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1.
The two major steroidal saponins from the roots of Asparagus racemosus were isolated by RP-HPLC and their structure determined by extensive NMR studies. Their structures did not match those reported previously for shatavarins I and IV and were found to be 3-O-{[β-d-glucopyranosyl(1→2)][α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranosyl}-26-O-(β-d-glucopyranosyl)-(25S)-5β-furostan-3β,22α,26-triol and 3-O-{[β-d-glucopyranosyl(1→2)][α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranosyl}-(25S)-5β-spirostan-3β-ol. 相似文献
2.
Furostanol saponins with inhibitory action against COX-2 production from Tupistra chinensis rhizomes
Kun Zou Jun Zhi Wang Jun Wu Yuan Zhou Chuang Liu Fei Jun Dan Ya Xiong Zhang Jin Yang 《中国化学快报》2007,18(10):1239-1242
Two furostanol saponins were obtained from the n-butanol fraction of methanol extract from Tupistra chinensis rhizomes,a folk medicine of Shennongjia Forest District of Hubei Province.Their structures were determined as (25S)-26-O-(β-D-glucopyranosyl)- furost-1β,3β,22α,26-tetrol-3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (1) and (25R)- 26-O-(β-D-glucopyranosyl)-furost-1β,3β22α,26-tetrol 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-β-D-glu- copyranoside (2),on basis of chemical and spectroscopic evidences.1 and 2 displayed marked inhibitory action towards COX-2 production in macrophages of the rat abdomen induced by LPS at 20μg/mL. 相似文献
3.
A new triterpene and a saponin from Centella asiatica 总被引:1,自引:0,他引:1
Quan Lin Yu Hong Quan Duan Wen Yuan Gao Yoshihisa Takaishi 《中国化学快报》2007,18(1):62-64
A new triterpene and a saponin,named 2α,3β,23-trihydroxyurs-20-en-28-oic acid(1)and 2α,3β,23-trihydroxyurs-20-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester(2),have been isolated from the aerial part of Centella asiatica.Their structures were elucidated by spectral methods,including 2D-NMR spectra. 相似文献
4.
5.
Three new triterpenoidal glucosides, justiciosides E, F and G, were isolated from the aerial portion of Justicia betonica. Their structures were established through chemical and spectroscopic analyses, and showed an unusual A-nor-B-homo oleanan-12-ene skeleton type for the aglycone moiety as A-nor-B-homo-oleanan-10,12-diene-3β,11α,28-triol 28-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside, A-nor-B-homo-oleanan-10,12-diene-3β,11α,28-triol 28-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside, and 11α-methoxy-A-nor-B-homo-oleanan-10,12-diene-3β,11α,28-triol 28-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside, respectively. 相似文献
6.
A new steroidal saponin, shatavarin V, (3-O-{[α-l-rhamnopyranosyl(1→2)][β-d-glucopyranosyl(1→4)]-β-d-glucopyranosyl}-(25S)-5β-spirostan-3β-ol), was isolated from the roots of Asparagus racemosus by RP-HPLC, and its structure determined by 1D and 2D NMR studies. This data permits clarification of the structures reported for several known saponins: asparinins A and B; asparosides A and B; curillin H; curillosides G and H and shavatarins I and IV. 相似文献
7.
The structures of two saponins, thyonosides A and B, isolated from the holothurian Thyone aurea collected in Namibia, were elucidated by 1D and 2D NMR (1H, 13C, 1H-1H COSY, 1H-1H J-resolved, TOCSY, HMQC, HMBC and NOESY). The two compounds have the same aglycon but different oligosaccharidic chains. Thyonoside A has a 3-O-methyl-β-d-xylopyranosyl-(1→3)-6-O-sodium sulphate-β-d-glucopyranosyl-(1→4)-β-d-quinovopyranosyl-(1→2)-4-O-sodium sulphate-β-d-xylopyranosyl chain, and thyonoside B a 3-O-methyl-β-d-xylopyranosyl-(1→4)-β-d-xylopyranosyl-(1→4)-β-d-quinovopyranosyl-(1→2)-4-O-sodium sulphate-β-d-xylopyranosyl chain. The holostane-type aglycon features an endocyclic double bond at position 7-8, a double bond at position 25-26 and a β-acetoxy group at C16. 相似文献
8.
