Chemical constituents of Lycium barbarum leaves and their anti-rheumatoid arthritis activity in vitro

doi:10.1007/s13659-025-00516-9

Natural Products and Bioprospecting ›› 2025, Vol. 15 ›› Issue (4): 35-35.DOI: 10.1007/s13659-025-00516-9

• ORIGINAL ARTICLES • Previous Articles Next Articles

Chemical constituents of Lycium barbarum leaves and their anti-rheumatoid arthritis activity in vitro

Zi-Jiao Wang^1,3, Bang-Yin Tan^1,3, Yun Zhao^1,3, Chang-Bin Wang^1,3, Yun-Li Zhao², Xiao-Dong Luo^1,2

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, P. R. China;
2. Yunnan Characteristic Plant Extraction Laboratory Co. Ltd, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, School of Chemical Science and Technology, Yunnan University, Southwest United Graduate School, Kunming, 650091, P. R. China;
3. University of Chinese Academy of Sciences, Beijing, 100049, P. R. China

Received:2025-03-27 Accepted:2025-04-21 Online:2025-05-30 Published:2025-08-23
Supported by:
This research received financial backing from the High-level Talent Promotion and Training Project of Kunming (grant number 2022SCP003), Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform (grant numbers 2022YKZY001, 2023YKZY001, 2023YKZY004), Yunnan Provincial Science and Technology Project at Southwest United Graduate School (No. 202302AP370006), the Major Science and Technology Project of Yunnan Province (202302AA310013), and the Guiding Funds of the Central Government for Supporting the Development of Local Science and Technology (202407AD110002). Special thanks are extended to the Analysis and Measurement Center of Kunming Institute of Botany for their technical assistance.

Chemical constituents of Lycium barbarum leaves and their anti-rheumatoid arthritis activity in vitro

Zi-Jiao Wang^1,3, Bang-Yin Tan^1,3, Yun Zhao^1,3, Chang-Bin Wang^1,3, Yun-Li Zhao², Xiao-Dong Luo^1,2

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, P. R. China;
2. Yunnan Characteristic Plant Extraction Laboratory Co. Ltd, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, School of Chemical Science and Technology, Yunnan University, Southwest United Graduate School, Kunming, 650091, P. R. China;
3. University of Chinese Academy of Sciences, Beijing, 100049, P. R. China

通讯作者: Yun-Li Zhao, E-mail:zhaoyunli@ynu.edu.cn;Xiao-Dong Luo, E-mail:xdluo@mail.kib.ac.cn
基金资助:
This research received financial backing from the High-level Talent Promotion and Training Project of Kunming (grant number 2022SCP003), Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform (grant numbers 2022YKZY001, 2023YKZY001, 2023YKZY004), Yunnan Provincial Science and Technology Project at Southwest United Graduate School (No. 202302AP370006), the Major Science and Technology Project of Yunnan Province (202302AA310013), and the Guiding Funds of the Central Government for Supporting the Development of Local Science and Technology (202407AD110002). Special thanks are extended to the Analysis and Measurement Center of Kunming Institute of Botany for their technical assistance.

Abstract

Abstract: Two new together with 32 known compounds were isolated from the leaves of Lycium barbarum. Their structures were elucidated using 1D and 2D NMR, HRESIMS, and ECD spectroscopic techniques. Compounds 1–34 were evaluated for their anti-rheumatoid arthritis activities in a lipopolysaccharide (LPS)-induced MH7A cells inflammatory model. As a result, compounds 1–3, 6, 8, 10, 14, 17–19, 29 and 31 inhibited the activity of lactate dehydrogenase (LDH) and nitric oxide (NO) at concentrations 20 μM. Among them, compound 1 showed the best effectiveness, with inhibition rates of 46.7% for NO and 32.8% for LDH.

