acetylamino-2-deoxy-β-d-glucopyranosylentagenic acid 28-O-β-apiofuranosyl-(1  3)-β-d-xylopyranosyl-(1  2)-β-d-glucopyranoside (Rheediinoside A, 1) and 3-O-β-d-glucopyranosyl-(1  3)-O-[β-d-xylopyranosyl-(1  3)-α-l-arabinopyranosyl-(1  6)]-2-acetylamino-2-deoxy-β-d-glucopyranosylentagenic acid 28-O-β-apiofuranosyl-(1  3)-β-d-xylopyranosyl-(1  2)-β-d-glucopyranoside (Rheediinoside B, 2). Compounds 1 and 2 were tested for their antiproliferative activity against T98G, A431, PC3 and B16-F1 cell lines, and further for their antioxidant properties. Moderate cytotoxic potency and antioxidant properties were found for these compounds whereas Rheediinoside B was in all assays more active than Rheediinoside A.  相似文献   

7.
Two new steroidal saponins, 25(R)-3β [(O-β-d-glucopyranosyl-(1  3)-β-d-glucopyranosyl-(1  2)-O-[β-d-xylopyranosyl-(1  3)-O-β-d-glucopyranosyl-(1  4)-β-d-galactopyranosyl)oxy]-5α, 15β, 22R, 25R-spirostan-3,15-diol (1, named parquispiroside) and 25R-26-[(β-d-glucopyranosyl)Oxy]-(3β [(O-β-d-glucopyranosyl-(1  3)-β-d-glucopyranosyl-(1  2)-O-[β-d-xylopyranosyl-(1  3)-O-β-d-glucopyranosyl-(1  4)-β-d-galactopyranosyl)oxy], 5α, 15β, 22R, 25R)-furostane-3,15,22-triol (2, named parquifuroside), along with the known saponins, capsicoside D (3) and 22-OMe-capsicoside D (4) and the known glycoside, benzyl primeveroside (5), were isolated from the leaves of Cestrum parqui. The structures of these compounds were elucidated by careful analysis of 1D and 2D NMR spectra and ESIMS data. Parquispiroside (1) exhibited moderate inhibition of Hela, HepG2, U87, and MCF7 cell lines with IC50 values in the range of 3.3–14.1 μM.  相似文献   

8.
Five new steroidal saponins were isolated from the fruits of Tribulus terrestris. Their structures were fully established by spectroscopic and chemical analysis as (23S,25S)-5α-spirostane-24-one-3β,23-diol-3-O-{α-l-rhamnopyranosyl-(1  2)-O-[β-d-glucopyranosyl-(1  4)]-β-d-galactopyranoside} (1), (24S,25S)-5α-spirostane-3β,24-diol-3-O-{α-l-rhamnopyranosyl-(1  2)-O-[β-d-glucopyranosyl-(1  4)]-β-d-galactopyranoside} (2), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-2α,3β,22α,26-tetraol-3-O-{β-d-glucopyranosyl-(1  2)-O-β-d-glucopyranosyl-(1  4)-β-d-galactopyranoside} (3), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-20(22)-en-2α,3β,26-triol-3-O-{β-d-glucopyranosyl-(1  2)-O-β-d-glucopyranosyl-(1  4)-β-d-galactopyranoside} (4), and 26-O-β-d-glucopyranosyl-(25S)-5α-furostan-12-one-22-methoxy-3β,26-diol-3-O-{α-l-rhamnopyranosyl-(1  2)-O-[β-d-glucopyranosyl-(1  4)]-β-d-galactopyranoside} (5). The isolated compounds were evaluated for cytostatic activity against HL-60 cells.  相似文献   