Masaru Kojima 《Tetrahedron letters》2009,50(45):6143-3663
The total synthesis of clemochinenoside A and the first total syntheses of clemochinenoside B and berchemolide were achieved simultaneously via macrocyclization of 4-O-(4-O-F13benzyl-β-d-glucopyranosyl)syringic acid with 4-O-(4-O-F17benzyl-β-d-glucopyranosyl)vanillic acid by a fluorous mixture synthetic method. The spectroscopic data of the synthetic products were identical with those of the natural products, although the optical rotation of clemochinenoside A differed from the published values in sign and magnitude. 相似文献
9.
Shu Yun Shi Qi Zhou Hua Peng Chang Xin Zhou Ming Hui Hu Qiao Feng Tao Xiao Jiang Hao Joachim Stoeckigt Yu Zhao 《中国化学快报》2007,18(11):1367-1370
Two new flavone glycosides,isoetin-7-O-β-D-glucopyranosyl-2′-O-α-L-arabinopyranoside (1) and isoetin-7-O-β-D-glucopyr- anosyl-2′-O-α-D-glucopyranoside (2),a new lignan,mongolicumin A (3),and a new guaianolide,mongolicumin B (4) were isolated from the aerial part of Taraxacum mongolicum.Their structures were elucidated mainly by spectral analyses. 相似文献
10.
Bolleddula JayaprakasamMuraleedharan G Nair 《Tetrahedron》2003,59(6):841-849
Four novel withanolide glycosides and a withanolide have been isolated from the leaves of Withania somnifera. The structures of the novel compounds were elucidated as physagulin D (1→6)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (1), 27-O-β-d-glucopyranosyl physagulin D (2), 27-O-β-d-glucopyranosyl viscosalactone B (3), 4,16-dihydroxy-5β, 6β-epoxyphysagulin D (4), and 4-(1-hydroxy-2,2-dimethylcyclo-propanone)-2,3-dihydrowithaferin A (5) on the basis of 1D-, 2D NMR and MS spectral data. In addition, seven known withanolides withaferin A (6), 2,3-dihydrowithaferin A (7), viscosalactone B (8), 27-desoxy-24,25-dihydrowithaferin A (9), sitoindoside IX (10), physagulin D (11), and withanoside IV (12) were isolated. These withanolides were assayed to determine their ability to inhibit cycloxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes and lipid peroxidation. The withanolides tested, except compound 9, showed selective COX-2 enzyme inhibition ranging from 9 to 40% at 100 μg/ml. Compounds 4, 10 and 11 also inhibited lipid peroxidation by 40, 44 and 55%, respectively. The inhibition of COX-2 enzyme by withanolides is reported here for the first time. 相似文献
11.
Fan Qiu Jianguang Luo Shun Yao Li Ma Lingyi Kong 《Journal of separation science》2009,32(12):2146-2151
High-speed counter-current chromatography (HSCCC) was applied to the preparative isolation and purification of peonidin 3-O-(6-O-(E)-caffeoyl-2-O-β-D -glucopyranosyl-β-D -glucopyranoside)-5-O-β-D -glucoside ( 1 ), cyanidin 3-O-(6-O-p-coumaroyl)-β-D -glucopyranoside ( 2 ), peonidin 3-O-(2-O-(6-O-(E)-caffeoyl-β-D -glucopyranosyl)-6-O-(E)-caffeoyl-β-D -glucopyranoside)-5-O-β-D -glucopyranoside ( 3 ), peonidin 3-O-(2-O-(6-O-(E)-feruloyl-β-D -glucopyranosyl)-6-O-(E)-caffeoyl-β-D -glucopyranoside)-5-O-β-D -glucopyranoside ( 4 ) from purple sweet potato. Separation of crude extracts (200 mg) from the roots of purple sweet potato using methyl tert-butyl ether/n-butanol/acetonitrile/water/trifluoroacetic acid (1:4:1:5:0.01, v/v) as the two-phase solvent system yielded 1 (15 mg), 2 (7 mg), 3 (10 mg), and 4 (12 mg). The purities of 1 – 4 were 95.5%, 95.0%, 97.8%, and 96.3%, respectively, as determined by HPLC. Compound 2 was isolated from purple sweet potato for the first time. The chemical structures of these components were identified by 1H NMR, 13C NMR and ESI-MSn. 相似文献
12.
