Research Progress on Chemical Constituents of Lonicerae japonicae flos

Lingna Wang, Qiu Jiang, Jinghong Hu, Yongqing Zhang, Jia Li, Lingna Wang, Qiu Jiang, Jinghong Hu, Yongqing Zhang, Jia Li

Abstract

Lonicerae japonicae flos is commonly used in traditional Chinese medicine for thousands of years with confirmed curative effects. Except for medicine, it is also used in healthy food, cosmetics, and soft beverages for its specific activities. Therefore, the chemical constituents, mainly including organic acids, flavonoids, iridoids, triterpenoids, and volatile oils, have been well studied by many scholars in recent years and a comprehensive and systematic review on chemical constituents of Lonicerae japonicae flos is indispensable. This paper aims at reviewing the chemical components of LJF in recent years through searching for the literatures both at home and abroad. Our results show that 212 components have been isolated from Lonicerae japonicae flos, including 27 flavonoids, 40 organic acids, 83 iridoids, 17 triterpenoids, and 45 other compounds, which could lay a foundation for the further application of Lonicerae japonicae flos.

Figures

Figure 1
Figure 1
Skeleton of flavonoids.
Figure 2
Figure 2
The structures of 40 organic acids (28)–(67).
Figure 3
Figure 3
The structures of 83 iridoids (68)–(150).
Figure 4
Figure 4
The structures of compounds of (151)-(152).
Figure 5
Figure 5
Skeleton of triterpenoids.
Figure 6
Figure 6
The structures of compounds of (168)–(212).

