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Functional identification of the terpene synthase family involved in diterpenoid alkaloids biosynthesis in Aconitum carmichaelii

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Acta Pharmaceutica Sinica B 2021年第10期11卷 3310-3321页

作者： Liuying Mao Baolong Jin Lingli Chen Mei Tian Rui Ma Biwei Yin Haiyan Zhang Juan Guo Jinfu Tang Tong Chen Changjiangsheng Lai Guanghong Cui Luqi Huang College of Pharmacy Shandong University of Chinese MedicineJinan 250355China State Key Laboratory of Dao-di Herbs National Resource Center for Chinese Materia MedicaChina Academy of Chinese Medical SciencesBeijing 100700China

Aconitum carmichaelii is a high-value medicinal herb widely used across China,Japan,and other Asian ***-type diterpene alkaloids(DAs)are the characteristic compounds in *** six transcriptomes,based on short-read next generation sequencing technology,have been reported from the Aconitum species,the terpene synthase(TPS)corresponding to DAs biosynthesis remains *** apply a combination of Pacbio isoform sequencing and RNA sequencing to provide a comprehensive view of the *** *** TPSs and five alternative splicing isoforms belonging to TPS-b,TPS-c,and TPS-e/f subfamilies were *** vitro enzyme reaction analysis functional identified two sesqui-TPSs and twelve di *** of the TPS-c subfamily genes reacted with GGPP to produce the intermediate ent-copalyl *** Ac KSLs separately reacted with ent-CPP to produce ent-kaurene,ent-atiserene,and ent-13-epi-sandaracopimaradie:a new diterpene found in *** TPSs gene expression in conjunction DAs content analysis in different tissues validated that ent-CPP is the sole precursor to all DAs biosynthesis,with Ac KSL1,Ac KSL2 s and Ac KSL3-1 responsible for C20 atisine and napelline type DAs biosynthesis,*** data clarified the molecular basis for the C20-DAs biosynthetic pathway in *** and pave the way for further exploration of C19-DAs biosynthesis in the Aconitum species.

关键词： Aconitum carmichaelii Full-length transcriptome Diterpene synthase diterpenoid alkaloids

New diterpenoid alkaloids from the Roots of Aconitum excelsum Reichb

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Chinese Chemical Letters 1999年第2期10卷 133-134页

作者： Shu Xiang ZHANG Shi Shan JIA(Pharmcy Department, Inner Monglia Medical College Hohhot, Inner Monglia, China 010059) Pharmcy Department Inner Monglia Medical College Hohhot Inner Monglia 010059 China

Two new diterpenoid alkaloids have been isolated from roots of Aconitum excelsum Reichb. These new compounds were named excecoitine I and exceconidine II. The two structures were elucidated by spectroscopic methods as... 详细信息

关键词： diterpenoid alkaloids exceconitine exceconidine

New diterpenoid alkaloids from Spiraea japonica var. Ovalifolia

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Chinese Chemical Letters 2001年第2期12卷 147-150页

作者： Guo Ying ZUO Hong Ping HE Xin HONG Wei Ming ZHU Yi Ming HU Xiao Sheng YANG Xiao Jiang HAO Laboratory of Phytochemistry Kunming Institute of BotanyChinese Academy of SciencesKunming 650204 Kunming 43 Hospital PLAKunming 650032 The Key Laboratory of Chemistry for Natural Products ofGuizhou Province and Chinese Academy of Sciences Guiyang 550002

Five new diterpenoid alkaloids. 19-O-deethlyspiramine N (1), deacetylspiramine S (2), spiramidine A (3), spiramidine B (4) and deacetylspiramine F (5) were isolated from the aerial parts of Spirae japonica L. f. var o... 详细信息

关键词： Rosaceae Spireae japonica L. f. var. ovalifolia diterpenoid alkaloids

TWO NORditerpenoid alkaloids FROM ACONITUM LEUCOSTOMUM

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Chinese Chemical Letters 1996年第8期7卷 725-728页

作者： Yue, JM Xu, J Sun, HD Chen, SN Chen, YZ ACAD SINICA KUNMING INST BOTLAB PHYTOCHEMKUNMING 650204PEOPLES R CHINA LANZHOU UNIV DEPT CHEMLANZHOU 730000PEOPLES R CHINA

Two new norditerpenoid alkaloids leucostines A (1) and B (2) have been isolated from the soot of Aconitum leucostomum. Their structures were elucidated on the basis of spectral data and chemical evidence.

