Structural identification of nonvolatile dimerization products of glucosamine by gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and nuclear magnetic resonance analysis     

Jun M  Shao Y  Ho CT  Koetter U  Lech S 《Journal of agricultural and food chemistry》2003,51(21):6340-6346

The degradation profile of glucosamine bulk form stressed at 100 degrees C for 2 h in an aqueous solution was studied. Column chromatography of acetylated product mixture led to isolation of two pure compounds (1b and 2b) and a mixture of at least three isomers (3b). 1a and 2a were identified as 5-(hydroxymethyl)-2-furaldehyde (5-HMF) and 2-(tetrahydroxybutyl)-5-(3',4'-dihydroxy-1'-trans-butenyl)pyrazine, respectively, by utilizing a variety of analytical techniques, such as GC-MS, LC-MS, on-line UV spectrum, (1)H and (13)C NMR, and DEPT, as well as (1)H-(1)H COSY. 3a was identified as 2-(tetrahydroxybutyl)-5-(2',3',4'-trihydroxybutyl)pyrazine, commonly known as deoxyfructosazine. In addition, glucosamine solid dosage form was exposed to 40 degrees C/75% relative humility for 10 weeks. Methanol extract of glucosamine solid dosage form was analyzed after acetylation by LC-MS, resulting in degradants 3b and 4b. 3a and 4a were, therefore, determined as deoxyfructosazine and 2,5-bis(tetrahydroxybutyl)pyrazine (fructosazine), respectively. Furthermore, the mechanisms of formation of identified degradation products are proposed and briefly discussed.  相似文献   

New prenylated benzoic acid and other constituents from almond hulls (Prunus amygdalus Batsch).   总被引：2，自引：0，他引：2  

Shengmin Sang  Karen Lapsley  Robert T Rosen  Chi-Tang Ho 《Journal of agricultural and food chemistry》2002,50(3):607-609

One new prenylated benzoic acid derivative, 3-prenyl-4-O-beta-D-glucopyranosyloxy-4-hydroxylbenzoic acid, and three known constituents, catechin, protocatechuic acid, and ursolic acid, have been isolated from the hulls of almond (Prunus amygdalus). Complete assignments of the proton and carbon chemical shifts for the new prenylated benzoic acid derivative were accomplished on the basis of high-resolution 1D and 2D nuclear magnetic resonance data. All of these compounds except ursolic acid are being reported from almond hulls (P. amygdalus) for the first time.  相似文献   

New spirostanol saponins from Chinese chives (Allium tuberosum)     

Sang S  Zou M  Xia Z  Lao A  Chen Z  Ho CT 《Journal of agricultural and food chemistry》2001,49(10):4780-4783

Three new spirostanol saponins have been isolated from the seeds of Allium tuberosum. On the basis of acid hydrolysis and comprehensive spectroscopic analysis, their structures were established as tuberoside J, (25R)-5alpha-spirostan-2alpha,3beta,27-triol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside; tuberoside K, (25R)-5alpha-spirostan-2alpha,3beta,27-triol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside; and tuberoside L, 27-O-beta-D-glucopyranosyl-(25R)-5alpha-spirostan-2alpha,3beta,27-triol 3-O-alpha-D-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside.  相似文献   

Characteristics of soil microbiostasis     

W.C. Ho  W.H. Ko 《Soil biology & biochemistry》1982,14(6):589-593

No increase in numbers of fungi, actinomycetes and bacteria in 3 days, as measured by selective media, was used as an indication of the presence of fungistasis, actinostasis and bacteriostasis in soil, respectively. The population of fungi, actinomycetes and bacteria did not increase in 9 of 10 soils tested indicating concurrent existence of fungistasis, actinostasis and bacteriostasis in a wide range of soils. When Penicillium funiculosum, Streptomyces scabies and Agrobacterium radiobacter were used as test organisms, these three types of microbiostasis were detected simultaneously in all 8 soils tested. All three groups of microorganisms flourished in autoclaved soil, and microbiostasis was restored to sterilized soil by reinoculation with 1% natural soil or microorganisms including antibiotic and non-antibiotic producers. Soil microbiostasis was annulled completely or partially by addition of different nutrie0nts. Bacteriostasis appeared to be the easiest to overcome with nutrients among these three types of microbiostasis.  相似文献   

Inhibition of xanthine oxidase and suppression of intracellular reactive oxygen species in HL-60 cells by theaflavin-3,3'-digallate, (-)-epigallocatechin-3-gallate, and propyl gallate   总被引：6，自引：0，他引：6  

Lin JK  Chen PC  Ho CT  Lin-Shiau SY 《Journal of agricultural and food chemistry》2000,48(7):2736-2743

