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Steroidal scaffold decorations in Solanum alkaloid biosynthesis

Molecular Plant 2024年第8期17卷 1236-1254页

作者： Rosalind Lucier Mohamed O.Kamileen Yoko Nakamura Sofiia Serediuk Ranjit Barbole Jens Wurlitzer Maritta Kunert Sarah Heinicke Sarah E.O'Connor Prashant D.Sonawane department of natural product biosynthesis Max Planck Institute for Chemical Ecology07745 JenaGermany Research Group biosynthesis and NMR Max Planck Institute for Chemical Ecology07745 JenaGermany Biochemical Sciences Division CSIR-National Chemical LaboratoryPune 411008MaharashtraIndia

Steroidal glycoalkaloids(SGAs)are specialized metabolites produced by hundreds of Solanum species,including important vegetable crops such as tomato,potato,and *** it has been known that SGAs play important roles in defense in plants and“anti-nutritional"effects(e.g.,toxicity and bitterness)to humans,many of these molecules have documented anti-cancer,anti-microbial,antiinflammatory,anti-viral,and anti-pyretic *** these,α-solasonine andα-solamargine isolated from black nightshade(Solanum nigrum)are reported to have potent anti-tumor,anti-proliferative,and anti-inflammatory ***,α-solasonine andα-solamargine,along with the core steroidal aglycone solasodine,are the most widespread SGAs produced among the Solanum ***,it is still unknown how plants synthesize these bioactive steroidal *** comparative metabolomictranscriptome-guided approach,biosynthetic logic,combinatorial expression in Nicotiana benthamiana,and functional recombinant enzyme assays,here we report the discovery of 12 enzymes from *** that converts the starting cholesterol precursorto solasodine aglycone,and the downstreamα-solasonine,α-solamargine,and malonyl-solamargine SGA *** further identified six enzymes from cultivated eggplant that catalyze the production ofα-solasonine,α-solamargine,and malonyl-solamargine SGAs from solasodine aglycone via glycosylation and atypical malonylation *** work provides the gene tool box and platform for engineering the production of high-value,steroidal bioactive molecules inheterologoushosts usingsyntheticbiology.

关键词： steroidal glycoalkaloids Solanum biosynthetic pathway α-solamargine malonyl-solamargine specialized metabolites

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Diverse Ring-seco Limonoids from Munronia unifoliolata and Their Biological Activities

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Chinese Journal of Chemistry 2022年第1期40卷 123-136页

作者： Yunpeng Sun Qiurong Li Letian Cui Pengfei Tang Yongyi Li Lingyi Kong Jun Luo Jiangsu Key Laboratory of Bioactive natural product Research State Key Laboratory of Natural MedicinesDepartment of Natural Medicinal ChemistryChina Pharmaceutical UniversityNanjingJiangsu 210009China

Twenty-two new limonoids,mufolinoids A—V(1—22),including six rings A,B-seco limonoids(1—6),twelve ring A-seco limonoids(7—18),four ring-intact limonoids(19—22),together with thirteen known compounds(23—35)were isolated from Munronia *** structures including absolute configurations were elucidated by combination of NMR,HR-MS,single-crystal X-ray diffraction and calculations of ECD and NMR *** 24,25,33,34 could be significantly reversed the multidrug resistance of MCF-7/doxorubicin(DOX)cells,and the reversal fold(RF)was much higher than that of positive drug *** 24,28,and 29 exhibited significant anti-inflammatory activity with the IC50 values in the range of 17.7—39.4μmol/***,compound 29 could markedly inhibit the release of IL-1βby inhibiting the initiation and assembly of NLRP3 inflammasome,which demonstrates the great potential of limonoids as an anti-inflammatory agent.

关键词： Munronia unifoliolata Limonoids Structure elucidation Inflammatory natural products

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Novel and efficient supramolecular synthesis of pyrroles in the presence of β-cyclodextrin in water

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Chinese Chemical Letters 2012年第12期23卷 1331-1334页

作者： K.Ramesh K.Karnakar G.Satish Y.V.D.Nageswar CSIR-natural product Chemistry Indian Institute of Chemical Technology

A simple and efficient synthesis of highly substituted pyrroles was achieved in water medium via multi-component strategy, using amine, DMAD/DEAD as well as phenacyl bromide catalyzed by β-CD. Utilizing this protocol... 详细信息

关键词： Amine DMAD/DEAD Phenacyl bromide Water Recyclability β-Cyclodextrin

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Two natural molecules preferentially inhibit azole-resistant Candida albicans with MDR1 hyperactivation

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Chinese Journal of natural Medicines 2019年第3期17卷 209-217页

