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1.
Terpenic acids are under development as therapeutic agents in numerous treatments. In support of pharmacokinetic and toxicological evaluations, a robust assay based on high-performance liquid chromatography (HPLC) was developed for the analysis of the terpenoids in human serum. For a clear understanding of the differences in biological activity of these compounds, the interactions between oleanolic or betulinic acids and human serum protein have been studied by ultraviolet-visible (UV-vis) absorption under physiological conditions. A combination of liquid/liquid extraction, centrifugation, and consecutive HPLC resulted in simultaneous separation, identification, and quantification of the oleanolic, betulinic, and ursolic acids. The validity of the developed method was established by determining linearity, recovery, precision, accuracy, limit of detection, and quantification. Detection limits were in the range of 3.3-4.3 ng/mL, and linearity values ranged up to 1 μg/mL. The repeatability of the method was good. All compounds can be well-distinguished by order of elution during liquid chromatography. The pentacyclic triterpenoids have been identified by retention time comparison to pure standards and quantified by an internal standard. The results by UV-vis absorption spectra experiments (240-340 nm) indicate that protein structures have been perturbed in the presence of oleanolic and betulinic acids.  相似文献   

2.
Investigation on the anthelminthic bioactive compounds of the ethanol extract of Tadehagi triquetrum resulted in the isolation of three new prenylated isoflavones, triquetrumones A (1), B (2), and C (3), and one new prenylated biisoflavanone, (R)-triquetrumone D (4), along with 16 known compounds, cyclokievitone (5), yukovanol (6), aromadendrin (7), kaempferol (8), astragalin (9), 2-O-methyl-l-chiro-inositol (10), galactitol (11), p-hydroxycinnamic acid (12), ursolic acid (13), betulinic acid (14), beta-sitosterol (15), daucosterol (16), stigmasterol (17), stigmasta-5,22-dien-3-O-beta-d-glucopyranoside (18), saccharose (19), and docosanoic acid (20). The structures of 1-4 were elucidated on the basis of spectroscopic and spectrometric methods. Compounds 1-3 displayed mild anthelminthic bioactivity, and compound 3 showed a significant binding ability to the estrogen receptor.  相似文献   

3.
Triterpenic acids are widespread in plants and have multiplicity of biological properties. Unfortunately the method for accurate analysis of these compounds remains poorly investigated. This study proposed a highly sensitive and selective precolumn derivatization method for accurate determination of five triterpenic acids (betulinic acid, betulonic acid, maslinic acid, ursolic acid and oleanolic acid) in fruits using acridone-9-ethyl-p-toluenesulfonate (AETS) as fluorescent labeling reagent by HPLC with fluorescence detection (FLD). Response surface methodology was employed to optimize the derivatization reaction, ensuring the sufficient labeling of the analyzed components. The rapid separation of five triterpenic acids could be achieved in as little as 16 min. This developed method offered the exciting detection limits of 1.68-2.04 ng/mL. When applied to several popular fruits in China, it revealed satisfactory applicability and reproducibility. This developed method also exhibits powerful potential for accurate detection of triterpenic acids from other foodstuffs and nature products.  相似文献   

4.
Bioassay-guided isolation and purification of hexane and ethyl acetate extracts of Cabernet Sauvignon grape skin yielded nine compounds (1-9), which were identified as beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside (1), beta-sitosterol (2), beta-sitosterol-3-O-beta-D-glucoside (3), oleanolic acid (4), oleanolic aldehyde (5), resveratrol (6), (+)-epsilon-viniferin (7), (-)-catechin (8), and 1-triacontanol (9). The structures of these compounds were established by spectroscopic methods. The compounds were assayed for insulin production using an INS-1 cell assay. In a dose-response study, compound 4 stimulated insulin production of INS-1 cells by 20.23, 87.97, 1.13, and 6.38 ng of insulin/mg of protein at 6.25, 12.5, 25, and 50 microg/mL, respectively. This trend was similar to the dose-dependent insulin production of INS-1 cells by glucose. Compound 5 also showed a dose-dependent insulin production in this assay. The isolated compounds were also assayed for cyclooxygenase-1 and -2 (COX) enzyme inhibitory activities. At 100 microg/mL, compounds 2, 3, and 4 inhibited the COX-2 enzyme by 11, 12, and 10%, respectively, but did not show activities on the COX-1 enzyme. Compounds 6, 7, and 8 at 100 microg/mL inhibited the COX-1 enzyme by 98, 99, and 98%, respectively, and the COX-2 enzyme by 0, 47, and 72%, respectively. This is the first report of beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside (1) from grape skin and insulin secretion activities of compounds 4 and 5.  相似文献   