The inhibitory effects of five tea polyphenols, namely theaflavin (TF1), theaflavin-3-gallate (TF2), theaflavin-3,3'-digallate (TF3), (-)-epigallocatechin-3-gallate (EGCG), and gallic acid, and propyl gallate (PG) on xanthine oxidase (XO) were investigated. These six antioxidant compounds reduce oxidative stress. Theaflavins and EGCG inhibit XO to produce uric acid and also act as scanvengers of superoxide. TF3 acts as a competitive inhibitor and is the most potent inhibitor of XO among these compounds. Tea polyphenols and PG all have potent inhibitory effects (>50%) on PMA-stimulated superoxide production at 20 approximately 50 microM in HL-60 cells. Gallic acid (GA) showed no inhibition under the same conditions. At 10 microM, only EGCG, TF3, and PG showed significant inhibition with potency of PG > EGCG > TF3. The superoxide scavenging abilities of these six compunds are as follows: EGCG > TF2 > TF1 > GA > TF3 > PG. PG was the most potent inhibitor of PMA-stimulated H(2)O(2) production in HL-60 cells. The order of H(2)O(2) scavenging ability was TF2 > TF3 > TF1 > EGCG > PG > GA. Therefore, the antioxidative activity of tea polyphenols and PG is due not only to their ability to scavenge superoxides but also to their ability to block XO and related oxidative signal transducers.  相似文献   

Epicatechin and catechin in cocoa inhibit amyloid beta protein induced apoptosis   总被引：4，自引：0，他引：4  

Heo HJ  Lee CY 《Journal of agricultural and food chemistry》2005,53(5):1445-1448

To elucidate additional health benefits of cocoa phytochemicals on the neurotoxicity induced by amyloid beta protein (Abeta), PC12 cells were treated with toxic peptide (Abeta(25)(-)(35)) and the effects of epicatechin, catechin, and cocoa were studied using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction, lactate dehydrogenase (LDH) release, and trypan blue exclusion methods. Significant increase in neuronal cell death was observed on PC12 cells treated with Abeta(25)(-)(35) (25 microM), while epicatechin and catechin and their mixture prevented the Abeta-induced neuronal cell death. Abeta treatment also led to the increased membrane instability of PC12 cells. The membrane protective effects of the phenolics determined by LDH release and trypan blue exclusion assays demonstrated that epicatechin, catechin, and their mixture protect cellular membrane from Abeta-induced cytotoxicity. In these three different cell viability assays, the mixture of epicatechin and catechin showed the highest protective effect and synergistic activity. The present results showed that the major flavonoids of cocoa, epicatechin and catechin, protect PC12 cells from Abeta-induced neurotoxicity, and suggest that cocoa may have anti-neurodegenerative effect in addition to other known chemopreventive effects.  相似文献   

Induction of apoptosis by garcinol and curcumin through cytochrome c release and activation of caspases in human leukemia HL-60 cells   总被引：5，自引：0，他引：5  

Pan MH  Chang WL  Lin-Shiau SY  Ho CT  Lin JK 《Journal of agricultural and food chemistry》2001,49(3):1464-1474

Garcinol, a polyisoprenylated benzophenone, was purified from Garcinia indica fruit rind. The effects of garcinol and curcumin on cell viability in human leukemia HL-60 cells were investigated. Garcinol and curcumin displayed strong growth inhibitory effects against human leukemia HL-60 cells, with estimated IC(50) values of 9.42 and 19.5 microM, respectively. Garcinol was able to induce apoptosis in a concentration- and time-dependent manner; however, curcumin was less effective. Treatment with garcinol caused induction of caspase-3/CPP32 activity in a dose- and time-dependent manner, but not caspase-1 activity, and induced the degradation of poly(ADP-ribose) polymerase (PARP). Pretreatment with caspase-3 inhibitor inhibited garcinol-induced DNA fragmentation. Treatment with garcinol (20 microM) caused a rapid loss of mitochondrial transmembrane potential, release of mitochondrial cytochrome c into cytosol, and subsequent induction of procaspase-9 processing. The cleavage of D4-GDI, an abundant hematopoietic cell GDP dissociation inhibitor for the Ras-related Rho family GTPases, occurred simultaneously with the activation of caspase-3 but preceded DNA fragmentation and the morphological changes associated with apoptotic cell death. Of these, Bcl-2, Bad, and Bax were studied. The level of expression of Bcl-2 slightly decreased, while the levels of Bad and Bax were dramatically increased in cells treated with garcinol. These results indicate that garcinol allows caspase-activated deoxyribonuclease to enter the nucleus and degrade chromosomal DNA and induces DFF-45 (DNA fragmentation factor) degradation. It is suggested that garcinol-induced apoptosis is triggered by the release of cytochrome c into the cytosol, procaspase-9 processing, activation of caspase-3 and caspase-2, degradation of PARP, and DNA fragmentation caused by the caspase-activated deoxyribonuclease through the digestion of DFF-45. The induction of apoptosis by garcinol may provide a pivotal mechanism for its cancer chemopreventive action.  相似文献   

