A new flavanone glycoside with antimicrobial and cytotoxic activities from Camellia hakodae Ninh leaves

Nguyen Thanh Tuyen, Pham Gia Dien, Nguyen The Hung, Nguyen Thi Hanh, Vu Minh Tin, Tran Hong Ngoc, Cao Duc Tuan, Pham Quang Duong, Tran Thi Thu Thuy
Author affiliations

Authors

  • Nguyen Thanh Tuyen 1Soc Son Cooperative for the Conservation and Development of Medicinal Herbs, Soc Son District, Ha Noi, Vietnam
  • Pham Gia Dien 2Institute of Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Ha Noi, Viet Nam
  • Nguyen The Hung 3Ha Noi University of Pharmacy, 15 Le Thanh Tong, Ha Noi, Vietnam
  • Nguyen Thi Hanh Soc Son Cooperative for the Conservation and Development of Medicinal Herbs, Soc Son District, Ha Noi, Vietnam
  • Vu Minh Tin Soc Son Cooperative for the Conservation and Development of Medicinal Herbs, Soc Son District, Ha Noi, Vietnam
  • Tran Hong Ngoc K16, Faculty of Pharmacy, Phenikaa University, Yen Nghia, Ha Dong, Ha Noi, Vietnam
  • Cao Duc Tuan Hai Phong University of Medicine and Pharmacy, 72A Nguyen Binh Khiem, Hai Phong, Vietnam https://orcid.org/0000-0001-9129-8241
  • Pham Quang Duong Center for High Technology Development, VAST, 18 Hoang Quoc Viet, Cau Giay, Ha Noi, Vietnam
  • Tran Thi Thu Thuy Institute of Natural Products Chemistry, VAST, 18 Hoang Quoc Viet, Cau Giay, Ha Noi, Viet Nam https://orcid.org/0000-0002-6770-3291

DOI:

https://doi.org/10.15625/2525-2518/18758

Keywords:

Camellia hakodae Ninh, flavanone glycoside, flavonoid, cytotoxicity, antimicrobial, cytotoxicity

Abstract

ABSTRACT – HCTN8: Camellia hakodae Ninh, belonging to the golden subgroup of Camellia (Theaceae), is a Camellia species native to Vietnam and primarily found in Tam Dao, Vinh Phuc province. This study aimed to isolate and identify the flavonoids from the leaves of Camellia hakodae Ninh. As a results, a new flavanone glycoside, named camehakonin A (1), was discovered alongside six known flavonoids including isoxanthohumol (2), naringenin (3), taxifolin (4), (-)epicatechin (5), macarangin (6), and 3,5,7,3’,4’-pentahydroxy-6-geranylflavonol (7). The chemical structures of these compounds were elucidated based on analysis of their spectroscopic data and by comparison with reported NMR spectroscopy data of known compounds. All isolated flavonoids were evaluated for their antimicrobial activity against various microorganisms, including Enterococcus faecalis, Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica and Candida albicans. Compound 1 exhibited significant inhibition of the tested Gram-positive bacteria (E. faecalis, S. aureus, and B. cereus) with MIC values of 128, 64, and 256 µg/mL respectively, as well as the human-pathogenic fungus C. albicans (MIC: 16 µg/mL). Furthermore, compound 1 displayed weak cytotoxicity in vitro against two cancer cell lines (KB and Hep-G2) with IC50 values of 73.70 and 221.11 µM, respectively. Notably, compounds 1-7 were isolated from the leaves of Camellia hakodae Ninh for the first time.

Downloads

Download data is not yet available.

References

1. Trinh T. D. - Yellow Camellias: A review of chemical constituents and biological activities. DaLat University J. Sci. 12 (3) (2022) 117-144. https://doi.org/ 10.37569/DalatUniversity. 12.3.977(2022).

2. Tran D. M., Nguyen T. T., Hoang T. S., Dang V. T., Phung D. T., Nguyen V. T., Dao T. D., Mai T. L., Vu T. L., Nguyen H. T. et al. - Golden Camellias: A review, Arch. Curr. Res. Inter. 16 (2) (2019) 1-8. https://doi.org/10.9734/acri/2019/v16i230085.

3. He, D., Li X., Sai X., Wang L., Li S., and Xu Y. - Camellia nitidissima C.W. Chi: A review of botany, chemistry, and pharmacology, Phytochem. Rev. 17 (2) (2018) 327-349. https://doi.org/10.1007/s11101-017-9537-x.

4. Chai S. F., Tang J. M., Chen Z. Y., Xie W. L., Yang X., and Wei X. - Analysis of chemical components and physiological active substances in flowers of Camellia nitidissima, Lishizhen Med. Mat. Med. Res. 27 (3) (2016) 575-577.