The synthesis of the 1,3–1,4-β-glucanase substrate analogue 4-nitrophenyl O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→3)-2-desoxi-β-d-glucopyranoside 2 is reported. Starting from the main tetrasaccharide obtained by enzymatic depolymerization of barley β-glucan, the synthetic scheme involves preparation of the corresponding 3-O-substituted glycal which was converted into a 2-deoxy-α-glycosyl iodide as a glycosyl donor. The key glycosylation step was successfully achieved by nucleophilic substitution of the iodide donor with 4-nitrophenolate with high β-selectivity. 相似文献
13.
Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al3+ in an aqueous solution around pH 4.0. To clarify the mechanism of blue sepal-color development of hydrangea, we tried to reproduce the blue color in vitro by mixing 1 with designed synthetic co-pigments in the presence of Al3+ at pH 4.0. We at first succeeded in clarifying the essential functional structure in the co-pigment that could form the stable blue solution. Here, we present the structure of the blue pigment caused by an Al-complex coordinating of 1 at ortho-dihydroxyl groups of the B-ring, 1-hydroxy, 1-carboxylic acid, and the carbonyl residue in the ester at 5-position of 2 and/or 3. The hydrophobic interaction between the aromatic acyl residue at 5-position and the nucleus of 1 may also contribute to stabilize the complex. 相似文献
14.
Xing Zeng Zhao Xu Feng Xiao Dong Jia Yun Fa Dong Ming Wang Jiangsu Center for Research & Development of Medicinal Plants Jiangsu Institute of Botany Chinese Academic of Science/Nanjing Botanical Garden Mem. Sun Yat-Sen. Nanjing China 《中国化学快报》2007,18(2):168-170
A new neolignan glycoside, 4-O-β-D-glucopyranosyl-9-O-β-D-glucopyranosyl-(7R,8S)-dehydrodiconiferyl alcohol was isolated from the fresh roots of Angelica dahurica. The structure of the new compound was elucidated on the basis of spectral analysis. 相似文献
15.
A new ceramide and its glycoside were isolated from the flower of Albizia julibrissin. Their structures were established as(2S,3S,4R,8E)-2-[(2'R)-hydroxyhexadecanoylamino]-8-tetra-cosene-1,3,4-triol (Ⅰ) and 1-O-β-D-glucopyranosyl-(2S,3S,4R,8E)-2-[(2'R)-hydroxy-hexade-canoylamino]-8-tetracosene-1,3,4-triol (H) on the basis of chemical and spectroscopic studies. 相似文献
16.
Kumi Yoshida Mihoko MoriMiki Kawachi Reiko OkunoKiyoshi Kameda Tadao Kondo 《Tetrahedron letters》2003,44(43):7875-7880
Prevention of E,Z-isomerization of caffeoyl residues of a tri-(E)-caffeoyl anthocyanin, heavenly blue anthocyanin (HBA), and its stability under UV-B irradiation conditions were studied. We isolated four photoproducts from irradiated HBA and their structures were determined to be mono- or di-Z-caffeoyl isomers of HBA and mono-deglucosylated HBA. Under such conditions one caffeoyl residue, the innermost one, never isomerized to the Z-form, suggesting that intramolecular stacking must prevent photoisomerization. In general, anthocyanins are considered to be more stable in strong acidic than neutral aqueous media. However, with UV-B irradiation HBA was most stable in aqueous solution at pH 7.5 and most unstable in acidic methanol solutions. It was found to emit strong fluorescence on excitation with UV-B, possibly resulting from intramolecular association of caffeoyl moieties with the anthocyanidin nucleus. The finding that pigment in petals is more tolerant of UV-irradiation may be rational in the context of the necessity to resist strong solar radiation. 相似文献
17.