Key words: Lycium barbarum leaves, Chemical constituents, Anti-rheumatoid arthritis

摘要： Two new together with 32 known compounds were isolated from the leaves of Lycium barbarum. Their structures were elucidated using 1D and 2D NMR, HRESIMS, and ECD spectroscopic techniques. Compounds 1–34 were evaluated for their anti-rheumatoid arthritis activities in a lipopolysaccharide (LPS)-induced MH7A cells inflammatory model. As a result, compounds 1–3, 6, 8, 10, 14, 17–19, 29 and 31 inhibited the activity of lactate dehydrogenase (LDH) and nitric oxide (NO) at concentrations 20 μM. Among them, compound 1 showed the best effectiveness, with inhibition rates of 46.7% for NO and 32.8% for LDH.

关键词: Lycium barbarum leaves, Chemical constituents, Anti-rheumatoid arthritis

Zi-Jiao Wang, Bang-Yin Tan, Yun Zhao, Chang-Bin Wang, Yun-Li Zhao, Xiao-Dong Luo. Chemical constituents of Lycium barbarum leaves and their anti-rheumatoid arthritis activity in vitro[J]. Natural Products and Bioprospecting, 2025, 15(4): 35-35.

References

[1] Zhang L, Li Y, Yan Q, Ning Y, Wang Y, Liu K, Qiang Y, Ma X, Sun X. Establishment of high performance liquid chromatographic fingerprint and determination of 4 kinds of phenolic acid bioactive substances of fruitless Lycium barbarum leaves from Ningxia at different harvesting periods. Heliyon. 2024;10: e24614.
[2] Zhang B, Wang M, Wang C, Yu T, Wu Q, Li Y, Lv Z, Fan J, Wang L, Zhang B. Endogenous calcium attenuates the immunomodulatory activity of a polysaccharide from Lycium barbarum L. leaves by altering the global molecular conformation. Int J Biol Macromol. 2019;123:182-8.
[3] Gong G, Fan J, Sun Y, Wu Y, Liu Y, Sun W, Zhang Y, Wang Z. Isolation, structural characterization, and antioxidativity of polysaccharide LBLP5-A from Lycium barbarum leaves. Process Biochem. 2016;5:314-24.
[4] Li Y, Li A, Xing Y, Jiang Y, Pei H, He Z, Li J, Zhao Y, Shi K, Zong Y, Du R. Gastrodin targets the system Xc-/GPX4 axis to inhibit abnormal proliferation of fibroblast-like synoviocytes and improve rheumatoid arthritis. Phytomedicine. 2025;139: 156493.
[5] Pan L, Zhou T, Maimaiti K, Xu H, Ma G. Anti-rheumatoid arthritis effects of Caragana acanthophylla Kom. on collagen-induced arthritis and the anti-inflammatory activity of polyphenols as main active components. J Ethnopharmacol. 2025;346:119637.
[6] Jing R, Ban Y, Xu W, Nian H, Guo Y, Geng Y, Zang Y, Zheng C. Therapeutic effects of the total lignans from Vitex Negundo seeds on collagen-induced arthritis in rats. Phytomedicine. 2019;58: 152825.
[7] Wessig P, Schwarz J, Lindemann U, Holthausen MC. Photochemical synthesis of 3, 4-dihydro-2H-1, 3-oxazin-4-ones. Synthesis. 2001;112:1258-62.
[8] Hu X, White KM, Jacobsen NE, Mangelsdorf DJ, Canfield LM. Inhibition of growth and cholesterol synthesis in breast cancer cells by oxidation products of β-carotene. J Nutr Biochem. 1998;6:567-74.
[9] Yan J, Shi X, Donkor PO, Zhu H, Gao X, Ding L, Qiu F. Nine pairs of megastigmane enantiomers from the leaves of Eucommia ulmoides Oliver. J Nat Med. 2017;71:780-90.
[10] Serra S, Barakat A, Fuganti C. Chemoenzymatic resolution of cis- and trans-3,6-dihydroxy-α-ionone. Synthesis of the enantiomeric forms of dehydrovomifoliol and 8,9-dehydrotheaspirone. Tetrahedron Asymmetry. 2007;8:2573-80.
[11] Jin Q, Lee C, Lee JW, Yeon ET, Lee D, Han SB, Hong JT, Kim Y, Lee MK, Hwang BY. 2-Phenoxychromones and prenylflavonoids from Epimedium koreanum and their inhibitory effects on LPS-induced nitric oxide and interleukin-1β production. J Nat Prod. 2014;77:1724-8.
[12] Fan XZ, Song JQ, Shi XY, Zhou JF, Yuan RJ, Liu T, Kong XQ, Huang YS, Zhang LJ, Liao HB. New sesquiterpenoids with neuroprotective effects in vitro and in vivo from the Picrasma chinensis. Fitoterapia. 2024;175: 105908.
