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Xu XY, Wang DY, Li YP, Deyrup ST, Zhang HJ. Plant-derived lignans as potential antiviral agents: a systematic review. PHYTOCHEMISTRY REVIEWS : PROCEEDINGS OF THE PHYTOCHEMICAL SOCIETY OF EUROPE 2022; 21:239-289. [PMID: 34093097 PMCID: PMC8165688 DOI: 10.1007/s11101-021-09758-0] [Citation(s) in RCA: 34] [Impact Index Per Article: 11.3] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Subscribe] [Scholar Register] [Received: 11/04/2020] [Accepted: 04/20/2021] [Indexed: 05/04/2023]
Abstract
Medicinal plants are one of the most important sources of antiviral agents and lead compounds. Lignans are a large class of natural compounds comprising two phenyl propane units. Many of them have demonstrated biological activities, and some of them have even been developed as therapeutic drugs. In this review, 630 lignans, including those obtained from medicinal plants and their chemical derivatives, were systematically reviewed for their antiviral activity and mechanism of action. The compounds discussed herein were published in articles between 1998 and 2020. The articles were identified using both database searches (e.g., Web of Science, Pub Med and Scifinder) using key words such as: antiviral activity, antiviral effects, lignans, HBV, HCV, HIV, HPV, HSV, JEV, SARS-CoV, RSV and influenza A virus, and directed searches of scholarly publisher's websites including ACS, Elsevier, Springer, Thieme, and Wiley. The compounds were classified on their structural characteristics as 1) arylnaphthalene lignans, 2) aryltetralin lignans, 3) dibenzylbutyrolactone lignans, 4) dibenzylbutane lignans, 5) tetrahydrofuranoid and tetrahydrofurofuranoid lignans, 6) benzofuran lignans, 7) neolignans, 8) dibenzocyclooctadiene lignans and homolignans, and 9) norlignans and other lignoids. Details on isolation and antiviral activities of the most active compounds within each class of lignan are discussed in detail, as are studies of synthetic lignans that provide structure-activity relationship information.
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Affiliation(s)
- Xin-Ya Xu
- School of Chinese Medicine, Hong Kong Baptist University, Kowloon, Hong Kong SAR, P. R. China
- Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning, 530200 P. R. China
| | - Dong-Ying Wang
- School of Chinese Medicine, Hong Kong Baptist University, Kowloon, Hong Kong SAR, P. R. China
- College of Food Science and Technology, Henan University of Technology, Zhengzhou, 450001 P. R. China
| | - Yi-Ping Li
- Institute of Human Virology, Key Laboratory of Tropical Disease Control of Ministry of Education, Zhongshan School of Medicine, Sun Yat-Sen University, Guangzhou, 510080 P. R. China
| | - Stephen T. Deyrup
- Department of Chemistry and Biochemistry, Siena College, Loudonville, NY 12211 USA
| | - Hong-Jie Zhang
- School of Chinese Medicine, Hong Kong Baptist University, Kowloon, Hong Kong SAR, P. R. China
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Liu J, Wei X, Zhang X, Qi Y, Zhang B, Liu H, Xiao P. A Comprehensive Comparative Study for the Authentication of the Kadsura Crude Drug. Front Pharmacol 2019; 9:1576. [PMID: 30740055 PMCID: PMC6357937 DOI: 10.3389/fphar.2018.01576] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/25/2018] [Accepted: 12/31/2018] [Indexed: 11/18/2022] Open
Abstract
The stems and roots of Kadsura species have been used as the folk medicine in Traditional Chinese medicine (TCM) and have good traditional efficacy and medicinal application with a long history. Among these species, K. coccinea, K. heteroclita and K. longipedunculata are the most widely distributed species in the regions of south and southwest China. Owing to their similar appearance, the crude drugs are often confusedly used by some folk doctors, even some pharmaceutical factories. To discriminate the crude drugs, haplotype analysis based on cpDNA markers and ITS was firstly employed in this study. Generic delimitation, interspecific interrelationships, and the identification of medicinal materials between K. longipedunculata and K. heteroclita remained unresolved by the existing molecular fragments. The original plant could be identified through the morphological character of flower, fruit and leaf. However, in most situation collectors have no chance to find out these characters due to lack of reproductive organs, and have no experience with the minor difference and transitional variation of leaf morphology. The chemical characterization show that the chemometric of chemical composition owned higher resolution to discriminate three herbs of Kadsura species. In conclusion, this integrative approach involving molecular phylogeny, morphology and chemical characterization could be applied for authentication of the Kadusra. Our study suggests the use of this comprehensive approach for accurate characterization of this closely related taxa as well as identifying the source plant and confused herbs of TCM.