5.
Fourteen triterpene saponins (1-14) have been isolated from the roots of Medicago hybrida and their structures elucidated by FAB-MS and NMR analysis. Two of them are new compounds and were identified as hederagenin 3-O-[alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl]-28-O-beta-D-glucopyranoside (7) and oleanolic acid 3-O-[beta-D-galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl]-28-O-[alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranoside] (14). Seven saponins being mono- and bidesmosides of hederagenin (1, 5, 6, 9), one bidesmoside of bayogenin (2), and two bidesmosides of 2beta,3beta-dihydroxyolean-12-en-23-al-28-oic acid (11) and oleanolic acid (13) are known compounds but not previously reported as saponin constituents of Medicago, whereas five other saponins, being mono- and bidesmosides of medicagenic acid (3, 4, 8, 10, 12), and one monodesmoside of hederagenin (8) have been previously isolated from other Medicago species. The presence of 2beta,3beta-dihydroxyolean-12-en-23-al-28-oic acid might represent an interesting intermediate in the biosynthesis of these substances.  相似文献   

6.
Three triterpenic acids, oleanolic acid, ursolic acid and maslinic acid, at 2 or 4 μmol/L were used to study their antiangiogenic potential in human liver cancer Hep3B, Huh7 and HA22T cell lines. The effects of these compounds upon the level and/or expression of hypoxia-inducible factor (HIF)-1α, basic fibroblast growth factor (bFGF), vascular endothelial growth factor (VEGF), interleukin (IL)-8, urokinase plasminogen activator (uPA), reactive oxygen species (ROS), nitric oxide (NO) and cell invasion and migration were examined. Results showed that these triterpenic acids at 4 μmol/L significantly suppressed HIF-1α expression in three cell lines (P < 0.05); and these compounds at test doses failed to affect bFGF expression (P > 0.05). Three triterpenic acids dose-dependently decreased production and expression of VEGF and IL-8, retained glutathione level, lowered ROS and NO levels, and declined cell invasion and migration in test cell lines (P < 0.05). These compounds also dose-dependently reduced uPA production and expression in Hep3B and Huh7 cell lines (P < 0.05); but these agents only at 4 μmol/L significantly suppressed uPA production and expression in HA22T cells (P < 0.05). These findings suggest that these triterpenic acids are potent antiangiogenic agents to retard invasion and migration in liver cancer cells.  相似文献   

7.
This study investigates the antioxidant activity and cytotoxicity of Glossogyne tenuifolia extract on various cancer cell lines. The 5.8s DNA of G. tenuifolia was isolated, and the species of this plant was confirmed by NCBI's DNA database. G. tenuifolia was then extracted with ethanol and separated into several fractions using the partition procedure with water, n-butanol, and ethyl acetate (EA). Among these, the EA fraction most significantly affected the activity of DPPH(*) and superoxide anion scavenging. Additionally, only the EA fraction exhibited cytotoxicity on breast cancer cells (MCF-7 and MDA-MB-231) and liver cancer cells (Hep G2 and Hep 3B). Next, the EA fraction was further separated by column chromatography, and 15 fractions were obtained. Three effective components were isolated and identified separately from the active fractions: oleanolic acid (OA) from fraction 6, luteolin from fractions 8-10, and luteolin-7-glucoside from fraction 12. The test of these three compounds on scavenging activity of DPPH(*) and superoxide anion indicates that luteolin had the highest antioxidant activity, whereas the effect of OA was negligible. Additionally, a synergistic effect between luteolin and luteolin-7-glucoside was observed. Kick-out experiments showed that the activities were vanished or decreased. Especially on MDA-MB-231 and MCF-7 cells, the cytotoxicity completely disappeared when luteolin was eliminated from fractions 8-10. These findings demonstrate that luteolin plays a crucial role in the inhibition of the growth of hepatoma cancer cell lines. Fraction 3, which did not contain luteolin, luteolin-7-glucoside, and oleanolic acid, had cytotoxicity on MDA-MB-231, MCF-7, Hep G2, Hep 3B, and A549, which implies that this fraction contained some other effective ingredients and requires further study. The investigation is currently underway in our laboratory.  相似文献   

