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Frontiers of Chemical Science and Engineering 2021年第3期15卷 615-629页

作者： Yu Xin Qiuyue Gao Yu Gu Mengyao Hao Guangming Fan Liang Zhang Key laboratory of Industry Biotechnology(Ministry of Education) School of BiotechnologyJiangnan UniversityWuxi 214122China National Engineering laboratory for Cereal Fermentation Technology Jiangnan UniversityWuxi 214122China

A cholesterol oxidase(COD)was hybridized with Ca^(2+),Zn^(2+),Al^(3+),Fe^(2+) and Mn^(2+).After precipitation with PO_(4)^(3-) at 4℃ for 72 h,the resulting pellets were *** scanning electron microscopy assays,the metal-COD complexes revealed flower-like or granular structures after *** transform infrared spectroscopy assay revealed the characteristic peaks of both the enzyme and metal materials.X-ray diffraction analysis indicated that COD was encapsulated in CaHPO_(4)·2H_(2)O-,Zn_(3)(PO_(4))_(2)·4H_(2)O-,AlPO_(4-),FeP_(4-) and Mn_(3)(PO_(4))_(2)·3H_(2)O-based nanostructures,*** scanning calorimetry assay indicated significant increases in thermo-denaturation temperatures from 60.5℃ to 167.02℃,167.02℃,137.70℃,172.85℃ and 160.99℃,*** steroid derivatives as substrates,this enzyme could convert cholesterol,pregnenolone,dehydroepiandrosterone,ergosterol,b-sitosterol and stigmasterol to related single *** in metal-based nanostructures could significantly enhance the initial conversion ratio and reaction stability of the *** addition,substrate selectivity could be affected by various metal ***,using Ca^(2+),Zn^(2+),Al^(3+),Fe^(2+) and Mn^(2+) as hybrid raw materials could help to encapsulate COD in related metal-enzyme nanostructures,and could help to promote the stability and tolerant properties of the enzyme,while also enhancing its catalytic characteristics.

关键词： cholesterol oxidase metal-enzyme hybridization nanostructures sterol derivatives bioconversion

Low-protein diet accelerates wound healing in mice post-acute injury

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Burns & Trauma 2021年第1期9卷 339-350页

作者： Jonathan J.Hew Roxanne J.Parungao Craig P.Mooney Julian K.Smyth Sarah Kim Kevin H.-Y.Tsai Huaikai Shi Cassandra Chong Renee C.F.Chan Beba Attia Caroline Nicholls Zhe Li Samantha M.Solon-Biet David G.Le Couteur Stephen J.Simpson Marc G.Jeschke Peter K.Maitz Yiwei Wang Burns Research and Reconstructive Surgery ANZAC Research InstituteConcord HospitalUniversity of SydneySydneyAustralia 2139 Bone Biology Group ANZAC Research InstituteConcord HospitalUniversity of SydneySydneyAustralia 2139 adrenal steroids laboratory ANZAC Research InstituteConcord HospitalUniversity of SydneySydneyAustralia 2139 Electron Microscopy Unit Anatomical PathologyConcord HospitalSydneyAustralia 2139 Burns Unit Concord Repatriation General HospitalConcordAustralia 2139 Ageing and Alzheimer Institute and ANZAC Research Institute Concord HospitalUniversity of SydneySydneyAustralia 2139 Charles Perkins Centre and School of Life and Environmental Sciences University of SydneyAustralia 2006 Sunnybrook Research Institute TorontoOntarioCanadaM4N 3M5 School of Pharmacy Nanjing University of Chinese MedicineNanjingPR China 210023

Background:Wound healing processes are influenced by macronutrient intake(protein,carbohydrate and fat).The most favourable diet for cutaneous wound healing is not known,although highprotein diets are currently favoured *** experimental study investigates the optimal macronutrient balance for cutaneous wound healing using a mouse model and the Geometric Framework,a nutrient modelling method,capable of analyzing the individual and interactive effects of a wide spectrum of macronutrient ***:Two adjacent and identical full-thickness skin excisions(1 cm^(2))were surgically created on the dorsal area of male C57BL/6 *** were then allocated to one of 12 high-energy diets that varied in protein,carbohydrate and fat *** select diets,wound healing processes,cytokine expression,energy expenditure,body composition,muscle and fat reserves were ***:Using the Geometric Framework,we show that a low-protein intake,coupled with a balanced intake of carbohydrate and fat is optimal for wound *** fed a low-protein diet progressed quickly through wound healing stages with favourable wound inflammatory cytokine expression and significantly accelerated collagen *** local processes were associated with an increased early systemic inflammatory response and a higher overall energy expenditure,related to metabolic changes occurring in key macronutrient reserves in lean body mass and fat ***:The results suggest that a low-protein diet may have a greater potential to accelerate wound healing than the current clinically used high-protein diets.