Ying Peng Yu Jing Zhang Zhi Qiang Ma Wei San Pan Yu Qing Sun Shao Jiang Song School of Pharmacy Shenyang Pharmaceutical University Shenyang China No. Herbal Factory Haerbin Phamarceuticals Group Haerbin China 《中国化学快报》2007,18(2):171-174
Two new saponins 3-O-β-D-glucopyranosyl (1→2)-β-D-mannopyranosyl sarsasapogenin, named timosaponin A IV(1) and (5β, 25S)-26-O-β-D-glucopyranosyl-furost-20(22)-en-3,26-diol-3-O-β-D-glucopyranosyl (1→4) glucopyranosyl (1→2)-β-D-galacopyranoside, named timosaponin B IV(2), were isolated by silica gel column chromatography and preparative HPLC from Anemarrhena asphodeloides Bge. Their structures were elucidated by chemical characters and spectroscopic analysis. 相似文献
18.
Kin-ichi Oyama 《Tetrahedron》2004,60(9):2025-2034
We have succeeded in the first total synthesis of apigenin 7,4′-di-O-β-d-glucopyranoside (1a), a component of blue pigment, protodelphin, from naringenin (2). Glycosylation of 2 according to Koenigs-Knorr reaction provided a monoglucoside 4a in 80% yield, and this was followed by DDQ oxidation to give apigenin 7-O-glucoside (12a). Further glycosylation of 4′-OH of 12a with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl fluoride (5a) was achieved using a Lewis acid-and-base promotion system (BF3·Et2O, 2,6-di-tert-butyl-4-methylpyridine, and 1,1,3,3-tetramethylguanidine) in 70% yield, and subsequent deprotection produced 1a. Synthesis of three other chiral isomers of 1a, with replacement of d-glucose at 7 and/or 4′-OH by l-glucose (1b-d), and four chiral isomers of apigenin 7-O-β-glucosides (6a,b) and 4′-O-β-glucosides (7a,b) also proved possible. 相似文献
19.
Éva Bokor Attila Fekete Gergely Varga Béla Szőcs Katalin Czifrák István Komáromi László Somsák 《Tetrahedron》2013
Synthesis of O-perbenzoylated 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazoles, precursors of potent inhibitors of glycogen phosphorylase, was studied by ring closures of N1-acyl-carboxamidrazone type intermediates. Reactions of C-(β-d-glucopyranosyl)formimidate or C-(β-d-glucopyranosyl)formamidine with acid hydrazides as well as acylation of C-(β-d-glucopyranosyl)formamidrazone by acid chlorides unexpectedly gave the corresponding 1,3,4-oxadiazoles instead of 1,2,4-triazoles. The desired triazoles were obtained in reactions of C-(β-d-glucopyranosyl)formamidine or C-(β-d-glucopyranosyl)formyl chloride with arenecarboxamidrazones, and also in acylations of N1-tosyl-C-(β-d-glucopyranosyl)formamidrazone with acid chlorides. Theoretical calculations (B3LYP and M06-2X DFT with the standard 6-31G(d,p) basis set) on simple model compounds with methyl and phenyl substituents to understand the bifurcation of the ring closure of N1-acyl-carboxamidrazones indicated that in general the reaction led to 1,2,4-triazoles. However, the probability of the 1,3,4-oxadiazole forming pathway was shown to be significantly higher with N1-benzoyl-acetamidrazones, which were closest analogues of the intermediates resulting in C-glucosyl-1,3,4-oxadiazoles. It was thereby demonstrated that the substitution pattern of the N1-acyl-carboxamidrazones played a fundamental role in determining the direction of the ring closing reaction. 相似文献
20.
Fernanda Peres Ferreira 《Tetrahedron letters》2010,51(52):6856-6859
A new phenylpropanoid and two new diterpenes were isolated from the leaves of the plant Mikania laevigata Shultz Bip. ex Baker. The structures of these compounds were established by 1D- and 2D-nuclear magnetic resonance spectroscopic techniques and mass spectrometry data. Taraxerol, lupeol, coumarin, syringaldehyde, trans-melilotoside, cis-melilotoside, adenosine, patuletin 3-O-β-d-glucopyranoside, kaempferol 3-O-β-d-glucopyranoside, quercetin 3-O-β-d-glucopyranoside, methyl 3,5-di-O-caffeoyl quinate, and 3,3′,5-trihydroxy-4′,6,7-trimethoxyflavone were isolated too. In addition, the compounds dihydrocoumarin, spathulenol, caryophyllene oxide, kaurenoic acid, beyerenoic acid, and lupeol acetate were identified by GC-MS. 相似文献