9.
Six new compounds including two oleanane-type triterpenoid saponins (1, 2) and four C-glycosyl flavones (36), along with a known saponin (7), three di-C-glycosyl flavones (810) and a glycosyl auronol (11), were isolated from the stem bark of Erythrina abyssinica Lam. The structures of the new compounds, identified as 3-O-[α-l-rhamnopyranosyl-(1  2)-β-d-galactopyranosyl-(1  2)-β-d-glucuronopyranosyl]-22-O-β-d-glucopyranosyl sophoradiol (1), 3-O-[α-l-rhamnopyranosyl-(1  2)-β-d-glucopyranosyl-(1  2)-β-d-glucuronopyranosyl]-22-O-β-d-glucopyranosyl sophoradiol (2), 6-C-β-glucopyranosyl-8-C-β-quinovopyranosyl apigenin (3), 6-C-β-quinovopyranosyl-8-C-β-glucopyranosyl apigenin (4), 8-C-[6″-O-α-l-rhamnopyranosyl-(1‴  6″)]-β-glucopyranosyl 7,4′-dihydroxyflavone (5) and 8-C-[6″-O-β-d-xylopyranosyl-(1‴  6″)]-β-glucopyranosyl 7,4′-dihydroxyflavone (6), were determined by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and acid hydrolysis. These new compounds together with the known saponins 7 were evaluated for their cytotoxic activity against MCF-7 (estrogen dependent) and MDA-MB-231 (estrogen independent) cell lines. The new saponin 2 exhibited the highest cytotoxic activity among tested compounds, exerting a selective inhibitory effect against the proliferation of MCF-7 cells, with lower IC50 value (12.90 μM) than that of the positive control, resveratrol (13.91 μM). Structure–activity relationship of these compounds is also discussed.  相似文献   

10.
Three cycloartane-type triterpene glycosides were isolated from Astragalus wiedemannianus together with eight known secondary metabolites namely cycloastragenol, cycloascauloside B, astragaloside IV, astragaloside VIII, brachyoside B, astragaloside II, astrachrysoside A, and astrasieversianin X. The structures were established mainly by a combination of 1D and 2D-NMR techniques as 3-O-[α-L-rhamnopyranosyl-(1  2)-β-D-glucopyranosyl]-25-O-β-D-glucopyranosyl-20(R),24(S)-epoxy-3β,6α,16β,25-tetrahydroxycycloartane, 3-O-[α-L-rhamnopyranosyl-(1  2)-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-24-O-α-(4’-O-acetoxy)-L-arabinopyranosyl-16-O-acetoxy-3β,6α,16β,24(S),25-pentahydroxycycloartane, 3-O-[α-L-rhamnopyranosyl-(1  2)-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-24-O-α-L-arabinopyranosyl-16-O-acetoxy-3β,6α,16β,24(S),25-pentahydroxycycloartane. To the best of our knowledge, the presence of an arabinose moiety on the acyclic side chain of cycloartanes is reported for the first time.  相似文献   

11.
A new flavonol glycoside, kaempferol 7-O-(6-E-p-coumaroyl)-β-d-glucopyranosyl-(1  3)-α-l-rhamnopyranoside 3-O-β-d-galactopyranoside (1), together with other five known compounds (26), were identified from the flowers and leaves of Aconitum angustifolium Bernh. Their chemical structures were elucidated by extensive NMR spectral studies, as well as by ESI-MS analysis.  相似文献   

12.
Two new ursane-type triterpene saponins, 3-O-β-d-glucopyranosyl(1  3)-[α-l-rhamnopyranosyl(1  2)]-α-l-arabinopyranosylurs-12,19(29)-dien-28-oic acid 28-O-α-l-rhamnopyranosyl(1  2)-β-d-glucopyranosyl ester (1) and 3-O-β-d-glucopyranosyl(1  3)-[α-l-rhamnopyranosyl(1  2)]-α-l-arabinopyranosyl-19α,20α-dihydroxyurs-12-en-28-oic acid 28-O-α-l-rhamnopyranosyl(1  2)-β-d-glucopyranosyl ester (2), along with thirteen known triterpene saponins were isolated from the n-BuOH part of the MeOH extraction of the leaves of Ilex kudingcha C.J. Tseng (also called “Ku-Ding-Cha”). The structures of new compounds were elucidated on the basis of detailed spectroscopic analysis, including HR-ESI-TOF-MS, 1D and 2D-NMR experiments, and by acid hydrolysis. All the compounds were screened for antiplatelet aggregation activity in vitro, and compounds 1, 2, 3, 7, 12 and 15 showed significant inhibition of platelet aggregation induced by ADP (5 μM) with IC50 values of 14.7 ± 3.7, 11.3 ± 2.5, 17.4 ± 4.6, 20.5 ± 3.1, 8.1 ± 1.5 and 18.9 ± 4.2 μM, respectively.  相似文献   

