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(1) Iridoids from Gardenia jasminoides contain six categories according to the structure of iridoids.
(2) Iridoids from Gardenia jasminoides possess anti-inflammatory, antioxidant, anti-tumor, and neuroprotection biological activities.
(3) The potential mechanisms of anti-inflammatory, antioxidant, anti-tumor and neuroprotective effects of iridoids from Gardenia jasminoides were summarized.
Iridoids compounds are one of the main active components of Gardenia jasminoides, which were divided into two categories: iridoid glycosides and non-glucosylated iridoids according to their chemical structures. Relevant studies have shown that components such as geniposide, deacetyl asperulosidic acid methyl ester, and geniposidic acid play an important role in anti-inflammatory, hypoglycemia, and the protection of cardiomyocytes. While the pharmacological effects of most iridoid glycosides are still not clear. This paper’s systematic summary was created by searching for relevant iridoids material on websites such as Google Scholar, PubMed, SciFinder Scholar, Science Direct, and others. Up to now, a total of 94 iridoids had been identified in G. jasminoides, among which 40 iridoids had extensive biological activities and the mechanisms involved in MAPK, NF-κB, JNK signal pathways. This paper reviews the literature on types and pharmacological effects of iridoid compounds in G. jasminoides, in order to provide a reference for its development and application.
Sampaio-Santos, M. I., Kaplan, M. A. C. Biosynthesis significance of iridoids in chemosystematics. Journal of the Brazilian Chemical Society, 2010, 12: 144–153. https://doi.org/10.1590/S0103-50532001000200004
Franzyk, H. Synthetic aspects of iridoid chemistry. Organic Chemistry Frontiers, 2000, 79: 1–114. https://doi.org/10.1007/978-3-7091-6341-21
Kong, Y. F. Research progress on structures and structure-activity relationships of iridoids. Natural Product Research, 2021, 33: 1236–1250. https://doi.org/10.7501/j.issn.0253-2670.2013.19.025
Çelikel, F. G., Reid, M. S., Jiang, C. Z. Postharvest physiology of cut Gardenia jasminoides flowers. Scientia Horticulturae, 2020, 261: 108983. https://doi.org/10.1016/j.scienta.2019.108983
Feng, J., He X., Zhou, S., et al. Preparative separation of crocins and geniposide simultaneously from gardenia fruits using macroporous resin and reversed-phase chromatography. Journal of Separation Science, 2014, 37: 314–322. https://doi.org/10.1002/jssc.201300601
Hobbs, C. A., Koyanagi. M., Swartz, C., et al. Genotoxicity evaluation of the naturally-derived food colorant, gardenia blue, and its precursor, genipin. Food and Chemical Toxicology, 2018, 118: 695–708. https://doi.org/10.1016/j.fct.2018.06.001
Zhang, Q. H. Homology of medicine and food and Chinese herb taken as food. Journal of Liaoning University of Traditional Chinese Medicine, 2009, 11: 54–55. https://doi.org/10.13194/j.jlunivtcm.2009.07.56.zhangqh.096
Li, H. B., Ma, J. F., Mei, Y. D., et al. Two new iridoid glycosides from the fruit of Gardenia jasminoides. Natural Product Research, 2022, 36: 186–192. https://doi.org/10.1080/14786419.2020.1775227
Chen, Y. F., Zhang, J. Y., Zhao, M., et al. The analgesic activity and possible mechanisms of deacetyl asperulosidic acid methyl ester from Ji Shi Teng in mice. Pharmacology Biochemistry and Behavior, 2012, 102: 585–592. https://doi.org/10.1016/j.pbb.2012.07.005
