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Deciphering fungal metabolon coupling tandem inverse-electrondemand Diels-Alder reaction and semipinacol rearrangement for the biosynthesis of spiro polycyclic alkaloids

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Science China Chemistry 2025年第1期68卷 288-296页

作者： Shuai Liu Wen-Qiang Xu Ying-Tong Di Man-Cheng Tang Ding-Kang Chen Ming-Ming Cao Yao-Wen Chang Hong-Yu Tang Chun-Mao Yuan Jun-Bo Yang Zhi-Li Zuo Han Guo Zi-Fei Xu Ying Zeng Yun-Dong Wu Xiao-Jiang Hao Key Laboratory of Phytochemistry and natural Medicines (Chinese Academy of Sciences) Kunming Institute of Botany Chinese Academy of Sciences University of Chinese Academy of Sciences Lab of Computational Chemistry and Drug Design State Key Laboratory of Chemical Oncogenomics Peking University Shenzhen Graduate School Shenzhen Bay Laboratory State Key Laboratory of Microbial Metabolism School of Life Sciences & Biotechnology Shanghai Jiao Tong University State Key Laboratory of Functions and Applications of medicinal Plants Guizhou Medical University Molecular Biology Experimental center Germplasm Bank of Wild Species in Southwest China Kunming Institute of Botany Chinese Academy of Sciences Yunnan Key Laboratory for Wild Plant Resources Kunming Institute of Botany Chinese Academy of Sciences research Unit of Chemical Biology of natural Anti-Virus products Chinese Academy of Medical Sciences

In the intricate process of natural product biosynthesis, a metabolon can enhance metabolic flux by associating sequential enzymes. A fungal metabolon, comprising of flavin-dependent monooxygenase Spe F and P450 monooxygenase Spe G, is identified in the biosynthesis of spiro polycyclic alkaloids(+)-notoamide B and its diastereomer(+)-versicolamide B. Using notoamide E as a substance, Spe F/Spe G metabolon can control the stereoselectivity of its 2,3-epoxidation, followed by hydrogen atom ion at C-17 to generate reactive epoxide tau-m A with dienyl iminium unit. Subsequently,(+)-notoamide B and(+)-versicolamide B are produced via tandem nonenzymatic inverse-electron-demand Diels-Alder reaction and semipinacol rearrangement. This provides the first example of metabolon in the biosynthesis of spiro-prenylated indole alkaloids.

关键词： metabolon Diels-Alder reaction semipinacol rearrangement biosynthesis notoamides spiro polycyclic alkaloids

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Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes

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Chinese Chemical Letters 2024年第4期35卷 346-351页

作者： Lei Shen Yang Zhang Linlin Zhang Chuanwang Liu Zhixian Ma Kangjiang Liang Chengfeng Xia Key Laboratory of medicinal Chemistry for natural Resource Ministry of EducationYunnan Provincial Center for Research&Development of Natural ProductsSchool of PharmacyYunnan UniversityKunming 650500China

Spectroscopic investigations discovered that the in-situ generated phenylhydrazone anion was significantly bathochromically shifted to visible light region for photoactivation under irradiation. The photoexcited phenylhydrazone anion was potential to reduce aryl iodides via single electron transfer process for the subsequent radical chain reaction. A redox-neutral photochemical carbonylation of aryl iodides was developed on basis of the special spectroscopic features of phenylhydrazone anion. This protocol provided a convenient and efficient synthetic tool for accessing carbonylation products under redox neutral conditions without the need of transition-metals.

关键词： Organic anion Hydrazone Carbonylation Visible light Single electron transfer

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Harnessing generative AI to decode enzyme catalysis and evolution for enhanced engineering

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National Science Review 2023年第12期10卷 13-25页

作者： Wen Jun Xie Arieh Warshel Department of medicinal Chemistry Center for Natural Products Drug Discovery and DevelopmentGenetics InstituteUniversity of Florida Department of Chemistry University of Southern California

Enzymes, as paramount protein catalysts, occupy a central role in fostering remarkable progress across numerous fields. However, the intricacy of sequence-function relationships continues to obscure our grasp of enzyme behaviors and curtails our capabilities in rational enzyme engineering. Generative artificial intelligence(AI), known for its proficiency in handling intricate data distributions, holds the potential to offer novel perspectives in enzyme research. Generative models could discern elusive patterns within the vast sequence space and uncover new functional enzyme sequences. This review highlights the recent advancements in employing generative AI for enzyme sequence analysis. We delve into the impact of generative AI in predicting mutation effects on enzyme fitness, catalytic activity and stability, rationalizing the laboratory evolution of de novo enzymes, and decoding protein sequence semantics and their application in enzyme engineering. Notably, the prediction of catalytic activity and stability of enzymes using natural protein sequences serves as a vital link, indicating how enzyme catalysis shapes enzyme evolution. Overall,we foresee that the integration of generative AI into enzyme studies will remarkably enhance our knowledge of enzymes and expedite the creation of superior biocatalysts.