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Affiliation(s)
- Jiushi Liu
- Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, China
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Beijing, China
| | - Xueping Wei
- Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, China
- Engineering Research Center of Traditional Chinese Medicine Resources, Ministry of Education, Beijing, China
| | - Xiaoyi Zhang
- Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, China
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Beijing, China
| | - Yaodong Qi
- Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, China
- Engineering Research Center of Traditional Chinese Medicine Resources, Ministry of Education, Beijing, China
| | - Bengang Zhang
- Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, China
- Engineering Research Center of Traditional Chinese Medicine Resources, Ministry of Education, Beijing, China
| | - Haitao Liu
- Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, China
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Beijing, China
| | - Peigen Xiao
- Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, China
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Beijing, China
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Werner B, Kalesse M. Pinacol Coupling Strategy for the Construction of the Bicyclo[6.4.1]tridecane Framework of Schiglautone A. Org Lett 2017; 19:1524-1526. [PMID: 28300417 DOI: 10.1021/acs.orglett.7b00288] [Citation(s) in RCA: 12] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
Abstract
The synthesis of the tricyclic carbon framework of schiglautone A (1) is reported herein. The generation of the bicyclo[6.4.1]tridecane 19 was accomplished via a SmI2-mediated pinacol coupling of dialdehyde 18. The side chain in 18 was introduced using a selective 1,4-addition. A further key step of the synthesis was the homologation of a Wieland-Miescher ketone derivative to establish the 7-membered ring.
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Affiliation(s)
- Bettina Werner
- Institute for Organic Chemistry, Leibniz Universität Hannover , Schneiderberg 1B, D-30167 Hannover, Germany
| | - Markus Kalesse
- Institute for Organic Chemistry, Leibniz Universität Hannover , Schneiderberg 1B, D-30167 Hannover, Germany.,Helmholtz Centre for Infection Research (HZI) , Inhoffenstrasse 7, D-38124 Braunschweig, Germany
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Liu HT, Liu JS, Zhang J, Guo YJ, Qi YD, Jia XG, Zhang BG, Xiao PG. Chemical Constituents in Plants of Genus Kadsura Kaempf. ex Juss. CHINESE HERBAL MEDICINES 2014. [DOI: 10.1016/s1674-6384(14)60028-9] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/25/2022] Open
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Liu J, Qi Y, Lai H, Zhang J, Jia X, Liu H, Zhang B, Xiao P. Genus Kadsura, a good source with considerable characteristic chemical constituents and potential bioactivities. PHYTOMEDICINE : INTERNATIONAL JOURNAL OF PHYTOTHERAPY AND PHYTOPHARMACOLOGY 2014; 21:1092-1097. [PMID: 24784528 DOI: 10.1016/j.phymed.2014.01.015] [Citation(s) in RCA: 24] [Impact Index Per Article: 2.2] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Received: 09/05/2013] [Revised: 11/11/2013] [Accepted: 01/31/2014] [Indexed: 06/03/2023]
Abstract
In China, the plants of genus Kadsura had been used as the folk medicines for a long time and showed good effect of activating blood and dissolving stasis, promoting qi circulation to relieve pain, dispelling wind and eliminating dampness. The bioactivities of genus Kadsura were attributed to the existence of its characteristic chemical constituents. This review systematically summarized the traditional efficacy and medicinal application of genus Kadsura in China, chemical constituents and bioactivities of the plants of genus Kadsura. And, lignans and triterpenoids were the main bioactive constituents, which exhibited good anti-HIV, anti-tumor, anti-hepatitis, anti-oxidant, anti-platelet aggregation activities and neuroprotective effect etc. Moreover, some structure-activity relationships mining would greatly enrich the opportunity of finding new and promising lead compounds and promote the reasonable development and utilization of the plants of genus Kadsura.