13.
Four new triterpenoidal saponins (14), oleanolic acid 3β-O-α-l-arabinopyranosyl-(1  2)-β-d-glucuronopyranoside-6-O-butyl ester (1), oleanolic acid 3β-O-[α-l-arabinopyranosyl-(1  2)-β-d-glucuronopyranoside-6-O-butyl ester]-28-O-β-d-glucopyranoside (2), 19α-hydroxy oleanolic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (3), and 19α-hydroxy urs-12-en-28-oic acid 3β-O-α-l-arabinopyranosyl-(1  2)-β-d-glucuronopyranoside-6-O-methyl ester (4) were isolated from the roots of Ilex cornuta. Their structures were determined by means of extensive spectroscopic analyses (IR, ESIMS, HRESIMS, 1D and 2D NMR). Compounds 19 were tested for their cytotoxic activities by MTT assay, and 1, 3, 5 and 6 showed moderate cytotoxic activities against HeLa, SMMC-7721, and HL-60 human tumor cell lines.  相似文献   

14.
Two new acylated flavonol pentaglycosides were isolated from the butanolic extract of Baphia nitida leaves by Sephadex LH-20 and preparative HPLC. Structural elucidation of kaempferol 3-O-β-d-xylopyranosyl(1  3)-(4-O-E-p-coumaroyl-α-l-rhamnopyranosyl(1  2))[β-d-glucopyranosyl(1  6)]-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside (1) and kaempferol 3-O-β-d-xylopyranosyl(1  3)-(4-O-Z-p-coumaroyl-α-l-rhamnopyranosyl(1  2))[β-d-glucopyranosyl(1  6)]-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside (2) was achieved using UV, NMR, and mass spectrometry, indicating the presence of trans or cis isomers of p-coumaric acid moiety in these novel structures. The antioxidant activity of the two compounds was assessed in the peroxynitrite assay.  相似文献   

15.
In the search of natural compounds inhibiting methane production in ruminants three novel steroidal saponins have been isolated from the aerial parts of Helleborus viridis L. Their structures have been established based on spectral analyses as: (25R)-26-O-β-d-glucopyranosyl-5β-furostan-3β,22α,26-triol 3-O-β-d-glucopyranosyl-(1  6)-O-β-d-glucopyranoside, (25R)-26-O-β-d-glucopyranosyl-5α-furostan-3β,22α,26-triol 3-O-β-d-glucopyranosyl-(1  6)-O-β-d-glucopyranoside and (25R)-26-O-β-d-glucopyranosyl-furost-5-ene-1β,3β,22α,26-tetraol 1-O-{α-l-rhamnopyranosyl-(1  2)-O-[β-d-glucopyranosyl-(1  3)]-6-O-acetoxy-β-d-glucopyranoside}.  相似文献   

16.
Grandulosides A-C, three new flavonoid glycosides, were isolated from the aerial parts of Graptophyllum grandulosum Turill and identified as chrysoeriol-7-O-β-d-apiofuranosyl-(1  2)-β-d-xylopyranoside (1), chrysoeriol-7-O-[4′′′-O-acetyl-β-d-apiofuranosyl-(1  2)]-β-d-xylopyranoside (2) and 7-O-α-l-rhamnopyranosyl-(1  6)-β-d-(4′′-Sodium hydrogeno sulfate) glucopyranoside (3). Four known compounds, chrysoeriol-7-O-β-d-xyloside (4), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1  6)-β-d-glucopyranoside (5), luteolin-7-O-β-d-apiofuranosyl-(1  2)-β-d-xylopyranoside (6) and sucrose (7) were also obtained. The structures of these compounds were established by interpretation of their spectral data, mainly HR-TOFESIMS, 1D-NMR (1H, 13C) and 2D-NMR (COSY, NOESY, HSQC and HMBC) and by comparison with the literature data.  相似文献   

