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A New Antimicrobial Flavonol Glycoside from Alchornea davidii

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Chinese Chemical Letters 2003年第2期14卷 179-180页

作者： Gui You CUI Jun Yan LIU ren xiang tan Institute of Functional Biomolecules School of Life SciencesNanjing UniversityNanjing 210093

A new flavonol glycoside, isorhamnetin-3-O-b-D-xyloside, was isolated from the extract of leaves and twigs of Alchornea davidii (Euphorbiaceae). Its structure was established on the basis of the spectral analysis and chemical degradation. Antimicrobial assay showed that it moderately inhibited the growth of test bacteria (Staphylococcus aureus, Bacillus subtilis and Pseudomonas fluorescens) and fungi (Candida albicans, Aspergillus niger and Trichophyton rubrum) with MICs at 50 g/mL.

关键词： Alchornea davidii Euphorbiaceae flavonol glycoside antimicrobial activity.

Antiosteoporotic Tetrahydroxanthone Dimers from Aspergillus brunneoviolaceus FB-2 Residing in Human Gut

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Chinese Journal of Chemistry 2021年第6期39卷 1580-1586页

作者： Xiao-Jing Lv Fei Ding Ying-Jie Wei ren-xiang tan State Key Laboratory Cultivation Base for TCM Quality and Efficacy Nanjing University of Chinese MedicineNanjingJiangsu 210023China State Key Laboratory of Pharmaceutical Biotechnology School of Life SciencesNanjing UniversityNanjingJiangsu 210023China

A complex community of human-associated microorganisms plays diversely important roles in maintaining health,and the metabolites help to define whether a particular human-associated microbe is a friend or a *** work shows that Aspergillus brunneoviolaceus FB-2,derived from the stool of a healthy individual,produces a family of antiosteoporotic xanthone dinners including penibishexahydroxanthone A(1)and brunneoxanthones A-E(2-6,undescribed previously).The structures of 1-6 were elucidated by MS and NMR spectroscopic analysis,and the absolute configuration of 2 was established by X-ray *** 4-6 are relatively rare examples of highly oxidized heterodimeric xanthones with an 8-ketone ***,the prednisolone-induced osteoporotic zebrafish enabled our demonstration that the antiosteoporotic effects of 1-6 are dose-dependent.

关键词： Aspergillus brunneoviolaceus Gut-associated fungus Natural products Structure elucidation Biological activity

Post-ingestion conversion of dietary indoles into anticancer agents

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National Science Review 2022年第4期9卷 128-138页

作者： Li Ping Lin Dan Liu Jia Cheng Qian Liang Wu Quan Zhao ren xiang tan State Key Laboratory of Pharmaceutical Biotechnology Institute of Functional BiomoleculesNanjing University State Key Laboratory Cultivation Base for TCM Quality and Efficacy Nanjing University of Chinese Medicine

There are health benefits from consuming cruciferous vegetables that release indole-3-carbinol(I3 C), but the in vivo transformation of I3 C-related indoles remains underinvestigated. Here we detail the post-ingestion conversion of I3 C into antitumor agents, 2-(indol-3-ylmethyl)-3,3′-diindolylmethane(LTr1) and 3,3′-diindolylmethane(DIM), by conceptualizing and materializing the reaction flux derailing(RFD) approach as a means of unraveling these stepwise transformations to be non-enzymatic but p H-dependent and gut microbe-sensitive. In the upper(or acidic) gastrointestinal tract, LTr1 is generated through Michael addition of 3-methyleneindolium(3 MI, derived in situ from I3 C) to DIM produced from I3 C via the formaldehyde-releasing(major) and CO-liberating(minor) pathways. In the large intestine,‘endogenous’ I3 C and DIM can form, respectively, from couplings of formaldehyde with one and two molecules of indole(a tryptophan catabolite). Acid-producing gut bacteria such as Lactobacillus acidophilus facilitate the H+-promotable steps. This work updates our understanding of the merits of I3 C consumption and identifies LTr1 as a drug candidate.

关键词： indole-3-carbinol reaction flux derailing (RFD) approach 2-(indol-3-ylmethyl)-3 3′-diindolylmethane (LTr1) anticancer Lactobacillus acidophilus

Anti-proliferative and pro-apoptotic effects of tectorigenin on hepatic stellate cells

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World Journal of Gastroenterology 2010年第31期16卷 3911-3918页

作者： Jun-Hua Wu Yu-Rong Wang Wu-Yang Huang ren-xiang tan Institute of Functional Biomolecules State Key Laboratory of Pharma ceutic al Biote chnologyNanjing UniversityNanjing 210093Jiangsu ProvinceChina