作者： SHI Hong-Zhuo CHANG Wen-Qiang ZHANG Ming LOU Hong-Xiang department of natural product Chemistry Key Laboratory of Chemical Biology of Ministry of Education School of Pharmaceutical Sciences Shandong University

Antifungal drug resistance is a significant clinical problem, and antifungal agents that can evade resistance are urgently needed. In infective niches, resistant organisms often co-existed with sensitive ones, or a subpopulation of antibiotic-susceptible organisms may evolve into resistant ones during antibiotic treatment and eventually dominate the whole population. In this study, we established a co-culture assay in which an azole-resistant Candida albicans strain was mixed with a susceptible strain labeled with green fluorescent protein to mimic in vivo conditions and screen for antifungal drugs. Fluconazole was used as a positive control to verify the validity of this co-culture assay. Five natural molecules exhibited antifungal activity against both susceptible and resistant C. albicans. Two of these compounds, retigeric acid B(RAB) and riccardin D(RD), preferentially inhibited C. albicans strains in which the efflux pump MDR1 was activated. This selectivity was attributed to greater intracellular accumulation of the drugs in the resistant strains. Changes in sterol and lipid compositions were observed in the resistant strains compared to the susceptible strain, and might increase cell permeability to RAB and RD. In addition, RAB and RD interfered with the sterol pathway, further aggregating the decrease in ergosterol in the sterol synthesis pathway in the MDR1-activated strains. Our findings here provide an alternative for combating resistant pathogenic fungi.

关键词： Candida albicans MDR1 Azole resistance Co-culture

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Effect of La,Ce on Taxus Cuspidata Cell Growth,biosynthesis and Release of Taxol

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Journal of Rare Earths 1998年第4期16卷 61-67页

作者：元英进胡国武王传贵景莹申泮文 department of Chemical Engineering and natural product Institute of Biochemical Engineering Tianjin University Tianjin 300072 China department of Chemistry Nankai University Tianjin 300071 China

The effect of La, Ce was firstly tested on growth of the Taxus(T.) cuspidata cell suspensions, biosynthesis and release of taxol. The results indicate that the growth pattern of *** cells is altered significantly by adding high concentration of rare earth in the medium. The lag and exponential phases of cell growth are shortened, the stationary phase disappears and the biomass fluctuates periodically during the decline phase. The rare earth compounds added in the exponential phase obviously increase the taxol biosyntheis and release yields of *** cells, and the supplement of carbon source in the medium containing rare earth is also favorable to taxol biosynthesis.

关键词： Rare earths Lathanum Cerium Taxol Cell suspension culture Taxus cuspidata

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Endless exploration for natural products: dedicated to the 80th birthday of Prof. SUN Han-Dong

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Chinese Journal of natural Medicines 2019年第12期17卷 881-882页

作者： KONG Ling-Yi Chinese Journal of natural Medicines Jiangsu Key Laboratory of Bioactive natural product Research and State Key Laboratory of natural Medicines Department of Natural Medicinal Chemistry China Pharmaceutical University

natural products always exhibit more intellectual bioactivities and atom economy,and it’s also an important source of innovative *** Han-Dong,Academician of Chinese Academy of Sciences from Kunming Institute of Botany,has made outstanding contributions to natural product chemistry,andsetagoodexamplefor *** occasion ofProfSun’s 80th birthday,I’d like to express my deep respect to him,and wish *** a happy birthday and good health.

关键词： Academician birthday drugs

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Design and synthesis of antiviral pseudo-natural products through effective one-step acylmethylation macrocyclization

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Chinese Journal of natural Medicines 2023年第10期21卷 721-722页

作者： LI Shang WANG Xiaobing Jiangsu Key Laboratory of Bioactive natural product Research Department of Natural Medicinal ChemistryChina Pharmaceutical UniversityNanjing 210009China

Influenza virus poses a significant threat to global public health,causing serious repercussions on human life and social *** the past decades,various antiviral drugs targeting either the virus itself or its host were ***,the emergence of drug-resistant influenza virus strains has posed a critical challenge to the effectiveness of these existing anti-influenza agents .Consequently,there is an urgent need to develop novel molecules with new chemical *** natural products serve as a crucial resource for validating targets and discovering lead ***,the number of naturlly crring macrocyclic natural products is limited due to inherent biosynthetic pathways,which restricts the development of macrocyclic *** contrast,artificially synthesized pseudonatural products show enhanced availability and greater structural diversity,while possessing similar biological functions[5]and have attracted significant interest from medicinal ***,it is valuable to develop effective synthetic methods to expedite the discovery of macrocyclic lead compounds.