Xia, T., Zhao, R., He, S., et al. Gardenoside ameliorates inflammation and inhibits ECM degradation in IL-1β-treated rat chondrocytes via suppressing NF-κB signaling pathways. Biochemical and Biophysical Research Communications, 2023, 640: 164–172. https://doi.org/10.1016/j.bbrc.2022.12.016
Liu, J., Zhao, N., Shi, G., et al. Geniposide ameliorated sepsis-induced acute kidney injury by activating PPARγ. Neurobiology of Aging, 2020, 12: 22744–22758. https://doi.org/10.18632/aging.103902
Yu, Y., Bian, Y., Shi, J. X., et al. Geniposide promotes splenic Treg differentiation to alleviate colonic inflammation and intestinal barrier injury in ulcerative colitis mice. Bioengineered, 2022, 13: 14616–14631. https://doi.org/10.1080/21655979.2022.2092678
Chen, J. Y., Li, H. H., Hu, S. L., et al. Anti-inflammatory effects and pharmacokinetics study of geniposide on rats with adjuvant arthritis. International Immunopharmacology, 2015, 24: 102–109. https://doi.org/10.1016/j.intimp.2014. 11.017
Yu, B., Shen, Y., Qiao, J., et al. Geniposide attenuates Staphylococcus aureus-induced pneumonia in mice by inhibiting NF-κB activation. Microbial Pathogenesis, 2017, 112: 117–121. https://doi.org/10.1016/j.micpath.2017.09.050
Song, X., Zhang, W., Wang, T., et al. Geniposide plays an anti-inflammatory role via regulating TLR4 and downstream signaling pathways in lipopolysaccharide-induced mastitis in mice. Inflammopharmacology, 2014, 37: 1588–1598. https://doi.org/10.1007/s10753-014-9885-2
Chang, C. H., Wu, J. B., Yang, J. S., et al. The suppressive effects of geniposide and genipin on Helicobacter pylori infections in vitro and in vivo. Journal of Food Science, 2017, 82: 3021–3028. https://doi.org/10.1111/1750-3841.13955
Li, C., Mu, Y. R. Penta-acetyl geniposide suppresses migration, invasion, and inflammation of TNF-α-stimulated rheumatoid arthritis fibroblast-like synoviocytes involving Wnt/β-catenin signaling pathway. Inflammopharmacology, 2021, 44: 2232–2245. https://doi.org/10.1007/s10753-021-01495-y
Tang, J. J., Zhao, N., Gao, Y. Q., et al. Phytosterol profiles and iridoids of the edible Eucommia ulmoides Oliver seeds and their anti-inflammatory potential. Food Bioscience, 2021, 43: 2212–4292. https://doi.org/10.1016/j.fbio.2021.101295
Sohn, Y. A., Hwang, I. Y., Lee, S. Y., Cho, et al. Protective Effects of Genipin on Gastrointestinal Disorders. Biological and Pharmaceutical Bulletin, 2017, 40: 151–154. https://doi.org/10.1248/ bpb.b16-00545
Kim, T. H., Yoon, S. J., Lee, S. M. Genipin attenuates sepsis by inhibiting Toll-like receptor signaling. Molecular Medicine, 2012, 18: 455–465. https://doi.org/10.2119/molmed.2011.00308
Li, Z., Ma, T., Zhang, W., et al. Genipin attenuates dextran sulfate sodium-induced colitis via suppressing inflammatory and oxidative responses. Inflammopharmacology, 2020, 28: 333–339. https://doi.org/10.1007/s10787-019-00639-9
Huertas-Bell, M., Cuéllar-Sáenz, J. A., Rodriguez, C. N., et al. A pilot study to evaluate genipin in Staphylococcus aureus and Pseudomonas aeruginosa keratitis models: modulation of pro-inflammatory cytokines and matrix metalloproteinases. International Journal of Molecular Sciences, 2023, 24: 6904. https://doi.org/10.3390/ijms24086904
Wang, J., Chen, L. Genipin inhibits LPS-induced inflammatory response in BV2 microglial cells. Neurochemical Research, 2017, 42: 2769–2776. https://doi.org/10.1007/s11064-017-2289-6