AIM: To investigate the effect of tectorigenin on proliferation and apoptosis of hepatic stellate cells (HSC)-T6 cells. METHODS: HSC-T6 cells were incubated with tectorigenin at different concentrations, and their proliferation was assessed by bromodeoxyuridine incorporation assay. Apoptosis was detected by flow cytometry assay with Hoechst 33342 staining. Also, generation of reactive oxygen species (ROS), intracellular [Ca2+]i, potential of mitochondrial membrane, activities of cytochrome c and caspase-9 and-3 were investigated to explore a conceivable apoptotic pathway. RESULTS: Tectorigenin suppressed the proliferation of HSC-T6 cells and induced apoptosis of HSC-T6 cells in a time-and dose-dependent manner. Tectorigenin at the concentration of 100 μg/mL greatly inhibited the viability of HSC-T6 cells and induced the condensation of chromatin and fragmentation of nuclei. When treated for 48 h, the percentage of cell growth and apoptosis reached 46.3% ± 2.37% (P = 0.004) and 50.67% ± 3.24% (P = 0.003), respectively. Furthermore, tectorigenin-induced apoptosis of HSC-T6 cells was associated with the generation of ROS, increased intracellular [Ca2+]i, loss of mitochondrial membrane potential, translocation of cytochrome c, and activation of caspase-9 and -3. CONCLUSION: Tectorigenin inhibits proliferation of HSC-T6 cells and induces apoptosis of HSC-T6 cells.

关键词： Tectorigenin Apoptosis Hepatic stellate cells Hepatic fibrosis Mitochondria Proliferation

Nitric Oxide Potentiates Oligosaccharide-induced Artemisinin Production in Artemisia annua Hairy Roots

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Journal of Integrative Plant Biology 2008年第1期50卷 49-55页

作者： Li-Ping Zheng Yu-Ting Guo Jian-Wen Wang ren-xiang tan Department of Horticultural Sciences Soochow University Suzhou 215006 China School of Pharmaceutical Sciences Soochow University Suzhou 215006 China Institute of Functional Biomolecules State Key Laboratory of Pharmaceutical Biotechnology Nanjing University Nanjing 210093 China

The purpose of the present study was to characterize the generation of nitric oxide （NO） in Artemisia annua roots induced by an oligosaccharide elicitor （OE） from Fusarium oxysporum mycelium and the potentiation role of NO in the elicitation of artemisinin accumulation. The OE （0.3 mg total sugar/mL） induced a rapid production of NO in cultures, which exhibited a biphasic time course, reaching the first plateau within 1.5 h and the second within 8 h of OE treatment. Artemisinin content in 20-day-old hairy roots was increased from 0.7mg/g dry wt to 1.3 mg/g dry wt by using the OE treatment for 4d. In the absence of OE, the NO donor sodium nitroprusside （SNP） at 10, 50 ~1 and 100 ~1 enhanced the growth of hairy roots, but had no effect on artemisinin synthesis, The combination of SNP with OE increased artemisinin content from 1.2 mg/g drywt to 2.2 mg/g dry wt, whereas the maximum production of artemisinin in cultures was 28.5 mg/L, a twofold increase over the OE treatment alone. The effects of SNP on the OE-induced artemisinin were suppressed strongly by the NO scavenger 2-（4- carboxyphenyl）-4,4,5,5-tetramethylimidazoline-l-oxyl-3-oxide （cPTIO）. The results suggest that NO can strongly potentiate elicitor-induced artemisinin synthesis in A. annua hairy roots.

关键词： Artemisia annua artemisinin hairy roots nitric oxide oligosaccharide elicitor.

Verticase:a Fibrinolytic Enzyme Produced by Verticillium sp,Tj33,an Endophyte of Trachelospermum jasminoides

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Journal of Integrative Plant Biology 2007年第11期49卷 1548-1554页

作者： Ying Li Jing-Lei Shuang Wei-Wei Yuan Wu-Yang Huang ren-xiang tan College of Horticulture Nanjing Agricultural University Nanjing 210095 China Institute of Functional Biomolecules Nanjing University Nanjing 210093 China

Plant endophytes are among the most important resources of biologically active metabolites. Twenty-three endophyte strains residing in Trachelospermum jasminoides were cultivated in vitro with the cultures assayed for the fibrinolytic substance production. As a result, the culture of VerticUlium sp. Tj33 was shown to be the most active. A fibrinolytic enzyme designated as verticase was subsequently purified from the supernatant of Verticillium sp. culture broth by a combination of DEAE-52, Sephadex G-75 and hydrophobic column chromatographies. Verticase, with its molecular mass of 31 kDa and pl of 8.5, was demonstrated to be homogeneous by sodium dodecyl suIfate-polyacrylamide gel electrophoresis and isoelectric focusing electrophoresis. Verticase is an enzyme that hydrolyzes fibrin directly without activation of plaminogen. It was stable in a broad pH range from 4 through to 11 with the optimal reaction pH value and temperature shown to be around 9-10 and 50-60℃, respectively. The fibrinolytic activity of verticase was severely inhibited by phenylmethylsulfony fluoride, indicating that verticase was a serine protease.