[13] Zheng JX, Zheng Y, Zhi H, Dai Y, Wang NL, Fang YX, Du ZY, Zhang K, Wu LY, Fan M. γ-Lactone derivatives and terpenoids from Selaginella uncinata. Chem Nat Compd. 2014;50:366-72.
[14] D’Abrosca B, Della GM, Fiorentino A, Monaco P, Oriano P, Temussi F. Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui. Phytochemistry. 2004;65:497-505.
[15] Luo Y, Li XZ, Xiang B, Luo Q, Liu JW, Yan YM, Sun Q, Cheng YX. Cytotoxic and renoprotective diterpenoids from Clerodendranthus spicatus. Fitoterapia. 2018;125:135-40.
[16] Shi YS, Liu YB, Ma SG, Li Y, Qu J, Li L, Yuan SP, Hou Q, Li YH, Jiang JD, Yu SS. Bioactive sesquiterpenes and lignans from the fruits of Xanthium sibiricum. J Nat Prod. 2015;78:1526-35.
[17] Yang C, Mao H, Qi X, Zhang Y, Cao Y, Tao L, Dong X, Zhang Y. Chemical constituents from the stems of Ostodes paniculata Bl. (Euphorbiaceae). Biochem Syst Ecol. 2024;113:104807.
[18] Wang W, Jiang L, Zhu Y, Mei L, Tao Y, Liu Z. Bioactivity-guided isolation of cyclooxygenase-2 inhibitors from Saussurea obvallata (DC.) Edgew. using affinity solid phase extraction assay. J Ethnopharmacol. 2022;284:114785.
[19] Ramabulana T, Scheepers LM, Moodley T, Maharaj VJ, Stander A, Gama N, Ferreira D, Sonopo MS, Selepe MA. Bioactive lignans from Hypoestes aristata. J Nat Prod. 2020;83:2483-9.
[20] Zhou H, Ren J, Li Z. Antibacterial activity and mechanism of pinoresinol from Cinnamomum camphora leaves against food-related bacteria. Food Control. 2017;79:192-9.
[21] Li BB, Li JL, Li N, Qi SZ, Lee HS, Zhang L, Xing SS, Tuo ZD, Cui L. Diacylglycerol acyltransferase 1 (DGAT1) inhibition by furofuran lignans from stems of Acanthopanax senticosus. Arch Pharm Res. 2017;40:1271-7.
[22] Bajpai VK, Shukla S, Paek WK, Lim J, Kumar P, Kumar P, Na M. Efficacy of (+)-lariciresinol to control bacterial growth of Staphylococcus aureus and Escherichia coli O157:H7. Front Microbiol. 2017;8:804.
[23] Huang Y, Hou P, Pan L, Li J, Liang X, Ren C, Peng L, Gan C, Xu W, Yang R, Li J, Guan X. Lignans and phenols with potential anti-inflammatory effect from the stems of Mallotus paxii Pamp. Fitoterapia. 2024;179: 106253.
[24] Wang L, Li F, Yang CY, Khan AA, Liu X, Wang MK. Neolignans, lignans and glycoside from the fruits of Melia toosendan. Fitoterapia. 2014;99:92-8.
[25] Wang J, Zhang X, Yu J, Du J, Wu X, Chen L, Wang R, Wu Y, Li Y. Constituents of the fruits of Rubus chingii Hu and their neuroprotective effects on human neuroblastoma SH-SY5Y cells. Food Res Int. 2023;173: 113255.
[26] Zhou H, Jian R, Kang J, Huang X, Li Y, Zhuang C, Yang F, Zhang L, Fan X, Wu T, Wu X. Anti-inflammatory effects of caper (Capparis spinosa L.) fruit aqueous extract and the isolation of main phytochemicals. J Agric Food Chem. 2010;58:12717-21.
[27] Oh CH, Kim NS, Yang JH, Lee H, Yang S, Park S, So UK, Bae JB, Eun JS, Jeon H, Lim JP, Kwon J, Kim YS, Shin TY, Kim DK. Effects of isolated compounds from Catalpa ovata on the T Cell-mediated immune responses and proliferation of leukemic cells. Arch Pharm Res. 2010;33:545-50.
[28] Nukulkit S, Nalinratana N, Aree T, Suriya U, Suttisri R, Nuengchamnong N, Chang HS, Chansriniyom C. Maeruines A-E, elusive indole alkaloids from stems of Maerua siamensis and their inhibitory effects on cyclooxygenases and HT-29 colorectal cancer cell proliferation. Phytochemistry. 2025;22: 114291.
[29] Kang U, Park J, Han AR, Woo MH, Lee JH, Lee SK, Chang TS, Woo HA, Seo EK. Identification of cytoprotective constituents of the flower buds of Tussilago farfara against glucose oxidase-induced oxidative stress in mouse fibroblast NIH3T3 cells and human keratinocyte HaCaT cells. Arch Pharm Res. 2016;39:474-80.
[30] Xiao H, Parkin K. Isolation and identification of phase II enzyme-inducing agents from nonpolar extracts of green onion (Allium Spp.). J Agric Food Chem. 2006;54:8417-24.
