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1.
A general scheme of synthesis of antibiotic doxorubicin derivatives is based on the 13-dimethyl ketal of 14-bromodaunorubicin (4). The interaction of 4 with melibiose (5), lactose (6), 3-methoxy-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-4-oxybenzaldehyde (12) or 4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-4-oxybenzaldehyde (13) by reductive alkylation followed by hydrolysis of the corresponding intermediate bromoketals produced 3'-N-[alpha-D-galactopyranosyl-(1-->6)-O-1-deoxy-D-glucit-1-yl]doxorubicin (7), 3'-N-[beta-D-galactopyranosyl-(1-->4)-O-1-deoxy-D-glucit-1-yl]doxorubicin (8), 3'-N-[3"-methoxy-4"-O-(beta-D-galactopyranosyl)-4"-oxybenzyl]doxorubicin (16), and 3'-N-[4"-O-(beta-D-galactopyranosyl)-4"-oxybenzyl]doxorubicin (17). Cytotoxic and antitumor activity of the synthesized drug candidates compared to the parent doxorubicin was studied using various experimental models, in particular, on mice bearing lymphocyte leukemia P-388 at single and multiple i.v. injection regimens.  相似文献   

2.
Four acylated pelargonidin glycosides and pelargonidin 3-sophoroside-5-glucoside were isolated from 23 red-purple cultivars of Pharbitis nil. The acylated anthocyanins were all based on pelargonidin 3-sophoroside-5-glucoside and were identified as the 3-O-[2-O-(beta-D-glucopyranosyl)-6-O-(trans-caffeyl)-beta-D- glucopyranoside]-5-O-(beta-D-glucopyranoside), the 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta- D-glucopyranosyl)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), the 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta- D-glucopyranosyl)-6-O-(trans-caffeyl)-beta-D-glucopyranoside]-5-O-(beta- D-glucopyranoside); and the 3-O-[2-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)caffeyl)-beta-D- glucopyranosyl)-6-O-(trans-4-O-(6-O-(trans-3-O-(beta-D- glucopyranosyl)caffeyl)- beta-D-glucopyranosyl)caffeyl)-beta-D-glucopyranoside]-5-O-(beta-D- glucopyranoside). By the analysis of these anthocyanin constituents variously in 23 cultivars, it was found that the red flower colour gradually changed into more bluish colour with increasing numbers of caffeic acid residues in the acylated pelargonidin glycosides. The stabilities of these anthocyanins increased in the order of increasing caffeyl substitution.  相似文献   

3.
Each of a series of synthetic peptidoglycan subunits and subunit analogues was injected in combination with streptococcus type M24 antigen extract. The substances tested were: (8a) N-acetylmuramyldipeptide (MDP) and the following derivatives thereof: MDP modified in positions C3 and C4, or with L-alanine substituted by L-2-aminobutyric acid or with the peptide chain prolonged (by three lysines or a polylysine); (b) some synthetically prepared peptides: a hexapeptide, a tridecapeptide and an octadecapeptide. Configurations in positions C3 and C4 were found essential for the adjuvant effect. Adjuvant activity, though somewhat lower than in MDP, was pronounced in the analogue containing the L-2-aminobutyryl residue. Surprisingly, potent adjuvant effect was displayed by the hexapeptide; prolongation of the peptidic chain was not effective. The use of a polymeric carrier for MDP increased the adjuvant effect. Contrary to expectation, streptococcal antigens used with immunoadjuvant materials showed that induced delayed hypersensitivity was type related.  相似文献   

