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The biosynthetic pathway of the hallucinogen mescaline and its heterologous reconstruction

Molecular Plant 2024年第7期17卷 1129-1150页

作者： Paula Berman Luis Alejandro de Haro Ana-Rita Cavaco Sayantan Panda Younghui Dong Nikolay Kuzmich Gabriel Lichtenstein Yoav Peleg Hila Harat Adam Jozwiaki Jianghua Cai Uwe Heinig Sagit Meir Ilana Rogachev Asaph Aharoni Department of Plant and Environmental Sciences Weizmann Institute of ScienceRehovot 7610001Israel Life Sciences Core Facilities Weizmann Institute of ScienceRehovot 7610001Israel The Maurice and Vivienne Wohl Institute for Drug Discovery Weizmann Institute of ScienceRehovot 7610001Israel Present address:Department of Cell and Metabolic Biology Leibniz Institute of Plant BiochemistryWeinberg 306120 Halle(Saale)Germany Department of Molecular&Cellular Pharmacology University of Miami Miler School of MedicineMiamiFL 33136USA Department of Botany and Plant Sciences University of California RiversideRiversideCA 92521USA Laboratory of Plant Hormones and Development Regulation of Chongqing School of Life SciencesChongqing UniversityChongqing 401331China

Mescaline,among the earliest identified natural hallucinogens,holds great potential in psychotherapy ***,despite the existence of a postulated biosynthetic pathway for more than half a century,the specific enzymes involved in this process are yet to be *** this study,we investigated the cactus Lophophora williamsii(Peyote),the largest known natural producer of the phenethylamine *** employed a multi-faceted approach,combining de novo whole-genome and transcriptome sequencing with comprehensive chemical profiling,enzymatic assays,molecular modeling,and pathway engineering for pathway *** identified four groups of enzymes responsible for the six catalytic steps in the mescaline biosynthetic pathway,and an N-methyltransferase enzyme that N-methylates all phenethylamine intermediates,likely modulating mescaline levels in ***,we reconstructed the mescaline biosynthetic pathway in both Nicotiana benthamiana plants and yeast cells,providing novel insights into several challenges hindering complete heterologous mescaline *** together,our study opens up avenues for exploration of sustainable production approaches and responsible utilization of mescaline,safeguarding this valuable natural resource for future generations.

关键词： mescaline Lophophora williamsi Peyote biosynthetic pathway de novo genome sequencing mo-lecular modeling

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biosynthetic pathway of terpenoid indole alkaloids in Catharanthus roseus

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Frontiers of Medicine 2014年第3期8卷 285-293页

作者： Xiaoxuan Zhu Xinyi Zeng Chao Sun Shilin Chen Institute of Medicinal Plant Development China Academy of Medical Sciences & Peking Union Medical College Beijing 100193 China Institute of Chinese Materia Medica China Academy of-Chinese Medical Sciences Beijing 100700 China

Catharanthus roseus is one of the most extensively investigated medicinal plants, which can produce more than 130 alkaloids, including the powerful antitumor drugs vinblastine and vincristine. Here we review the recent advances in the biosynthetic pathway of terpenoid indole alkaloids （TIAs） in C. roseus, and the identification and characterization of the corresponding enzymes involved in this pathway. Strictosidine is the central intermediate in the biosynthesis of different TIAs, which is formed by the condensation of secologanin and tryptamine. Secologanin is derived from terpenoid （isoprenoid） biosynthetic pathway, while tryptamine is derived from indole biosynthetic pathway. Then various specific end products are produced by different routes during downstream process. Although many genes and corresponding enzymes have been characterized in this pathway, our knowledge on the whole TIA biosynthetic pathway still remains largely unknown up to date. Full elucidation of TIA biosynthetic pathway is an important prerequisite to understand the regulation of the TIA biosynthesis in the medicinal plant and to produce valuable TIAs by synthetic biological technology.

关键词： Catharanthus roseus terpenoidindole alkaloids biosynthetic pathway vinblastine vincristine

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De novo nucleotide biosynthetic pathway and cancer

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Genes & Diseases 2023年第6期10卷 2331-2338页

作者： Jie Chen Siqi Yang Yingge Li Xu Ziwen Pingfeng Zhang Qibin Song Yi Yao Huadong Pei Cancer Center Renmin Hospital of Wuhan UniversityWuhanHubei 430062China Lombardi Comprehensive Cancer Center Georgetown University Medical CenterWashingtonD.C.20057USA

De novo nucleotide biosynthetic pathway is a highly conserved and essential biochemical pathway in almost all *** purine nucleotides and pyrimidine nucleotides are necessary for cell metabolism and ***,the dysregulation of the de novo nucleotide biosynthetic pathway contributes to the development of many human diseases,such as *** has been shown that many enzymes in this pathway are overactivated in different *** this review,we summarize and update the current knowledge on the de novo nucleotide biosynthetic pathway,regulatory mechanisms,its role in tumorigenesis,and potential targeting opportunities.

