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1.
The protected structure of -oxoacteoside (tomentoside A), 2-oxo-2-(3,4-dihydroxyphenyl)ethyl 3-O-(2,3,4-tri-O-acetyl--l-rhamnopyranosyl)-4-O-caffeoyl--d-glucopyranoside 14 was synthesized in 14% overall yield in 11 steps, starting from d-glucose for biological and medicinal studies of phenylpropanoid glycosides. The first step was the preparation of a 3-O-rhamnopyranosyl disaccharide sugar core 2 from a suitably protected rhamnosyl trichloroacetimidate 10 and glucose derivative (diacetone-d-glucose 1) in 71% yield. To the glucose moiety of this sugar core, several protection/deprotection procedures were performed sequentially to obtain a fully acetylated sugar core 7 with a 4-OH group on the glucose moiety, in 57% yield in five steps. Thereafter, to the 4-OH group of the glucose moiety, selective 4-O-caffeoylation was achieved by proton-transfer esterification with 3,4-di-O-allylcaffeic acid 16 to give the caffeoyl disaccharide 11 in 97% yield. Then, it was converted to trichloroacetimidate 13 for a glycosylation donor in 90% in two steps. Finally, anomeric glycosylation was conducted with 2-oxo-2-(3,4-di-allyloxyphenyl)ethyl alcohol 19 with catalytic amounts of BF3·Et2O to give 2-oxo-2-(3,4-di-allyloxyphenyl)ethyl 2,6-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl--l-rhamnopyranosyl)-4-O-(3,4-di-allyloxycaffeoyl)--d-glucopyranoside 14 in 60% yield. Deprotected intermediates of compounds 2, 11, 14, and 19 which were obtained in high yield would be useful for biological and medicinal studies of phenylpropanoid glycosides.Part of this study was presented at the 52nd Annual Meeting of the Japan Wood Research Society, Gifu, April, 2002  相似文献   

2.
Synthesis of isoacteoside, a dihydroxyphenylethyl glycoside   总被引：1，自引：0，他引：1  
The total chemical synthesis of isoacteoside (1), 2-(3,4-dihydroxyphenyl)ethyl 6-O-caffeoyl-3-O-(-l-rhamnopyranosyl)--d-glucopyranoside, is described. An acteoside acetate with benzyl groups at the catechols (3: 2-(3,4-dibenzyloxyphenyl)ethyl 2,6-di-O-acetyl-4-O-[3,4-bis(O-benzyl)caffeoyl]-3-O-(-l-rhamnopyranosyl)--d-glucopyranoside) was treated with a solution of methy-lamine in methanol (MeNH2 in MeOH) to perform both deacetylation and caffeoyl migration, affording an isoacteoside derivative with benzyl groups at the catechols4b: 2-(3,4-dibenzyloxyphenyl)ethyl 6-O-[3,4-bis(O-benzyl) caffeoyl] -3-O-(-l-rhamnopyranosyl)--d-glucopyranoside —in 34% yield. Debenzylation of4b was successfully accomplished by catalytic transfer hydrogenation using 1,4-cyclohexadiene to give the target compound isoacteoside (1) in 54% yield.1H and13C nuclear magnetic resonance spectral data of the synthesized isoacteoside (1) were identical with those of the natural isoacteoside isolated fromPaulownia tomentosa (Thumb.) Steud.Part of this research was presented at the 51st Annual Meeting of the Japan Wood Research Society, Tokyo, April 2001  相似文献   

3.
Xylan prepared from culms of kumaizasa (Sasa senanensis Rehd.), a representative species of bamboo grass, was hydrolyzed with-xylanase ofStreptomyces olivaceoviridis E-86. Four arabinoxylo-oligosaccharides and two glucuronoxylo-oligosaccharides were isolated from the enzymatic hydrolysate of the xylan by chromatography on a charcoal column, a Dowex 1-x8 column, a Toyo-pearl HW-40S column, and a LiChrospher 100 NH2 column and on preparative paper chromatography. The results of the structural analyses of the saccharides showed that the isolated oligosaccharides had the structures of 32--l-arabinofuranosyl-xylobiose, 32--l-arabinofuranosyl-xylotriose, 32--[-d-xylopyranosyl-(1 2)-l-arabinofuranosyl]-xylobiose, 33--[-d-xylopyranosyl-(1 2)-l-arabinofuranosyl]-xylotriose, 23--4-O-methyl-d-glucuronosyl-xylotriose, and 23--d-glucuronosyl-xylotriose. From the structural analysis of the oligosaccharides derived from the xylan, kumaizasa xylan was concluded to be a kind of arabinoglucuronoxylan having not only stubs of singlel-arabinose and singled-glucuronic acid but also stubs of disaccharide units such as-d-xylopyranosyl-(1 2)-l-arabinofuranose.  相似文献   

