To study the chemical constituents from the stems and leaves of Humulus scandens, this study isolated thirteen compounds by different chromatographic methods including silica gel column, ODS, Sephadex LH-20 and preparative HPLC. Based on comprehensive analysis, the chemical structures were elucidated and identified as citrunohin A(1), chrysosplenetin(2), casticin(3), neoechinulin A(4), ethyl 1H-indole-3-carboxylate(5), 3-hydroxyacetyl-indole(6),(1H-indol-3-yl) oxoacetamide(7), inonotusic acid(8), arteannuin B(9), xanthotoxol(10), α-tocopherol quinone(11), eicosanyl-trans-p-coumarate(12), and 9-oxo-(10E,12E)-octadecadienoic acid(13). Among them, compound 1 was a new dihydrochalcone, and the other compounds were obtained from H. scandens for the first time.
Humulus ; Chalcones ; Indoles ; Drugs, Chinese Herbal/chemistry*

AIMTo investigate the chemical constituents of tetraploidy Banlangen (Isatis indigotica Fort.).

METHODSCompounds were separated by chromatography on silica gel. Their structures were determined by spectral analysis and chemical evidence.

RESULTSThree compounds were isolated. Their structures were identified as (E)-2-[(3'-indole) cyanomethylene]-3-indolinone (I), 2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxy-phenyl)-methyl]-3- hydroxymethyl-tetrahydro-furan (II) and 2-methoxy-4-[tetrahydro-4-[(4-hydroxy-3-methoxy-phenyl)-methyl]-3- hydroxymethyl-2-furanyl] phenyl-1-O-beta-D-glucopyranoside (III).

CONCLUSIONCompound I is a new compound.

Indoles ; chemistry ; Isatis ; chemistry ; genetics ; Molecular Structure ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; genetics ; Polyploidy

Chuangxinmycin (CM) from Actinoplanes tsinanensis was an antibiotic discovered by Chinese scientists about 40 years ago. It contains a new heterocyclic system of indole fused with dihydrothiopyran, whose biosynthetic mechanism remains unclear. CM is used as an oral medicine in the treatment of bacterial infections in China. The simple structure makes CM as an attractive candidate of structure modification for improvement of antibacterial activity. Recently, we analyzed the secondary metabolites of Actinoplanes tsinanensis CPCC 200056, a CM producing strain, as a natural CM analogue. We discovered the first natural CM analogue 3-demethylchuangxinmycin (DCM) as a new natural product. Compared to CM, DCM exhibited a much weaker activity in the inhibition of the bacterial strains tested. The finding provides valuable information for the structure-activity relationship in the biosynthesis of CM.
Anti-Bacterial Agents ; chemistry ; isolation & purification ; China ; Indoles ; chemistry ; isolation & purification ; Micromonosporaceae ; chemistry ; Structure-Activity Relationship

AIMTo study the synthesis of 5-(3'-indolyl)-oxazoles and their antioxidative activity.

METHODSThe amides were prepared from tryptophan and different acid derivatives by the catalytic dehydration of dicyclohexyl carbodiimide (DCC). The characteristic heterocyclic ring system of 5-(3'-indolyl)-oxazoles was constructed by oxidative cyclization of amide, using dicholorodicyanoquinone (DDQ). Their antioxidative activity in vitro was tested using DPPH system.

RESULTSEleven 2-substituted phenyl-5-(3'-indolyl)-oxazoles were prepared, the compounds 21 and 22 have shown antioxidative activity 3-4 times stronger than that of Vit E, and the compound 29 showed antioxidative activity almost as same as Vit E.

CONCLUSIONThree 5-(3'-indoyl)-oxazole compounds synthesized showed potent antioxidative effect and they would be a good antioxidants.

Antioxidants ; chemical synthesis ; chemistry ; Indoles ; chemistry ; isolation & purification ; Molecular Structure ; Oxazoles ; chemistry ; isolation & purification

OBJECTIVETo study the chemical constituents of Hedysarum polybotrys.

METHODChromatographic methods were used to isolate compounds from H. polybotrys and chemical and spectral methods were used to elucidate the structures of the isolated compounds.

RESULTFive compounds, N,N,N-trimethyl-tropaphone inner salt (hypaphorine) (1), octadecyl-3-methoxy-4-hydroxy-benzeneacrylate (2), 5,7,4'-trihydroxy-dihydroflavanone 5,7-di-O-beta-D-glucopyranoside (3), 3,4,5-trimethoxy cinnamic acid methy ester (4) and vanillic acid (5), were isolated from the roots of H. polybotrys.

