共查询到20条相似文献,搜索用时 8 毫秒
1.
Huifeng Li Min Ye Hongzhu Guo Yin Tian Jie Zhang Jianping Zhou Yuchi Hu Dean Guo 《Phytochemistry》2009,70(11-12):1416-1420
Biotransformation of 20(S)-protopanaxadiol (1) by the fungus Mucor spinosus AS 3.3450 yielded eight metabolites (2–9). On the basis of NMR and MS analyses, the metabolites were identified as 12-oxo-15α,27-dihydroxyl-20(S)-protopanaxadiol (2), 12-oxo-7β,11α,28-trihydroxyl-20(S)-protopanaxadiol (3), 12-oxo-7β,28-dihydroxyl-20(S)-protopanaxadiol (4), 12-oxo-15α,29-dihydroxyl-20(S)-protopanaxadiol (5), 12-oxo-7β,15α-dihydroxyl-20(S)-protopanaxadiol (6), 12-oxo-7β,11β-dihydroxyl-20(S)-protopanaxadiol (7), 12-oxo-15α-hydroxyl-20(S)-protopanaxadiol (8), and 12-oxo-7β-hydroxyl-20(S)-protopanaxadiol (9), respectively. Among them, 2–5, 7, and 8 are new compounds. These results indicated that M. spinosus could catalyze the specific C-12 dehydrogenation of 20(S)-protopanaxadiol, as well hydroxylation at different positions. These biocatalytic reactions may be difficult for chemical synthesis. The biotransformed products showed weak in vitro cytotoxic activities. 相似文献
2.
M.H. Haron B. Avula I.A. Khan S.K. Mathur A.K. Dasmahapatra 《Comparative biochemistry and physiology. Toxicology & pharmacology : CBP》2013,157(3):287-297
Alcohol consumption by women during pregnancy often induces fetal alcohol spectrum disorder (FASD) in children who have serious central nervous system (CNS), cardiovascular, and craniofacial defects. Prevention of FASD, other than women abstaining from alcohol drinking during pregnancy, is not known. A limitation of the use of synthetic anti-alcoholic drugs during pregnancy led us to investigate herbal products. In particular, many plants including Asian ginseng (Panax ginseng) have therapeutic potential for the treatment of alcoholism. We used Japanese ricefish (medaka) (Oryzias latipes), an animal model of FASD, for identifying herbal medicines that can attenuate ethanol toxicity. Fertilized eggs in standard laboratory conditions were exposed to ginseng (PG) root extract (0–2 mg/mL) either 0–2 (group A) or 1–3 (group B) day post fertilization (dpf) followed by maintenance in a clean hatching solution. The calculated IC50 as determined 10 dpf in A and B groups were 355.3 ± 1.12 and 679.7 ± 1.6 μg/mL, respectively. Simultaneous exposure of embryos in sub-lethal concentrations of PG (50–200 μg/mL) and ethanol (300 mM) for 48 h disrupted vessel circulation and enhanced mortality. However, PG (100 μg/mL) may partially protect trabecular cartilage (TC) deformities in the neurocranium in B group embryos induced by ethanol (300 mM). To understand the mechanism, embryonic ethanol concentration was measured at 2 dpf and adh5, adh8, aldh2, aldh9a, catalase, GST, and GR mRNAs were analyzed at 6 dpf. It was observed that although ethanol is able to reduce adh8 and GST mRNA contents, the simultaneous addition of PG was unable to alter ethanol level as well as mRNA contents in these embryos. Therefore, antagonistic effects of PG on ethanol toxicity are mediated by a mechanism which is different from those regulating ethanol metabolism and oxidative stress. 相似文献
3.
The volatile constituents of the roots of Panax ginseng C.A. Meyer have been investigated after hydrodistillation and analysed by means of different analytical methods. Besides several compounds already known three sesquiterpene hydrocarbons have been isolated from the essential oil. Structure elucidation of the bicyclic panaxene as well as of the tricyclic panaginsene and ginsinsene was performed by MS and NMR. They have been identified as (1R*,2S*,5S*)-2-ethenyl-1(1-methylethenyl)-2,6,6-trimethylbicyclo[3.2.0]heptane (panaxene), (1S*,8S*,11R*)-4,7,7,11-tetramethyltricyclo[6.3.0.0(1,5)]undec-4-ene (panaginsene) und (1R*,6R*,7R*)-3,7,10,10-tetramethyltricyclo[4.3.2.0(2,6)]undec-2-ene (ginsinsene). 相似文献
4.