关键词： generative AI mutation effects evolution–catalysis relationship enzyme engineering enzyme evolution

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One stone three birds:Ni-catalyzed asymmetric allenylic substitution of allenic ethers,hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers

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Chinese Chemical Letters 2024年第8期35卷 282-287页

作者： Zhirong Yang Shan Wang Ming Jiang Gengchen Li Long Li Fangzhi Peng Zhihui Shao Key Laboratory of medicinal Chemistry for natural Resource Ministry of EducationSchool of Chemical Science and TechnologyYunnan Provincial Center for Research&Development of Natural Productsand State Key Laboratory for Conservation and Utilization of Bio-Resources in YunnanYunnan UniversityKunming 650091China

The development of low-cost,earth-abundant and environmentally benign transition metal catalysts,which can catalyze multiple different types of asymmetric reactions,is an important objective in mod-ern asymmetric *** we demonstrate that a chiral Ni/P-Phos catalyst achieves three types of asymmetric reactions:allenylic substitution of racemic allenic ethers,1,4-hydroalkylation of prochiral 1,3-enynes and double alkylation of newly designed enynyl ether *** methods complement each other and produce various axially chiral allene derivatives bearing a pyrazolidine-3,5-dione unit,which is widely present in drugs and biologically active molecules with versatile pharmacological activities.

关键词： Nickel Asymmetric catalysis Allenylic substitution Hydroalkylation Double alkylation Allene 1,3-Enyne Pyrazolidine-3,5-dione

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Aspect of QOL Assessment and Proposed New Scale for Evaluation

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Open Journal of Immunology 2015年第3期5卷 147-182页

作者： Nobuo Yamaguchi Matsuo Arai Tsugiya Murayama Department of Fundamental research for CAM Kanazawa Medical University Ishikawa Japan ishikawa natural medicinal products research center Ishikawa Japan Faculty of Pharmaceutical Sciences Department of Microbiology and Immunology Hokuriku University Ishikawa Japan

According to the reports from Ministry of Health in each country, the average life span is elongated over the past decade. This trend is expected to be keeping constant further in the future and at the same time continued efforts should be made. Next, it is necessary for us to consent about improving the quality of life. In an effort of improving the quality of life, other than the western medicine, we have attempted to introduce many traditional medical practices, including the oriental medicine, from various parts of the world into the medical field as a complementary & alternative medicine (CAM). Judging both positive and negative aspects by the evaluation standard of the Western medicine, we try to obtain numerical aspects in termed of QOL. Some methods of alternative medicine involved in this review are acupuncture, moxibustion, TCM and other traditional medicine. Above all, WHO suggests selecting the suzerain nation of acupuncture moxibustion, which has been developed in the oriental countries as a specialized cure, by identifying merits & demerits and ascertaining which nation can be a the best model for special field. At the moment for evaluating CAM, for example, what kind of methods is/are suitable for evaluating each CAM. We have been trying to propose the peripheral leukocyte, that is one of the best marker for evaluating CAM. Our trial is a hot spring hydrotherapy, acupuncture and moxibution, light exercise and Ondle/floor heating etc. In these trials, we find the common results from leukocyte effects which exhibit a strong correlation for the regulation in number and function, as a new scale for evaluating QOL. The contents are the result from the data showing the much in number of volunteer tend to down regulate, on the other hand, lower number of volunteer is up-regulated at next day by each menu of CAM as a constitution dependent manner. However, even in western medical methodology, double blind and cross over system are the better way to evaluation

关键词： QOL Leukocyte Subset Granulocyte Lymphocyte Constitution Dependent Assay System Double Blind-Cross Over System Immunological Factors Emotional Hormone Adrenalin Dopamine Anti-Oxidative Assay by Macrophage

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Fermented Ethnic Medicine (<i>Pueraria mirifica</i>) Designed by Lactobacillus Regulated Leukocyte Subsets via Activation of Complement Components