[31] Stefani T, Romo-Mancillas A, Carrizales-Castillo JJJ, Arredondo-Espinoza E, Ramírez-Estrada K, Alcantar-Rosales VM, González-Maya L, Sánchez-Carranza JN, Balderas-Renterías I, Camacho-Corona MDR. Cytotoxic fractions from Hechtia glomerata extracts and p-coumaric acid as MAPK inhibitors. Molecules. 2021;26:1096.
[32] Chang SW, Kim KH, Lee IK, Choi SU, Ryu SY, Lee KR. Phytochemical constituents of Bistorta manshuriensis. Nat Prod Sci. 2009;15:234-40.
[33] Abo-Qotb SMS, Hassanein AMM, Desoukey SY, Wanas AS, Tawfik HM, Orabi MAA. In vivo anti-inflammatory and hepatoprotective activities of Orobanche crenata (Forssk) aerial parts in relation to its phytomolecules. Nat Prod Res. 2022;36:1067-72.
[34] Reis B, Martins M, Barreto B, Milhazes N, Garrido EM, Silva P, Garrido J, Borges F. Structure-property-activity relationship of phenolic acids and derivatives. protocatechuic acid alkyl esters. J Agric Food Chem. 2010;58:6986-93.
[35] Luo JR, Jiang HE, Zhao YX, Zhou J, Qian JF. Components of the heartwood of Populus euphratica from an ancient tomb. Chem Nat Compd. 2008;44:6-9.
[36] Zhang YW, Sun WX, Li X, Zhao CC, Meng DL, Li N. Two new compounds from Helichrysum arenarium (L.). J Asian Nat Prod Res. 2009;11:289-93.
[37] Wang Y, Zhang H, Su X, Yang H, Sun W. Flavonoids and phenolic compounds of Petrosimonia sibirica. Chem Nat Compd. 2016;52:482-3.
[38] Wu Q, Zou L, Yang XW, Fu DX. Novel sesquiterpene and coumarin constituents from the whole herbs of Crossostephium chinense. J Asian Nat Prod Res. 2009;11:85-90.
[39] Wang W, Yang H, Chen Y. Constituents of Microsorum insigne. Chem Nat Compd. 2017;53:789-90.
[40] Xiao BK, Yang JY, Liu YR, Dong JX, Huang RQ. Chemical constituents of Pittosporum illicioides. Chem Nat Compd. 2015;51:1126-9.
[41] Luo S, Li H, Liu J, Xie X, Wan Z, Wang Y, Zhao Z, Wu X, Li X, Yang M, Li X. Andrographolide ameliorates oxidative stress, inflammation and histological outcome in complete freund’s adjuvant-induced arthritis. Chem-Biol Interact. 2020;319: 108984.
[42] Ma X, Yang Y, Li H, Luo Z, Wang Q, Yao X, Tang F, Huang Y, Ling Y, Ma W. Periplogenin inhibits pyroptosis of fibroblastic synoviocytes in rheumatoid arthritis through the NLRP3/Caspase-1/GSDMD signaling pathway. Int Immunopharmacol. 2024;133: 112041.
[43] Tong S, Liu J, Zhang C. Platelet-rich plasma inhibits inflammatory factors and represses rheumatoid fibroblast-like synoviocytes in rheumatoid arthritis. Clin Exp Med. 2017;17:441-9.
[44] Mo X, Chen J, Wang X, Pan Z, Ke Y, Zhou Z, Xie J, Lv G, Luo X. Krüppel-like factor 4 regulates the expression of inducible nitric oxide synthase induced by TNF-α in human fibroblast-like synoviocyte MH7A cells. Mol Cell Biochem. 2018;438:77-84.
[45] Akinloye OA, Alagbe OA, Ugbaja RN, Omotainse SO. Evaluation of the modulatory effects of Piper guineense leaves and seeds on egg albumin-induced inflammation in experimental rat models. J Ethnopharmacol. 2020;255: 112762.
[46] Zhang Y, Cai X, Wang B, Zhang B, Xu Y. Exploring the molecular mechanisms of the involvement of GZMB-Caspase-3-GSDME pathway in the progression of rheumatoid arthritis. Mol Immunol. 2023;161:82-90.
[47] Zhu PF, Dai Z, Wang B, Wei X, Yu HF, Yan ZR, Zhao XD, Liu YP, Luo XD. The anticancer activities phenolic amides from the stem of Lycium barbarum. Natur Prod & Bioprosp. 2017;7:421-31.
[48] Chen YC, Liu YY, Chen L, Tang DM, Zhao Y, Luo XD. Antimelanogenic effect of isoquinoline alkaloids from Plumula nelumbinis. J Agric Food Chem. 2023;71:16090-101.
[49] Li C, Tang S, Hu T, Zhou C, Chen Y, Hu Z, Pan J, Chen J, Wang Y. Exploring the potential mechanism of action of Wutou-Guizhi decoction in the treatment of rheumatoid arthritis through network pharmacology analysis. Comput Biol Chem. 2025;115: 108314.
[50] Chen S, Tian CB, Bai LY, He XC, Lu QY, Zhao YL, Luo XD. Thrombosis inhibited by Corydalis decumbens through regulating PI3K-Akt pathway. J Ethnopharmacol. 2024;329: 118177.