Shindo, S., Hosokawa, Y., Hosokawa, I., et al. Genipin inhibits MMP-1 and MMP-3 release from TNF-a-stimulated human periodontal ligament cells. Biochimie, 2014, 107: 391–395. https://doi.org/10.1016/j.biochi.2014.10.008
Jeon, W. K., Hong, H. Y., Kim, B. C. Genipin up-regulates heme oxygenase-1 via PI3-kinase-JNK1/2-Nrf2 signaling pathway to enhance the anti-inflammatory capacity in RAW264.7 macrophages. Archives of Biochemistry and Biophysics, 2011, 512: 119–125. https://doi.org/10.1016/j.abb.2011.05.016
Luo, X., Lin, B., Gao, Y., et al. Genipin attenuates mitochondrial-dependent apoptosis, endoplasmic reticulum stress, and inflammation via the PI3K/AKT pathway in acute lung injury. International Immunopharmacology, 2019, 76: 105842. https://doi.org/10.1016/j.intimp
Zhang, X., Wang, L., Zheng, Z., et al. Online microdialysis-ultra performance liquid chromatography–mass spectrometry method for comparative pharmacokinetic investigation on iridoids from Gardenia jasminoides Ellis in rats with different progressions of type 2 diabetic complications. Journal of Pharmaceutical and Biomedical Analysis, 2017, 140: 146–154. https://doi.org/10.1016/j.jpba.2017.03.040
Zeng, X., Jiang, J., Liu, S., et al. Bidirectional effects of geniposide in liver injury: preclinical evidence construction based on meta-analysis. Journal of ethnopharmacology, 2023, 319: 117061. https://doi.org/10.1016/j.jep.2023.117061
He, J., Lu, X., Wei, T., et al. Asperuloside and asperulosidic acid exert an anti-inflammatory effect via suppression of the NF-κB and MAPK signaling pathways in LPS-Induced RAW 264.7 macrophages. International Journal of Molecular Sciences, 2018, 19: 2027. https://doi.org/10.3390/ijms19072027
Chen, Y. E., Xu, S. J., Lu, Y. Y., et al. Asperuloside suppressing oxidative stress and inflammation in DSS-induced chronic colitis and RAW 264.7 macrophages via Nrf2/HO-1 and NF-κB pathways. Chemico-Biological Interactions, 2021, 344: 109512. https://doi.org/10.1016/j.cbi.2021.109512
Zhang, H., Feng, N., Xu, Y. T., et al. Chemical constituents from the flowers of wild Gardenia jasminoides J. Ellis. Chemistry & Biodiversity, 2017, 14: 1600437. https://doi.org/10.1002/cbdv.201600437
Ijaz, F., Haq, A. U., Ahmad, I., et al. Antioxidative iridoid glycosides from the sky flower ( Duranta repens Linn). Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, 26: 88–92. https://doi.org/ 10.3109/14756361003724778
Wei, D., Liu, B. L., Shi, Y., et al. Genipin inhibited on oxidative stress injury of ARPE-19 cells by regulating Nrf2/HO-1 pathway. International Journal of Molecular Medicine, 2022, 51: 83–86. https://doi.org/10.3892/ijmm.2018.4027
Cheng, S., Jia, H., Zhang, Y., et al. Geniposidic acid from Eucommia ulmoides oliver staminate flower tea mitigates cellular oxidative stress via activating AKT/NRF2 signaling. Molecules, 2022, 27: 8568. https://doi.org/10.3390/molecules27238568
Li, J., Ge, H., Xu, Y., et al. Geniposide alleviates oxidative damage in hepatocytes through regulating miR-27b-3p/Nrf2 axis. Journal of Agricultural and Food Chemistry, 2022, 70: 11544–11553. https://doi.org/10.1021/acs.jafc.2c03856
Wu, Q., Gai, S., Zhang, H. J. Asperulosidic acid, a bioactive iridoid, alleviates placental oxidative stress and inflammatory responses in gestational diabetes mellitus by suppressing NF-κB and MAPK signaling pathways. Pharmacology, 2022, 107: 197–205. https://doi.org/10.1159/000521080
