ABSTRACT
The present study investigated the chemical constituents from the leaves of Craibiodendron yunnanense. The compounds were isolated and purified from the leaves of C. yunnanense by a combination of various chromatographic techniques including column chromatography over polyamide, silica gel, Sephadex LH-20, and reversed-phase HPLC. Their structures were identified by extensive spectroscopic analyses including MS and NMR data. As a result, 10 compounds, including melionoside F(1), meliosmaionol D(2), naringenin(3), quercetin-3-O-α-L-arabinopyranoside(4), epicatechin(5), quercetin-3'-glucoside(6), corbulain Ib(7), loliolide(8), asiatic acid(9), and ursolic acid(10), were isolated. Compounds 1 and 2 were two new compounds, and compound 7 was isolated from this genus for the first time. All compounds showed no significant cytotoxic activity by MTT assay.
Subject(s)
Quercetin , Ericaceae , Plant Leaves , Catechin , Chromatography, High Pressure LiquidABSTRACT
Eight compounds,(R)-2-[5-(methoxycarbonyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]acetic acid(1),(3S,4R)-3,4-dihydro-3,4-epoxy-5-hydroxynaphthalen-1(2H)-one(2),(-)-mitorubrinol(3),(-)-mitorubrin(4),(±)-asperlone A(5), terreusinone(6), verrucisidinol(7) and cerebroside C(8) were isolated from the endophytic fungus Talaromyces purpurogenus by using various column chromatographic techniques. Their structures were identified by NMR, MS, CD and optical rotation. Compounds 1 and 2 were new compounds. Their anti-diabetic activities in vitro were evaluated, and compound 1 showed moderate inhibitory activity toward XOD at 10 μmol·L~(-1) with the inhibition rate of 69.9%.
Subject(s)
Endophytes/chemistry , Hypoglycemic Agents/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Secondary Metabolism , Talaromyces/chemistry , Tylophora/microbiology , Xanthine Oxidase/antagonists & inhibitorsABSTRACT
One new compound ()-2,3-dihydroxybutyl 2-hydroxy-3,5,6-trimethylbenzoate (1) and six known compounds xylariphthalide A (2), convolvulol (3), cis-4-hydroxy-6-deoxytalone (4), phomoxydienes B (5), 5,6-dihydroxy-2,3,6-trimethylcyclohex-2-enone (6), trans-cyclo-(D-tryptophanyl-L-tyrosyl) (7) were isolated from Diaporthe sp., an endophytic fungus hosted in the leaves of the toxic Chinese folk medicine Tylophora ouata, using the combination methods of silica gel column chromatography, medium-pressure ODS column chromatography and RP-preparative HPLC. The structure of compound 1 was elucidated by NMR and MS data analyses. The absolute configurations were established according to the ¹H-NMR data and exciton chirality method. Compound 1 inhibited the activation of human lung fibroblasts MRC-5 cells by 64.0% at 10 μmol·L⁻¹. The MTT assay showed that compounds 2 and 4 displayed cytotoxic activity against human tumor cell lines BGC-823 cells with IC₅₀ values of 1.5 and 8.6 μmol·L⁻¹, respectively.
ABSTRACT
Endophytic fungi Penicillium dangeardii, isolated from Lysidice rhodostegia Hance root, was fermented and the secondary metabolites were studied. By means of Sephadex LH-20 column chromatography, ODS column chromatography and PHPLC over the fermented culture, 5 compounds were isolated. By using ESI-MS and NMR, the structures of the compounds were determined as N-[9-(β- D-ribofuranosyl)-9H-purin-6-yl]-L-aspartic acid (1), 3-caffeoylquinic acid (2), 4-caffeoylquinic acid (3), and 5-caffeoylquinic acid (4), 3-hydroxy-benzoic acid-4-O-β-D-glucopyranoside (5).
