ABSTRACT
1. Butyrolactone I (BL-I), one of the major secondary metabolites of fungus Aspergillus terreus, is a selective cdc2 kinase inhibitor. In the present study, the metabolism of BL-I in male Wistar rats was investigated by characterizing metabolites excreted into feces. 2. Following an oral dose of 40 mg/kg BL-I, 10 phase I metabolites were isolated from the feces of rats, and their structures were identified on the basis of a range of spectroscopic data and ICD analysis. These metabolites were fully characterized as butyrolactone VI (M1), aspernolide E (M2), 7''S-hydroxy-9''-ene-butyrolactone I (M3), 7''R-hydroxy-9''-ene-butyrolactone I (M4), 7â³S, 8â³R-dihydroxy-aspernolide E (M5), 7â³R, 8â³S-dihydroxy-aspernolide E (M6), 7â³R-acetyl-8â³S-hydroxy-aspernolide E (M7), 7â³S-acetyl-8â³R-hydroxy-aspernolide E (M8), 7â³R-methoxy-8â³S-hydroxy-aspernolide E (M9), butyrolactone V (M10), respectively. It is the first time to describe the metabolites of BL-I in vivo, and metabolites M3 to M9 are new compounds. 3. BL-I and metabolites M2 to M10 were evaluated for their antimicrobial activity and in vitro antiproliferative activities. Only M-3 and M-4 showed inhibitory effect against staphylococcus aureus both with MIC of 125 µg/ml. BL-I and metabolites M-4 and M-5 exhibited potent cancer cell growth inhibitory activities against HL-60 (human leukemia) cell lines with the IC50 values of 13.2, 28.8 and 35.7 µM, respectively. 4. On the basis of metabolites profile, a possible metabolism pathway for BL-I in rats has been proposed. This is the first systematic study on the phase I metabolites of BL-I.
Subject(s)
4-Butyrolactone/analogs & derivatives , 4-Butyrolactone/isolation & purification , 4-Butyrolactone/metabolism , Animals , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/metabolism , Rats , Rats, Wistar , Staphylococcus aureusABSTRACT
Two new diketopiperazines, PJ147 (1) and PJ157 (2), were isolated from the mycelium of a fungus, Gliocladium sp. YUP08, which was separated from sea mud collected in Rushan, Shandong, China. Their structures were elucidated by spectroscopical and chemical methods.
Subject(s)
Diketopiperazines/isolation & purification , Gliocladium/chemistry , Diketopiperazines/chemistry , Magnetic Resonance SpectroscopyABSTRACT
A new tannin-related compound named bistortaside A (1) and a known compound have been isolated from the rhizome of Polygonum bistorta L. A new compound was elucidated as 3-methyl-gallic acid 4-O-beta-d-(6'-O-3''-methyl-galloyl)-glucopyranoside and a known compound was quercetin-3'-O-beta-d-glucopyranoside (2) on the basis of spectroscopic analysis.
Subject(s)
Monosaccharides/chemistry , Polygonum/chemistry , Quercetin/analogs & derivatives , Rhizome/chemistry , Tannins/chemistry , Molecular Structure , Monosaccharides/isolation & purification , Quercetin/chemistry , Quercetin/isolation & purification , Tannins/isolation & purificationABSTRACT
A novel coumarone, platyphyllin A (1), was isolated from the leaves of Betula platyphylla Suk.. The structure elucidation was accomplished by the analysis of spectroscopic data. Compound 1 was identified as a new coumarone skeleton, which was first isolated from plants.
Subject(s)
Benzofurans/isolation & purification , Betula/chemistry , Benzofurans/chemistry , China , Drugs, Chinese Herbal/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Structures/chemistry , Plants, Medicinal/chemistryABSTRACT
OBJECTIVE: To isolate the chemical constituents of the peelings of Citrus grandis and determine their structure. METHOD: Column chromatography and PTLC were applied to isolating and purifying the chemical constituents, and 1H NMR and 13C NMR were used to elucidate their structure. RESULT: 4 compounds were isolated as meranzin hydrate(1), roseoside(2), 8-(3-beta-D-syl-2-hydrox-3-methylbutyl)-7-methoxycoumarin(3) and glucose(4). CONCLUSION: Compound 2 was isolated as a carotenoid from this genus for the first time.
Subject(s)
Citrus/chemistry , Glucosides/isolation & purification , Norisoprenoids , Plants, Medicinal/chemistry , Fruit/chemistry , Glucose/chemistry , Glucose/isolation & purification , Glucosides/chemistryABSTRACT
Four naphthoic acid esters including a new compound were isolated from the roots of Rubia cordifolia L. The new one was named as rubilactone and its structure was elucidated as 3'-carbomethoxy-4'-hydroxy-naphtho[1',2'-2,3] pyran-6-one (I) based on the physicochemical properties and spectrometric analyses (UV, IR, MS, 1HNMR and 13CNMR). The other three were 3'-carbomethoxy-4'-hydroxy-naphtho [1',2'-2,3] furan (II), dihydromollugin (III) and 3-carbomethoxy-2-(3'-hydroxy)isopentyl-1,4-naphthohydroquinone-1-O -beta-D-glucoside (IV).
Subject(s)
Drugs, Chinese Herbal/chemistry , Naphthols/isolation & purification , Pyrones/isolation & purificationABSTRACT
Seven anthraquinones were isolated from the ethyl alcohol extracts of the roots of Rubia Cordifolia L. By means of spectrometric data combined with physico-chemical properties, six of them were identified as 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone (I), 1-hydroxy-9,10-anthraquinone(II), 1,2,4-trihydroxy-9,10-anthrequinone(III), 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone-3-O-beta-D-glucoside(IV), 1,2-dijhydroxy-9,10-anthraquinone-2-O-beta-D-xylosyl(1-->6)-beta-D -glucoside(V) and 1,3-dihydroxy-2-hydroxymethyl1-9,10-anthraquinone-3-O-beta-D- xylosyl(1-->6)-beta-D-glucoside(VI). VII is a new compound. Its structure was elucidated to be 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone-3-O-beta-D-xylosyl(1-->2)-b eta-D- (6'-O-acetyl)glucoside.
