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The ERF transcription factor LTF1 activates DIR1 to control stereoselective synthesis of antiviral Lignans and stress defense in Isatis indigotica roots

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Acta Pharmaceutica Sinica B 2024年第1期14卷 405-420页

作者： Ruibing Chen Jian Yu Luyao Yu Liang Xiao Ying Xiao Junfeng Chen Shouhong Gao Xianghui Chen Qing Li Henan Zhang Wansheng Chen Lei Zhang Department of Pharmaceutical Botany School of PharmacyNaval Medical UniversityShanghai 200433China Research and Development Center of Chinese Medicine Resources and Biotechnology Shanghai University of Traditional Chinese MedicineShanghai 201203China Department of Pharmacy Shanghai Changzheng HospitalNaval Medical UniversityShanghai 200003China School of Medicine Shanghai UniversityShanghai 200433China Institute of Edible Fungi Shanghai Academy of Agricultural SciencesNational Engineering Research Center of Edible FungiKey Laboratory of Edible Fungi Resources and Utilization(South)Ministry of AgricultureShanghai 201403China College of Life Sciences and Medicine Key Laboratory of Plant Secondary Metabolism and Regulation of Zhejiang ProvinceZhejiang Sci-Tech UniversityHangzhou 310018China State Key Laboratory of Dao-di Herbs Beijing 100700China

Lignans are a powerful weapon for plants to resist stresses and have diverse bioactive functions to protect human health.Elucidating the mechanisms of stereoselective biosynthesis and response to stresses of Lignans is important for the guidance of plant improvement.Here,we identified the complete pathway to stereoselectively synthesize antiviral(-)-lariciresinol glucosides in Isatis indigotica roots,which consists of three-step sequential stereoselective enzymes DIR1/2,PLR,and UGT71B2.DIR1 was further identified as the key gene in respoJanuary 2024nse to stresses and was able to trigger stress defenses by mediating the elevation in lignan content.Mechanistically,the phytohormone-responsive ERF transcription factor LTF1 colocalized with DIR1 in the cell periphery of the vascular regions in mature roots and helped resist biotic and abiotic stresses by directly regulating the expression of DIR1.These systematic results suggest that DIR1 as the first common step of the lignan pathway cooperates with PLR and UGT71B2 to stereoselectively synthesize(-)-lariciresinol derived antiviral Lignans in I.indigotica roots and is also a part of the LTF1-mediated regulatory network to resist stresses.In conclusion,the LTF1-DIR1 module is an ideal engineering target to improve plant Defenses while increasing the content of valuable Lignans in plants.

关键词： Lignans Stereoselective synthesis Stress resistance Dirigent protein ERF

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Lignans and sesquiterpenoids from the stems of Schisandra bicolor var. tuberculata

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Natural Products and Bioprospecting 2022年第1期12卷 256-264页

作者： Shui-Mei Zhang Kun Hu Xiao-Nian Li Han-Dong Sun Pema-Tenzin Puno State Key Laboratory of Phytochemistry and Plant Resources in West China Yunnan Key Laboratory of Natural Medicinal ChemistryKunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China University of Chinese Academy of Sciences Beijing 10039People’s Republic of China

A pair of new tetrahydrofuran lignan enantiomers,(±)-schibiculatin A[(±)-1],a new enedione lignan,schibiculatin B(2),two new cadinane-type sesquiterpenoids,schibiculatins C(3)and D(4),along with two known seco-cadinane-type sesquiterpenoids(5 and 6)and seven known miscellaneous Lignans(7-13)were isolated from the stems of Schisandra bicolor var.tuberculata.The structures of 1-4 were elucidated by comprehensive analysis of their spectro-scopic data,quantum chemical calculations,as well as single-crystal X-ray diffraction.A few isolated compounds were tested for their protective activities against corticosterone-induced apoptosis in PC12 cells.Among them,compounds 5 and 6 showed moderate activities.