8.
Two new lactams, coixspirolactam D (1) and coixspirolactam E (2), and a new spiroenone, coixspiroenone (3), together with seven known compounds, coixspirolactam A (4), coixspirolactam B (5), coixspirolactam C (6), coixlactam (7), coixol (8), ethyl dioxindole-3-acetate (9), and isoindol-1-one (10), and two neolignans, zhepiresionol (11) and ficusal (12), were isolated from the bioactive subfraction of adlay bran ethanolic extract (ABE). Compounds 9 and 10 are the first isolates from natural resources. The structures of new compounds were identified by spectroscopic methods, including infrared (IR) spectrum, 1D and 2D nuclear magnetic resonance (NMR), and mass spectrum (MS). All of the isolated compounds were tested for antiproliferative effects on MCF-7, MDA-MB-231, and T-47D cells. Results showed that compounds 1, 3, 4, 6, and 7 at 50 μM significantly inhibited MCF-7 cell proliferation by 30.2, 19.2, 21.0, 13.5, and 32.4%, respectively; compounds 2, 4, and 7 significantly inhibited T-47D cells at 50 μM by 20.7, 24.8, and 28.9%; and compounds 1, 2, and 12 significantly inhibited MDA-MB-231 cells at 50 μM by 47.4, 25.3, and 69.3%, respectively. In conclusion, ABE has antiproliferative activities, and this effect is partially related to the presence of lactams and spiroenone.  相似文献   

9.
Bioactivity-guided fractionation of Red Delicious apple peels was used to determine the chemical identity of bioactive constituents, which showed potent antiproliferative and antioxidant activities. Twenty-nine compounds, including triterpenoids, flavonoids, organic acids and plant sterols, were isolated using gradient solvent fractionation, Diaion HP-20, silica gel, and ODS columns, and preparative HPLC. Their chemical structures were identified using HR-MS and 1D and 2D NMR. Antiproliferative activities of isolated pure compounds against HepG2 human liver cancer cells and MCF-7 human breast cancer cells were evaluated. On the basis of the yields of isolated flavonoids (compounds 18- 23), the major flavonoids in apple peels are quercetin-3-O-beta-D-glucopyranoside (compound 20, 82.6%), then quercetin-3-O-beta-D-galactopyranoside (compound 19, 17.1%), followed by trace amounts of quercetin (compound 18, 0.2%), (-)-catechin (compound 22), (-)-epicatechin (compound 23), and quercetin-3-O-alpha-L-arabinofuranoside (compound 21). Among the compounds isolated, quercetin (18) and quercetin-3-O-beta-D-glucopyranoside (20) showed potent antiproliferative activities against HepG2 and MCF-7 cells, with EC 50 values of 40.9 +/- 1.1 and 49.2 +/- 4.9 microM to HepG2 cells and 137.5 +/- 2.6 and 23.9 +/- 3.9 microM to MCF-7 cells, respectively. Six flavonoids (18-23) and three phenolic compounds (10, 11, and 14) showed potent antioxidant activities. Caffeic acid (10), quercetin (18), and quercetin-3-O-beta-D-arabinofuranoside (21) showed higher antioxidant activity, with EC 50 values of <10 microM. Most tested flavonoids and phenolic compounds had high antioxidant activity when compared to ascorbic acid and might be responsible for the antioxidant activities of apples. These results showed apple peel phytochemicals have potent antioxidant and antiproliferative activities.  相似文献   

10.
In order to reinvestigate the key molecules inducing bitter off-taste of carrots ( Daucus carota L.), a sensory-guided fractionation approach was applied to bitter carrot extracts. Besides the previously reported bitter compounds, 6-methoxymellein (1), falcarindiol (2), falcarinol (3), and falcarindiol-3-acetate (4), the following compounds were identified for the first time as bitter compounds in carrots with low bitter recognition thresholds between 8 and 47 micromol/L: vaginatin (5), isovaginatin (6), 2-epilaserine oxide (7), laserine oxide (8), laserine (14), 2-epilaserine (15), 6,8-O-ditigloyl- (9), 6-O-angeloyl-, 8-O-tigloyl- (10), 6-O-tigloyl-, 8-O-angeloyl- (11), and 6-, 8-O-diangeloyl-6 ss,8alpha,11-trihydroxygermacra-1(10) E,4 E-diene (12), as well as 8-O-angeloyl-tovarol (13) and alpha-angeloyloxy-latifolone (16). Among these bitter molecules, compounds 9, 10, 13, and 16 were not previously identified in carrots and compounds 6, 11, and 12 were yet not reported in the literature.  相似文献   