CONCLUSIONCompounds 1, 2 and 3 were obtained from this plant for the first time, while compounds 1 and 2 were isolated from Hedysarum for the first time.

Acrylates ; chemistry ; isolation & purification ; Fabaceae ; chemistry ; Indoles ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry

Taking application of some isolation and purification technologies, such as solvent extraction, preliminary solvent isolation, column chromatographies over silica gel and Sephadex LH-20 gel and preparative HPLC, 10 compounds were obtained from Gynura nepalensis cultivated in the suburban area of Beijing. Their structures were identified by spectroscopic methods and comparison with literature as (3R) -3-hydroxy-β-ionone (1), (3S,5R, 6S, 7E) -5, 6-epoxy-3-hydroxy-7-megastigmen-9-one (2), (+) -boscialin (3), 3, 6-trans-3-hydroxy-α-ionone (4), 3, 6-cis-3-hydroxy-α-ionone (5), 3, 4-cis-3, 4-dihydroxy-β-ionone (6), ethyl caffeate (7), loliolide (8), 1H-indole-3-carbaldehyde (9), and 3-(hydroxyacetyl)indole (10), respectively. All compounds were isolated from the title plant for the first time, and with compounds 1, 2, 4-7, 9 and 10 being isolated from Gynura species for the first time. Structurally, the above compounds 1-6 belong to C13 nor-sesquiterpenoids, sharing the same carbon skeleton of megastigmane. According to this study, they are one of major kinds of chemical constituents of Gynura nepalensis and have important reference value for the investigation on phytotaxonomy of this species.
Asteraceae ; chemistry ; Caffeic Acids ; chemistry ; Cyclohexanones ; Drugs, Chinese Herbal ; chemistry ; Glucosides ; Indoles ; chemistry ; Mass Spectrometry ; Molecular Structure ; Norisoprenoids ; chemistry

OBJECTIVETo study the chemical constituents of the leaf of Isatis indigotica.

METHODChromatography and spectral analysis were respectively used to isolate and identify the constituents.

RESULTThree compounds were isolated from the ethanol extracts of theleaf of I. indigotica, and identified as indirubin, tryptanthrin and L-pyroglutamic acid.

CONCLUSIONL-pyroglutamic acid was isolated from the genus for the first time, and tryptanthrin was isolated from the leaf of this plant for the first time.

Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Indoles ; chemistry ; isolation & purification ; Isatis ; chemistry ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Pyrrolidonecarboxylic Acid ; chemistry ; isolation & purification ; Quinazolines ; chemistry ; isolation & purification

Three compounds were isolated from solid culture of endophyte Myrothecium roridum IFB-E091 in Artemisia annua. Their structures were determined as (S)-(-)-N-[2-(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-ethyl]-acetamide (1), N-(4-hydroxyphenethyl)acetamide (2) and asperfumoid (3), in which compound 1 was a new indole derivative. In cytotoxicity assay, the compound 1 had no obvious inhibition activity in human hepatoma cell line SMMC-7721 and human cervical carcinoma cell line HeLa.
Artemisia annua ; microbiology ; Cell Line, Tumor ; drug effects ; Endophytes ; chemistry ; Humans ; Hypocreales ; chemistry ; Indoles ; chemistry ; isolation & purification

OBJECTIVETo study the chemical constituents in the root of Cichorium intybus.

METHODThe compounds were isolated and identified by column chromatography and NMR, IR, MS data.

RESULTTwelve compounds were isolated and identified.

CONCLUSION2,3,4,9-tetrahydro-1H-pyrido-(3,4-b)indole-3-carboxylic acid was isolated from the Cichorium genus for the first time, azelaic acid and daucosterol were isolated from the the plant for the first time.

Chicory ; chemistry ; Dicarboxylic Acids ; chemistry ; isolation & purification ; Indoles ; chemistry ; isolation & purification ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Sitosterols ; chemistry ; isolation & purification

Accessed to literatures at home and abroad, we introduced the process of indigo naturalis transforming from dyestuff industry into pharmaceutical industry. It is affirmed that the precursors of indigo and indirubin are isatan A, isatan B, isatan C and indicant. Meanwhile, author clarified the mechanism of transformation for these precursors transforming into indigo and indirubin. And we summarized methods of determination for these precursors. In summary, these references provide us accordance of study on processing principle of Indigo naturalis, and lay the foundation for technics of making indigo and indirubin entering into modern industry.
Indigo Carmine ; Indoles ; chemistry ; metabolism ; Oxidation-Reduction ; Pigmentation ; Plants ; metabolism ; Temperature