关键词： natural products C-H activation Macrocyclization H1N1 inhibitors

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MKK4 inhibitor:the hope for liver failure prevention and potential small liver graft transplantation

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Chinese Journal of natural Medicines 2024年第6期22卷 483-485页

作者： ZHANG Yanqiu ZHANG Hao Jiangsu Key Laboratory of Bioactive natural product Research Department of Natural Medicinal ChemistryChina Pharmaceutical UniversityNanjing 210009China

Liver regeneration represents a fascinating concept that spans from ancient mythology to modern medical *** Greek mythology,Prometheus,a hero who defied Zeus by stealing fire and giving it to humanity,was subjected to a severe *** was bound to a rock where,each day,an eagle would feast on his liver,which would then miracu-lously regenerate *** myth underscores the liver’s unique regenerative abilities,a feature that is not just le-gendary but also scientifically recognized.

关键词： Liver regeneration Partial hepatectomy MKK4 Drug discovery and development First-in-human phase I trial

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The parallel biosynthesis routes of hyperoside from naringenin in Hypericum monogynum

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Horticulture Research 2023年第9期10卷 247-259页

作者： Yingying Wang Zhirong Cui Qianqian Li Shuai Zhang Yongyi Li Xueyan Li Lingyi Kong Jun Luo Jiangsu Key Laboratory of Bioactive natural product Research and State Key Laboratory of natural Medicines Department of Traditional Chinese PharmacyChina Pharmaceutical UniversityNanjing 210009China

Hyperoside is a bioactive flavonoid galactoside in both medicinal and edible *** plays an important physiological role in the growth of flower ***,the hyperoside biosynthesis pathway has not been systematically elucidated in plants,including its original source,*** group found abundant hyperoside in the flower buds of Hypericum monogynum,and we sequenced its transcriptome to study the biosynthetic mechanism of *** gene screening and functional verification,four kinds of key enzymes were ***,HmF3Hs(flavanone 3-hydroxylases)and HmFLSs(flavonol synthases)could catalyze flavanones into dihydroflavonols,as well as catalyzing dihydroflavonols into *** could also convert flavanones into flavonols and flavones with varying ***3′H(flavonoid 3′-hydroxylase)was found to act broadly on 4′-hydroxyl flavonoids to produce 3′,4′-diydroxylated flavanones,dihydroflavonols,flavonols,and ***(flavonoid 3-O-galactosyltransferase)would transform flavonols into the corresponding 3-O-galactosides,including *** parallel hyperoside biosynthesis routes were thus depicted,one of which was successfully reconstructed in Escherichia coli BL21(DE3)by feeding naringenin,resulting in a hyperoside yield of 25 mg/***,this research not only helped us understand the interior catalytic mechanism of hyperoside in *** concerning flower development and bioactivity,but also provided valuable insights into these enzyme families.

关键词： interior concerning hyper

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Evidence Based Validation of Indian Traditional Medicine–Way Forward

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World Journal of Traditional Chinese Medicine 2016年第1期2卷 48-61页

作者： Pulok K Mukherjee Ranjit K Harwansh Shiv Bahadur Subhadip Banerjee Amit Kar School of natural product Studies Department of Pharmaceutical Technology Jadavpur University

Evidence based validation of the ethno-pharmacological claims on traditional medicine(TM) is the need of the day for its globalization and reinforcement. Combining the unique features of identifying biomarkers that are highly conserved across species, this can offer an innovative approach to biomarker-driven drug discovery and development. TMs are an integral component of alternative health care systems. India has a rich wealth of TMs and the potential to accept the challenge to meet the global demand for them. Ayurveda, Yoga, Unani, Siddha and Homeopathy(AYUSH) medicine are the major healthcare systems in Indian Traditional Medicine. The plant species mentioned in the ancient texts of these systems may be explored with the modern scientific approaches for better leads in the healthcare. TM is the best sources of chemical diversity for finding new drugs and leads. Authentication and scientific validation of medicinal plant is a fundamental requirement of industry and other organizations dealing with herbal drugs. Quality control(QC) of botanicals, validated processes of manufacturing, customer awareness and post marketing surveillance are the key points, which could ensure the quality, safety and efficacy of TM. For globalization of TM, there is a need for harmonization with respect to its chemical and metabolite profiling, standardization, QC, scientific validation,documentation and regulatory aspects of TM. Therefore, the utmost attention is necessary for the promotion and development of TM through global collaboration and co-ordination by national and international programme.

关键词： Indian traditional medicine AYUSH Ayurveda Chemical profiling Plant metabolomics

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