11.
Plants from Iryanthera genus have been traditionally used as food supplements by South American Indians. The MeOH extract of leaves of Iryanthera juruensis, one of the plants endemic to the Amazon region and consumed in Brazil, and the hexane extract from its seeds inhibited lipid peroxidation (LPO) and cyclooxygenase (COX-1 and -2)) enzymes in in vitro assays. Further analyses of these extracts yielded 5-deoxyflavones (1-5) from the leaf extract and sargachromenol (6), sargaquinoic acid (7), a novel juruenolic acid (8), omega-arylalkanoic acids (9a-c), and the lignan guaiacin (10) from the seed extract. Compounds 3-5 inhibited LPO by 86%, 77%, and 88% at 10 ppm, respectively, and compounds 6 and 9a-c showed inhibition at 76% and 78% at 100 ppm, respectively. However, compounds 7 and 8 were inactive and lignan 10 exhibited LPO inhibitory activity by 99% at 100 ppm compared to commercial antioxidants butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), and vitamin E. The flavones 1-5 also inhibited COX-1 and -2 enzymes by 50-65% at 100 ppm. Compound 6 showed high but nonselective inhibition of COX-1 and COX-2 enzymes, when compared to aspirin and Celebrex, a nonsteroidal anti-inflammatory drug (NSAID). Compounds 7 and 10 inhibited COX-1 by 60% and 65% and COX-2 by 37% and 18%, respectively, whereas compounds 8 and 9a-c showed little or no activity against these enzymes.  相似文献   

12.
Six azaphilones, monascin (1), ankaflavin (2), rubropunctatin (3), monascorburin (4), rubropunctamine (5), and monascorburamine (6), two furanoisophthalides, xanthomonasin A (7) and xanthomonasin B (8), and two amino acids, (+)-monascumic acid (9) and (-)-monascumic acid (10), isolated from the extracts of Monascus pilosus-fermented rice (red-mold rice) were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice, on the induction of Epstein-Barr virus early antigen (EBV-EA) by TPA in Raji cells, and on the activation of (+/-)-(E)-methyl-2[(E)-hydroxy-imino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor. Among the compounds tested, seven compounds (1-6 and 10) on TPA-induced inflammation, and six compounds (1, 3-5, 9, and 10) on EBV-EA activation, exhibited potent inhibitory effects. All of the compounds tested showed moderate inhibitory effects on NOR 1 activation.  相似文献   

13.
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14.
Bioactivity-guided fractionation of black bean (Phaseolus vulgaris) seed coats was used to determine the chemical identity of bioactive constituents, which showed potent antiproliferative and antioxidative activities. Twenty-four compounds including 12 triterpenoids, 7 flavonoids, and 5 other phytochemicals were isolated using gradient solvent fractionation, silica gel and ODS columns, and semipreparative and preparative HPLC. Their chemical structures were identified using MS, NMR, and X-ray diffraction analysis. Antiproliferative activities of isolated compounds against Caco-2 human colon cancer cells, HepG2 human liver cancer cells, and MCF-7 human breast cancer cells were evaluated. Among the compounds isolated, compounds 1, 2, 6, 7, 8, 13, 14, 15, 16, 19, and 20 showed potent inhibitory activities against the proliferation of HepG2 cells, with EC50 values of 238.8 +/- 19.2, 120.6 +/- 7.3, 94.4 +/- 3.4, 98.9 +/- 3.3, 32.1 +/- 6.3, 306.4 +/- 131.3, 156.9 +/- 11.8, 410.3 +/- 17.4, 435.9 +/- 47.7, 202.3 +/- 42.9, and 779.3 +/- 37.4 microM, respectively. Compounds 1, 2, 3, 5, 6, 7, 8, 9, 10, 11, 14, 15, 19, and 20 showed potent antiproliferative activities against Caco-2 cell growth, with EC50 values of 179.9 +/- 16.9, 128.8 +/- 11.6, 197.8 +/- 4.2, 105.9 +/- 4.7, 13.9 +/- 2.8, 35.1 +/- 2.9, 31.2 +/- 0.5, 71.1 +/- 11.9, 40.8 +/- 4.1, 55.7 +/- 8.1, 299.8 +/- 17.3, 533.3 +/- 126.0, 291.2 +/- 1.0, and 717.2 +/- 104.8 microM, respectively. Compounds 5, 7, 8, 9, 11, 19, 20 showed potent antiproliferative activities against MCF-7 cell growth in a dose-dependent manner, with EC50 values of 129.4 +/- 9.0, 79.5 +/- 1.0, 140.1 +/- 31.8, 119.0 +/- 7.2, 84.6 +/- 1.7, 186.6 +/- 21.1, and 1308 +/- 69.9 microM, respectively. Six flavonoids (compounds 14-19) showed potent antioxidant activity. These results showed the phytochemical extracts of black bean seed coats have potent antioxidant and antiproliferative activities.  相似文献   