4.
Ten new alpha-glucosylginsenosides were found to be synthesized from dextrin and four ginsenosides, -Rb1, -Rc, -Re, and -Rg1, by the successive actions of B. stearothermophilus cyclomaltodextrin glucanotransferase and Rhizopus glucoamylase. Seven of them were isolated in the pure state by extraction with n-butanol saturated with water, silica gel column chromatography, and high pressure liquid chromatography, and identified as 3-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[beta-D-glcp-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[alpha-L-araf-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[(4G-alpha-D-glcp)-alpha-L-araf-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 6-O-[alpha-L-rhap-(1-->2)-beta-D-glcp]-20-O-[alpha-D-glcp-(1-->4)-beta-D-glcp]-20(S)-protopanaxatriol, 6-O-[alpha-D-glcp-(1-->4)-beta-D-glcp]-20-O-(beta-D-glcp)-20(S)-protopanaxatriol, and 6-O-[alpha-D-glcp-(1-->3)-beta-D-glcp]-20-O-(beta-D-glcp)-20(S)-protopanaxatriol, by spectroscopy (FAB-MS, IR, 1H-NMR and 13C-NMR) and hydrolysis products in 50% acetic acid. The bitterness of these alpha-glucosyl-ginsenosides was less than that of ginsenosides.  相似文献   

5.
Acylated anthocyanins from red radish (Raphanus sativus L.)   总被引:5,自引:0,他引:5  
Twelve acylated anthocyanins were isolated from the red radish (Raphanus sativus L.) and their structures were determined by spectroscopic analyses. Six of these were identified as pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-beta-D-glucopyranosyl]-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-caffeoyl-2-O-(6-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-p-coumaroyl-2-O-(6-(E)-caffeoyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-(6-(E)-caffeoyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-p-coumaroyl-2-O-(6-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), and pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-(2-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside).  相似文献   

6.
Acylated anthocyanins from the blue-violet flowers of Anemone coronaria   总被引:2,自引:0,他引:2  
Five polyacylated anthocyanins were isolated from blue-violet flowers of Anemone coronaria 'St. Brigid'. They were identified as delphinidin 3-O-[2-O-(2-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(malonyl)-beta-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-beta-D-glucopyranoside]-3'-O-[beta-D-glucuronopyranoside], and its demalonylated form, delphinidin 3-O-[2-O-(2-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(2-O-tartaryl)malonyl)-beta-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-beta-D-glucopyranoside]-3'-O-[beta-D-glucuronopyranoside], and its cyanidin analog as well as delphinidin 3-O-[2-O-(2-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(2-O-(tartaryl)malonyl)-beta-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-beta-D-glucopyranoside].  相似文献   

7.
Six new triterpenoid saponins have been isolated from the stem bark of Elattostachys apetala together with four known triterpenoid saponins. Three of these new compounds are glycosides of a newly described genin, 29-hydroxyhederagenin (1). On the basis of spectral evidence, the structures of the new saponins were concluded to be alpha-hederin 28-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl] ester (2), sapindoside B 28-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl] ester (3), 3-O-beta-D-xylopyranosyl astrantiasaponin VII (4), 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (5), 3-O-[alpha-L-arabinopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (6), and 3-O-[beta-D-xylopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-gluco pyranosyl-(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (7).  相似文献   

8.
6-Phosphomannosylated bovine serum albumin (Man6P-BSA), a neoglycoprotein endocytosed by macrophages, bearing either 3-(2-pyridyldithio)propionyl or 3-[(carbamoylmethyl)thio]propionyl residues coming from alkylation of thiol residues by iodoacetamide were prepared and tested for their immunomodulator properties. The supernatants of mouse peritoneal macrophages incubated with Man6P-BSA bearing 3-[(carbamoylmethyl)thio]propionyl groups, and by a lesser extent 3-(2-pyridyldithio)propionyl groups, were cytotoxic to L929 cells, suggesting the presence of a tumor necrosis factor like compound. This macrophage-activation process is linked to the capacity of Man6P-BSA to be endocytosed via membrane lectins of macrophages, because the supernatants of macrophages incubated with unglycosylated conjugates were not cytotoxic. The cytotoxic activity induced by 3-[(carbamoylmethyl)thio]propionyl groups bound onto Man6P-BSA was similar to that induced by Man6P-BSA bearing muramyl dipeptide, indicating that endocytosed neoglycoproteins bearing 3-[(carbamoylmethyl)thio]propionyl residues are potent macrophage activators.  相似文献   