关键词： biosynthetic pathway Cancer de novo synthesis Metabolism Nucleotide

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Functional characterization of CYP81C16 involved in the tanshinone biosynthetic pathway in Salvia miltiorrhiza

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Chinese Journal of Natural Medicines 2023年第12期21卷 938-949页

作者： REN Li LUO Linglong HU Zhimin MA Ying WANG Jian CHENG Yatian JIN Baolong CHEN Tong TANG Jinfu CUI Guanghong GUO Juan HUANG Luqi State Key Laboratory of Dao-di Herbs National Resource Center for Chinese Materia MedicaChina Academy of Chinese Medical SciencesBeijing 100000China

Danshen,the dried roots and rhizomes of Salvia miltiorrhiza Bunge(***),is widely used in the treatment of cardiovascular and cerebrovascular ***,the bioactive compounds from Danshen,exhibit a wide spectrum of pharmacological properties,suggesting their potential for future therapeutic *** biosynthesis is a complex process involving at least six P450 enzymes that have been identified and characterized,most of which belong to the CYP76 and CYP71 *** this study,CYP81C16,a member of the CYP71 clan,was identified in *** in vitro assay revealed that it could catalyze the hydroxylation of four para-quinone-type tanshinones,namely neocryptotanshinone,deoxyneocryptotanshinone,and danshenxinkuns A and ***81C16 emerged as a potential broad-spectrum oxidase targeting the C-18 position of para-quinone-type tanshinones with an impressive relative conversion rate exceeding 90%.Kinetic evaluations and in vivo assays underscored its highest affinity towards neocryptotanshinone among the tested *** overexpression of SmCYP81C16 promoted the accumulation of(iso)tanshinone in hairy root *** characterization of SmCYP81C16 in this study accentuates its potential as a pivotal tool in the biotechnological production of tanshinones,either through microbial or plant metabolic engineering.

关键词： Salvia miltiorrhiza Tanshinone biosynthetic pathway Cytochrome P450 Hydroxylation Neocryptotanshinone

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Clinical metabolic analysis combined with traceability of biosynthetic pathway:a new approach to quality marker of Chinese materia medica

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TMR Modern Herbal Medicine 2019年第1期2卷 3-10页

作者： Zhi-Rui Yang Ai-Ting Wang Juan Liu Xin-Yu Yang Xiao-Fang Wang Lei Zhang Na Guo Jia-Chen Zi Cheng Peng Shu-Xun Yan Dan Yan Beijing Shijitan Hospital Capital Medical UniversityBeijingChina Beijing Key Laboratory of Bio-characteristic Profiling for Evaluation of Rational Drug Use BeijingChina International Cooperation&Joint Laboratory of Bio-characteristic Profiling for Evaluation of Rational Drug Use BeijingChina Experimental Research Center China Academy of Chinese Medical SciencesBeijingChina JiNan University GuangzhouChina Chengdu University of Traditional Chinese Medicine ChengduChina The first affiliated hospital Henan University of China MedicineZhengzhouChina

Quality marker(Q-marker)of Chinese materia medica(CMM)plays an important role in quality control of CMM ***,its research strategy and technique remain *** on the fact that quality standard of CMM should be associated with clinical efficacy,taking Jinqi Jiangtang tablet treating type 2 diabetes as an example,the Q-marker related to activity via the reverse analysis of drug metabolism in clinic and traceability of botanic biosynthetic pathways is discovered and ***,we proposed a new research strategy of Q-marker of CMM with"Discovery of clinical active constituents as guidance,Reverse analysis of metabolic transformations as link,and Traceability of biosynthesis pathways as key",to improve quality control of CMM products.

关键词： Chinese materia medica Quality marker Clinical metabolic analysis biosynthetic pathway Jinqi Jiangtang Tablet Type 2 diabetes

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High-yielding Heparin Induced by Modifying Its biosynthetic pathway

High-yielding Heparin Induced by Modifying Its Biosynthetic ...