关键词： Schisandra bicolor var.tuberculata Cadinane-type sesquiterpenoids Lignans Quantum chemical calculation

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Anti-HIV Lignans from Justicia procumbens

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Chinese Journal of Natural Medicines 2019年第12期17卷 945-952页

作者： XU Xin-Ya WANG Dong-Ying KU Chuen-Fai ZHAO Yang CHENG Han LIU Kang-Lun RONG Li-Jun ZHANG Hong-Jie School of Chinese Medicine Hong Kong Baptist UniversityHong Kong SARChina Institute of Marine Drugs Guangxi University of Chinese MedicineGuangxi 530200China College of Food Science and Technology Henan University of TechnologyZhengzhou 450001China Department of Microbiology and Immunology College of MedicineUniversity of Illinois at ChicagoIL 60612United States

Twenty-one Lignans including three new ones(1, 2 and 13) were isolated from Justicia procumbens. The chemical structures of the new Lignans were determined by spectroscopic means including 1 D and 2 D NMR analysis. These compounds were evaluated for their cytotoxic and anti-HIV activities. The new secoisolariciresinol dimethyl ether acetate(13) exhibited anti-HIV-1 activity with an IC50 value of 5.27 μmol·L^-1 and a selective index(SI) value of 2.2. The known arylnaphthalene lignan procumbenoside A(3) and diphyllin(8) demonstrated inhibitory activity against HIV-1 with IC50 values of 4.95(SI > 6.2) and 0.38 μmol·L^-1(SI = 5.3), respectively.

关键词： Justicia procumbens Antiviral plant Lignans Anti-HIV-1 activity

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Improved stability and oral bioavailability of Ganneng dropping pills following transforming Lignans of herpeto- spermum caudigerum into nanosuspensions

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Chinese Journal of Natural Medicines 2018年第1期16卷 70-80页

作者： LI Juan-Juan CHENG Ling SHEN Gang QIU Ling SHEN Cheng-Ying ZHENG Juan XU Rong YUAN Hai-Long Department of Pharmacy Air Force General Hospital of PLA Beijing 100142 China Department of Pharmacy Guangyuan Central Hospital Guanyuan 628000 China Department of Pharmacy Shuangliu District Maternal and Child Health Hospital Chengdu 610075 China Chengdu Institute of Chinese Herbal Medicine Chengdu 610045 China

The present study was designed to improve storage stability and oral bioavailability of Ganneng dropping pills(GNDP) by transforming Lignans of Herpetospermum caudigerum(HL) composed of herpetrione(HPE) and herpetin(HPN) into nanosuspension(HL-NS), the main active ingredient of GNDP, HL-NS was prepared by high pressure homogenization and lyophilized to transform into solid nanoparticles(HL nanoparticles), and then the formulated HL nanoparticles were perfused into matrix to obtain NS-GNDP by melting method. For a period of 3 months, the content uniformity, storage stability and pharmacokinetics test in vivo of NS-GNDP were evaluated and compared with regular GNDP at room temperature. The results demonstrated that uniformity of dosage units of NS-GNDP was acceptable according to the criteria of Chinese Pharmacopoeia 2015 J. Physical stability of NS-GNDP was investigated systemically using photon correlation spectroscopy(PCS), zeta potential measurement, and scanning electron microscopy(SEM). There was a slight increase in particles and PI of HL-NS re-dispersed from NS-GNDP after storage for 3 months, compared with new formulated NS-GNDP, which indicated a good redispersibility of the NS-GNDP containing HL-NS after storage. Besides, chemical stability of NS-GNDP was studied and the results revealed that HPE and HPN degradation was less when compared with that of GNDP, providing more than 99% of drug residue after storage for 3 months. In the dissolution test in vitro, NS-GNDP remarkably exhibited an increased dissolution velocity compared with GNDP and no distinct dissolution difference existed within 3 months. The pharmacokinetic study showed that HPE and HPN in NS-GNDP exhibited a significant increase in AUC0–t, Cmax and decrease in Tmax when compared with regular GNDP. These results indicated that NS-GNDP possessed superiority with improved storage stability and increased dissolution rate and oral bioavailability.

关键词： Ganneng dropping pills Lignans Herpetospermum caudigerum Nanosuspensions Stability Oral bioavailability

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Lignans-Rich Extract from Herpetospermum caudigerum Alleviate Physical Fatigue in Mice

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Chinese Journal of Integrative Medicine 2016年第11期22卷 840-845页

作者：靳世英李瑞生申宝德白金霞徐平华戴领徐和靳士晓韩晋袁海龙 Department of Pharmacy 302 Hospital of People's Liberation Army Beijing 100039 China Pharmacy College Chengdu University of Traditional Chinese Medicine Chengdu 610075China Animal Laboratory Center 302 Hospital of People's Liberation Army Beijing 100039 China Key Lab of Modern Preparation of Traditimal Chinese Medicine Ministry of Education Jiangxi University of Traditional Chinese MedicineNanchang 330004 China