Ethephon at 50 μM enhanced both root growth and ginsenoside accumulation in ginseng (Panax ginseng C.A. Meyer) adventitious root cultures, but at 100 μM it inhibited only ginsenoside accumulation. Ginsenoside productivity with 50 μM ethephon was the highest at 1.7 mg l−1 d−1 after 8 days of elicitation. However, elicitation with 50 μM ethephon and 100 μM methyl jasmonate (MJ) improved productivity (6.3 mg l−1 d−1) whereas elicitation with 100 μM MJ alone gave only 2.9 mg l−1 d−1. 相似文献
5.
The role of ginseng saponins (ginsenosides) as modulators or inhibitors of disease is vague, but our earlier work supports the existence of an allelopathic relationship between ginsenosides and soilborne microbes. Interestingly, this allelopathy appears to significantly promote the growth of the important ginseng pathogen, Pythium irregulare while inhibiting that of an antagonistic non-pathogenic fungus, Trichoderma hamatum. Herein we report on the apparent selective metabolism of 20(S)-protopanaxadiol ginsenosides by an extracellular glycosidase from P. irregulare. Thus, when P. irregulare was cultured in the presence of a purified (> 90%) ginsenoside mixture, nearly all of the 20(S)-protopanaxadiol ginsenosides (Rb1, Rb2, Rc, Rd, and to a limited extent G-XVII) were metabolized into the minor ginsenoside F2, at least half of which appears to be internalized by the organism. No metabolism of the 20(S)-protopanaxatriol ginsenosides (Rg1 and Re) was evident. By contrast, none of the ginsenosides added to the culture medium of the non-pathogenic fungus T. hamatum were metabolized. The metabolism of 20(S)-protopanaxadiol ginsenosides by P. irregulare appears to occur through the hydrolysis of terminal monosaccharide units from disaccharides present at C-3 and/or C-20 of ginsenosides Rb1, Rc, Rb2, Rd and G-XVII to yield one major product, ginsenoside F2 and one minor product (possibly G-III). A similar transformation of ginsenosides was observed using a crude protein preparation isolated from the spent medium of P. irregulare cultures. 相似文献
6.
Ginseng occupies a prominent position in the list of best-selling natural products in the world. Compared to the long history of use and widespread research on Asian ginseng, the study of American ginseng is relatively limited. In the past decade, some promising advances have been achieved in understanding the chemistry, pharmacology and structure-function relationship of American ginseng. To date, there is no systematic review of American ginseng. In this review, the different structures of the ginsenosides in American ginseng are described, including naturally occurring compounds and those resulting from steaming or biotransformation. Preclinical and clinical studies published in the past decade are also discussed. Highlighted are the chemical and pharmacological diversity and potential structural-activity relationship of ginsenosides. The goal is that this article is a useful reference to chemists and biologists researching American ginseng, and will open the door to agents in drug discovery. 相似文献
7.
Zhao JM Li N Zhang H Wu CF Piao HR Zhao YQ 《Bioorganic & medicinal chemistry letters》2011,21(3):1027-1031
Three new dammarane-type sapogenins (1, 3, and 5) together with two known ones (2 and 4) were isolated from the total hydrolyzed saponins extracted from Panax ginseng berry. Their structures were elucidated using a combination of 1D and 2D 1H and 13C NMR spectra and mass spectroscopy as 20(R)-25-methoxyl-dammarane-3β,12β,20-triol (1), 20(R)-25-methoxyl-dammarane-3β,6α,12β,20-tetrol (2), 20(R)-20-methoxyl-dammarane-3β,12β,25-triol (3), 20(R)-20,25-dimethoxyl-dammarane-3β,12β-diol (4), and (12R,20S,24S)-20,24-; 12,24-diepoxy-dammarane-3β-ol (5). Their antitumor activities were evaluated in six human cancer cell lines. The novel compounds 1 and 3 showed significant cytotoxic activity against the six cell lines. The IC50 values of 3 against HepG2, Colon205, and HL-60 were the lowest (8.78, 8.64, and 3.98 μM, respectively). Compounds 1 and 20(S)-25-OCH3-PPD, which are a pair of configuration isomers, showed a 10- to 100-fold greater growth inhibition than ginsenoside-Rg3 (an anti-cancer clinical agent in China). The data presented here may be useful for the development of novel anti-cancer agents. 相似文献
8.