5. Cheng J. W., Wei Z. H., Chen X. Y., Zheng Q., Liang X., and Ouyang X. - In vitro antioxidant experiment research of total saponins in the flower of Camellia nitidissima C.W. Chi, Chin. J. Ethnomed. Ethnopharmacol. 25 (10) (2016) 27-30.

6. Dai L., Li J., Liang X., Li L., Feng Y., Liu H., Wei W., Ning S., and Zhang L. - Flowers of Camellia nitidissima cause growth inhibition, cell-cycle dysregulation and apoptosis in a human esophageal squamous cell carcinoma cell line, Mol. Med. Reports 14 (2) (2016) 1117-1122. https://doi.org/10.3892/mmr.20 16.5385.

7. He D., Wang N., Sai X., Li X., and Xu Y. - Camellia euphlebia protects against corticosterone-induced apoptosis in differentiated PC12 cells by regulating the mitochondrial apoptotic pathway and PKA/CREB/BDNF signaling pathway, Food Chem. Toxicol. 126 (2019) 211-222. https://doi.org/10.1016/j.fct.2019. 02.028.

8. Lin J. L., Lin H.Y., Yang N.S., Li Y.H., Lee M. R., Chuang C. H., Ho C. T., Kuo S. C., and Way T. D. - Chemical constituents and anticancer activity of yellow camellias against MDA-MB-231 human breast cancer cells, J. Agric. Food Chem. 61 (2013) 9638–9644. https://doi.org/10.1021/jf4029877.

9. Ge L., Lin B., Mo J., Chen Q., Su L., Li Y., and Yang K. - Composition and antioxidant and antibacterial activities of essential oils from three yellow Camellia species, Trees 33 (1) (2019) 205-212. https://doi.org/10.1007/s00468-018-1769-x.

10. He D., Jia S., and Xu Y. - Effect of different processing methods on phytochemical contents and neuroprotective activity of Camellia euphlebia leaves extract, Bio. Med. Res. Inter. 2019 (2) (2019) 1-8. https://doi.org/10.1155/2019/ 1717090.

11. Huang Y. L., Chen Y. Y., Wen Y. X., Li D. P., Liang R. G., and Wei X. - Effects of the extracts from Camellia nitidissima leaves on blood lipids, Lishizhen Med. Mat. Med. Res. 20 (2009) 776-777.

12. He D., Wang X., Zhang P., Luo X., Li X., Wang L., Li S., and Xu Y. - Evaluation of the anxiolytic and antidepressant activities of the aqueous extract from Camellia euphlebia Merr. ex Sealy in mice, Evid. Based Complementary Altern. Med. 2015 (2015) 618409. https://doi.org/10.1155/2015/618409.

13. He D., Sai X., Wang N., Li X., Wang L., and Xu Y. - Camellia euphlebia exerts its antidepressant-like effect via modulation of the hypothalamic-pituitary-adrenal axis and brain monoaminergic systems, Metab. Brain Dis. 33 (1) (2018) 301-312. https://doi.org/10.1007/s11011-017-0167-1.

14. Nguyen H. H., Nguyen H. N., and Truong V. C. - Assessment of acute and sub-acute-chronic toxicity of Camellia hakodae Ninh leaves aqueous extracts in experimental animals, Afric. J. Pharm. Pharmaco. 14 (7) (2020) 203-211. https://doi.org/ 10.5897/AJPP2020.5140.

15. Nguyen T. T., Tran V. H., Pham G. D., Tran N., Nguyen T. H., and Vu D. H. - A new sexangularetin derivative from Camellia hakodae, Nat. Prod. Commun. 14 (9) (2019) 1934578X1987620. https://doi.org/10.1177/1934578X19876209.

16. Nguyen T. T., Tran V. H., Pham G. D., Tran N., Nguyen T. H., and Vu D. H. - Flavonoids from the Camellia hakodae Ninh flowers, Proceeding of International Camellia Congress, Goto (Japan), 2020, pp. 196-202.

17. Sarker S. D., Nahar L., and Kumarasamy Y. - Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals, Methods 42 (2007) 321-324. https://doi.org/10.1016/j.ymeth.2007.01.006.

18. Mosmann T. - Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol. Methods 65 (1983) 55-63. https://doi.org/10.1016/0022-1759(83)90303-4.

19. Lee E. H., Kim H. J., Song Y. S., Jin C., Lee K. T., Cho J., and Lee Y. S. - Constituents of the stems and fruits of Opuntia ficus-indica var. saboten, Arch. Pharm. Res. 26 (12) (2003) 1018-1023. https://doi.org/10.1007/BF02994752.