4.
The reference compound (9), with a partial structure of acteoside, was synthesized to elucidate the relation between structural features and the precipitation or solubility of the oxidation products of acteoside: 2-(3,4-dihydroxyphenyl)-ethyl 3-O-(-L-rhamnopyranosyl)--D-glucopyranoside (9). The glycosyl acceptor 2-O-benzoyl-3-O-(2,3,4-tri-O-acetyl--L-rhamnopyranosyl)-4,6-O-benzylidene--D-glucopyranosyl trichloroacetimidate (7) was prepared from allyl 2-O-benzoyl-3-O-(2,3,4-tri-O-acetyl--L-rhamnopyranosyl)-4,6-O-benzylidene--D-glucopyranoside (4) via isomerization of the allyl group with an iridium complex to the 1-propenyl group and its hydrolysis with HgCl2lHgO, followed by treatment with CCl3CN and DBU in a 65.5% overall yield. The glycosyl acceptor 3,4-diacetoxyphenethyl alcohol (16) was prepared from homoveratric acid via demethylation with 57% HI and its acetylation with Ac2O and 85% H3PO4, followed by selective reduction of the carboxyl group to the alcohol with a borane-tetrahydrofurane complex in a 61% overall yield. The glycosylation of7 with16 in dichloromethane promoted by BF3-Et2O gave a 74.3% yield of8. Hydrolysis of8 with 90% CF3COOH gave the debenzylidenated product, which was treated with NaOMe to afford a 32% overall yield of the desired compound9. This compound9 was identical with the natural specimen.This study was presented in part at the 46th annual meeting of the Japan Wood Research Society, Kumamoto, April 3–5, 1996  相似文献   

5.
In our efforts to find new whitening agent from natural resources, we focused on wood of Artocarpus heterophyllus which shows anti-melanogenesis activity. By activity-guided fractionation of A. heterophyllus wood extract, a new prenylated flavonoid, 3-prenyl luteolin (1) was isolated. The IC50 of mushroom tyrosinase inhibitotry activity of 1 was 76.3 µM. The results of the comparison with that of luteolin showed the prenyl substituent at C-3 position of 1 play an important role for revealing tyrosinase inhibition. In melanin formation inhibition on B16 melanoma cells, IC50 of 1 was 56.7 µM with less cytotoxicity.  相似文献   

6.
Two new chromones, 5-((S)-2′-oxo-4′-hydroxypentyl)-2-(β-glucopyranosyl-oxy-methyl)chromone (1) and 5-((S)-2′-oxo-4′-hydroxypentyl)-2-methoxychromone (2), together with four known analogues, 8-C-glucosyl-7-O-methyl-(S)-aloesol (3), isoaloeresin D (4), 8-C-glucosyl-(R)-aloesol (5), and aloesin (6) were isolated from the aqueous extract of Aloe barbadensis Miller. Their structures were determined on the basis of spectroscopic evidences (1-D and 2-D NMR, HRMS, UV, and IR data), chemical methods and the literature data. The Mosher's method was applied to establish the absolute configuration of compounds 1 and 2. The inhibitory effects of these chromones on the activity of mushroom tyrosinase were examined, and compound 6 was identified as a noncompetitive tyrosinase inhibitor with an IC50 value of 108.62 μg·mL− 1.  相似文献   