To develop an experimental system for studying ginsenoside biosynthesis, we generated thousands of ginseng (Panax ginseng C.A. Meyer) hairy roots, genetically transformed roots induced by Agrobacterium rhizogenes, and analyzed the ginsenosides in the samples. 27 putative ginsenosides were detected in ginseng hairy roots. Quantitative and qualitative variations in the seven major ginsenosides were profiled in 993 ginseng hairy root lines using LC/MS and HPLC-UV. Cluster analysis of metabolic profiling data enabled us to select hairy root lines, which varied significantly in ginsenoside production. We selected hairy root lines producing total ginsenoside contents 4-5 times higher than that of a common hairy root population, as well as lines that varied in the ratio of the protopanaxadiol to protopanaxatriol type ginsenoside. Some of the hairy root lines produce only a single ginsenoside in relatively high amounts. These metabolites represent the end product of gene expression, thus metabolic profiling can give a broad view of the biochemical status or biochemical phenotype of a hairy root line that can be directly linked to gene function. 相似文献
9.
C. S. Jeong H. N. Murthy E. J. Hahn H. L. Lee K. Y. Paek 《Acta Physiologiae Plantarum》2009,31(1):219-222
The effect of the root-inoculum size and axuin concentration on growth of adventitious roots and accumulation of ginsenosides
were studied during suspension cultures of ginseng (Panax ginseng C.A. Meyer). Of the various concentrations of indole-3-butyric acid (IBA) and γ-naphthaleneacetic acid (NAA) used as supplementary
growth regulators along with Murashige and Skoog medium, 25 μM IBA was found suitable for lateral root induction and growth,
as well as accumulation of ginsenosides. Inoculum size of 5 g L−1 was found suitable for optimal biomass (10.5 g L−1 dry biomass) and ginsenosides (5.4 mg g−1 DW) accumulation. Of the various length of root inocula tested (chopped to 1–3, 4–6, 7–10 mm and un-chopped), root inocula
of 7–10 mm was found suitable for biomass and ginsenoside accumulation. 相似文献
10.
Jian-Fang Cui Ingemar Björkhem Peter Eneroth 《Journal of chromatography. B, Analytical technologies in the biomedical and life sciences》1997,689(2):818
An improved gas chromatographic-mass spectrometric method (GC-MS) with a fast solid-phase extraction on a newly introduced C18 microcolumn, was applied to study the urinary excretion of 20(S)-protopanaxadiol and 20(S)-protopanaxatriol glycosides in man after oral administration of ginseng preparations. Using panaxatriol as internal standard, 20(S)-protopanaxadiol and 20(S)-protopanaxatriol (the aglucones of ginesenosides) could be determined at a detection level of a few ng per ml urine by GC-MS with selected-ion monitoring after their release from glycosides which occur in urine. The extraction recovery of ginsenosides from urine was more than 80% and the intra-assay coefficient of variation was less than 5.0%. The results after intake of single doses of ginseng preparations demonstrated a linear relation between the amounts of ginsenosides consumed and the 20(S)-protopanaxatriol glycosides excreted in urine. About 1.2% of the dose was recovered in five days. 相似文献
11.
Ginseng saponins (ginsenosides) were isolated from soil associated with the roots of commercially grown American ginseng (Panax quinquefolius L.), identified via LC-MS and quantified via analytical HPLC. The ginsenosides, including F(11), Rb(1), Rb(2), Rc, Rd, Re and Rg(1), represented between 0.02 and 0.098% (average 0.06%) of the mass of the soil collected from roots annually between 1999 and 2002. The same ginsenosides were also isolated from run-off of undisturbed plants grown in pots in a greenhouse using a root exudate trapping system. To investigate (1) whether these saponins could influence the growth of pythiaceous fungi pathogenic to ginseng, and (2) whether soil levels of ginsenosides were sufficient to account for any effects, bioassays were completed using a crude saponin extract and an ecologically relevant concentration of purified ginsenosides. Thus, when cultured on media containing crude saponins, the colony weight of both Phytophthora cactorum and Pythium irregulare was significantly greater than that of control, indicating a strong growth stimulation by ginsenosides. The growth of Pythium irregulare was also significantly stimulated after addition of an ecologically relevant, low concentration (i.e. 0.06%) of purified ginsenosides to culture medium. By contrast, growth of the saprotrophic fungus Trichoderma hamatum was slightly (but not significantly) inhibited under the same conditions. These results imply that ginsenosides can act as allelopathic stimulators of the growth of pythiaceous fungi in the rhizosphere, and this may contribute to the disease(s) of this crop. 相似文献
12.