关键词： Wound healing Macronutrients Cutaneous Geometric Framework Mouse model Low-protein diet Nutrition

steroids hydroxylation catalyzed by the monooxygenase mutant 139-3 from Bacillus megaterium BM3

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Acta Pharmaceutica Sinica B 2017年第4期7卷 510-516页

作者： Xing Liu Jian-qiang Kong State Key laboratory of Bioactive Substance and Function of Natural Medicines&Ministry of Health Key laboratory of Biosynthesis of Natural Products Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

The search of new substrates with pharmaceutical and industrial potential for biocatalysts including cytochrome P450 enzymes is always challenging. Cytochrome P450 BM3 mutant 139-3, a versatile biocatalyst, exhibited hydroxylation activities towards fatty acids and alkanes. However, there were limited reports about its hydroxylation activity towards steroids. Herein, an Escherichia coli-based whole-cell extract containing the recombinant 139-3 protein was used as the biocatalyst to screen 13 steroids. Results revealed that 139-3 was able to specifically hydroxylate androstenedione (1) at 1α-position, generating a hydroxylated steroid 1α-OH-androstenedione (1a). To investigate whether C-1α hydroxylation catalyzed by BM3 mutant 139-3 could be industrially used, an optimization of catalyzing conditions was performed. Accordingly, the BM3 mutant 139-3 enzyme was observed to display maximum activity at 37 °C, under pH 7.0 for 4 h, with 37% transformation rate. Moreover, four 139-3 variants were generated by random mutagenesis with the aim of improving its activity and expanding substrate scope. Surprisingly, these mutants, sharing a common mutated site R379S, lost their activities towards androstenedione (1). These data clearly indicated that arginine residue located at site 379 played key role in the hydroxylation activities of 139-3. Overall, these new findings broadened the substrate scope of 139-3 enzyme, thereby expanding its potential applications as a biocatalyst on steroids hydroxylation in pharmaceutical industry.

关键词： Cytochrome P450 BM3 139-3 steroids hydroxylation 1α-OH-androstenedione Biocatalyst

Multi-Residue Determination of Eight Anabolic steroids by GC-MS in Muscle Tissues from Pigs

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Agricultural Sciences in China 2010年第2期9卷 306-312页

作者： ZENG Dong-ping, LIN Cui-ping, ZENG Zhen-ling, HUANG Xian-hui and HE Li-min laboratory of Veterinary Pharmacology, College of Veterinary Medicine, South China Agricultural University, Guangzhou 510640, P.R. China laboratory of Veterinary Pharmacology College of Veterinary Medicine South China Agricultural University Guangzhou 510640 China

A gas chromatography-mass spectrometry （GC-MS） method to determine eight anabolic steroids （diethylstilbestrol, methyltestosterone, norethindrone, 17α-ethynylestradiol, estradiol, 6α-methyl-17α-hydroxy-progesterone, estradiol benzoate, and chlormadinone acetate） was developed. Muscle samples were extracted with liquid-liquid extraction and clean-up was performed in two steps, the extracts obtained were derivatized with heptafluorbutyric （HBF） anhydride and analyzed by GC-MS. In the above method, the linear scope was 2.5-50 μg kg^-1. The range of the recoveries was 78.5-148% for diethylstilbestrol, 70.8-109% for methyltestosterone, 69.8-87.2% for norethindrone, 67.7-120% for 17α-ethynylestradiol, 82.8-103% for estradiol, 70.3-99.2% for 6α-methyl-17α-hydroxy-progesterone, 73.0-104% for estradiol benzoate, and 72.9- 91.8% for chlormadinone acetate. The range of the coefficients of variation within batches was 0.4-12%; the range of the coefficients of variation between batches was 6.4-11%. The limit of detections and the detection capability were 0.99 and 3.30 μg kg^-1 for diethylstilbestrol, 1.05 and 3.50 μg kg^-1 for methyltestosterone, 1.19 and 3.97 μg kg^-1 for norethindrone, 0.94 and 3.13 μg kg^-1 for 17α-ethynylestradiol, 1.45 and 4.83 μg kg^-1 for estradiol, 1.56 and 5.20 μg kg^-1 for 6α-methyl-17α- hydroxy-progesterone, 1.92 and 6.40 μg kg^-1 for estradiol benzoate, and 2.41 and 8.03 μg kg^-1 for chlormadinone acetate, respectively. These results showed that the method was widely available, accurate, and sensitive.