9.
Five acylated peonidin glycosides were isolated from the pale gray-purple flowers of a duskish mutant in the Japanese morning glory (Ipomoea nil or Pharbitis nil) as major pigments, along with a known anthocyanin, Heavenly Blue Anthocyanin (HBA). Three of these were based on peonidin 3-sophoroside and two on peonidin 3-sophoroside-5-glucoside as their deacylanthocyanins; both deacylanthocyanins were acylated with caffeic acid and/or glucosylcaffeic acids. By spectroscopic and chemical methods, the structures of the former three pigments were determined to be 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-beta-D-glucopyranoside], 3-O-[2-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-glucopyranoside], and 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside] of peonidin. The structures of the latter two pigments were also confirmed as 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-beta-D-glucopyranoside]-5-O-beta-D-glucopyranoside, and 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside]-5-O-beta-D-glucopyranoside of peonidin. The mutation affecting glycosylation and acylation in anthocyanin biosynthesis of Japanese morning glory was discussed.  相似文献   

10.
彩色马铃薯富含花色苷,是一种天然抗氧化食品.本研究采用高效液相色谱质谱联用技术以引进品种“黑美人”为对照分析了云南马铃薯地方特色品种“剑川红”和“转心乌”花色苷的主要成分.结果表明:“剑川红”色素主要为酰化天竺葵色素类花色苷,其主要成分为天竺葵素3-[ 6-O-( 4-O-E-p-香豆酰-O-α-吡喃鼠李糖苷)-β-D-吡喃葡萄糖苷]-5-O-β-D-毗喃葡萄糖苷.“转心乌”和“黑美人”所含色素相似,主要为酰化矮牵牛色索、锦葵色素、芍药色素类衍生物,主要成分均为矮牵牛花色素3-[ 6-O-( 4-O-E-p-香豆酰-O-α-吡喃鼠李糖苷)-β-D-毗喃葡萄糖苷]-5-O-β-D-毗喃葡萄糖苷.  相似文献   

11.
A phytochemical investigation of the extracts obtained from bulbs of leek. Allium porrum L. has led to the isolation of five flavonoid glycosides based on the kaempferol aglycone. Two of them are new compounds and have been identified as kaempferol 3-O-[2-O-(trans-3-methoxy-4-hydroxycinnamoyl)-beta-D-galactopyranosyl]-(1-->4)-O-beta-D-glucopyranoside, and kaempferol 3-O-[2-O-(trans-3-methoxy-4-hydroxycinnamoyl)-beta-D-glucopyranosyl]-(1-->6)-O-beta-D-glucopyranoside, on the basis of spectroscopic methods, including 2D NMR. The isolated compounds have been evaluated for their human platelet anti-aggregation activity.  相似文献   

12.
Zou K  Zhao Y  Tu G  Cui J  Jia Z  Zhang R 《Carbohydrate research》2000,324(3):182-188
Two diastereomeric saponins, julibrosides J1 (1) and J9 (2), both of which show cytotoxic activity, were obtained from the stem bark of Albizia julibrissin Durazz. On the basis of chemical and spectral evidence [L.B. Ma et al., Carbohydr. Res., 281 (1996) 35-46], the structure of 1 was revised as 3-O-[beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6) -beta-D-glucopyranosyl]-21-O-[(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O- [4-O-((6R)-2-trans-2,6-dimethyl-6-O-(beta-D-quinovopyranosyl)-2,7- octadienoyl)-beta-D-quinovopyranosyl]-2,7-octadienoyl] acacic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->4 )]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester. The diastereoisomer 2 of 1 was identified as 3-O-[beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6) -beta-D-glucopyranosyl]-21-O-[(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O- [4-O-((6S)-2-trans-2,6-dimethyl-6-O-(beta-D-quinovopyranosyl)-2,7- octadienoyl)-beta-D-quinovopyranosyl]-2,7-octadienoyl] acacic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->4 )]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester. Saponin 2 is a new saponin named julibroside J9. Both julibrosides J1 and J9 show good inhibitory action against the KB cancer cell line in vitro.  相似文献   