The defatted seed meal of common vetch (Vicia sativa L.) served as a source of (R)-oxynitrilase which catalyzed the enantioselective addition of HCN to aromatic, heteroaromatic, fluoro-substituted aromatic aldehydes to produce the corresponding enantiomeric pure cyanohydrins in yields of 52–100% and 88–99% ee at 12°C under micro-aqueous medium (diisopropyl ether) without addition of buffer solution. 相似文献
13.
Pectin-like acidic polysaccharide from Panax ginseng with selective antiadhesive activity against pathogenic bacteria 总被引:1,自引:0,他引:1
Previous studies have revealed the inhibitory effects of an acidic polysaccharide purified from the root of Panax ginseng against the adhesion of Helicobacter pylori to gastric epithelial cells and the ability of Porphyromonas gingivalis to agglutinate erythrocytes. In this study, this acidic polysaccharide from P. ginseng, PG-F2, was investigated further, in order to characterize its antiadhesive effects against Actinobacillus actinomycetemcomitans, Propionibacterium acnes, and Staphylococcus aureus. The minimum inhibitory concentrations (MIC) were found to be in a range of 0.25-0.5mg/mL. However, results showed no inhibitory effects of PG-F2 against Lactobacillus acidophilus, Escherichia coli, or Staphylococcus epidermidis. PG-F2 is a pectin-type polysaccharide with a mean MW of 1.2 x 10(4) Da, and consists primarily of galacturonic and glucuronic acids along with rhamnose, arabinose, and galactose as minor components. The complete hydrolysis of PG-F2 via chemical or carbohydrolase enzyme treatment resulted in the abrogation of its antiadhesive activity, but limited hydrolysis via treatment with pectinase (EC. 3.2.1.15) yielded an oligosaccharide fraction, with activity comparable to the precursor PG-F2 (the MIC of ca. 0.01 mg/mL against H. pylori and P. gingivalis). Our results suggest that PG-F2 may exert a selective antiadhesive effect against pathogenic bacteria, while having no effects on beneficial and commensal bacteria. 相似文献
14.
We have described the synthesis of (+)-(2R,3S,4R)-2,3,4-trihydroxycyclohexanone by the reduction of a keto-conduritol derivative, the latter being prepared in five steps from (-)-(2S,3R,4S,5S)-2,3,4-tribenzyloxy-5-hydroxycyclohexanone, which is in turn readily synthesized from D-glucose. 相似文献
15.
A single-chained ribonuclease was isolated from the aqueous extract of sanchi ginseng (Panax pseudoginseng) flowers. It exhibited a molecular mass of 23 kDa, an N-terminal sequence with some similarity to other enzymes involved in RNA metabolism but different from known ribonucleases, and considerably higher activity toward poly U than poly C and only slight activity toward poly A and poly G. The purification protocol entailed ion exchange chromatography on diethylaminoethyl (DEAE)-cellulose, affinity chromatography on Affi-gel blue gel, ion exchange chromatography on carboxymethyl (CM)-cellulose, and gel filtration on Superdex 75. The ribonuclease was unadsorbed on DEAE-cellulose and adsorbed on Affi-gel blue gel and CM-cellulose. Maximal activity of the ribonuclease was attained at pH 7. On either side of this pH the enzyme activity underwent a drastic decline. The enzyme activity was at its highest at 50 degrees C and dropped to about 20% of the maximal activity when the temperature was decreased to 20 degrees C or elevated to 80 degrees C. The characteristics of sanchi ginseng flower ribonuclease were different from those of the ribonucleases previously purified from sanchi ginseng and Chinese ginseng roots including ribonuclease from Chinese ginseng flowers which are morphologically very similar to sanchi ginseng flowers. 相似文献
16.
The most abundant root proteins of ginseng (Panax ginseng) have been detected and identified by comparative proteome analysis with cultured hairy root of ginseng. Four abundant proteins (28, 26, 21 and 20 kDa) of P. ginseng had isoforms with different pl values on two-dimensional gel electrophoresis (2DE). The results of N-terminal and internal amino acid sequencing, however, showed that all of them originate from a 28 kDa protein, known as ginseng major protein (GMP). The GMP gene was searched for in the expressed sequence tag database of P. ginseng and found to encode a 27.3 kDa protein having 238 amino acid residues. Analysis of the amino acid sequences indicates that GMP exhibits high sequence homology with plant RNases and RNase-like proteins. However, purified GMP had no RNase activity even though it has conserved amino acid residues known to be essential for active sites of RNase. The GMPs present in ginseng main root were not expressed in cultured hairy roots of ginseng. 2DE analysis showed that the amounts of GMPs in main roots change according to seasonal fluctuation. These results suggest that the GMPs are root-specific RNase-like proteins, which function as vegetative storage proteins of ginseng for survival in the natural environment. 相似文献
17.