Lin, L., Cheng, X. L., Li, M. Z., et al. Antitumor effects of iridomyrmecin in HeLa cervical cancer cells are mediated via apoptosis induction, loss of mitochondrial membrane potential, cell cycle arrest and down-regulation of PI3K/Akt and up-regulation of lncRNA CCAT2 expression. Bangladesh Journal of Pharmacology, 2016, 11: 856. https://doi.org/10.3329/bjp.v11i4.27539
Zhang, C., Wang, N., Tan, H. Y., et al. Direct inhibition of the TLR4/MyD88 pathway by geniposide suppresses HIF-1α-independent VEGF expression and angiogenesis in hepatocellular carcinoma. British Journal of Pharmacology, 2020, 14: 3240–3257. https://doi.org/10.1111/bph.15046
Alamri, M. A., Alawam, A. S., Alshahrani, M. M., et al. Establishing the role of iridoids as potential Kirsten rat sarcoma viral oncogene homolog G12C inhibitors using molecular docking; molecular docking simulation; molecular mechanics poisson–boltzmann surface area; frontier molecular orbital theory; molecular electrostatic potential; and absorption, distribution, metabolism, excretion, and toxicity analysis. Molecules, 2023, 28: 5050. https://doi.org/10.3390/molecules28135050
Moon, A. Genipin, a constituent of Gardenia jasminoides Ellis, induces apoptosis and inhibits invasion in MDA-MB-231 breast cancer cells. Oncology Reports, 2011, 27: 567–572. https://doi.org/10.3892/or.2011.1508
Li, Z., Zhang, T. B., Jia, D. H., et al. Genipin inhibits the growth of human bladder cancer cells via inactivation of PI3K/Akt signaling. Oncology Letters, 2018, 15: 2619–2624. https://doi.org/10.3892/ol.2017.7588
Jo, M. J., Jeong, S., Yun, H. K., et al. Genipin induces mitochondrial dysfunction and apoptosis via downregulation of Stat3/mcl-1 pathway in gastric cancer. BMC Cancer, 2019, 19: 739. https://doi.org/10.1186/s12885-019-5957-x
Cao, H., Feng, Q., Xu, W., et al. Genipin induced apoptosis associated with activation of the c-Jun NH2-terminal kinase and p53 protein in HeLa cells. Biological & pharmaceutical bulletin, 2010, 33: 1343–1348. https://doi.org/10.1248/bpb
Yang, X., Yao, J., Luo, Y., et al. P38 MAP kinase mediates apoptosis after genipin treatment in non-small-cell lung cancer H1299 cells via a mitochondrial apoptotic cascade. Journal of Pharmacological Sciences, 2013, 121: 272–281. https://doi.org/10.1254/jphs.12234fp
Peng, C., Huang, C., Wang, C. The anti-tumor effect and mechanisms of action of penta-acetyl geniposide. Current Cancer Drug Targets, 2005, 5: 299–305. https://doi.org/10.2174/1568009054064633
Qi, Z. M., Wang, X., Liu, X., et al. Asperuloside promotes apoptosis of cervical cancer cells through endoplasmic reticulum stress-mitochondrial pathway. Chinese Journal of Integrative Medicine, 2024, 30: 34–41. https://doi.org/10.1007/s11655-023-3695-z
Zhang, H., Sun, Y., Yau, S., et al. Synergistic effects of two natural compounds of iridoids on rapid antidepressant action by up-regulating hippocampal PACAP signaling. British Journal of Pharmacology, 2022, 179: 4078–4091. https://doi.org/10.1111/bph.15847
Sun, Z. W., Zhan, H. G.,Wang, C., et al. Shanzhiside methylester protects against depression by inhibiting inflammation via the miRNA-155-5p/SOCS1 axis. psychopharmacology, 2022, 239: 2201–2213. https://doi.org/10.1007/s00213-022-06107-7
Luo, X. F., Li, Y., Hu, J. Regulatory effect of gardenoside on sleep disorder in rats with Parkinson’s disease and itsmechanism. Journal of Jilin University Medicine Edition, 2020, 46: 1177–1181. https://doi.org/10.13481/j.1671-587x.20200611