13.
Two triacylated and tetraglucosylated anthocyanins derived from cyanidin were isolated from the flowers of Ipomoea asarifolia and their structures elucidated using chemical, GC, MS and NMR methods (1H and 13C, TOCSY-1D, DQF-COSY, DIFFNOE and HMBC). These complex pigments were found to consist of cyanidin 3-O-[2-O-(6-O-E-caffeoyl-beta-D-glucopyranosyl)]-[6-O-[4-O-(6-O-E-3,5-dihydroxycinnamoyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl]-5-O-beta-D-glucopyranoside and cyanidin 3-O-[2-O-(6-O-E-p-coumaroyl-beta-D-glucopyranosyl)]-[6-O-[4-O-(6-O-E-p-coumaroyl-beta-D-glucopyranosyl)-E-caffeoyl]-beta-D-glucopyranosyl]-5-O-beta-D-glucopyranoside.  相似文献   

14.
The synthesis of 3′-O-{3-[N-(4-azido-2-nitrophenyl) amino] propionyl} 8-azido-adenosine 5′-triphosphate—a 3′-arylazido-8-azido ATP—is described. The ATP derivative is characterized by thin layer chromatography, infrared spectroscopy, and optical spectroscopy. Its photolysis upon irradiation with uv light and its stability in dependence on pH are tested. Its two photolabile azido groups allow the use of this ATP analog as a photoaffinity label for cross-linking the subunits of ATP binding proteins.  相似文献   

15.
The triacyl anthocyanins, Leschenaultia blue anthocyanins 1 and 2 (LBAs 1 and 2) were isolated from the blue flowers of Leschenaultia R. Br. cv. Violet Lena (Goodeniaceae), in which LBA 1 was present as a dominant pigment. The structure of LBA 1 was elucidated to be delphinidin 3-O-[6-O-(malonyl)-beta-D-glucopyranoside]-7-O-[6-O-(4-O-(6-O-(4-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside] by application of chemical and spectroscopic methods. Since LAB 2 was isolated in small amount, its structure was tentatively assigned as either delphinidin 3-(malonylglucoside)-7-[(glucosyl-p-coumaroyl)-(glucosylcaffeoyl)-glucoside] or delphinidin 3-(malonyl-glucoside)-7-[(glucosyl-caffeoyl)(glucosyl-p-coumaroyl)-glucoside]. This is the first report of the occurrence of 7-polyacylated anthocyanins in the family of Goodeniaceae, although others have been found in the families of the Ranunculaceae, Campanulaceae, and Compositae. Moreover, delphinidin 3-glycoside-7-di-(glucosylcaffeoyl)-glucoside has been reported only in the flowers of Platycodon grandiflorum (Campanulaceae). From a chemotaxonomical viewpoint, the Goodeniaceae may be closely related to the Campanulaceae.  相似文献   

16.
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   

17.
Targeting of synthetically glycosylated human placental glucocerebrosidase   总被引:1,自引:0,他引:1  
Human placental beta-glucocerebrosidase modified by covalent attachment of N2-(N2, N6-bis [3-(alpha-D-mannopyranosylthio)propionyl]-L- lysyl)-N6-[3-(alpha-D-mannopyranosylthio)propionyl]-L-lysine was administered to rats by intravenous injection. Comparison of enzyme distribution in isolated liver cell populations indicates an increase in enzyme-specific activity of 18-fold in nonparenchymal cells and only 1.5-fold to hepatocytes compared to uninjected control animals. This macrophage-specific delivery of an active lysosomal enzyme has potential for application in enzyme replacement trials.  相似文献   