关键词： anabolic steroids GC-MS multi-residue determination pigs

Four new polyhydroxylated steroids from the South Sea sponge Plakortis sp.

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Chinese Journal of Natural Medicines 2020年第11期18卷 844-849页

作者： WANG Kun-Ya LI Ping-Lin SUN Jing-Fan de Voogd Nicole J TANG Xu-Li LI Guo-Qiang Key laboratory of Marine Drugs Chinese Ministry of EducationSchool of Medicine and PharmacyOcean University of ChinaQingdao 266003China laboratory of Marine Drugs and Biological Products National Laboratory of Marine Science and TechnologyQingdao 266235China National Museum of Natural History PO Box 95172300 RA Leidenthe Netherlands Collge of Chemistry and Chemical Engineering Ocean Universiy of ChinaQingdao 266100China

Four new polyhydroxylated steroids plaksterols A–D(1–4), together with two known related steroids ergost-7,9(11),22-trien-3β,5α,6α-triol(5) and ergosta-6β-methoxy-7,22-diene-3β,5α-diol(6), were isolated from methanol extract of the South China Sea marine sponge Plakortis sp. Their structures were identified by spectroscopic analysis, including NMR, MS, and IR. The cytotoxicity of the polyhydroxylated steroids were evaluated, and compound 6 showed moderate inhibitory activities against K562, HL-60 and BEL-7402 cells.

关键词： Polyhydroxylated steroids Plakortis sp. Cytotoxic activity

steroids and dihydroisocoumarin glycosides from Xylaria *** the one strain many compounds strategy and their bioactivities

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Chinese Journal of Natural Medicines 2023年第2期21卷 154-160页

作者： GAN Dong LI Chenzhe SHU Yan WANG Jiapeng WANG Chengyao ZHU Li YANG Yujun LIU Jiaqi HE Bijian CAI Le DING Zhongtao Functional Molecules Analysis and Biotransformation Key laboratory of Universities in Yunnan Province Key Laboratory of Medicinal Chemistry for Natural ResourceMinistry of EducationSchool of Chemical Science and TechnologyYunnan UniversityKunming 650091China College of Pharmacy Dali UniversityDali 671003China

The fungus Xylaria ***-15 was isolated from Illigera *** on the one strain many compounds(OSMAC)strategy,the strain was fermented on potato and rice solid media,*** a result,two novel steroids,xylarsteroids A(1)and B(2),which are the first examples of C28-steroid with an unusualβ-andγ-lactone ring,respectively,along with two new dihydroisocoumarin glycosides,xylarglycosides A(3)and B(4),were *** structures were elucidated by spectroscopic methods,X-ray diffraction and electronic circular dichroism(ECD)*** isolated compounds were evaluated for cytotoxicity,DPPH radical scavenging activity,acetylcholinesterase inhibitory and antimicrobial *** 1 exhibited potent AChE inhibitory activity with an IC50 value of 2.61±0.05μmol·L^(−1).Theβ-lactone ring unit of 1 is critical for its AChE inhibitory *** finding was further confirmed through exploring the interaction of 1 with AChE by molecular *** addition,both compounds 1 and 2 exhibited obvious antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration(MIC)of 2μg·mL^(−1).Compounds 3 and 4 exhibited antibacterial activities against Staphylococcus aureus with MICs of 4 and 2μg·mL^(−1),respectively,which also exhibited DPPH radical scavenging activity comparable to the positive control with IC50 values of 9.2±0.03 and 13.3±0.01μmol·L^(−1),respectively.

关键词： Xylaria sp. OSMAC strategy Secondary metabolite Bioactivity

Structural Modification for Antitumor Nitrogenous steroids

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Chinese Journal of Structural Chemistry 2017年第12期36卷 2007-2019页

作者：谢田鹏杨康张立志陈德胜邹坤黄年玉 Hubei Key laboratory of Natural Products Research and Development College of Biological and Pharmaceutical Sciences China Three Gorges University

Natural steroids have been showing notable cytotoxic activities, which are quite interesting lead compounds for the development of anticancer drug including estramustine and prednimustine. Considering that these semi-synthetic molecules are nitrogen mustard functionalized steroidal derivatives, the present review is focused on the methodologies of introducing nitrogen atom or nitrogen-containing heterocycles on A^D rings or side chains of steroids, and analysis of the structure-activity relationship（SAR） for these man-made cytotoxic steroids.