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Open Journal of Rheumatology and Autoimmune Diseases 2017年第1期7卷 65-79页

作者： Yoshiichiroh Mastuba Kazuhiro Okamoto Yuma Kato Nobuo Yamaguchi Sumiyo Akazawa-Kudoh ishikawa natural medicinal products research center Ishikawa Japan Department of Rehabilitation Kanazawa Medical University Uchinada-machi Japan Department of General Medicine Kanazawa Medical University Ishikawa Japan

A plant fermentation was carried out by Lactobaccilli against the Rhizome from Pueraria milifica (f-PMF). This material was evidenced by safe in animal toxic study. The main aim of this study was to revise the traditional way of hot water extraction to fermentation so as to use up the original material and finding new activity. We tried to show the new activity through phytoestrogen and immune-competent cells from the host that administrated either of original remedy and the new fermented sample, plus activated water SRE. In mice, compromised host was prepared by cancer chemotherapeutic agent (Mitomycin-C). After administration of f-PMF to immno-suppressed animals, the effects by both samples were augmented by lymphocyte in number and functions, macrophage activities, anti-oxidative activity. However, the intense of effect was much more by fermented one but not by conventional one. The anti-oxidative assay was also carried out ex-vivo system by peritoneal macrophage that we proposed as suitable system for evaluating anti-oxidative assay. In our clinical study by 20 healthy volunteers, granulocyte and lymphocyte ratio was regulated as neutral in peripheral white blood cells, increasing one, two and three weeks after the administration of f-PMF. We have found the significant regulation of blood chemical factors that were important makers for the lifestyle-related diseases. The mechanism of augmentation by probing directory with immuno-electrophoretic method, generating new complement component, especially found by alternative pathway of complement. So we discussed the process concerning designed f-PMF molecule for activation of complement component and bound for the biological activity of each physical component. In a limited condition, fewer numbers of volunteers, the breast size was tending to increase along with the administration time. Including these evidences, we discussed the possibility of this traditional ethnic medicine, originally found and spread in the hi

关键词： Family Pueraria Fermentation Lactobacilli Cancer Chemotherapeutic Agent Immune-Compromised Host Lymphocyte Granulocyte Ant-Oxidative Activity Complement Alternative Complement Activation

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~1H–^(15)N HMBC spectra of C_(18)-diterpenoid alkaloids

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Chinese Chemical Letters 2015年第6期26卷 804-806页

作者： Qian Mei Yao-Nan Wang Ming Zhao Xiao-Yu Liu Shi-Qi Peng Feng-Peng Wang Department of Chemistry of medicinal natural products West China College of PharmacySichuan University Medical Experiment and Test center Capital Medical University College of Pharmaceutical Sciences Capital Medical University

The normally underused ^1H-^15N HMBC spectra of thirteen C18-diterpenoid alkaloids have been determined for the first time. As a result, the significant effects of the substituents of nitrogen atoms, the conformations... 详细信息

关键词： Diterpenoid alkaloid ^15N NMR ^1H-^15N HMBC

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An Anomeric Base-Tolerant Ester of 8-Alkynyl-1-naphthoate for Gold(I)-Catalyzed Glycosylation Reaction

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Chinese Journal of Chemistry 2023年第11期41卷 1305-1312页

作者： Xiaojuan Zhang Peng Xu Zhengbing Zhou Yazhou Zhang Biao Yu Yugen Zhu Zhongshan Institute for Drug Discovery Shanghai Institute of Materia MedicaChinese Academy of SciencesZhongshanGuangdong528400 China Key Laboratory of medicinal Chemistry for natural Resource Ministry of EducationYunnan Provincial Center for Research&Development of Natural ProductsSchool of Chemical Science and TechnologyYunnan UniversityKunmingYunnan650091 China State Key Laboratory of Bioorganic and natural products Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai200032 China

Given the extreme complexity and diversity of carbohydrates,efficient approaches to the homogeneous oligosaccharide remain *** synthesis represents one of the most reliable methods to access homogeneous samples,which mainly relies on the key glycosylation *** with enormous efforts to develop leaving groups for establishing robust glycosylation protocols,we herein disclose a structurally novel leaving group of 8-phenylethynyl-1-naphthoate that is able to enable efficient glycosylation reactions under the extremely mild condition of gold(I)-***,the anomeric naphthoate possesses the unprecedent character of base-stability in sharp contrast to the conventional ester groups at anomeric position of carbohydrates,which endows high compatibility with a variety of chemical ***,the present glycosylation protocol with 8-phenylethynyl-1-naphthoate as leaving group is able to realize minimally protected glycosylation *** studies reveal a unique structure of 8-phenylethynyl-1-naphthoate that accounts for the reason for these characteristics.