18.
Among chemically synthesized analogues corresponding to the nonreducing sugar part of lipid A, we have found an analogue (GLA-27) which exhibits Limulus, mitogenic, polyclonal B cell activation (PBA), interferon-inducing, and tumor necrosis factor (TNF)-inducing activities but not pyrogenic activity. The structure of GLA-27 comprises 4-O-phosphono-D-glucosamine with tetradecanoyl and 3-tetradecanoyloxytetradecanoyl (C14-O-(C14] groups as the 3-O- and 2-N-acyl substituents, respectively. Derivatives of GLA-27 with different backbone structures, such as the 1-deoxy, 3-epimeric, 3-amino, and 1-deoxy-3-epimeric derivatives of glucosamine, were chemically synthesized, and their mediator-inducing activities such as interferon- and TNF-inducing activities were investigated in comparison with their B cell activation activities including mitogenic and PBA activities. Among these derivatives, a derivative with a 1-deoxyglucosamine backbone (GLA-40) exhibited stronger B cell activation activities than those of GLA-27 while the mediator-inducing activities of GLA-40 were weaker than those of GLA-27. In addition to these derivatives, stereoisomers of GLA-27 which possess the (R) and (S) forms of C14-O-(C14) as the 2-N-acyl substituent were also synthesized and their biological activities compared. The (S) isomer exhibited much stronger mediator-inducing activities than the (R) isomer. On the other hand, B cell activation activities of the (R) isomer were strong and those of the (S) isomer weak. These results clearly demonstrate that mediator-inducing activities and B cell activation activities can be selectively expressed by modifying the structures of lipid A analogues.  相似文献   

19.
From the aerial parts of Astragalus suberi L., Fabaceae, seven saponins were isolated. Based on spectral data (IR, 1H and 13C NMR and HR-FABMS), the structures were established as 3-O-(beta-D-glucopyranosyl)-soyasapogenol B (1); 3-O-(beta-D-glucuronopyranosyl)-soyasapogenol B (2); 3-O-[beta-D-galactopyranosyl (1-->2)-beta-D-glucopyranosyl]-soyasapogenol B (3); 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucopyranosyl]-soyasapogenol B (4); 3-O-[beta-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucopyranosyl]-11-hydroxy-soyasapogenol B (5); 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucuronopyranosyl]-soyasapogenol B (6) and 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucuronopyranosyl]-complogenin (7). The isolated saponins exhibited antibacterial activities against Gram-positive and Gram-negative bacteria with minimum inhibitory concentration values >100 microg/ml, antifungal activity against all the strains tested with minimum fungicidal concentration values between 25 and 50 microg/ml and inhibited the growth of Hep-2 (human carcinoma of larynx), with IC50 values between 50 microg/ml (compounds 5-7) and 100 microg/ml (compounds 1-4), and Hela (human carcinoma of cervix) cell lines in culture with different IC50 values [74 (compound 7), 98 (compound 5) and 180 microg/ml (compounds 1-4 and 6)].  相似文献   

20.
Three acylated cyanidin 3-sambubioside-5-glucosides (1-3) were isolated from the violet-blue flowers of Orychophragonus violaceus, and their structures were determined by chemical and spectroscopic methods. Two of those acylated anthocyanins (1 and 3) were cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-xylopyranosyl)-6-O-(4-O-(beta-D-glucopyranosyl)-trans-acyl)-beta-D-glucopyranoside]-5-O-(6-O-malonyl-beta-D-glucopyranoside)s, in which the acyl groups were p-coumaric acid for 1, and sinapic acid for 3, respectively. The last anthocyanin 2 was cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-xylopyranosyl)-6-O-(4-O-(beta-D-glucopyranosyl)-trans-feruloyl)-beta-D-glucopyranoside]-5-O-beta-D-glucopyranoside. In these flowers, the anthocyanins 2 and 3 were present as dominant pigments, and 1 was obtained in rather small amounts.  相似文献   

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