Xin Chen Jian Zhang Ji-Hua Liu Bo-Yang Yu 《Journal of Molecular Catalysis .B, Enzymatic》2008,54(3-4):72-75
The regioselective glycosylation of three isomers of hydroxybenzoic acids was observed in Panax ginseng hairy root cultures. p-Hydroxybenzoic acid (1) and m-hydroxybenzoic acid (2) were converted into their corresponding glycosides (1a and 2a) and glycosyl esters (1b and 2b) while no metabolite of o-hydroxybenzoic acid (3) was detected. A new compound, m-hydroxybenzoic acid β-d-xylopyranosyl (1 → 6)-β-d-glycopyranosyl ester (2c) was identified as a biotransformation product of 2. Further time-course studies of the biotransformation reactions showed that the glycosides were major products in the latter stage. The addition of carbohydrates or antioxidants increased glycosyl esters formation. 相似文献
18.
Production of highly pure (2S,3S)-2,3-butanediol ((2S,3S)-2,3-BD) and (3S)-acetoin ((3S)-AC) in high concentrations is desirable but difficult to achieve. In the present study, glucose was first transformed to a mixture of (2S,3S)-2,3-BD and meso-2,3-BD by resting cells of Klebsiella pneumoniae CICC 10011, followed by biocatalytic resolution of the mixture by resting cells of Bacillus subtilis 168. meso-2,3-BD was transformed to (3S)-AC, leaving (2S,3S)-2,3-BD in the reaction medium. Using this approach, 12.5 g l(-1) (2S,3S)-2,3-BD and 56.7 g l(-1) (3S)-AC were produced. Stereoisomeric purity of (2S,3S)-2,3-BD and enantiomeric excess of (3S)-AC was 96.9 and 96.2%, respectively. 相似文献
19.
The contents of five ginsenosides (Rg1, Re, Rb1, Rc and Rd) were measured in American ginseng roots collected from 10 populations grown in Maryland. Ginsenoside contents and compositions varied significantly among populations and protopanaxatriol (Rg1 and Re) ginsenosides were inversely correlated within root samples and among populations. The most abundant ginsenoside within a root and by population was either Rg1 or Re, followed by Rb1. Ginseng populations surveyed grouped into two chemotypes based on the relative compositions of Rg1 and Re. Four populations, including the control population in which plants were grown from TN and WI seed sources, contained roots with the recognized chemotype for American ginseng of low Rg1 composition relative to Re. The remaining 6 populations possessed roots with a distinctive chemotype of high relative Rg1 to Re compositions. Chemotype did not vary by production type (wild versus cultivated) and roots within a population rarely exhibited chemotypes different from the overall population chemotype. These results provide support for recent evidence that relative Rg1 to Re ginsenoside contents in American ginseng roots vary by region and that these differences are likely influenced more by genotype than environmental factors. Because the physiological and medicinal effects of different ginsenosides differ and can even be oppositional, our findings indicate the need for fingerprinting ginseng samples for regulation and recommended usage. Also, the High Rg1/Low Re chemotype discovered in MD could potentially be used therapeutically for coronary health based on recent evidence of the positive effects of Rg1 on vascular growth. 相似文献
20.
Microbial transformation of cadina-4,10(15)-dien-3-one, aromadendr-1(10)-en-9-one and methyl ursolate by Mucor plumbeus ATCC 4740 总被引:2,自引:0,他引:2
The sesquiterpenes cadina-4,10(15)-dien-3-one (1) and aromadendr-1(10)-en-9-one (squamulosone) (14) along with the triterpenoid methyl ursolate (21) were incubated with the fungus Mucor plumbeus ATCC 4740. Substrates 1, 14 and ursolic acid (20) were isolated from the plant Hyptis verticillata in large quantities. M. plumbeus hydroxylated 1 at C-12 and C-14. When the iron content of the medium was reduced, however, hydroxylation at these positions was also accompanied by epoxidation of the exocyclic double bond. In total nine new oxygenated cadinanes have been obtained. Sesquiterpene 14 was converted to the novel 2alpha,13-dihydroxy derivative along with four other metabolites. Methyl ursolate (21) was transformed to a new compound, methyl 3beta,7beta,21beta-trihydroxyursa-9(11),12-dien-28-oate (22). Two other triterpenoids, 3beta,28-dihydroxyurs-12-ene (uvaol) (23) and 3beta,28-bis(dimethylcarbamoxy)urs-12-ene (24) were not transformed by the micro-organism, however. 相似文献