Four new steroidal saponins from the seeds of Allium tuberosum   总被引：3，自引：0，他引：3  

Sang S  Mao S  Lao A  Chen Z  Ho CT 《Journal of agricultural and food chemistry》2001,49(3):1475-1478

Four new steroidal saponins, 26-O-beta-D-glucopyranosyl-(25S,20R)-20-O-methyl-5alpha-furost-22(23)-en-2alpha,3beta,20,26-tetraol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (1); 26-O-beta-D-glucopyranosyl-(25S,20R)-5alpha-furost-22(23)-en-2alpha,3beta,20,26-tetraol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L- rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (2); 26-O-beta-D-glucopyranosyl-(25S,20S)-5alpha-furost-22(23)-en-2alpha,3beta,20,26-tetraol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L- rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (3); and 26-O-beta-D-glucopyranosyl-(25S,20S)-5alpha-furost-22(23)-en-3beta,20,26-triol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (4), have been isolated from the seeds of Allium tuberosum. Their structures were established by spectroscopic studies such as MS, IR, NMR, and 2D-NMR and the results of acid hydrolysis and named tuberosides F, G, H, and I, respectively.  相似文献   

Novel trisaccharide fatty acid ester identified from the fruits of Morinda citrifolia (Noni)   总被引：4，自引：0，他引：4  

Wang M  Kikuzaki H  Csiszar K  Boyd CD  Maunakea A  Fong SF  Ghai G  Rosen RT  Nakatani N  Ho CT 《Journal of agricultural and food chemistry》1999,47(12):4880-4882

Two known glycosides and a novel trisaccharide fatty acid ester were isolated from the n-butanol-soluble fraction of the fruits of Morinda citrifolia (noni). Structure determination was carried out by spectral techniques such as MS, IR, NMR, and 2D-NMR. The novel trisaccharide fatty acid ester was elucidated as 2, 6-di-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-glucopyranose. The known compounds were identified as rutin and asperulosidic acid.  相似文献   

Novel polyphenol molecule isolated from licorice root (Glycrrhiza glabra) induces apoptosis, G2/M cell cycle arrest, and Bcl-2 phosphorylation in tumor cell lines   总被引：4，自引：0，他引：4  

Rafi MM  Vastano BC  Zhu N  Ho CT  Ghai G  Rosen RT  Gallo MA  DiPaola RS 《Journal of agricultural and food chemistry》2002,50(4):677-684

Herbal therapies are commonly used by patients with cancer, despite little understanding about biologically active chemical derivatives. We recently demonstrated that the herbal combination PC-SPES, which contains licorice root, had anti-prostate cancer activity attributable to estrogen(s) that produced a chemical castration. A recent study also demonstrated that licorice root alone decreased circulating testosterone in men. Other studies demonstrated antitumor activity of PC-SPES in vitro associated with decreased expression of the anti-apoptotic protein Bcl-2 and in patients independent of chemical castration, suggesting that other mechanisms of antitumor activity exist separate from chemical castration. In the present study, we assessed licorice root extract for effects on Bcl-2 to identify novel cytotoxic derivatives. Licorice root extract induced Bcl-2 phosphorylation as demonstrated by immunoblot and G2/M cell cycle arrest, similarly to clinically used antimicrotubule agents such as paclitaxel. Bioassay-directed fractionations resulted in a biologically active fraction for Bcl-2 phosphorylation. HPLC separation followed by mass spectrometry and NMR identified 6 compounds. Only one molecule was responsible for Bcl-2 phosphorylation; it was identified as 1-(2,4-dihydroxyphenyl)-3-hydroxy-3-(4'-hydroxyphenyl) 1-propanone (beta-hydroxy-DHP). The effect on Bcl-2 was structure specific, because alpha-hydroxy-DHP, 1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(4'-hydroxyphenyl) 1-propanone, in contrast to beta-hydroxy-DHP, was not capable of Bcl-2 phosphorylation. Pure beta-hydroxy-DHP induced Bcl-2 phosphorylation in breast and prostate tumor cells, G2/M cell cycle arrest, apoptosis demonstrated by Annexin V and TUNEL assay, decreased cell viability demonstrated by a tetrazolium (MTT) assay, and altered microtubule structure. Therefore, these data demonstrate that licorice root contains beta-hydroxy-DHP, which induced Bcl-2 phosphorylation, apoptosis, and G2/M cell cycle arrest, in breast and prostate tumor cells, similarly to the action of more complex (MW >800) antimicrotubule agents used clinically.  相似文献