References

    1. Shang X., Pan H., Li M., Miao X., Ding H. Lonicera japonica Thunb.: ethnopharmacology, phytochemistry and pharmacology of an important traditional Chinese medicine. Journal of Ethnopharmacology. 2011;138(1):1–21. doi: 10.1016/j.jep.2011.08.016.
    1. Kang O.-H., Choi J.-G., Lee J.-H., Kwon D.-Y. Luteolin isolated from the flowers of Lonicera japonica suppresses inflammatory mediator release by blocking NF-κB and MAPKs activation pathways in HMC-1 cells. Molecules. 2010;15(1):385–398. doi: 10.3390/molecules15010385.
    1. Liu Y., Wang G. L. Effect of Flos Lonicerae extracts on herpes simplex keratitis. Herald of Medicine. 2011;30(11):1421–1424. doi: 10.3870/yydb.2011.11.006.
    1. Tian J., Che H., Ha D., Wei Y., Zheng S. Characterization and anti-allergic effect of a polysaccharide from the flower buds of Lonicera japonica . Carbohydrate Polymers. 2012;90(4):1642–1647. doi: 10.1016/j.carbpol.2012.07.044.
    1. Ning W., Peng X., Ma L., et al. Enhanced secondary metabolites production and antioxidant activity in postharvest Lonicera japonica Thunb. in response to UV radiation. Innovative Food Science and Emerging Technologies. 2012;13:231–243. doi: 10.1016/j.ifset.2011.10.005.
    1. Han J. M., Kim M. H., Choi Y. Y., Lee H., Hong J., Yang W. M. Effects of Lonicera japonica Thunb. on type 2 diabetes via PPAR-γ activation in rats. Phytotherapy Research. 2015;29(10):1616–1621. doi: 10.1002/ptr.5413.
    1. National Health and Family Planning Commission ofthe People's Republic of China. Diagnostic and Treatment Protocol for Human Infections with Avian Influenza A (H7N9), 2014, .
    1. Liu N., Lin X. F., Zuo J. L., Ye Z. Z., Huang X. P. Treatment of 70 cases of SARS clinical observation by clear away heat and toxic material. Journal of Sichuan Traditional Chinese Medicine. 2005;23(3):54–57.
    1. Pan Z. Z., Wang X. F., Yan L. J., Nan C. H., Yue Z. J. Inhibitory effect of extracts from Lonicerae on influena A virus FM1 strain in vitro. Chinese Journal of Information on TCM. 2007;14(6):37–38.
    1. Wang X. Y. Study on health beverage of honeysuckle and mungbean skin fiber. Food Research and Development. 2013;34(10):65–68.
    1. Jeong Y. T., Jeong S. C., Hwang J. S., Kim J. H. Modulation effects of sweroside isolated from the Lonicera japonica on melanin synthesis. Chemico-Biological Interactions. 2015;238:33–39. doi: 10.1016/j.cbi.2015.05.022.
    1. Shen T. C., Cheng Q. Q., Shan W. G., Tang L. Study on preparation of Lonicerae japonicae flos effervescent tables for beverage. Science and Technology of Food Industry. 2012;33(12):255–258.
    1. Chu X. B., Yan B. X. Application and prospect of medicinal ornamental plant Lonicera in the landscape field. Journal of Anhui Agricultural Sciences. 2014;13:3854–3862. doi: 10.3969/j.issn.0517-6611.2014.13.030.
    1. Li Y., Cai W., Weng X., et al. Lonicerae japonicae flos and Lonicerae flos: a systematic pharmacology review. Evidence-Based Complementary and Alternative Medicine. 2015;2015:16. doi: 10.1155/2015/905063.905063
    1. Huang L. Y., Lv Z. Z., Li J. B., Zhou B. N. Studies on the chemical constituents of Japanese honeysuekle. Chinese Traditional and Herbal Drugs. 1996;27(11):645–647.
    1. Bi Y. F., Tian Y., Pei S. S., Zhang C. The chemical constituents of Lonicera japonica Thunb. Journal of Zhengzhou University (Natural Science Edition) 2007;39(2):184–186.
    1. Tian Y. Study on chemical constituents of Lonicera japonica thunb [M.S. dissertation] Zhengzhou, China: Zhengzhou University; 2007.
    1. Jiang N. H. Study on chemical constituents of Lonicera japonica bud. Journal of Chinese Medicinal Materials. 2015;38(2):315–317.
    1. Wang F., Jiang Y. P., Wang X. L., Lin S., Pu P. B., Zhu C. G. Chemical constituents from flower buds of Lonicera japonica . China Journal of Chinese Materia Medica. 2013;38(9):1378–1384.
    1. Feng W.-S., Chen X., Zheng X.-K., Zhang C.-L., Li D.-D. Study on chemical constituents of Lonicerae japonicae flos. Chinese Pharmaceutical Journal. 2011;46(5):338–340.
    1. Yu Y., Song W. X., Guo Q. L., et al. Studies on chemical constituents of aqueous extract of Lonicera japonica flower buds. The Journal of Chinese Medicine & Traditional Chinese Medicine. 2015;40(17):3496–3504.
    1. Xu D. D., Jiang X. Z., Gao Y., Zheng W., He M., Gao Q. P. Studies on chemical constituents of effective fraction of Honeysuckle on inhibition of Escherichia coli biofilms. Chinese Journal of Experimental Traditional Medical Formulae. 2012;18(20):122–125.
