Direct biodegradation of eugenol to coniferyl aldehyde and other higher value-added products by Gibberella fujikuroi ZH-34

BACKGROUND: Eugenol is an economically favorable substrate for the microbial biotransformation of aromatic compounds. Coniferyl aldehyde is one kind of aromatic compound that is widely used in condiment and medical industries; it is also an important raw material for producing other valuable products such as vanillin and protocatechuic acid. However, in most eugenol biotransformation processes, only a trace amount of coniferyl aldehyde is detected, thus making these processes economically unattractive. As a result, an investigation of new strains with the capability of producing more coniferyl aldehyde from eugenol is required. RESULTS: We screened a novel strain of Gibberella fujikuroi, labeled as ZH-34, which was capable of transforming eugenol to coniferyl aldehyde. The metabolic pathway was analyzed by high-performance liquid chromatography­mass spectrometry and transformation kinetics. The culture medium and biotransformation conditions were optimized. At a 6 h time interval of eugenol fed-batch strategy, 3.76 ± 0.22 g/L coniferyl aldehyde was obtained, with the corresponding yield of 57.3%. CONCLUSIONS: This work improves the yield of coniferyl aldehyde with a biotechnological approach. Moreover, the fed-batch strategy offers possibility for controlling the target product and accumulating different metabolites

Chemical constituents from stems of Acanthopanax henryi / 中草药

Objective To study the chemical constituents from stems of Acanthopanax henryi based on LPS-induced macrophages RAW264.7 and microglia BV2 as the bioactivity guided model. Methods The compounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography, as well as Prep-TLC and recrystallization methods. Their structures were identified on the basis of their physicochemical properties and spectroscopic data. Results Eighteen compounds were obtained from A. henryi and their chemical structures were identified as p-hydroxybenzoic acid (1), trans-p-hydroxycinnamic acid (2), (E)-caffeic acid methyl ester (3), caffeic acid (4), trans-coniferyl aldehyde (5), syringaldehyde (6), vanillin (7), 6-methoxy-7-hydroxycoumarin (8), trans-sinapaldehyde (9), undecane-1,11-dioic acid monomethyl ester (10), (-)-sesamin (11), 3-O-caffeoyl-quinic acid (12), 5-O-caffeoyl-quinic acid (13), 1,3-di-O-caffeoyl-quinic acid (14), 1,4-di-O-caffeoyl-quinic acid (15), 1,5-di-O-caffeoyl-quinic acid (16), stigmasterol (17), and β-sitosterol (18), respectively. Conclusion To the best of our knowledge, compound 10 was isolated from Araliaceae for the first time. Except compounds 12, 14, 17, and 18, all of other compounds were obtained from this species for the first time.

Chemical constituents of Phyllanthus emblica and its anti-inflammation activities / 中草药

Objective: To study the chemical constituents and its anti-inflammtory activity effect of Phyllanthus emblica. Methods: The chemical constituents of P. emblica were isolated and purified by silica gel column chromatography, ODS column chromatography, Sephadex LH-20 column chromatography, semi-preparative high-performance liquid chromatography and recrystallization method. Through their spectra data, physical and chemical properties analysis, the structures of those compounds with high content were identified. LPS-induced RAW264.7 inflammatory cell model was established to evaluate the effect of compounds in P. emblica on proinflammatory factors (NO, IL-6, TNF-α, and MCP-1) of RAW264.7 inflammatory cells. Results: Totally, 14 compounds were isolated from P. emblica. and idetified as isovanillic acid (1), trans-cinnamic acid (2), p-hydroxybenzaldehyde (3), coniferyl aldehyde (4), quercetin (5), kaempferol-3-O-α-L-rhamnose (6), naringenin (7), 2-hydroxy-3-methyl phenylpropiolate (8), hydroquinone (9), myricetin (10), 2-furoic acid (11), methyl gallate (12), protocatechuic acid (13), gallic acid (14). The experiment of anti-inflammatroy effects showed that those compounds had different inhibitory effects on the production of inflammatory factors NO, IL-6, TNF-α and MCP-1. Conclusion: Compounds 1, 3, 4, 8-11 and 13 are isolated from P emblica for the first time. The anti-inflammatory effect of P. emblica is related to its phenolic acids.

Domain Analysis and Isolation of Coniferyl Alcohol Dehydrogenase Gene from Pseudomonas nitroreducens Jin1.