Objective: To ascertain anti-fatigue constituents and mechanisms of Herpetospermum caudigerum. Methods: The 80% ethanol extracts of Herpetospermum caudigerum were partitioned with chloroform, ethyl acetate and n-butanol, respectively. Male Kunming mice were divided into 13 groups with 16 mice in each group: a control group fed with water, 9 groups treated with 3 fractions of Herpetospermum caudigerum(chloroform fraction, ethyl acetate fraction and n-butanol fraction) at dose of 80, 160 and 320 mg/kg for the low-dose group, medium-dose group and high-dose group, 3 herpetrione(HPE) treated groups fed with HPE at dose of 15, 30, and 60 mg/kg for the low-dose group, medium-dose group and high-dose group. All animals were treated once per day for 30 days. Anti-fatigue activity was assessed through the forced swimming test and serum biochemical parameters including blood lactic acid(BLA), blood urea nitrogen(BUN), malondialdehyde(MDA), hepatic glycogen(HG), lactic dehydrogenase(LDH), superoxide dismutase(SOD) and glutathione peroxidase(GPx) determined following the recommended procedures provided by the commercial kits. Results: Compared with the control group, the Lignans extract(ethyl acetate fraction) of Herpetospermum caudigerum and HPE could significantly prolonged the exhaustive swimming time(PLignans extract and HPE treated groups(PLignans extract had antifatigue activities and HPE may be partly responsible for the anti-fatigue effects of Herpetospermum caudigerum. The possible mechanisms of anti-fatigue activity were related to the decrease of BUN and BLA, the increase of the HG storage and

关键词： Herpetospermum caudigerum Lignans herpetrione anti-fatigue activity

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Lignans and diterpenes isolated from Tirpitzia ovoidea and their biological activities

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Chinese Journal of Natural Medicines 2017年第12期15卷 938-943页

作者： YANG Xue-Yan ZHANG Yi-Fan LIU Li-Jia WANG Yi SHANG Ming-Ying XU Feng LIU Guang-Xue CAI Shao-Qing Department of Natural Medicine School of Pharmaceutical Sciences Peking University Health Science Center Beijing 100191China

A new lignan, tirpitzin A(17) together with 20 known compounds(1-16, and 18-21) were isolated from the ethyl acetate soluble fraction of ethanol extract of the aerial parts of Tirpitzia ovoidea. The structure of new compound was elucidated by means of spectroscopic analysis. Of the known compounds, 7-21 were isolated from Linaceae family for the first time. The pharmacological activity of the crude extracts was tested using a mouse inflammation model induced by dimethyl benzene. The results demonstrated that the ethyl acetate soluble fraction had anti-inflammatory activity. Moreover, the cytotoxic and anti-inflammatory activities of some compounds were studied. The new compound 17 showed moderate cytotoxic effect against Bx PC-3 cell line(IC_50 = 19.51μmol·L^(-1)) and Compound 10 showed significant cytotoxicity against Hep G2, HL-60, U87 and Bx PC-3 cell lines with IC_50 values in the range 4.2-8.3μmol·L^(-1). Additionally, Compounds 2, 10, 11, and 13 exhibited potent inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages at the concentration of 50μmol·L^(-1).

关键词： Tirpitzia ovoidea Linaceae Lignans Diterpenes Cytotoxic activity Anti-inflammatory activity

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A review of Lignans from genus Kadsura and their spectrum characteristics

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Chinese Herbal Medicines 2021年第2期13卷 157-166页

作者： Liu Zhang Yan-zhe Jia Bin Li Cai-yun Peng Yu-pei Yang Wei Wang Chang-xiao Liu TCM and Ethnomedicine Innovation&Development International Laboratory School of PharmacyHunan University of Chinese MedicineChangsha 410208China State Key Laboratory of Drug Delivery Technology and Pharmacokinetics Tianjin Institute of Pharmaceutical ResearchTianjin 300193China

Kadsura belongs to the Schisandroideae subfamily of Magnoliaceae.Plants from genus Kadsura are widely distributed in the South and Southwest of China.The plants of the genus are widely used as folk medicine for a long time in history,with the functions of relieving pain,promoting 'qi' circulation,activating blood resolve stasis,and applications in the treatment of rheumatoid arthritis and gastroenteric disorders.Lignans are the primary characteristic constituents with various biological activities of plants from genus Kadsura.This paper summarized 81 Lignans isolated from the plants of genus Kadsura over the past eight years(from 2014 to 2021),which belong to five types:dibenzocyclooctadienes,spirobenzofuranoid dibenzocyclooctadienes,aryltetralins,diarylbutanes and tetrahydrofurans.Each type of these Lignans possess typical characteristics in proton magnetic resonance(^(1)H NMR) and carbon-13 nuclear magnetic resonance(^(13)C NMR) spectra,the NMR regularities of these types of lingans were summarized,which provided a useful reference for the structural analysis of Lignans.The relationships between Lignans and pharmacodynamics were also systematically analyzed,Lignans were predicted to be the quality markers(Q-marker) of Kadsura genus.