    1. Bai X., Huang H. F., Wu X. H., Chi L. L. Analysis on chemical constituents in Lonicerae japonicae flos by HPLC-DAD-MS/MS. Food Drug. 2015;17(1):5–8.
    1. Lin L.-M., Zhang X.-G., Zhu J.-J., Gao H.-M., Wang Z.-M., Wang W.-H. Two new triterpenoid saponins from the flowers and buds of Lonicera japonica . Journal of Asian Natural Products Research. 2008;10(10):925–929. doi: 10.1080/10286020802217366.
    1. Zhang L. Y., Li Y. B., Li L. X., Wang Y. M., Jin J. Chemical constituent of Lonicera japonica Thunb. by RRLC-O-TOF/MS. Central South Pharmacy. 2012;10(3):204–208. doi: 10.3969/j.issn.1672-2981.2012.03.014.
    1. Lee E. J., Kim J. S., Kim H. P., Lee J.-H., Kang S. S. Phenolic constituents from the flower buds of Lonicera japonica and their 5-lipoxygenase inhibitory activities. Food Chemistry. 2010;120(1):134–139. doi: 10.1016/j.foodchem.2009.09.088.
    1. Ma S. C., Bi P. X., Huang R. C., Lee S. H., Lee S. F. Determination of the antiviral caffeoyl quinic acids isolaetd from Lonicera japonica Thunb. Chinese Journal of Pharmaceutical Analysis. 2005;25(7):751–755.
    1. Wang Q. Study on chemical constituents of Lonicare japonica flos [M.S. thesis] Shenyang, China: Shenyang Pharmaceutical University; 2008.
    1. Peng L.-Y., Mei S.-X., Jiang B., Zhou H., Sun H.-D. Constituents from Lonicera japonica . Fitoterapia. 2000;71(6):713–715. doi: 10.1016/s0367-326x(00)00212-4.
    1. Zheng Z.-F., Zhang Q.-J., Chen R.-Y., Yu D.-Q. Four new N-contained iridoid glycosides from flower buds of Lonicera japonica . Journal of Asian Natural Products Research. 2012;14(8):729–737. doi: 10.1080/10286020.2012.688038.
    1. Yu Y., Jiang Z. B., Song W. X., et al. Glucosylated caffeoylquinic acid derivatives from the flower buds of Lonicera japonica . Acta Pharmaceutica Sinica B. 2015;5(3):210–214. doi: 10.1016/j.apsb.2015.01.012.
    1. Liu Z.-X., Liu C.-T., Liu Q.-B., et al. Iridoid glycosides from the flower buds of Lonicera japonica and their nitric oxide production and α-glucosidase inhibitory activities. Journal of Functional Foods. 2015;18, article 1255:512–519. doi: 10.1016/j.jff.2015.08.017.
    1. Kakuda R., Imai M., Yaoita Y., Machida K., Kikuchi M. Secoiridoid glycosides from the flower buds of Lonicera japonica . Phytochemistry. 2000;55(8):879–881. doi: 10.1016/s0031-9422(00)00279-x.
    1. Song Y., Li S.-L., Wu M.-H., Li H.-J., Li P. Qualitative and quantitative analysis of iridoid glycosides in the flower buds of Lonicera species by capillary high performance liquid chromatography coupled with mass spectrometric detector. Analytica Chimica Acta. 2006;564(2):211–218. doi: 10.1016/j.aca.2006.01.068.
    1. Li H. J., Li P., Wang M. C., Ye W. C. A new secoiridoid glucoside from Lonicera japonica . Chinese Journal of Natural Medicines. 2003;1(3):132–133.
    1. Song W.-X., Guo Q.-L., Yang Y.-C., Shi J.-G. Two homosecoiridoids from the flower buds of Lonicera japonica . Chinese Chemical Letters. 2015;26(5):517–521. doi: 10.1016/j.cclet.2014.11.035.
    1. Li C., Dai Y., Zhang J.-B., Liu M.-L., Yao X.-S. A new iridoid glycoside from Lonicerae flos. Chinese Traditional and Herbal Drugs. 2013;44(21):2951–2954. doi: 10.7501/j.issn.0253-2670.2013.21.001.
    1. Ma S. C., Paul B. X., Huang R. C., Lee S. H., Lee S. F. Determination of the antiviral Caeffoyl quinie acids isolated from Lonicera japonica Thunb. Chinese Journal of Pharmaceutical Analysis. 2005;25(7):751–755.
    1. Yu Y., Song W., Zhu C., et al. Homosecoiridoids from the flower buds of Lonicera japonica . Journal of Natural Products. 2011;74(10):2151–2160. doi: 10.1021/np2004566.
    1. Kashiwada Y., Omichi Y., Kurimoto S.-I., et al. Conjugates of a secoiridoid glucoside with a phenolic glucoside from the flower buds of Lonicera japonica Thunb. Phytochemistry. 2013;96:423–429. doi: 10.1016/j.phytochem.2013.09.021.
    1. Song W.-X., Yang Y.-C., Shi J.-G. Two new β-hydroxy amino acid-coupled secoiridoids from the flower buds of Lonicera japonica: isolation, structure elucidation, semisynthesis, and biological activities. Chinese Chemical Letters. 2014;25(9):1215–1219. doi: 10.1016/j.cclet.2014.05.037.
    1. Jiang Z.-B., Song W.-X., Shi J.-G. Two 1-(6′-O-acyl-β-d-glucopyranosyl)pyridinium-3-carboxylates from the flower buds of Lonicera japonica . Chinese Chemical Letters. 2015;26(1):69–72. doi: 10.1016/j.cclet.2014.10.011.