Chemical constituents of Lycium barbarum leaves and their anti-rheumatoid arthritis activity in vitro

Chemical constituents of Lycium barbarum leaves and their anti-rheumatoid arthritis activity in vitro

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 4

Recommended Articles

Metrics

Comments

[1]	Xiao-Na Wang, Zhao-Jie Wang, Yun Zhao, Huan Wang, Mei-Ling Xiang, Yang-Yang Liu, Li-Xing Zhao, Xiao-Dong Luo. Antifungal alkaloids from Mahonia fortunei against pathogens of postharvest fruit [J]. Natural Products and Bioprospecting, 2023, 13(2): 10-10.
[2]	Jin-Tao Ma, Da-Wei Li, Ji-Kai Liu, Juan He. Advances in Research on Chemical Constituents and Their Biological Activities of the Genus Actinidia [J]. Natural Products and Bioprospecting, 2021, 11(6): 573-609.
[3]	Yan-Jie Huang, Xing-Rong Peng, Ming-Hua Qiu. Progress on the Chemical Constituents Derived from Glucosinolates in Maca (Lepidium meyenii) [J]. Natural Products and Bioprospecting, 2018, 8(6): 405-412.
[4]	Ya-Mei Pan, Yu Zhang, Xiao-Nan Wang, He-Ping Chen, Shun-Lin Li, Ying-Tong Di, Duo-Zhi Chen, Ling-Li Guo, Xiao-Jiang Hao, Hong-Ping He. Chemical Constituents from the Stems of Manihot esculenta [J]. Natural Products and Bioprospecting, 2015, 5(1): 55-59.