7.
When (±)--oxo-guaiacylglycerol--(vanillic acid) ether (1) is degraded byFusarium solani M-13-1, the-ketone is initially reduced to giveerythro andthreo guaiacylglycerol--(vanillic acid) ethers (2), arylglycerol--aryl ethers, both of which are enantiomerically pure. The absolute configuration in each2 was determined by Mosher's method; the products were converted to,-di-(R)--methoxy--trifluoromethylphenylacetates (MTPA esters) (3) oferythro (-)- andthreo (+)-veratrylglycerol--(methyl vanillate) ethers (3), whose1H nuclear magnetic resonance (NMR) spectra were examined and compared with those of four di-(R)-MTPA ester (3) diastereomers from chemically synthesizederythro (±)-3 andthreo (±)-3. To assign the- and-MTPA-OCH3 peaks, the1H NMR scans of several compounds that have substructures of 3 and their 3,4,5-trimethoxyphenyl analogues were examined. When a racemic alcohol reacts with (R)-MTPA to give a pair of (R)-MTPA ester diastereomers, the value was defined as the absolute value of the difference in the1H chemical shifts of the peak between the diastereomers. It was found that the values of-MTPA-OCH3 were larger than those of-MTPA-OCH3 owing to a shielding effect of the veratryl ring located on the-MTPA-OCH3, and that the-MTPA-OCH3 peaks in the 3,4,5-trimethoxyphenyl compounds shifted downfield relative to those in the veratryl compounds. On the basis of the1h NMR data of (R)-MTPA esters, the absolute configuration of the four chemically prepared diastereomers (3) were determined. The catabolicerythro 3 [fromerythro (-)-3] andthreo 3 [fromthreo (+)-3] were identical to (R, S, R)-erythro 3 and (R, S, S)- threo 3, respectively. An hydrogen species in the fungal reduction would attack the-ketone fromre-face of both (R)-1 and (S)-1, givingerythro (S, R)-2 andthreo (S, S)-2, respectively.Part of this paper was presented at the 33rd Lignin Symposium, Tsukuba, November 1988  相似文献   

8.
Ding G  Chen L  Chen A  Tian X  Chen X  Zhang H  Chen H  Liu XZ  Zhang Y  Zou ZM 《Fitoterapia》2012,83(3):541-544
Two new cytochalasans, trichalasins C (1) and D (2) together with known cytochalasans aspochalasins D (3), M (4) and P (5) were isolated from one endophytic fungus Trichoderma gamsii inhabiting in traditional medicinal plant Panax notoginseng (BurK.) F.H.Chen. The structures for the new compounds 1 and 2 were determined by NMR and HRESIMS, and their relative configurations were established by analysis of coupling constants and NOESY correlations. Compound 3 displaying inhibitory activity with EC50 value 5.72 μM, whereas the EC50 values for compounds 1, 2 and 4, 5 are more than 40 μM.  相似文献   

9.
The extractives of shirakamba (Betula platyphylla Sukatchev var.japonica Hara) leaves were investigated. Two lignan glycosides were isolated, and their structures were elucidated to be 1-(4-hydroxy-3-methoxyphenyl)-2-[1-(3--l-rhamnopyranosyloxypropyl)-3-hydroxyphenoxy]-1,3-propanediol (I) and a new 2,3-dihydro-2-arylbenzofuran configuration neolignan,cis-2,3-dihydro-2-(4--l-rhamnopyranosyloxy-3-methoxyphenyl)-3-hydroxymethyl-7-hydroxy-5-benzofuranpropanol (II). These neolignan rhamnosides were newly found in shirakamba.  相似文献   

10.
Chemically synthesized (1 5)--d-glucofuranan, (1 5)--d-galactofuranan, (1 5)--d-xylofuranan, (1 5)--L-arabinofuranan, natural xylan, and curdlan were sulfated to investigate their inhibitory activities on B16-BL6 lung metastasis and anticoagulant activities. (1 5)--d-Glucofuranan sulfate, (1 5)--d-galactofuranan sulfate, xylan sulfate, and curdlan sulfate had binding abilities with B16-BL6 melanoma lysate. The inhibitory activities of sulfated polysaccharides on B16-BL6 lung metastasis selected by heparin binding assay were in the order (1 5)--d-galactofuranan sulfate > (1 5)---d-glucofuranan sulfate > xylan sulfate curdlan sulfate. Furthermore, (1 5)--d-galactofuranan sulfate, (1 5)--d-glucofuranan sulfate, and xylan sulfate had not only high inhibitory activity on B16-BL6 lung metastasis but also low anticoagulant activity. The correlation between chemical structure and biological activity is discussed.Part of this paper was presented at the 10th International Synposium on Wood and Pulping Chemistry, Yokohama, Japan, June 1999  相似文献   

11.
A series of novel 4-O-alkoxytrityl chlorides (1) with different chain lengths was synthesized as a novel reagent for obtaining 6-O-alkylated cellulose with high regioselectivity via trityl groups in one reaction step without the use of any protective groups. These chlorides were reacted with methyl -d-glucoside, which was used as a model compound, to examine the reactivities toward the primary hydroxyl groups of cellulose to afford a series of 6-O-alkylated methyl -d-glucosides in high yields. The product compounds were found to have interesting solubilities and thermal properties. Thus, newly prepared trityl chloride derivatives were found to be useful regioselective derivatization reagents on the primary hydroxyl group in carbohydrates, especially in cellulose.  相似文献   