关键词： fibrinolytic serine protease plant endophyte protein purification Trachelosperrnum jasminoides verticase.

Carbon-nitrogen bond formation to construct novel polyketide-indole hybrids from the indole-3-carbinol exposed culture of Daldinia eschscholzii

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Synthetic and Systems Biotechnology 2022年第2期7卷 750-755页

作者： Li Ping Lin Min Wu Nan Jiang Wei Wang ren xiang tan State Key Laboratory Cultivation Base for TCM Quality and Efficacy Nanjing University of Chinese MedicineNanjing210023China State Key Laboratory of Pharmaceutical Biotechnology Institute of Functional BiomoleculesNanjing UniversityNanjing210023China Key Laboratory of Cardiovascular&Cerebrovascular Medicine School of PharmacyNanjing Medical UniversityNanjing211166China Key Laboratory of Marine Drugs Ministry of EducationOcean University of ChinaQingdao266003China

A plenty of cytochrome P450s have been annotated in the Daldinia eschosholzii *** by the fact that some P450s have been reported to catalyze the carbon-nitrogen(C-N)bond formation,we were curious about whether hybrids through C-N bond formation could be generated in the indole-3-carbinol(I3C)exposed culture of *** expected,two skeletally undescribed polyketide-indole hybrids,designated as indolpolyketone A and B(1 and 2),were isolated and assigned to be constructed through C-N bond *** structures were elucidated by 1D and 2D NMR *** absolute configurations of 1 and 2 were determined by comparing the recorded and calculated electronic circular dichroism(ECD)***,the plausible biosynthetic pathways for 1 and 2 were *** 1 and 2 exhibited significant antiviral activity against H1N1 with IC_(50) values of 45.2 and 31.4μM,*** brief,compounds 1 and 2 were reported here for the first time and were the first example of polyketide-indole hybrids pieced together through C-N bond formation in the I3C-exposed culture of ***,this study expands the knowledge about the chemical production of *** through precursor-directed biosynthesis(PDB).

关键词： Polyketide-indole hybrids Daldinia eschosholzii Indole-3-carbinol C-N bond formation P450 Precursor-directed biosynthesis

A New Jatrophane Diterpenoid Ester from Euphorbia turczaninowii

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Chinese Chemical Letters 2006年第2期17卷 201-203页

作者： Li Gen LIU ren xiang tan You Ming GONG China Pharmaceutical University Nanjing 210009 Nanjing University Nanjing 210093

A new jatrophane diterpenoid ester （2S, 3S, 4R, 5R, 7S, 8R, 13R, 15R） - 3, 5, 7, 8, 15- pentaacetoxy-9, 14-dioxojatropha-6（17）, 11E-diene was isolated from the whole plant of Euphorbia turczaninowii Kar. ＆ Kit.. ... 详细信息

关键词： Euphorbia turczaninowii Kar. & Kit. jatrophane diterpenoid ester ( 2S 3S 4R 5R 7S,8R 13R 15R)-3 5 7 8 15-pentaacetoxy-9 14-dioxojatropha-6(17) llE-diene.

Discovery of daspyromycins A and B,2-aminovinyl-cysteine containing lanthipeptides,through a genomics-based approach

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Chinese Chemical Letters 2022年第1期33卷 511-515页

作者： Jing Shi Jia-Qi Ma Yong-Chao Wang Zi-Fei Xu Bo Zhang Rui-Hua Jiao ren-xiang tan Hui-Ming Ge State Key Laboratory of Pharmaceutical Biotechnology Institute of Functional BiomoleculesSchool of Life SciencesNanjing UniversityNanjing 210023China Chemistry and Biomedicine Innovation Center(ChemBIC) Nanjing UniversityNanjing 210023China

Lanthipeptides are one of the largest groups of ribosomally synthesized and post-translationally modified peptides(RiPPs)and are characterized by the presence of lanthionine(Lan)or methyllanthionine residues(MeLan).Only very few lanthipeptides contain a C-terminal 2-aminovinyl-cysteine(AviCys)motif,but all of them show potent antibacterial *** advances of genome sequencing led to the rapid accumulation of new biosynthetic gene clusters(BGCs)for *** this study,through our genome mining strategy,we found the AviCys containing lanthipeptides are widespread in the bacterial kingdom.A lanthipeptide-type biosynthetic gene cluster was identified from public bacterial genome *** new lanthipeptides,daspyromycins A and B(1 and 2)containing AviCys motif,along with two degraded products,daspyromycins C and D(3 and 4),were obtained after heterologous expression of the gene cluster in Streptomyces albus *** A and B showed potent antimicrobial activity against a spectrum of Gram-positive and-negative bacteria including methicillin-resistant Staphylococcus aureus(MRSA)and vancomycin-resistant Enterococci(VRE).

关键词： Lanthipeptides Genomics-based approach Daspyromycin RiPPs 2-Aminovinyl-cysteine motif