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第十一届全国化学生物学学术会议

作者： Mingjia Yu Tianwei Tan Jinping Li College of Life Science and Technology Beijing University of Chemical Technology

Heparin is an animal tissue extract that is widely used as an anticoagulant drug with more than 100 tons produced annually worldwide in clinics for the treatment of patients with thrombotic disorders. Heparin is a linear polysaccharide primarily comprising of a trisulfated disaccharide repeating unit,2-O-sulfo-α-L-iduronic acid 1-4 linked to 6-O-sulfo-N-sulfo-α-D-glucosamine with the help of three key enzymes in sulfated modification process. At present,the high proportion of heparin is still derived from animal sources such as porcine intestine and bovine lung though with potential risk of prion and other ***,with the increasingly urgent need to have alternative non-animal source heparin to replace the animal derived medicine,the biosynthetic pathway of heparin becomes a popular research topic(Figure 1).Our aim is to identify strategies on increasing catalytic activity of three key enzymes in sulfated modification process of *** the calculation of enzymes’ reaction mechanism and the homology modeling of enzymes,we analyze the catalytic center of the enzymes and design strategies on improving catalytic activity so as to produce high-yielding heparin and its mimetics by modifying its biosynthetic pathway.

关键词： Heparin Reaction mechanism Homology modeling biosynthetic pathway

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Multiomics analyses of two Leonurus species illuminate leonurine biosynthesis and its evolution

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Molecular Plant 2024年第1期17卷 158-177页

作者： Peng Li Meng-Xiao Yan Pan Liu Dan-Jie Yang Ze-Kun He Yun Gao Yan Jiang Yu Kong Xin Zhong Sheng Wu Jun Yang Hong-Xia Wang Yan-Bo Huang Le Wang Xiao-Ya Chen Yong-Hong Hu Qing Zhao Ping Xu shanghai Key Laboratory of Plant Functional Genomics and Resources Shanghai Chenshan Botanical GardenShanghai Chenshan Plant Science Research CenterChineseAcademy of SciencesShanghaiChina College of Life Sciences Shanghai Normal UniversityShanghai 200234China State Key Laboratory of Plant Molecular Genetics CAS Center for Excellence in Molecular Plant SciencesChinese Academy of SciencesShanghaiChina University of the Chinese Academy of Sciences Beijing 100049China The Research Center of Chiral Drugs Innovation Research Institute of Traditional Chinese MedicineShanghai University of Traditional Chinese Medicine1200 Cailun RoadShanghai 201203China College of Chemistry and Chemical Engineering Shanghai University of Engineering ScienceShanghai 201620China

The Lamiaceae family is renowned for its terpenoid-based medicinal components,but Leonurus,which has traditional medicinal uses,stands out for its alkaloid-rich ***,the principal active compound found in Leonurus,has demonstrated promising effects in reducing blood lipids and treating ***,the biosynthetic pathway of leonurine remains largely ***,we present the chromosome-level genome sequence assemblies of Leonurus japonicus,known for its high leonurine production,and Leonurus sibiricus,characterized by very limited leonurine *** integrating genomics,RNA sequencing,metabolomics,and enzyme activity assay data,we constructed the leonurine biosynthesis pathway and identified the arginine decarboxylase(ADC),uridine diphosphate glucosyltransferase(UGT),and serine carboxypeptidase-like(SCPL)acyltransferase enzymes that catalyze key reactions in this *** analyses revealed that the UGT–SCPL gene cluster evolved by gene duplication in the ancestor of Leonurus and neofunctionalization of SCPL in ***,which contributed to the accumulation of leonurine specifically in ***,our comprehensive study illuminates leonurine biosynthesis and its evolution in Leonurus.

关键词： Lamiaceae Leonurus japonicus Leonurus sibiricus genome sequence alkaloids leonurine gene cluster biosynthetic pathway evolution

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Steroidal scaffold decorations in Solanum alkaloid biosynthesis

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

作者： Rosalind Lucier Mohamed O.Kamileen Yoko Nakamura Sofia 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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Antibacterial and cytotoxic metabolites produced by Streptomyces tanashiensis BYF-112 isolated from Odontotermes formosanus

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Chinese Journal of Natural Medicines 2024年第9期22卷 822-830页

作者： WU J. SONG T. ZHANG L. HUANG Z. HUANG F. YIN C. ZHANG S. LIU X. ZHANG Y. School of Life Science Anhui Agricultural University Hefei 230036 China School of Pharmacy Anhui Medical University Hefei 230036 China