关键词： diterpenoid alkaloids DELPHINIUM

STRUCTURE　OF　6-EPICHASMANINE

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Chinese Chemical Letters 1996年第5期7卷 443-444页

作者： Li, ZB Wang, FP W CHINA UNIV MED SCI SCH PHARMDEPT CHEM & MED NAT PRODCHENGDU 610044PEOPLES R CHINA

Abstract: A new norditerpenoid alkaloid, 6-epichasmanine, was isolated from the roots of Aconitum kusnezoffii. Its structure was determind on the basis of spectrscopic analysis.

关键词： DELPHINIUM-STAPHISAGRIA LINNE diterpenoid alkaloids ACONITUM

Identification and comparative analysis of the major chemical constituents in the extracts of single Fuzi herb and FuziGancao herb-pair by UFLC-IT-TOF/MS

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Chinese Journal of Natural Medicines 2014年第7期12卷 542-553页

作者： YANG Yan YIN Xin-Juan GUO Hui-Min WANG Ru-Lin SONG Rui TIAN Yuan ZHANG Zun-Jian Key Laboratory of Drug Quality Control and Pharmacovigilance China Pharmaceutical UniversityMinistry of Education State Key Laboratory of Natural Medicines China Pharmaceutical University

AIM: The aim of this work was to establish a specific and sensitive method to comprehensively investigate and compare chemical constituents of Fuzi-Gancao herb pair(FG), consisting of Aconitum carmichaelii Debeaux(Fuzi, Chinese) and Roast Radix Glycyrrhizae(Glycyrrhiza glabra L., Gancao, in Chinese) and Fuzi alone to explore the underlying interaction mechanism of FG. METHOD: An ultra-fast liquid chromatography-ion trap/time-of-flight mass spectrometry(UFLC/MS-IT-TOF) method using diazepam as internal standard was developed for the identification and semi-quantitative analysis of the phytochemical constituents of Fuzi and FG. Chromatographic separation was achieved on a UFLC column using a gradient program with 40 mmol?L-1 ammonium acetate and acetonitrile as the mobile phase. RESULTS: Fifty-one of the sixty compounds, including forty-five C19-diterpenoid alkaloids and six C20-diterpenoid alkaloids were tentatively identified in the extracts of Fuzi and FG through accurate mass measurements and fragmentation patterns. Comparing the contents of these alkaloids in these two extracts, it was found that the diester-diterpenoid alkaloids(DDAs) and the alkylolamine-diterpenoid alkaloids(ADAs) were increased, while the monoester-diterpenoid alkaloids(MDAs) were decreased in the extracts of FG. CONCLUSION: This work provided comprehensive information for the quality control of Fuzi preparations, and the further investigation on the compatibility mechanisms of FG.

关键词： Aconitum carmichaelii Radix Rhizoma Glycyrrhizae diterpenoid alkaloids UFLC-IT-TOF/MS

Partial Synthesis of Crassicauline A from Yunaconitine

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Natural Products and Bioprospecting 2020年第2期10卷 105-108页

作者： Rong-Ping Zhang Yan-Jun Lin Hao-Fei Yu Si-Ying Chen Jun Zhou Yunnan University of Chinese Medicine KunmingChina Kunming Medical University KunmingChina Kunming Institute of Botany Chinese Academy of SciencesKunmingChina

Both Aconitum hemsleyanum and Aconitum geniculatun have abundant contents of yunaconitine(1).Yunaconitine(1)has similar skeleton to crassicauline A(3);the only difference between them is that 1 contains aα-hydroxyl group at *** team attempts to convert 1 into 3 because 3 owns pharmacological *** are two steps to achieve the transformation above:firstly,use dehydration reaction to transform yunaconitine(1)into dehydroyunaconitine(2);secondly,use hydrogen reduction to acquire crassicauline A(3).Compared with other methods,this one below is more suitable for production application and more concise;moreover,the cost is lower with higher yield.

关键词： diterpenoid alkaloids Yunaconitine Crassicauline A