关键词： Kadsura ^(1)H NMR and^(13)C NMR spectrum characteristics pharmacodynamics Q-marker Lignans structure classifications

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New seco-dibenzocyclooctadiene Lignans with nitric oxide production inhibitory activity from the roots of Kadsura longipedunculata

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Chinese Chemical Letters 2020年第2期31卷 423-426页

作者： Xinzhu Qi Jiabao Liu Jiabao Chen Qi Hou Shuai Li State Key Laboratory of Bioactive Substances and Functions of Natural Medicines Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

Four new seco-dibenzocyclooctadiene Lignans,kadlongiLignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) Lignans,were isolated from the roots of Kadsura longipedunculata.Their structures were elucidated by spectroscopic analysis,including extensive NM R,MS and ECD(electronic circular dichroism) spectra.Compounds 3 and 4 exhibited potent inhibitory activities against NO(nitric oxide) production of LPS(lipopolysaccharide)-induced murine macrophages with the inhibition rates of 36.3% and 26.9%,respectively.

关键词： Kadsura longipedunculata Seco-dibenzocyclooctadiene Lignans KadlongiLignans A-D Spectroscopic analysis NO production inhibition

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Natural products inspired [3+2] cycloaddition enables efficient construction of hydroxylated tetrahydrofuran acetals and concise syntheses of Lignans

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Science China Chemistry 2024年第7期67卷 2306-2313页

作者： Dong-Yue Cai Weiming Shi Zhao-Hui Jin Zhi-Xiang Yu Jin-Xin Zhao Jian-Min Yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences University of Chinese Academy of Sciences Beijing National Laboratory for Molecular Sciences(BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of EducationCollege of ChemistryPeking University

Mimicking biosynthetic pathways of hongkonoids led to the development of a new Cu(Ⅰ)-catalyzed [3+2] cycloaddition ofα-hydroxyketone and β-keto enol ethers, affording tetrahydrofuran acetals in a highly diastereoselective manner and 100% atom economy. Computational studies on the mechanism disclosed a concerted but asynchronous Michael addition/aldol reaction. Of the same importance, this methodology provides a practical biomimetic approach for one-step construction of the dibenzylbutyrolactol lignan backbone starting from two phenyl propane derivatives, opening up a powerful new approach for lignan synthesis, which is showcased by succinct total syntheses of two biologically important aryltetralin-type Lignans,β-apopicropodophyllin and cycloolivil. Given the mild and operationally simple conditions, the developed chemistry might have a promising prospect in potential industrial applications.

关键词： [3 + 2] cycloaddition transition-metal catalysis tetrahydrofuran Lignans natural products

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Two new Lignans from Dipteronia dyeriana

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Chinese Chemical Letters 2008年第10期19卷 1215-1217页

作者： Rong Guo Min Luo Chun Lin Long Ma Lin Li Zhi Qin Ouyang Yi Ping Zhou Yue Hu Wang Xing Yu Li Ya Na Shi Kunming Institute of Botany Chinese Academy of Sciences Kunming 650204 China Yunnan Agricultural University Kunming 650201 China Yunnan Laboratory of Pharmacology for Natural Products Kunming Medical College Kunming 650031 China Yunnan Introduction ＆ Propagation Center for Rare ＆ Endangered Plants Kunming 650032 China

A new sesquilignan, 7＇,8＇-didehydroherpetotriol （1）, and a new lignan glycoside, （＋）-isolariciresinol-9＇-O-α-L-rhamnopyra- nosy1-（1→6）-[3-D-glucopyranoside （2）, were isolated from the branches of Dipteronia dyeriana. Their structures were elucidated by spectroscopic methods and chemical evidence. Compound 1 possessed inhibitory activity against human leukaemia K562 cells with an IC50 value of 39 μmol/L.

关键词： Aceraceae Dipteronia dyeriana Lignans Didehydroherpetotriol Leukaemia

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