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Affiliation(s)
- Jiushi Liu
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193, China
| | - Yaodong Qi
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193, China
| | - Hongwu Lai
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193, China
| | - Jin Zhang
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193, China
| | - Xiaoguang Jia
- Xinjiang Institute of Chinese and Ethnic Medicine, Urumqi 830002, Xinjiang, China
| | - Haitao Liu
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193, China; Xinjiang Institute of Chinese and Ethnic Medicine, Urumqi 830002, Xinjiang, China.
| | - Bengang Zhang
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193, China.
| | - Peigen Xiao
- Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Peking Union Medical College), Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193, China
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Hsu YS, Kuo YH, Cheng HL, Flatt PR, Liu HK. Schizandra arisanensis extract attenuates cytokine-mediated cytotoxicity in insulin-secreting cells. World J Gastroenterol 2012; 18:6809-6818. [PMID: 23239919 PMCID: PMC3520170 DOI: 10.3748/wjg.v18.i46.6809] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 07/10/2012] [Revised: 09/18/2012] [Accepted: 09/22/2012] [Indexed: 02/06/2023] Open
Abstract
AIM To explore the bioactivity of an ethanolic extract of Schizandra arisanensis (SA-Et) and isolated constituents against interleukin-1β and interferon-γ-mediated β cell death and abolition of insulin secretion. METHODS By employing BRIN-BD11 cells, the effects of SA-Et administration on cytokine-mediated cell death and abolition of insulin secretion were evaluated by a viability assay, cell cycle analysis, and insulin assay. The associated gene and protein expressions were also measured. In addition, the bioactivities of several peak compounds collected from the SA-Et were tested against cytokine-mediated β cell death. RESULTS Our results revealed that SA-Et dose-dependently ameliorated cytokine-mediated β cell death and apoptosis. Instead of suppressing inducible nitric oxide synthase/nitric oxide cascade or p38MAPK activity, suppression of stress-activated protein kinase/c-Jun NH2-terminal kinase activity appeared to be the target for SA-Et against the cytokine mix. In addition, SA-Et provided some insulinotropic effects which re-activated the abolished insulin exocytosis in cytokine-treated BRIN-BD11 cells. Finally, schiarisanrin A and B isolated from the SA-Et showed a dose-dependent protective effect against cytokine-mediated β cell death. CONCLUSION This is the first report on SA-Et ameliorating cytokine-mediated β cell death and dysfunction via anti-apoptotic and insulinotropic actions.