15.
Three triterpenoids, betulinic acid, oleanolic acid, and ursolic acid, were isolated as their methyl esters (treatment with diazomethane) from diethyl ether extracts of almond hulls (Nonpareil variety) using flash chromatography and preparative high-performance liquid chromatography. The triterpenoids, which comprised approximately 1% of the hulls, were characterized using chromatographic and spectroscopic methods. These studies demonstrate that almond hulls are a rich source of these triterpenoids, which have reported anti-inflammatory, anti-HIV, and anti-cancer activities.  相似文献   

16.
G. Ogner  E.T. Gjessing 《Geoderma》1975,14(2):139-145
The chemical composition of aquatic humus was investigated by permanganate oxidation. Both methylated and non-methylated samples were investigated and the results compared with those of different soil humic fractions investigated earlier.The total amount of oxidation products identified from the methylated sample was 2%, and from the non-methylated sample 0.9%. The composition of the oxidation products from methylated aquatic humus was 42% benzenecarboxylic acid methyl esters (8 different compounds), 43% methoxy-benzenecarboxylic acid methyl esters (12 compounds), 10% dimethoxy-benzenecarboxylic acid methyl esters (4 compounds), and 5% of 1, 2, 3-propanetricarboxylic acid trimethyl ester. The unmethylated aquatic humus yielded 84% benzenecarboxylic acid methyl ester (7 compounds), 7% methoxy-benzenecarboxylic acid methyl esters (2 compounds), and 9% of 1, 2, 3-propanetricarboxylic acid trimethyl ester. Three diazines isolated from methylated material were believed to be artefacts from diazomethane treatment. Two of the diazines have earlier been found by oxidation of methylated soil samples, the third, C10H12N2O6, is an oxidation product of methylated aquatic humus only.Oxidation of aquatic humus yielded more benzenecarboxylic acids and methoxy-benzenecarboxylic acids than soil humic fractions, and less dimethoxy-benzenecarboxylic acids. No aliphatic dicarboxylic acids were detected among the oxidation products of the aquatic humus.The compounds identified are mainly the same as those found by oxidation of different soil humic fractions, although their yields clearly demonstrated that the aquatic humus differed in composition from the soil fractions.  相似文献   

17.
Four new abscisic acid related compounds (1-4), together with (+)-abscisic acid (5), (+)-beta-D-glucopyranosyl abscisate (6), (6S,9R)-roseoside (7), and two lignan glucosides ((+)-pinoresinol mono-beta-D-glucopyranoside (8) and 3-(beta-D-glucopyranosyloxymethyl)-2- (4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (9)) were isolated from the antioxidative ethanol extract of prunes (Prunus domestica L.). The structures of 1-4 were elucidated on the basis of NMR and MS spectrometric data to be rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (1), rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid 3'-O-beta-d-glucopyranoside (2), rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (3), and rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxabicyclo[3,2,1]- oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (4). The antioxidant activities of these isolated compounds were evaluated on the basis of oxygen radical absorbance capacity (ORAC). The ORAC values of abscisic acid related compounds (1-7) were very low. Two lignans (8 and 9) were more effective antioxidants whose ORAC values were 1.09 and 2.33 micromol of Trolox equiv/micromol, respectively.  相似文献   

