Chemical Constituents and Anti-dengue Activity of the Metabolites from Helicia Petelotii Collected in Sapa, Vietnam
Main Article Content
Abstract
From the leaves, twigs, and fruits of Helicia petelotii collected from the Hoang Lien mountain range in Sapa, Vietnam, six compounds were isolated including β-sitosterol (1), daucosterol (2), 3-O-[β-D-(6'-nonadecanoate)glucopyranosyl]-β-sitosterol (3), β-arbutin (4), breynioside B (5), and glycerol monostearate (6). Among them, compounds 3 and 6 were isolated from the fruits, while compounds 1, 2, 4, and 5 were obtained from the leaves and twigs. Advanced spectroscopic methods such as NMR and HR-ESI-MS were applied to accomplish the structures identification of the above compounds. The anti-denge potential of compounds 1-6 were examined against two dengue virus serotypes, DENV-1 and DENV-2. Among them compounds 3 and 5 demonstrated inhibitory activity against DENV-2, with PNRT₅₀ values of 18.25 µM and 159.43 µM, respectively, while the remaining compounds were inactive against all the virus serotypes. This is the first report of phytochemicals and antiviral properties of Helicia petelotii against Dengue virus.
Keywords
Helicia petelotii, phytochemical, anti-dengue activity, virus serotypes, PNRT50
Article Details
References
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https://doi.org/10.17485/IJST/v16sp1.msc2
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https://doi.org/10.15625/2525-2518/0/0/14783
[27] D. T. A. Nghia, H. T. N. H Hanh, L. T. Anh, L. T. H. Van, and H. V. Duc, Phenolic compounds and carotenoids from the leaves of gymnosporia chevalieri Tard, Hue Journal of Medicine and Pharmacy, vol. 15, iss. 2, pp. 170–179, May 2025.
https://doi.org/10.34071/jmp.2025.2.24
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http://doi.org/10.1007/BF02634442
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[2] S. O. T. Bello, A. S. A. Tapsoba, A. A. Zoure, Y. J. R. Bassole, W.-L.-S. K. Yogo, P. Bado, O. F. Kouta, F. Tassembedo, T. M. Zohoncon, F. W. Djigma, A. Diabate, J. Simpore, Molecular characterization of the four serotypes (DENV-1, DENV-2, DENV-3 and DENV-4) of dengue virus circulating in Ouagadougou, Burkina Faso, Open Journal Epidemiology, vol. 14, no. 4, pp. 565–578, 2024.
https://doi.org/10.4236/ojepi.2024.144040
[3] S. Melebari, A. Hafiz, H. A. Natto, M. O. Elamin, N. A. Jalal, A. Hakim, S. Rushan, O. Fallatah, K. Alzabeedi, F. Malibari, H. Mashat, A. Alsaadi, A. Alhakam, A. Hadidi, G. S. Alkhaldi, A. Alkhyami, A. Alqarni, A. Alzahrani, M. Alghamdi, A. Siddiqi, and A. Khogeer, Estimation and characterization of dengue serotypes in patients presenting with dengue fever at Makkah hospitals, Tropical Medicine Infectious Disease, vol. 10, iss. 1, pp. 27, Jan. 2025.
https://doi.org/10.3390/tropicalmed10010027
[4] World Health Organization- WHO: Dengue and severe dengue.. [Online]. Available: https://www.who.int/health-topics/dengue-and-severe-dengue#tab=tab_1
[5] Vietnam News Agency: 2023: The whole country recorded more than 172,000 cases of dengue fever, Jan. 8, 2024. [Online]. Available: https://vnanet.vn/vi/graphic/suc-khoe-7/nam-2023-ca-nuoc-ghi-nhan-hon-172000-ca-mac-sot-xuat-huyet-7201775.html
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[8] R. Shukla, V. Ramasamy, R. K. Shanmugam, R. Ahuja, and N. Khanna, Antibody-dependent enhancement: a challenge for developing a safe dengue vaccine, Frontiers in Cellular Infection Microbiology, vol. 10, pp. 572681, 2010. https://doi.org/10.3389/fcimb.2020.572681
[9] J. Pintado Silva, A. Fernandez-Sesma, Challenges on the development of a dengue vaccine: a comprehensive review of the state of the art, Journal of General Virology, vol. 104, iss. 3, pp. 001831, Mar. 2023.
https://doi.org/10.1099/jgv.0.001831
[10] B. Rehman, A. Ahmed, S. Khan, N. Saleem, F. Naseer, and S. Ahma, Exploring plant-based dengue therapeutics: from laboratory to clinic, Tropical Diseases, Travel Medicine and Vaccines, vol. 10, pp. 1–19, Nov. 2024, Art. no. 23.
https://doi.org/10.1186/s40794-024-00232-1
[11] T. P. T. Tran, Q. C. Nguyen, N. A. Ho, T. L. Nguyen, T. B. H. Vu, T. T. T. Nguyen, V. C. Tran, T. A. Nguyen, T. Q. Bui B., D. C. To, T. Q. Phan, T. T. Nguyen, V. S. Tran, and T. A. N. Nguyen, Anti-dengue screening on several Vietnamese medicinal plants: experimental evidences and computational analyses, Chemistry & Biodiversity, vol. 19, iss. 7, pp. e202101026, Jul. 2022.
https://doi.org/10.1002/cbdv.202101026
[12] T. P. T. Tran, D. T. Nguyen, N. T. Pham, C. V. Tran, A. N. Ho, H. B. T. Vu, and T. T. T. Nguyen, Phytochemistry of the unpolar extract of Carica papaya leaves and its antidengue activity, Vietnam Journal of Chemistry, vol. 60, iss. 6, pp. 777–783, Dec. 2022.