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Kadpolysperins A–N, lanostane triterpene acids possessing rich structure types from Kadsura polysperma. Tetrahedron 2012. [DOI: 10.1016/j.tet.2012.03.116] [Citation(s) in RCA: 17] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/23/2022]
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Song L, Ding JY, Tang C, Yin CH. Compositions and Biological Activities of Essential Oils of Kadsura longepedunculata and Schisandra sphenanthera. THE AMERICAN JOURNAL OF CHINESE MEDICINE 2012; 35:353-64. [PMID: 17436374 DOI: 10.1142/s0192415x07004874] [Citation(s) in RCA: 14] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 11/18/2022]
Abstract
The chemical compositions, antimicrobial activities, antioxidant activities and cytotoxicities of the essential oils isolated from the root of Kadsura longepedunculata Finet et Gagnep (KLREO) and the fruit of Schisandra sphenanthera Rehd. et Wills. (SSFEO) were investigated.The analyses of gas chromatography-mass spectrometry (GC-MS) showed that cadinane type compounds and their derivatives were rich in both oils (54.2% and 39.7%, respectively) and δ-cadinene was the major component of both oils (13.8% and 25.6%, respectively). The antimicrobial activities of both oils were evaluated against five microorganisms with the disc diffusion and the broth micro-dilution method. Results showed that Gram-positive bacteria were more sensitive to both oils than Gram-negative bacteria and the yeast. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of the oil of KLREO were lower than those of SSFEO, indicating that the former possessed slightly stronger antibacterial capability than the latter. The reducing power and lipid peroxidation assays were employed to study the potential antioxidant activities of both oils. Both oils remarkably decreased the content of malondialdehyde (MDA) in rat liver homogenate in a dose dependent manner. The antioxidant activities of KLREO appeared to be more potent than that of SSFEO. The oils of KLREO and SSFEO exhibited concentration-dependent cytotoxicities and were proved to be toxic to HepG2 cells with IC50 of 147 and 189 μg/ml, respectively.
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Affiliation(s)
- Lei Song
- State Key Laboratory of Genetic Engineering, Fudan University, 220 Handan Road, Shanghai, 200433, China
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Meng FY, Sun JX, Li X, Pi HF, Zhang P, Ruan HL. Triterpenoids from the Stems of Schisandra glaucescens. Helv Chim Acta 2011. [DOI: 10.1002/hlca.201100033] [Citation(s) in RCA: 12] [Impact Index Per Article: 0.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/07/2022]
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Ma W, Ma X, Huang H, Zhou P, Chen D. Dibenzocyclooctane Lignans from the Stems ofKadsura induta and Their Antiviral Effect on Hepatitis B Virus. Chem Biodivers 2007; 4:966-72. [PMID: 17511012 DOI: 10.1002/cbdv.200790087] [Citation(s) in RCA: 24] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/20/2023]
Abstract
Two new dibenzocyclooctane lignans, kadsurindutins A (1) and B (2), were isolated from the stems of Kadsura induta, together with the known, structurally related lignans schisantherin L (3), schisantherin P (4), kadsulignan L (5), and neokadsuranin (6). Their structures and configurations were elucidated by spectroscopic methods (UV, ORD, CD, IR, 1D- and 2D-NMR) in combination with mass-spectrometric (HR-MS) techniques. Compounds 1, 5, and 6 showed in vitro antiviral effects on hepatitis B virus.
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Affiliation(s)
- Wenhui Ma
- Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai 200032, PR China
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Huang SX, Yang J, Xiao WL, Zhu YL, Li RT, Li LM, Pu JX, Li X, Li SH, Sun HD. Three Novel Terpenoids fromSchisandra pubescens var.pubinervis. Helv Chim Acta 2006. [DOI: 10.1002/hlca.200690114] [Citation(s) in RCA: 39] [Impact Index Per Article: 2.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/07/2022]
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Li L, Ren HY, Yang XD, Zhao JF, Li GP, Zhang HB. Rubriflorin A and B, Two Novel Partially Saturated Dibenzocyclooctene Lignans fromSchisandra rubriflora. Helv Chim Acta 2004. [DOI: 10.1002/hlca.200490265] [Citation(s) in RCA: 7] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/08/2022]
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Abstract
The 18-(13-->12 beta)-abeo-lanostene triterpenoid acid, ananosic acid A (1), and the dibenzocyclooctadiene lignan, ananosin A (2), were isolated from the stem bark of Kadsura ananosma. Their structures were elucidated by extensive spectral studies and the structure of 1 was confirmed by single crystal X-ray diffraction analysis.
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Affiliation(s)
- Y G Chen
- Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, People's Republic of China
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