12.
Hot water extract (HWE) of Pinus radiata bark was separated into monomeric polyphenol (MPP), oligomeric proanthocyanidin (OPA), and polymeric proanthocyanidin (PPA) fractions by monitored chromatography using a Sephadex LH 20 column and an UV detector at 250 nm. The effects of these fractions on NIH/3T3 fibroblasts and B16 melanoma cells were examined by evaluating cell viability, melanogenesis (melanin content), morphological changes, and tyrosinase inhibitory activity. The polyphenolic fractions had a proliferation effect on fibroblasts, with cell growth increasing significantly (P < 0.01) even at the high concentration of 1250 μg/ml. At 125 μg/ml, HWE, MPP, and OPA had no effect on melanogenesis, whereas PPA significantly upregulated melanogenesis (P < 0.05). Melanogenesis was significantly upregulated in melanoma cells treated with these fractions at the high concentration of 600 μg/ml (P < 0.01). B16 melanoma cells cultured with the proanthocyanidin (PA)-rich fractions (HWE, OPA, and PPA) showed marked dendrite retraction, leading to significant morphological transformation. OPA in particular showed colored adhesion on the surface of melanoma cells. All four fractions significantly inhibited mushroom tyrosinase activity when compared to arbutin and ascorbic acid 2-glucoside (P < 0.05). The tyrosinase inhibitory activity of OPA and PPA did not differ significantly (P = 0.11), indicating that the inhibitory effects had a low correlation with molecular weight distribution. The inhibition kinetics of PPA determined using a Lineweaver-Burk plot indicated that PPA is a noncompetitive inhibitor of l-3,4-dihydroxyphenylalanine oxidation by mushroom tyrosinase.  相似文献   

13.
Summary Scolytidae and Platypodidae as well as other insects and mites found in imported wood. Part II The new list deals with insect and mite species collected in imported wood byWichmann () andCola last years. 40 species were found in 11 kinds of wood, most of them inPinus echinata Mill, imported from Norfolk, Virginia (U.S.A.). Nearer information onReticulitermes flavipes Koll, found byWichmann inPinus echinata in Mannheim, 1957, is given. Finally completitions are made of the list of species published in Anz. f. Schädlk. u. Pflanzenschtz. XLIV (5) p. 65–68, 1971. This list contents 41 species of insects and mites found in 9 kinds of imported wood.  相似文献   

14.
Screening and isolation of angiotensin I-converting enzyme (ACE) inhibitors from Japanese cedar (Cryptomeria japonica) based on the in vitro ACE inhibitory assay were attempted. The ethanol extract from outer bark showed the highest inhibitory activity (IC50 is 16g/ml) among 24 extracts prepared from roots, leaves, heartwood, sapwood, inner bark, and outer bark by successive extraction with four solvents. The fractionation of the outer bark ethanol extract followed by the bioassay resulted in the isolation of two strong ACE inhibitors, catechin and dimeric procyanidin B3. The bioassay of three flavan-3-ols including (+)-catechin and six flavones revealed that most of these compounds have high ACE inhibitory activity. The results suggest that the phenolic hydroxyl group at the C7 position and heterocyclic oxygen atom of these compounds are important for expressing the inhibitory activity.  相似文献   

15.
Li HF  Guan XY  Yang WZ  Liu KD  Ye M  Sun C  Lu S  Guo DA 《Fitoterapia》2012,83(1):44-48
Two new flavonoids, wushanicaritin (1) and wushankaempferol (2), along with 24 known flavonoids were isolated from the whole herb of Epimedium wushanense T.S. Ying (Berberidaceae). On the basis of NMR and ESI-MS spectroscopic analysis, structures of compounds 1 and 2 were elucidated as 8-γ-hydroxy-γ,γ-dimethylpropyl-3,5,7-trihydroxy-4′- methoxyflavone and kaempferol 3-O-α-l-[2,3-di-O-β-d-(6-E-p-coumaroyl) glucopyranosyl]-rhamnopyranosyl-7-O-α-l-rhamnopyranoside, respectively. DPPH radical scavenging activity tests indicated that 1 (IC50 35.3 μM) exhibited antioxidant activity comparable to Vitamin C (IC50 32.0 μM), while 2 (IC50 443.7 μM) showed weak activity.  相似文献   