https://doi.org/10.1002/vjch.202200049
[13] T. P. T. Tran, L. T. Nguyen, C. L. Nguyen, H. B. T. Vu, and T. T. T. Nguyen, The first phytochemical study of Elaeagnus latifolia in Vietnam, Vietnam Journal of Chemistry, vol. 59, iss. 3, pp. 376–382 , Jun. 2021.
https://doi.org/10.1002/vjch.202000204
[14] D. T. Nguyen, N. T. Pham, L. T. Nguyen, A. T. Nguyen, H. B. T. Vu, T. T. T. Nguyen, A. N. Ho, H. D. Pham, and T. P. T. Tran, Phytochemical study of Euphorbia cyathophora collected in Dan Phuong, Hanoi and its antidengue activity against DENV1-4 virus serotypes, Vietnam Journal of Chemistry, vol. 61, iss. 3, pp. 372–378, Jun. 2023.
https://doi.org/10.1002/vjch.202300123
[15] Pham Hoang Ho, Vietnamese plants, Youth Publishing House – Ho Chi Minh city, 1999, pp.16.
[16] H. Weston Peter and P. Barker Nigel, A new suprageneric classification of the Proteaceae, with an annotated checklist of genera, Telopea (Syd), vol. 11, iss. 3, pp. 314–344, 2006.
https://doi.org/10.7751/telopea20065733
[17] IUCN Red List of Threatened Species. [Online]. Available: https://www.iucnredlist.org
[18] P. C. Lalawmpuii, C. Malsawmtluangi, R. Vanlalruata, and B. B. Kakoti, Evaluation of anti-inflammatory activity of Helicia nilagirica Bedd on cotton pellet-induced granuloma in rats, International Journal of Pharmacy and Pharmaceutical Sciences, vol. 8, iss. 7, pp. 455–456, 2016.
[19 ] L. Tlau, L. Lalawmpuii, P. B. Lalthanpuii, V. Ralte, C. Lalnunfela, K. Lalchhandama, Study of the mizo medicinal plant, Helicia excelsa on its phytochemical components, antioxidant property and antibacterial activity, Indian Journal of Science and Technolology, vol. 16, iss. Special issue 1, pp. 10–18, 2023.
https://doi.org/10.17485/IJST/v16sp1.msc2
[20] G. C. Jagetia and J. Zoremsiami, Anticancer activity of Helicia nilagirica bedd in mice transplanted with Dalton’s lymphoma, IJCAM, vol. 11, iss. 2, pp. 209–220, Apr. 2018.
https://doi.org/10.15406/ijcam.2018.11.00380
[21] J. T. Roehrig, J. Hombach, and A. D. T. Barrett, Guidelines for plaque-reduction neutralization testing of human antibodies to dengue viruses, Viral Immunology, vol. 21, no. 2, pp. 123–132, 2008.
https://doi.org/10.1089/vim.2008.0007
[22] N. Kamal, C. Clements, A. I. Gray, R. A. Edrada-Ebel, Anti-infective activities of secondary metabolites from Vitex pinnata, Journal of Applied Pharmaceutical Science, vol. 6, iss. 1, pp. 102–106, Jan. 2016.
https://doi.org/10.7324/JAPS.2016.600117
[23] H. V. Do, H. T. Nguyen, T. T. T. Nguyen, N. T. Dang, B. H. T. Dao, A. H. T. Nguyen, H. L. T. Duong, T. H. Nguyen, Study on chemical constituentsfrom the roots of Panax bipinnatifidius seem, Collected in Sapa, Laocai, VNU Journal of Science, vol. 33, no. 2, pp. 50–55, Dec. 2017.
https://doi.org/10.25073/2588-1132/vnumps.4079
[24] N. Sultana and A. J. Afolayan, A novel daucosterol derivative and antibacterial activity of compounds from Arctotis arctotoides, Natural Product Research, vol. 21, iss. 10, pp. 889–896, Aug. 2007.
https://doi.org/10.1080/14786410601129606
[25] C. Avonto, Y. -H. Wang, B. Avula, M. Wang, D. Rua, and I. A. Khan, Comparative studies on the chemical and enzymatic stability of alpha- and beta-arbutin, International Journal of Cosmetic Science, vol. 38, iss. 2, pp. 187–193, Sep. 2015. https://doi.org/10.1111/ics.12275
[26] K. T. P. Linh, N. H. Quan, N. V. Chien, N. Q. Trung, V. H. Thong, N. V. Tuyen, and N. P. Thao, Secondary metabolites from the stem barks of rhizophora mucronata lamk, VJST, vol. 58, no. 6, pp. 653–664, 2020.
https://doi.org/10.15625/2525-2518/0/0/14783
[27] D. T. A. Nghia, H. T. N. H Hanh, L. T. Anh, L. T. H. Van, and H. V. Duc, Phenolic compounds and carotenoids from the leaves of gymnosporia chevalieri Tard, Hue Journal of Medicine and Pharmacy, vol. 15, iss. 2, pp. 170–179, May 2025.
https://doi.org/10.34071/jmp.2025.2.24
[28] N. O. V. Sonntag, Glycerolysis of fats and methyl esters – status, review and critique, Journal of the American Oil Chemists’ Society (JAOCS), vol. 59, iss. 10, pp.795–802A, Oct. 1982.
http://doi.org/10.1007/BF02634442