关键词： steroids structural modification N-hetercycles antitumor structure-activity relationship

Ecdysteroids： the overlooked sex steroids of insects？ Males： the black box

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Insect Science 2006年第5期13卷 325-338页

作者： ARNOLD DE LOOF laboratory for Developmental Physiology Genomics and Proteomics Zoological Institute K.U. Leuven Leuven Belgium

The paradigm, still around in textbooks, that ＇in insects sex is strictly genetic, thus that they do not have sex hormones＇, is mainly based on a wrong interpretation of the ＇gynandromorph argument＇. It is no longer tenable. Given the fact that vertebrates and invertebrates probably had a common, sexually reproducing ancestor, there is no reason to assume that only vertebrates need sex hormones. The major function of sex hormones is to inform the somatoplasm about developmental changes that take place in the gonads. In contrast to juvenile hormone and neuropeptides, ecdysteroids meet all criteria to act as sex hormones, which was probably their ancient role. Their much better documented role in moulting and metamorphosis was a secondary acquisition that enabled arthropods to cope with growth problems, imposed by a rigid cuticle. Female insects use 20-hydroxyecdysone （20E）, secreted by the follicle cells of the ovary, in a similar way as females of egg-laying vertebrates use estrogens. For a variety of reasons, the possibility that ecdysteroids, in particular ecdysone （E）, might also act as sex hormones in male insects, thus as the counterpart of testosterone of vertebrates, has been very much overlooked. Thanks to the recent discovery of the molecular basis of the haploid-diploid system of sex determination in the honeybee, the characterization of Halloween genes, proteomics, RNAi and so on, it now becomes possible to verify whether in insects, as with vertebrates, males are the endocrinologically default gender form.

关键词： ecdysone gynandromorph Halloween genes 20-hydroxylase juvenilehormone sex determination

Three Polyoxygenated steroids from the South China Sea Gorgonian Coral Subergorgia reticulata

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Chinese Journal of Chemistry 2005年第9期23卷 1218-1222页

作者：杨晋漆淑华张偲吴军肖志会 Guangdong Key laboratory of Marine Materia Medica South China Sea Institute of Oceanology Chinese Academy of Sciences Guangzhou Guangdong 510301 China Hainan Key laboratory of Tropical Marine Biology and Technology.South China Sea Institute of Oceanology Chinese Academy of Sciences Sanya Hainan 572000 China

Two new polyoxygenated steroids, reticulatic acid （1） and reticulatin （2）, together with a known compound 3,22,25-trihydroxy-16-24,20-24-bisepoxy-3β,16β,20S,22R,24S-cholest-5-ene （3）, were isolated from the CH2Cl2/ EtOH extract of the South China Sea gorgonian coral Subergorgia reticulata. Their structures were established on the basis of extensive spectroscopic analysis. The absolute stereochemistry of compounds 2 and 3 was determined by the X-ray crystallographic analysis and the Mosher ester determination.

关键词： Subergorgia reticulata steroid spectroscopic analysis X-ray Mosher ester

Elution of 17α 25-Norhopanes and Triaromatic steroids from Weathered Soils by Mixed Triton X-100/Na_2SiO_3 Surfactant Solution

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Chemical Research in Chinese Universities 2012年第3期28卷 419-423页

作者： JI Guo-dong ZHOU Guo-hui Key laboratory of Water and Sediment Sciences Ministry of EducationDepartment of Environmental EngineeringPeking UniversityBeo'ing 100871P.R.China

Sodium silicate（NazSiO3） was used to improve the elution of super heavy oil from weathered soil on an ultrasound-enhanced elution system by the solution containing 0-6000 mg/L surfactant Triton X-100. The removal extent of three markers[C26-34 17a 25-norhopanes, C26-28triaromatic steroids（TAS）, and C27-29methyl triaromatic steroids（MTAS）] was monitored. The average elution percentages of C26-34 norhopanes, C26-28 TAS, and C27-29 MTAS by Triton X-100/Na2SiO3 solutions were increased by 11%-13%, 9%-11% and 8%-13% with increasing Triton X-100 concentrations from 150 mg/L to 6000 mg/L. All the concentrations of Triton X-100 improved the elu- tion of TAS homologs containing fewer carbon atoms, whereas high concentrations improved the elution of larger 17a 25-norhopane and MTAS species. Addition of Na2SiO3 produced a noticeable increase in elution, particularly for lower-weight species. Scanning electron microscope（SEM） images and energy spectroscopy data reveal that surfac- rant solution of 6000 mg/L Triton X-100 and 4000 mg/L Na2SiO3 produced the greatest improvement in the elution of super heavy oil aggregates encapsulating the soil surface and the emulsification of particle dispersions. That is to say mixed solutions of Triton X-100 and Na2SiO3 in combination with ultrasound are a potential means of removing super heavy oil from weathered soils.

关键词： Triton X-100 surfactant solution Na2SiO3 17a 25-Norhopane Triaromatic steroid Biomarker