17.
Three new phenylethanoid glycosides, 2-(3-hydroxy-4-methoxyphenyl)ethyl 1-O-β-d-allopyranoside (hodgsonialloside A, 1), 2-(3-hydroxy-4-methoxyphenyl)ethyl 1-O-β-d-glucopyranosyl-(1  4)-β-d-allopyranoside (hodgsonialloside B, 2) and 2-(3-methoxy-4-hydroxyphenyl)ethyl 1-O-β-d-allopyranoside (hodgsonialloside C, 3) were isolated from the leaves of Magnolia hodgsonii in addition to six known compounds, tyrosol 4-O-β-d-xylopyranosyl-(1  6)-β-d-glucopyranoside (4), kaempferol 3-O-neohesperidoside (5), kaempferol 3-O-rutinoside (6), kaempferol 3-O-α-l-rhamnopyranosyl-(1  2)-[α-l-rhamnopyranosyl-(1  6)]-β-d-glucopyranoside (7), (+)-syringaresinol O-β-d-glucopyranoside (8), and oblongionoside C (9). The structure elucidation of these compounds was based on analyses of physical and spectroscopic data including 1D and 2D NMR experiments.  相似文献   

18.
Thirty-six naturally occurring compounds, including four C10-acetylenic glycosides and a lignan, were isolated from the whole plants of Saussurea cordifolia. Their structures were elucidated by means of spectroscopic and chemical methods to be 4,6-decadiyne-1-O-β-d-apiofuranosyl-(1  6)-β-d-glucopyranoside (1), 4,6-decadiyne-1-O-α-l-rhamnopyranosyl-(1  6)-β-d-glucopyranoside (2), (8E)-decaene-4, 6-diyn-1-O-α-l-rhamnopyranosyl-(1  6)-β-d-glucopyranoside (3), (8Z)-decaene-4,6-diyn-1-O-β-d-apiofuranosyl-(1  6)-β-d-glucopyranoside (4), and (2R, 3S, 4S)-4-(4-hydroxy-3-methoxybenzyl)-2-(5-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-tetrahydrofuran-3-ol (5).  相似文献   

19.
Six pentacyclic triterpenoid saponins, named antoniosides E–J along with two known alkaloids, were isolated from the leaves of Antonia ovata. Their structures were determined by the extensive use of 1D and 2D-NMR experiments along with HRESIMS analysis and acid hydrolysis. All isolated saponins contained the same pentasaccharide chain: 3-O-[β-d-glucopyranosyl-(1  2)]-[β-d-glucopyranosyl-(1  4)]-[β-d-glucopyranosyl-(1  3)-α-l-arabinopyranosyl(1  6)]-β-d-glucopyranoside, linked at C-3 of esterified derivatives of polyhydroxyoleanene triterpenoids (theasapogenol A and 15α-hydroxy-theasapogenol A). Isolated compounds were evaluated for their cytotoxic activity against KB cell line by a WST-1 assay, and the IC50 values ranged from 3.3 to 5.3 μM.  相似文献   

20.
From the leaves of Schefflera sessiliflora De P. V., two new oleanane-type triterpene saponins, named scheffleraside A (1), scheffleraside B (2); together with two known saponins, chikusetsusaponin IVa (3), 3-O-[α-l-rhamnopyranosyl-(1  3)]-β-d-glucuronopyranosyl hederagenin (4) were isolated by various chromatography methods. Its chemical structure was elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and comparison of their NMR data with previous reported data.  相似文献   

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