Ma, W. W., Tao, Y., Wang, Y. Y., et al. Effects of Gardenia jasminoides extracts on cognition and innate immune response in an adult Drosophila model of Alzheimer's disease. Chinese Journal of Natural Medicines, 2017, 15: 899–904. https://doi.org/10.1016/S1875-5364 (18)30005-0
Chen, G. H., Chen, Q. Role of gardenoside and its aglycone genipine in treatment of depression. Chinese Journal of Chemical Physics, 2022, 38: 1877–1882. https://doi.org/10.3969/j.issn.1000-4718.2022.10.018
Uczay, M., Pflüger, P., Picada, J. N., et al. Geniposide and asperuloside alter the COX-2 and GluN2B receptor expression after pilocarpine-induced seizures in mice. Naunyn-schmiedebergs Archives of Pharmacology, 2023, 396: 951–962. https://doi.org/10.1007/s00210-022-02367-4
Wei, H., Duan, G., He, J., et al. Geniposide attenuates epilepsy symptoms in a mouse model through the PI3K/Akt/GSK-3β signaling pathway. Experimental and Therapeutic Medicine, 2017, 1: 1136–1142. https://doi.org/10.3892/etm.2017.5512
Wang, M., Yang, L., Chen, Z., et al. Geniposide ameliorates chronic unpredictable mild stress induced depression-like behavior through inhibition of ceramide-PP2A signaling via the PI3K/Akt/GSK3β axis. Psychopharmacology, 2021, 238: 2789–2800. https://doi.org/10.1007/s00213-021-05895-8
Chen, Q. Y., Yin, Y., Li, L., et al. Geniposidic acid confers neuroprotective effects in a mouse model of Alzheimer's disease through activation of a PI3K/AKT/GAP43 regulatory axis. Journal of Prevention of Alzheimers Disease, 2022, 9: 158–171. https://doi.org/10.14283/jpad.2021.60
Gao, F. Y., Chen, X. F., Cui, L. X., et al. Gut microbiota mediates the pharmacokinetics of Zhi-Zi-Chi decoction for the personalized treatment of depression. Journal of Ethnopharmacology, 2023, 302: 115934. https://doi.org/10.1016/j.jep
Wang, Q. S., Tian, J. S., Cui, Y. L., et al. Genipin is active via modulating monoaminergic transmission and levels of brain-derived neurotrophic factor (BDNF) in rat model of depression. Neuroscience, 2014, 275: 365–373. https://doi.org/10.1016/j.neuroscience.2014.06.032
Li, Y., Li, L., Hölscher, C. Therapeutic potential of genipin in central neurodegenerative diseases. CNS Drugs, 2016, 30: 889–897. https://doi.org/10.1007/s40263-016-0369-9
Ramos, R. R., Gonçalo, M. P., Daniela, M. Genipin prevents alpha-synuclein aggrega tion and toxicity by affecting endocytosis, metabolism and lipid storage. Nature Communictions, 2023, 14: 1918. https://doi.org/10.1038/s41467-023-37561-2
Liu, X. Q., Wang, S. Y., Cui, L. L., et al. Flowers: precious food and medicine resources. Food Science and Human Wellness, 2023, 12: 1020–1052. https://doi.org/10.1016/j.fshw.2022.10.022
Chang, W. L., Wang, H. Y., Shi, L. S., et al. Immunosuppressive iridoids from the fruits of gardeniajasminoides. Journal of Natural Products, 2005, 68: 1683–1685. https://doi.org/10.1021/np0580816
Zhong, A. J., Li, G. Screening of active ingredients in Rehmannia glutinosa and its mechanism of action in the treatment of liver diseases. Indian Journal of Pharmaceutical Sciences, 2023, 85: 445–455. https://doi.org/10.36468/pharmaceutical-sciences.1110
Fan, H., Li, T. F., Gong, N., et al. Shanzhiside methylester, the principle effective iridoid glycoside from the analgesic herb Lamiophlomis rotata, reduces neuropathic pain by stimulating spinal microglial β-endorphin expression. Neuropharmacology, 2016, 101: 98–109. https://doi.org/10.1016/j.neuropharm.2015.09.010