    1. Song W. X., Li S., Wang S. J., et al. Pyridinium alkaloid-coupled secoiridoids from the flower buds of Lonicera japonica . Journal of Natural Products. 2008;71(5):922–925. doi: 10.1021/np800040k.
    1. Yu Y., Zhu C. G., Wang S. J., Song W. X., Yang Y. C., Shi J. G. Homosecoiridoid alkaloids with amino acid units from the flower buds of Lonicera japonica . Journal of Natural Products. 2013;76(12):2226–2233. doi: 10.1021/np4005773.
    1. Zheng Z. F. Studies on chemical constituents and bioactivities of Lonicera japonica and Morus australia [Ph.D. thesis] Beijing, China: Chinese Academy of Medical Science & Peking Union Medical College; 2010.
    1. Du C. Z., Feng X., Wang H. Analysis of volatile constituents in Lonicera japonica Thunb. from different originals by GC-MS. Agricultural Science & Technology. 2015;5:1081–1083.
    1. Yang M. L., Zhao Y. G. Analysis of volatile components of Honeysuckle in Ningxia by GC-MS. Journal of Zhengzhou University. (Natural Science Edition) 2006;38(1):95–97. doi: 10.3969/j.issn.1671-6841.2006.01.021.
    1. Guan R. W., Wang L., Qu Y. S., et al. Volatile constituents in Lonicarae japonicae flos ‘Jiu feng yi hao’ by GC-MS. Chinese Traditional Patent Medicine. 2014;36(11):2367–2371. doi: 10.3969/j.issn.1001-1528.2014.11.032.
    1. Du H. F., Zhang Y., Weng D. Q., Yang D. J. GC-MS analysis of volatile oils extracted from fresh Lonicarae japonicae flos by different methods. Chongqing Journal of Research on Chinese Drugs and Herbs. 2009;2:13–17.
    1. Kumar N., Singh B., Gupta A. P., Kaul V. K. Lonijaposides, novel cerebrosides from Lonicera japonica . Tetrahedron. 2006;62(18):4317–4322. doi: 10.1016/j.tet.2006.02.070.
    1. Song W. X. Study the water-soluble chemical constituents of the flower buds of Lonicera japonica [Ph.D. thesis] Beijing, China: Chinese Academy of Medical Science & Peking Union Medical College; 2008.
    1. Wang Y. Study the water-soluble chemical constituents of the flower buds of Lonicera japonica [M.S. thesis] Changsha, China: Human University of Traditional Chinese Medicine; 2008.
    1. Wang F., Jiang Y.-P., Wang X.-L., et al. Aromatic glycosides from the flower buds of Lonicera japonica . Journal of Asian Natural Products Research. 2013;15(5):492–501. doi: 10.1080/10286020.2013.785531.
    1. Bi Y.-F., Tian Y., Pei S.-S., Liu H.-M. Secoiridoid glycosides from Flos Lonicerae . Chinese Traditional and Herbal Drugs. 2008;39(1):18–21.
    1. Choi C.-W., Jung H. A., Kang S. S., Choi J. S. Antioxidant constituents and a new triterpenoid glycoside from flos Lonicerae . Archives of Pharmacal Research. 2007;30(1):1–7. doi: 10.1007/bf02977770.
    1. Han J.-T., Liu Y.-M., Wang H. Determination of eleven trace elements in chinese traditional and herbal drugs for relieving heat and toxic by FAAS. Spectroscopy and Spectral Analysis. 2006;26(10):1931–1934.
    1. Lai H. Y., Wu Y. Y. Analysis of primary chemical speciation of nine trace elements in Lonicera japonica . Journal of Anhui Agricultural Sciences. 2013;41(28):11326–11353.
    1. Song Y.-L., Wang H.-M., Ni F.-Y., et al. Study on anti-inflammatory activities of phenolic acids from Lonicerae Japonicae Flos . Chinese Traditional and Herbal Drugs. 2015;46(4):490–495. doi: 10.7501/j.issn.0253-2670.2015.04.006.
    1. Li X.-Q., Sun X.-H., Cai S., Ying X.-X., Li F.-M. Investigation on the chemical constituents and variation of the flower buds of Lonicera species by UPLC-ESI-MS/MS and principle component analysis. Acta Pharmaceutica Sinica. 2009;44(8):895–904.
    1. Chen Q. Z., Lin R. C., Wang G. L., Li F. M. Studies on chemical constituents of the extract of Lonicera japonica . Journal of Chinese Medicinal Materials. 2010;33(6):920–922.
    1. Xing J. B., Li H. J., Li P., Liu Y. Studies on chemical constituents in dried buds of Lonicera japonica Thunb. Chinese Journal of New Drugs. 2002;11(11):856–859.
    1. Cui C. Y., Liu Z. P., Zhou M., Su D. H., Tang X. Z. Chemical constituents of Lonicera japonica . Journal of Guangxi University: Natural Science Edition. 2012;37:530–533.
    1. Zhang X. G. Chemical studies on the water-soluble fraction extracted from flos Lonicerae japonicae [M.S. thesis] Xianyang, China: Shannxi University of Chinese Medicine; 2007.
    1. Chen C. X., Wang W. W., Ni W., Chen N. Y., Zhou J. Triterpenoid glycosides from the Lonicera japonica . Acta Botanica Yunnanica. 2000;22:201–208.

Source: PubMed

3
S'abonner