Subject(s)
Biological Factors , Chemistry , Metabolism , Endophytes , Chemistry , Metabolism , Fabaceae , Microbiology , Fermentation , Molecular Structure , Penicillium , Chemistry , Metabolism , Secondary MetabolismABSTRACT
Ten compounds, including seven sesquiterpenes, two phenols and one phenylpropanoid, were isolated from the roots of Illicium majus by means of silica gel, ODS, Sephadex LH-20, and preparative HPLC. On analysis of MS and NMR spectroscopic data , their structures were established as cycloparviflorolide (1), cycloparvifloralone (2), tashironin (3), tashironin A (4), anislactone A(5), anislactone B (6), pseudomajucin (7), syringaldehyde (8), methyl-4-hydroxy-3, 5-dimethoxybenzoate (9), and (E)-3-methoxy-4,5-methylenedioxycinnamic alchol (10), respectively. Compounds 1-4 and 8-10 were first isolated from this plant. In the in vitro assays, at a concentration of 1.0 x 10(-5) mol x L(-1), compounds 5 and 6 were active against LPS induced NO production in microglia with a inhibition rate of 75.31% and 53.7%, respectively.
Subject(s)
Drugs, Chinese Herbal , Chemistry , Illicium , Chemistry , Organic Chemicals , Chemistry , Plant Roots , ChemistryABSTRACT
The chemical constituents of Periploca forrestii were studied by means of macroporous resin, silica gel, ODS column chromatography and PHPLC. Nine compounds were isolated from this plant. By using ESI-MS and NMR, the structures of the nine compounds were determined as scopoletin (1), trans-3, 4-methylenedioxycinnamyl alcohol (2), syringaresinol (3), syringaresinol 4-0-beta-D-glucopyranoside (4), 6'-0-(E)-feruloylsucrose (5), loliolide (6), 4-hydroxy-3-methoxyl-benzaidehyde (7), delta5-pregnene-3beta, 17alpha, 20alpha-triol (8) and delta5-pregnene-3 beta, 17alpha, 20 alpha-triol-20-0-beta-D-canaropyranoside (9), respectively. Compounds 1, 2 and 5-7 are isolated from Periplocagenus for the first time.
Subject(s)
Drugs, Chinese Herbal , Chemistry , Glucosides , Chemistry , Mass Spectrometry , Molecular Structure , Periploca , Chemistry , Triterpenes , ChemistryABSTRACT
Aspergillus fumigatus, a type of endophytic fungi from Erthrophleum fordii, was fermented with GPY culture medium. Fermented liquid and mycelium were extracted from fermented products after freezing and thawing treatment. After alcohol extraction, mycelium was extracted with ethyl acetate and n-butyl alcohol, respectively. According to the results of cytotoxity of tumor cells, ethyl acetate extracts were studied for their chemical constituents. Five diketopiperazine compounds were separated and purified with silica gel, MCI and Sephadex LH-20 column chromatography, reversed-phase chromatographic column and preparative HPLC, their structures were identified as cyclo- (R-Pro-R-Phe) (1), cyclo- (trans-4-OH-D-Pro-D-Phe) (2), cyclo- (R-Tyr-S-Ile) (3), cyclo-(R-Phe-S-Ile) (4), and cyclo-(R-Val-S-Tyr) (5) by using spectral methods.
Subject(s)
Humans , Aspergillus fumigatus , Chemistry , Metabolism , Cell Line, Tumor , Diketopiperazines , Chemistry , Metabolism , Pharmacology , Endophytes , Chemistry , Metabolism , Fabaceae , Microbiology , Mycelium , Chemistry , MetabolismABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents of the roots of Capparis tenera.</p><p><b>METHOD</b>The chemical constituents were isolated and repeatedly purified by kinds of column chromatography and the structures were elucidated by the NMR spectra and physicochemical properties.</p><p><b>RESULT</b>Eight compounds were isolated and identified as erigeside C (1), glucosuringic acid (2), vanillic acid 4-O-beta-D-glucoside (3-methoxy 4-glucosyl-benzoic acid) (3), 4-O-beta-D-glucopyranosylbenzoate (4), 3', 5'-dimethoxy- 4-O-beta-D-glucopyranosyl-cinnamic acid (5), tachioside (6), 2, 3-dihydroxy-1-(4-hydroxyl-3, 5-dimethoxyphenyl)-1-propanone (7) and acacetin 7-rutinoside (8).</p><p><b>CONCLUSION</b>Compounds 1-8 were all isolated from this plant for the first time and the compound 8 was isolated from this gene for the first time.</p>