Aim: The Aim of present study is to analyse conserved functional Short Dehydrogenase Reductase (SDR) domain from bacteria. Based on the domain analysis selection of coniferyl alcohol dehydrogenase gene for isolation from Pseudomonas nitroreducens Jin1. Place and Duration of Study: Department of Biotechnology, Punjabi University, Patiala. From July, 2012 to November, 2012. Methodology: Bioinformatics tools were used to analyse various calA genes from bacteria based on the presence of conserved domain in members of SDR family. Based on insilico analysis, Pseudomonas nitroreducens Jin1 calA was selected. PCR was used for amplification of the gene from the genome of Pseudomonas nitroreducens Jin1. Result: Multiple sequence alignment results for conserved domains amongst members of SDR family identified presence of all domains of Short Dehydrogenase Reductase members in Pseudomonas nitroreducens Jin1 calA gene. Amongst the various sequences compared the P. nitroreducens Jin1, calA was found to be the smallest in size. The locus of calA in the genome resides at 103513-104280 bases. It was amplified from the genome of Pseudomonas nitroreducens Jin1. The calA gene that was amplified is of size 768bp. Conclusion: calA gene isolated from Pseudomonas nitroreducens Jin1 is a small gene with all the functional domains and can be used for biotransformation of coniferyl alcohol to coniferyl aldehyde.

Chemical constituents from Gnaphlium affine / 中草药

Objective: To investigate the chemical constituents from the stems of Gnaphlium affine. Methods: The constituents were isolated and purified by silica gel, Sephadex LH-20 column chromatography, and preparative TLC. The structures were identified on the basis of spectral data and physiochemical characteristics. Results: Fifteen compounds were isolated from 70% ethanol extracts of G. affine and identified as 3-methoxyphenol1-O-α-L-rhamnopyranosyl-(1→6)-O-β- D-glucopyranoside (1), 3', 5-dihydroxy-2-(4- hydroxybenzyl)-3-methoxybibenzyl (2), physcion (3), aldehyde (4), luteolin-4'-O-β-D-glucoside (5), faradiol 3-O-palmitate (6), betulinic acid (7), anabellamide (8), 4-O-D-glucopyranosyl-p-coumaric acid methyl ester (9), valene-1 (10)-ene-8, 11-diol (10), longumoside A (11), grossamiade K (12), quercetin-3-O-rutin-7-O-glucoside (13), luteolin-7-O-β-D-glucopyranosyl-(1→6)-[(6'''- O-caffeoylquinic)-β-D-glucopyranoside] (14), and isoverbascoside (15). Conclusion: Compounds 2 and 11 are reported from the plants in Gnaphalium L. for the first time. Compounds 2, 3, 6, 8, 13, and 14 are isolated from this plant material for the first time.

Chemical constituents from stems of Ficus auriculata / 中草药

Objective: To investigate the chemical constituents from the stems of Ficus auricalata. Methods: The constituents were isolated and purified by silica gel, Sephadex LH-20 column chromatography, and preparative TLC. Their structures were identified on the basis of spectral data and physiochemical characteristics. Results: Fourteen compounds were isolated from 95% ethanol extracts and identified as stigmast-4-ene-6β-ol-3-one (1), stigmast-4-ene-6α-ol-3-one (2), stigmast-4-ene-3-one (3), stigmast-5-ene-3β-ol-7-one (4), stigmast-4-ene-3, 6-dione (5), ergosterol peroxide (6), (20S)-3-oxo-hydroxytaraxastane (7), anabellamide (8), aurantiamide acetate (9) palmarumycin BG1 (10), 7-oxodehydroabietic acid (11), coniferyl aldehyde (12), S-(+)-dehydrovomifoliol (13), and 4-hydroxy-3-methoxy-benzoic acid (14). Conclusion: Compounds 2, 5, and 7-13 are reported from the plants in genus Ficus Linn. for the first time. All compounds are isolated from this plant material for the first time.

Chemical constituents of Syringae Cortex / 中国药学杂志

OBJECTIVE: To study the chemical constituents of Syringae Cortex. METHODS: The compounds were isolated and purified by silica (200-300), pre-HPLC and Sephadex LH-20 column chromatography. The structures were identified on the basis of spectral data and physiochemical properties. RESULTS: Twelve compounds were isolated and identified as syringin(I), sinapylal-dehyde 4-O-β-D-glucopyranoside(II), syringaldehyde(III), coniferyl aldehyde(IV), betulinic acid(V), oleuroprin(VI), oleoside dimethyl ester(VII), ligstroside(VIII), 2″-epifraxamoside (DC), β-sitosterol(X), n-triaconatanoic acid(XI) and 2-(4-hydroxyphe-nyl)-ethyl-l-dodecyloctadecanoate) (XII). CONCLUSION: Compounds II-V, VII and XI-XII are isolated from this plant for the first time.

Chemical constituents of Opuntia milpa (I) / 中草药

Objective: To investigate the chemical constituents of Opuntia milpa. Methods: The compounds were isolated by repeated silica gel chromatography and were elucidated by chemical and spectral analyses. Results: Ten compounds were isolated from the ethyl acelate extraction of O. milpa and identified as β-sitosterol (1), 1-heptadecanol (2), 5-hyadroxymemyl-2-furancarboxaldehyde (3), syringaldehyde (4), vanillin (5), p-hydroxybenzaldehyde (6), coniferyl aldehyde (7), p-hydroxyl-cinnamaldehyde (8), quercetin-3-methyl ether (9), and 2,6-dimethoxyphenol (10). Conclusion Compounds 3-10 are isolated from O. milpa for the first time.