20. Shia H., Liua M., Wanga R., Gaoa,B., Zhanga Z., Niua Y. and Yua L. - Separating four diastereomeric pairs of dihydroflavonol glycosides from Engelhardia roxburghiana using high performance counter-current chromatography, J. Chromatogr. A 1383 (2015) 79-87. https://doi.org/10.1016/j.chroma.2015.01.024.

21. Voutquenne-Nazabadioko L., Gevrenova R., Borie N., Harakat D., Sayagh C., Weng A., Thakur M., Zaharieva M., Henry M. - Triterpenoid saponins from the roots of Gypsophila trichotoma Wender, Phytochem. 90 (2013) 114-127. https://doi.org/10.1016/j.phytochem. 2013.03.001

22. Teng X. F., Yang J. Y., Yang C. R., and Zhang Y. J. - Five new flavonol glycosides from the fresh flowers of Camellia reticulate, Helv. Chim. Acta 91 (2008) 1305-1312. https://doi.org/10.1002/hlca.200890142.

23. Chen R., Liu X., Zou J., Yin Y., Ou B., Jianhua L., Wang R., Xie D., Zhang P., and Dai J. - Regio‐ and stereospecific prenylation of flavonoids by Sophora flavescens prenyltransferase, Adv. Synth. Catal. 355 (9) (2013) 1817-1828. https://doi.org/10.1002/ adsc.201300196.

24. Intelmann D., Haseleu G., and Hofmann T. - LC-MS/MS quantitation of hop-derived bitter compounds in beer using Echo technique, J. Agri. Food. Chem. 57(4) (2009) 1172-1182. https://doi.org/10.1021/jf803040g.

25. Olsen H. T., Stafford G. I., van Staden J., Christensen S. B., and Jager A. K. - Isolation of the MAO-inhibitor naringenin from Mentha aquatica L., J. Ethnopharmacol. 117 (3) (2008) 500-502. https://doi.org/10.1016/j.jep.2008.02.015.

26. Lee I. C., Bae J. S., Kim T., Kwon O. J., and Kim T. H. - Polyphenolic constituents from the aerial parts of Thymus quinquecostatus var. japonica collected on Ulleung island, J. Korean Soc., Appl. Biol. Chem. 54 (5) (2011) 811-816. https://doi.org/10.1007/ BF03253166.

27. Okushio, K., Suzuki M., Matsumoto N., Nanjo F., and Hara Y. - Identification of (−)-epicatechin metabolites and their metabolic fate in the rat, Drug Metab. Dispos. 27 (2) (1999) 309-316.

28. Sutthivaiyakit S., Unganont S., Sutthivaiyakit P., and Suksamrarn A. - Diterpenylated and prenylated flavonoids from Macaranga denticulata, Tetrahedron 58 (2002) 3619-3622. https://doi.org/10.1016/S0040-4020(02)00296-X.

29. Megawati, Saepudin E., Hanafi M., Darmawan A. and Lotulung P. D. N. – Identification and Bioactivity studies of flavonoid compounds from Macaranga hispida (Blume) Mull.Arg, Makara J. Sci. 19/3 (2015) 96-100. https://doi.org/10.7454/mss.v19i3.4848.

Downloads

Published

16-08-2024

How to Cite

[1]
T. T. Nguyen, “A new flavanone glycoside with antimicrobial and cytotoxic activities from Camellia hakodae Ninh leaves ”, Vietnam J. Sci. Technol., vol. 62, no. 4, pp. 686–696, Aug. 2024.

Issue

Vol. 62 No. 4 (2024)

Section

Natural Products

License

Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Vietnam Journal of Sciences and Technology (VJST) is an open access and peer-reviewed journal. All academic publications could be made free to read and downloaded for everyone. In addition, articles are published under term of the Creative Commons Attribution-ShareAlike 4.0 International (CC BY-SA) Licence which permits use, distribution and reproduction in any medium, provided the original work is properly cited & ShareAlike terms followed.

Copyright on any research article published in VJST is retained by the respective author(s), without restrictions. Authors grant VAST Journals System a license to publish the article and identify itself as the original publisher. Upon author(s) by giving permission to VJST either via VJST journal portal or other channel to publish their research work in VJST agrees to all the terms and conditions of https://creativecommons.org/licenses/by-sa/4.0/ License and terms & condition set by VJST.

Authors have the responsibility of to secure all necessary copyright permissions for the use of 3rd-party materials in their manuscript.