Yenigun, S., Basar, Y., Ipek, Y., et al. Comprehensive evaluation of Ixoroside: An iridoid glycoside from Nepeta aristata and N. baytopii, assessing antioxidant, antimicrobial, enzyme inhibitory, DNA protective properties, with computational and pharmacokinetic analyses. Journal of Biologically Active Products from Nature, 2024, 14: 286–315. https://doi.org/10.1080/22311866.2024.2358785
Zhou, J., Li, S. P., Feng, K. X., et al. Impact of gardenoside on insulin receptor and nuclear factor kappa B of insulin resistant in HepG2 cells. The Chinese Journal of Clinical Pharmacology, 2015, 31: 362–365. https://doi.org/10.13699/j.cnki.1001-6821.2015.05.013
Song, P., Shen, D. F., Meng, Y. Y., et al. Geniposide protects against sepsis-induced myocardial dysfunction through AMPK α-dependent pathway. Free Radical Biology and Medicine, 2020, 152: 186–196. https://doi.org/10.1016/j.freeradbiomed.2020.02.011
Fu, Y., Yuan, P., Cao, Y., et al. Geniposide in Gardenia jasminoides var. radicans Makino modulates blood pressure via inhibiting WNK pathway mediated by the estrogen receptors. Journal of Pharmacy and Pharmacology, 2020, 72: 1956–1969. https://doi.org/10.1111/jphp.13361
Zhang, Y., Ding, Y., Zhong, X., et al. Geniposide acutely stimulates insulin secretion in pancreatic β-cells by regulating GLP-1 receptor/cAMP signaling and ion channels. Molecular and Cellular Endocrinology, 2016, 430: 89–96. https://doi.org/10.1016/j.mce.2016.04.020
Kwak, J. H., Lee, D. U. Structure–antiamnesic activity relationship of iridoid glycosides from gardenia fruits. Chemistry Letters, 2015, 44: 837–839. https://doi.org/10.1246/cl.150172
Nakamura, K., Hosoo, S., Yamaguchi, S., et al. Geniposidic acid upregulates atrial natriuretic peptide secretion and lowers blood pressure in spontaneously hypertensive rats. Journal of Functional Foods, 2018, 40: 634–638. https://doi.org/10.1016/j.jff.2017.10.037
Huang, S. M., Lin, S. Y., Chen, M. K., et al. Effects of geniposide and geniposidic acid on fluoxetine-induced muscle atrophy in C2C12 cells. Processes, 2021, 9: 1649. https://doi.org/10.3390/pr9091649
L. Li, J. Zou, Q. Xia, et al. Anti-TMV and insecticidal potential of four iridoid glycosides from Gardenia jasminoides fruit. Chemical Research in Chinese Universities, 2018, 34: 697–699. https://doi.org/10.1007/s40242-018-8197-8
Kim, D. H., Lee, H. J., Kim, Y. J., et al. Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidation. Archives of Pharmacal Research, 2005, 28: 1156–1160. https://doi.org/10.1007/BF02972979
Akihisa, T., Watanabe, K., Yamamoto, A., et al. Melanogenesis inhibitory activity of monoterpene glycosides from Gardeniae Fructus. Chemistry & Biodiversity, 2012, 9: 1490–1499. https://doi.org/10.1002/cbdv.201200030
Hirata, T., Kobayashi, T., Wada, A., et al. Anti-obesity compounds in green leaves of Eucommia ulmoides. Bioorganic & Medicinal Chemistry Letters, 2011, 21: 1786–1791. https://doi.org/10.1016/j.bmcl.2011.01.060
Li, L., Zou, J., You, S., et al. Natural product cerbinal and its analogues Cyclopenta pyridines: synthesis and discovery as novel pest control agents. Journal of Agricultural and Food Chemistry, 2019, 18: 10498–10504. https://doi.org/10.1021/acs.jafc.9b03699
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