18.
Thirteen compounds, isolated from spinach (Spinacia oleracea), acted as antimutagens against the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline in Salmonella typhimurium TA 98. The antimutagens were purified by preparative and micropreparative HPLC from a methanol/water (70:30, v/v) extract of dry spinach (commercial product) after removal of lipophilic compounds such as chlorophylls and carotenoids by solid-phase extraction (SPE). Pure active compounds were identified by instrumental analysis including FT-IR, (1)H and (13)C NMR, UV-vis spectroscopy, and mass spectrometry. All of these compounds were flavonoids and related compounds that could be attributed to five groups: (A, methylenedioxyflavonol glucuronides) 5,3'-dihydroxy-4'-methoxy-6,7-methylenedioxyflavonol 3-O-beta-glucuronide (compound 1), 5,2',3'-trihydroxy-4'-methoxy-6,7-methylenedioxyflavonol 3-O-beta-glucuronide (compound 2), 5-hydroxy-3',4'-dimethoxy-6,7-methylenedioxyflavonol 3-O-beta-glucuronide (compound 3); (B, flavonol glucuronides) 5,6,3'-trihydroxy-7,4'-dimethoxyflavonol 3-O-beta-glucuronide (compound 4), 5,6-dihydroxy-7,3',4'-trimethoxyflavonol 3-O-beta-glucuronide (compound 5); (C, flavonol disaccharides) 5,6,4'-trihydroxy-7,3'-dimethoxyflavonol 3-O-disaccharide (compound 6), 5,6,3',4'-tetrahydroxy-7-methoxyflavonol 3-O-disaccharide (compounds 7 and 8); (D, flavanones) 5,8,4'-trihydroxyflavanone (compound 9), 7,8,4'-trihydroxyflavanone (compound 10); (E, flavonoid-related compounds) compounds 11, 12, and 13 with incompletely elucidated structures. The yield of compound 1 was 0.3%, related to dry weight, whereas the yields of compounds 2-13 ranged between 0.017 and 0.069%. IC(50) values (antimutagenic potencies) of the flavonol glucuronides ranged between 24.2 and 58.2 microM, whereas the flavonol disaccharides (compounds 7 and 8), the flavanones (compounds 9 and 10), and the flavonoid-related glycosidic compounds 11-13 were only weakly active. The aglycons of compounds 7 and 8, however, were potent antimutagens (IC(50) = 10.4 and 13.0 microM, respectively).  相似文献   

19.
Eleven apocarotenoids (1-11) including five new compounds, 4, 6, 9, 10 and 11, were isolated from the fruits of the red paprika Capsicum annuum L. The structures of new apocarotenoids were determined to be apo-14'-zeaxanthinal (4), apo-13-zeaxanthinone (6), apo-12'-capsorubinal (9), apo-8'-capsorubinal (10), and 9,9'-diapo-10,9'-retro-carotene-9,9'-dione (11) by spectroscopic analysis. The other six known apocarotenoids were identified to be apo-8'-zeaxanthinal (1), apo-10'-zeaxanthinal (2), apo-12'-zeaxanthinal (3), apo-15-zeaxanthinal (5), apo-11-zeaxanthinal (7), and apo-9-zeaxanthinone (8) which have not been previously found in paprika. These apocarotenoids were assumed to be oxidative cleavage products of C(40) carotenoid such as capsanthin in paprika.  相似文献   

20.
Caper (Capparis spinosa L.) fruits have been used as food as well as folk medicine in the treatment of inflammatory disorders, such as rheumatism. The present study was carried out to study the anti-inflammatory activities of C. spinosa L. fruit (CSF) aqueous extract and to isolate main phytochemicals from its bioactive fractions. The CSF aqueous extract were separated into three fractions (CSF1-CSF3) by macroporous adsorption resins. The fractions CSF2 and CSF3 effectively inhibited the carrageenan-induced paw edema in mice. Systematic fractionation and isolation from CSF2+3 led to the identification of 13 compounds (1-13). Their chemical structures were elucidated by spectroscopic analyses including nuclear magnetic resonance (NMR) and mass spectrometry (MS) and literature comparisons. Major compounds found in the bioactive fraction CSF2+3 are flavonoids, indoles, and phenolic acids. To our knowledge, 8 of these 13 compounds (1-4, 6-7, 10, and 13) were identified from caper fruits for the first time. The anti-inflammatory effects of these purified compounds are currently under investigation.  相似文献   

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