16.
Ying Xu  Zeng Jun Guo  Nan Wu 《Fitoterapia》2010,81(8):1091-1093
Two new amide alkaloids, named 3-isopropyl-tetrahydropyrrolo [1,2-a] pyrimidine-2,4(1H,3H)-dione (1) and 1-acetyl-2,3,6-triisopropyl-tetrahydropyrimidin-4(1H)-one (2), were isolated from the roots of Aconitum taipeicum. Their chemical structures were characterized on the basis of MS, 1D- and 2D NMR. The anti-leukaemia activities of the compounds were also tested. The results indicated that the compounds exhibited more significant cell growth inhibitory activities against HL-60 cells than adriamycin, with the IC50 of 1.1 ± 0.03 μg/mL and 1.6 ± 0.07 μg/mL respectively. In addition, two compounds showed anti-tumor activities against K562 cells as well.  相似文献   

17.
A new compound, 15,20-dinor-5,7,9-labdatriene-18-ol (1), named kujigamberol, was isolated from amber, fossilized tree resin from the Kuji area in Japan, has been dated as being 85 million years old (late Cretaceous). Kujigamberol was identified using the hypersensitive mutant yeast (zds1? erg3? pdr1? pdr3?) with respect to Ca2+-signal transduction. The structure was elucidated on the basis of spectroscopic analysis including 1D NMR, 2D NMR and HR-EI-MS. It was different from known diterpenoids with a similar activity isolated from Baltic amber (agathic acid 15-monomethyl ester (2), dehydroabietic acid (3) and pimaric acid (4)). Kujigamberol showed glycogen synthase kinase-3β (GSK-3β) inhibition activity involving the growth restored activity against the mutant yeast and was cytotoxic to HL60 cells (IC50 = 19.6 μM).  相似文献   

18.
From the ether extract of Porella densifolia, the first liverwort collected and chemically investigated in Vietnam, a kaurane diterpenoid, ent-kauren-15-one (1) and two sesquiterpene norpinguisone (2) and norpinguisone methyl ester (3) have been purified. Their structures were elucidated by spectroscopic analysis. In addition, an X-ray crystal structure of norpinguisone was obtained, allowing to determine its stereochemistry. Furthermore, the inhibitory activity of nitric oxide (NO) production in RAW 264.7 cells stimulated by lipopolysaccharide (LPS) of compounds 1–3 was examined with their IC50 values of 69.4, 45.5 and 1.68 μM, respectively.  相似文献   

19.
Twelve polar cardenolide monoglycosides, 1, 2, 4?C13, and oleagenin (3) were isolated from the methanol extract of stems and twigs of Nerium oleander. Among these, oleagenin (3) and cardenolide monoglycosides named cardenolide B-1 (1) and cardenolide B-2 (2) were isolated from natural sources for the first time. The in vitro antiinflammatory activity of compounds 1?C13 was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). Compounds 4?C7 were active at an IC50 value of less than 0.4 ??M. The cytotoxic activity of compounds 1?C13 was evaluated against three human cell lines: normal human fibroblast cells (WI-38), malignant tumor cells derived from WI-38 (VA-13), and human liver tumor cells (HepG2). Compounds 4, 6, and 7 were active toward these three cell lines at IC50 values of less than 0.7 ??M, and compounds 5 and 8 were active toward the cell lines at IC50 values of less than 1.5 ??M. The multidrug resistance (MDR) cancer-reversal activity of compounds 1?C13 was evaluated on the basis of the amount of calcein accumulated in MDR human ovarian cancer 2780AD cells in the presence of each compound. Compound 1 and 12 showed significant effects on calcein accumulation.  相似文献   

20.
Heartwoods of 22 African tropical wood species were extracted with methanol and the contents of total phenolic compounds in these extracts were measured. Three bioassays were conducted to evaluate the antioxidant activity, tyrosinase inhibitory activity, and antifungal activity of the methanol extracts. The results indicated that the extracts from 13 species exhibited high antioxidant potential, and their inhibitory concentrations that caused 50% scavenging of the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical (IC50) were less than 10 μg/ml. The crude extract from Cylicodiscus gabunensis showed the highest antioxidant activity, and was even higher than that of (+)-catechin, which is known as a potent antioxidant. There was a good correlation between the antioxidant activity and the content of total phenolic compounds, indicating that phenolic compounds played a predominant role in the antioxidant property of the wood extracts. Among all 22 species, only 1 species, Milicia excelsa, contained extractives that showed very high tyrosinase inhibitory activity. The extracts from 9 species showed high antifungal activity. No consistent relationship was observed between the tyrosinase inhibitory activity or antifungal activity and the content of total phenolics in the extracts. Part of this article was presented at the 56th Annual Meeting of the Japan Wood Research Society, Akita, August 2006  相似文献   

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