关键词： Glycosylation Leaving Group Gold Catalysis Anomeric Ester Base Tolerant Carbohydrates

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A New Activated Water Charged by Electrophoresis, Effect on the Experimentally Immuno-Suppressed Animal and Their Anti-Oxidative Activity

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Open Journal of Immunology 2015年第3期5卷 122-132页

作者： Yasuteru Eguchi Nobuo Yamaguchi Nurmuhamamt Amat Dilxat Yimit Parida Hoxur Kei Yokokawa ishikawa natural medicinal products research center Ishikawa Japan Department of Fundament research for CAM Kanazawa Medical University Ishikawa Japan Traditional Uighur Medicine Department Xinjiang Medical University Urumqi China Traditional Chinese Medicine Hospital Xinjiang Medical University Urumqi China

Every individuals expose to the lisk of conventional immunodeficiency in daily life with both internal and externals. In a series of investigation, we have been assessed the various health promoting menu such as hot spring hydrotherapy, acupuncture & moxibution, light excurse, evidenced Control water western medicine technique. In this report, we try to investigate the regulatory effect of hydrotherapy by activated water molecule as our representative menu under the influence of hypothalamus system. We set up both animal and human model for assessment of hydrotherapy. Before starting experimental assessment, six males and females seven-week-old ddY mice, are used for the acute oral toxicity study. There is no sign for toxicity as judged by body weight, organ inspection by veterinary doctor. Next, young ddY mice are experimentally induced diabetes and immune-deficient status by administrating cancer chemotherapeutic agent, Streptzotosin. Charged Water was evident to control the blood sugar level compared to the Control Water group together with conventional control group. Both experimental group of mice wear statistically significant for recovery from blood sugar level and antibody secreting cell both IgM and IgG plaque-forming cell. We confirm also activated water group delivered the granulocyte that slow down the oxidative stress by super oxide.

关键词： New Charged Water Hydrotherapy Peripheral Leukocyte Leukocyte Subsets Ratio Diabetes Meritesanti-Oxidative Activity CAM

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Plant Digestive Supplement Designed by Lactobacillus Regulated Leukocyte Subsets through Activation of Complement Components and Implication for Use against Tumor Bearing Host against Infection

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Open Journal of Immunology 2015年第3期5卷 133-146页

作者： Kohji Ohtubo Nobuo Yamaguchi Nurmuhamamt Amat Dilxat Yimit Parida Hoxur Hiroshi Ushijima Yousuke Watanabe ishikawa natural medicinal products research center Ishikawa Japan Department of Fundament research for CAM Kanazawa Medical University Ishikawa Japan Traditional Uighur Medicine Department Xinjiang Medical University Urumqi China Traditional Chinese Medicine Hospital Xinjiang Medical University Urumqi China

A plant material consisted by Family Poaceae was fermented by Yeast and Lactobaccilli (U-164). This material was proved by as safe in animal safety experiment for oral administration. In order to prove the effect of U-164 against physiological function, the animal and human trials were set up to look into mainly leukocyte functions. In animal experiment, anti-oxidative effect and antibody response in immune-compromised host and diabetes meritus were made up. For human use, peripheral lymphocyte in number and subset ratio were followed up to one month after administration. In order to understand its effect, human complement component analysis was made by immune-electrophoresis. Our results showed that U-164 augmented the level of lymphocytes, while U-164 down regulated the level of granulocytes. In our clinical study with 19 healthy volunteers, granulocyte and lymphocyte ratio was obtained as neutral in peripheral blood being increased significantly 30 days after the ingestion of U-164. In experimental animal study, the compromised host as well as normal animal was administered with cancer chemotherapeutic agent (Mytomycin-C). Our observations showed against antibody producing cell, this material recovered the antibody production in the host compromising the immure responsiveness. We also proposed an idea that U-164 exhibited tonic effects via activating complement components. Moreover, we tried to access further to the anti-oxidative activities of this U-164. This modification brought to the significant lifted up for anti-oxidative activity for phagocytic cell.

关键词： Family Poaceae Fermentation Yeast Lactobacillus Cancer Chemotherapeutic Agent Compromised Host Complement C3b Fragment Anti-Oxidant Diabetes Blood Sugar

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