Chemical investigations of the termite-associated Streptomyces tanashiensis BYF-112 resulted in the discovery of four novel alkaloid derivatives: vegfrecines A and B (1 and 2), exfoliazone A (3), and venezueline H (7), in addition to nine known metabolites (4−6, 8−13). The structures of these compounds were elucidated through comprehensive spectroscopic analysis and comparison with existing literature data. Antibacterial assays revealed that viridomycin A (11) exhibited potent antibacterial activity against Staphylococcus aureus, with a zone of inhibition (ZOI) of 12.67 mm, in comparison to a ZOI of 17.67 mm for the positive control gentamicin sulfate. Viridomycin A (11) showed moderate activity against Micrococcus tetragenus and Pseudomonas syringae pv. actinidae, with ZOI values of 15.50 and 14.33 mm, respectively, which were inferior to those of gentamicin sulfate (34.67 and 24.00 mm). Viridomycin F (12) also exhibited moderate antibacterial effects against S. aureus, M. tetragenus, and P. syringae pv. actinidae, with ZOI values of 8.33, 16.50, and 10.83 mm, respectively. Cytotoxicity assays demonstrated that viridobruunine A (5), exfoliazone (6), viridomycin A (11), and X-14881E (13) exhibited significant cytotoxicity against human malignant melanoma (A375), ovarian cancer (SKOV-3), and gastric cancer (MGC-803) cell lines, with IC50 values ranging from 4.61 to 19.28 μmol·L−1. Furthermore, bioinformatic analysis of the complete genome of S. tanashiensis suggested a putative biosynthetic gene cluster (BGC) responsible for the production of compounds 1−12. These findings indicate that the secondary metabolites of insect-associated S. tanashiensis BYF-112 hold promise as potential sources of novel antibacterial and anticancer agents. © 2024 China Pharmaceutical University

关键词： Alkaloid Antibacterial activity biosynthetic pathway Cytotoxic activity Odontotermes formosanus Streptomyces tanashiensis

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Elucidation of the melitidin biosynthesis pathway in pummelo

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Journal of Integrative Plant Biology 2023年第11期65卷 2505-2518页

作者： Shuangqian Shen Shouchuang Wang Chenkun Yang Chao Wang Qianqian Zhou Shen Zhou Ran Zhang Yufei Li Zixuan Wang Liupan Dai Wenjv Peng Yingchen Hao Hao Guo Guangping Cao Xianqing Liu Fan Yao Qiang Xu Alisdair RFernie Jie Luo Sanya Nanfan Research Institute of Hainan University Hainan UniversitySanya 572025China National Key Laboratory of Crop Genetic Improvement National Center of Plant Gene Research(Wuhan)Huazhong Agricultural UniversityWuhan 430070China Hubei Hongshan Laboratory College of Life Science and TechnologyCollege of Biomedicine and HealthHuazhong Agricultural UniversityWuhan 430070China Key Laboratory of Horticultural Plant Biology of Ministry of Education Huazhong Agricultural UniversityWuhan 430070China Max Planck Institute of Molecular Plant Physiology Potsdam-Golm 14476Germany Centre of Plant Systems Biology and Biotechnology Plovdiv 4000Bulgaria Yazhouwan National Laboratory Sanya 572025China

Specialized plant metabolism is a rich resource of compounds for drug *** acylated flavonoid glycoside melitidin is being developed as an anti-cholesterol statin drug candidate,but its biosynthetic route in plants has not yet been fully ***,we describe the gene discovery and functional characterization of a new flavonoid gene cluster(UDP-glucuronosyltransferases(Cg UGTs),1,2rhamnosyltransferase(Cg1,2Rha T),acyltransferases(Cg ATs))that is responsible for melitidin biosynthesis in pummelo(Citrus grandis(L.)Osbeck).Population variation analysis indicated that the tailoring of acyltransferases,specific for bitter substrates,mainly determine the natural abundance of ***,3-hydroxy-3-methylglutaryl-Co A reductase enzyme inhibition assays showed that the product from this metabolic gene cluster,melitidin,may be an effective anti-cholesterol statin drug ***-expression of these clustered genes in Nicotiana benthamiana resulted in the formation of melitidin,demonstrating the potential for metabolic engineering of melitidin in a heterologous plant *** study establishes a biosynthetic pathway for melitidin,which provides genetic resources for the breeding and genetic improvement of pummelo aimed at fortifying the content of biologically active metabolites.

关键词： bioactive metabolites biosynthetic pathway flavonoids melitidin natural variation

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