Subject(s)
Capparis , Chemistry , Chromatography , Drugs, Chinese Herbal , Chemistry , Glycosides , Chemistry , Magnetic Resonance Spectroscopy , Plant Roots , Chemistry , Solubility , Water , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents of Dregea sinensis var. corrugata.</p><p><b>METHOD</b>The chemical constituents were isolated by various column chromatographic techniques. Structures were elucidated on the basis of NMR data.</p><p><b>RESULT</b>Eight compounds were isolated and their structures were elucidated as syringaresinol (1), syringaresinol-O-3-D-glycopyranoside (2), 3, 4'-dimethoxyl-4, 9, 9'-trihydroxyl-benzofuranneolignan-7'-ene (3), 3, 4'-di- methoxyl-4, 9-dihydroxyl-9'-hydroethyl-benzofuranneolignan-7'-ene (4), conifer-aldehyde (5), sinapic aldehyde (6), 3-hydoxy-1-(4-hydroxy-3-methoxy-phenyl)-propan-1-one (7), 3-hydroxy-1-(3-methoxy-4-hydroxyphenyl)-propan-1-one (8).</p><p><b>CONCLUSION</b>Compounds 1-8 were isolated from Dregea sinensis var. corrugata for the first time.</p>
Subject(s)
Apocynaceae , Chemistry , Drugs, Chinese Herbal , Chemistry , Plants, Medicinal , Chemistry , Propane , ChemistryABSTRACT
<p><b>AIM</b>To study the chemical constituents of Corallodiscus flabellata.</p><p><b>METHODS</b>Fresh plant of Corallodiscus flabellata was extracted twice with boiling water, concentrated to small volume under reduced pressure at 55 degrees C. The concentrated material was partitioned with ether, ethyl acetate, and n-butanol. The fraction of ethyl acetate extract was chromatographed over macroporous adsorption resin (Diaion HP-20) eluted with a mixture of H2O and MeOH in increasing MeOH content. Their fractions from resin were repeatedly chromatographed over Sephadex LH-20, silica gel column chromatography. The compounds were identified on the basis of their physiochemical and spectral data.</p><p><b>RESULTS</b>Seven compounds were obtained and identified as 5,3',4'-trihydroxyl-6,7-dimethoxyl-8-C-[beta-D-xylocopyranosyl-(1-->2)]- beta-D-glucopyranosyl flavone (1), 5,4'-dihydroxyl-6,7-dimethoxyl-8-C- [beta-D-xylopyranosyl-(1-->2)]-beta-D-glucopyranosyl flavone (2), 5,4'-dihydroxyl-6,7-dimethoxyl-8-C-beta-D-glucopyranosyl flavone (3), 5,4'-dihydroxyl-6,7-dimethoxyl-8-C-[beta-D-apiofuranosyl- (1-->2)]-beta-D-glucopyranosyl flavone (4), 3,4-dihydroxyl benzoyl acetic acid glycol ester (5), hydroxytyrosol (6), apocynin (7).</p><p><b>CONCLUSION</b>Compound 1 and 2 are new compounds, the others were isolated from Corallodiscus flabellata for the first time.</p>
Subject(s)
Acetophenones , Chemistry , Flavonoids , Chemistry , Glucosides , Chemistry , Glycosides , Chemistry , Magnoliopsida , Chemistry , Molecular Conformation , Molecular Structure , Phenylethyl Alcohol , Chemistry , Plants, Medicinal , ChemistryABSTRACT
<p><b>AIM</b>To study the antivirus chemical constituents of Corallodiscus flabellata.</p><p><b>METHODS</b>The compounds were isolated with macroporous absorption resin, Diaion HP-20, Sephadex LH-20, silica gel column chromatography and identified on the basis of their physio-chemical and spectral data.</p><p><b>RESULTS</b>Four compounds were obtained and identified as 1'-O-beta-D-(3,4-dihydroxyphenyl)-ethyl-6'-O-vanilloylglucopyranoside (1); 1'-O-beta-(4-hydroxyphenyl)-ethyl-beta-D-apiofuranosyl-(1-->2')-glucopyranoside (2); 4-hydroxyphenethyl alcohol (3); bis (2-hydroxyethyl) ether (4).</p><p><b>CONCLUSION</b>Compound 1 is a new compound, compounds 2-4 were isolated from Corallodiscus flabellata for the first time.</p>