FOUR COMPOUNDS FROM DICRANOPTERIS LINEARIS SPORES
Main Article Content
Abstract
Dicranopteris linearis, a widely utilized plant species in traditional Vietnamese medicine, has been chemically investigated. Four compounds (1–4), including syringaresinol (1), shikimic acid (2), angelicin (3), and 3,4-dihydroxycinnamic acid (4) were isolated and structurally elucidated. Extensive spectroscopic methods were employed for structural elucidation. These isolates were subsequently evaluated for their alpha-glucosidase inhibitory activity and inhibitory effect on nitric oxide production in LPS-stimulated RAW 264.7 cells.Isolated compounds exhibited no inhibitory activity in either alpha-glucosidase or nitric oxide inhibition assays.
Keywords
alpha-glucosidase, angelicin, Dicranopteris linearis, nitric oxide inhibition, shikimic acid, syringaresinol
Article Details
References
Ban, N. K., Truong, L. H., Linh, T. M., Mai, N. C., Yen, D. T. H., Van Doan, V., Nhiem, N. X.,
Tai, B. H., & Van Kiem, P. (2020). Phenolic compounds from Trigonostemon honbaensis and their cytotoxic activity. Vietnam Journal of Chemistry, 58(6), 759-764. https://doi.org/10.1002/vjch.202000068
Bochkov, D. V., Sysolyatin, S. V., Kalashnikov, A. I., & Surmacheva, I. A. (2011). Shikimic acid: Review of its analytical, isolation, and purification techniques from plant and microbial sources. Journal of Chemical Biology, 5(1), 5-17. https://doi.org/10.1007/s12154-011-0064-8
Cao, H., Chai, T.-T., Wang, X., Morais-Braga, M. F. B., Yang, J.-H., Wong, F.-C., Wang, R., Yao, H., Cao, J., Cornara, L., Burlando, B., Wang, Y., Xiao, J., & Coutinho, H. D. M. (2017). Phytochemicals from fern species: Potential for medicine applications. Phytochemistry Reviews, 16(3), 379-440. https://doi.org/10.1007/s11101-016-9488-7
Chen, J., Chen, J.-J., & Gao, K. (2014). Chemical constituents and biological activities of Dicranopteris linearis. Chemistry of Natural Compounds, 49(6), 1129-1131. https://doi.org/10.1007/s10600-014-0839-6
Duong, T.-H., Tran, T.-M.-D., To, P.-M., Phan, N.-H.-N., Nguyen, T.-P., Le, H. T., & Sichaem, J. (2024). Potential antioxidant compounds from the spores of Dicranopteris linearis and the branches of Averrhoa bilimbi. Antioxidants, 13, 1319-1333.
Duong, T.-H., Vu, Y. T., Long, N. P., Phan, N.-H.-N., Pham, N.-K.-T., Sichaem, J., Kieu, N.-K.-D., Duong, C.-B., Nguyen, T.-T., Dang, V.-S., & Nguyen, H. T. (2023). Bioactive-guided phytochemical investigations, in vitro and in silico alpha-glucosidase inhibition of two vietnamese medicinal plants Dicranopteris linearis and Psychotria adenophylla. Pharmaceuticals, 16(9), Article 1253. https://doi.org/10.3390/ph16091253
Kamisan, F. H., Yahya, F., Mamat, S. S., Kamarolzaman, M. F. F., Mohtarrudin, N., Kek, T. L., Salleh, M. Z., Hussain, M. K., & Zakaria, Z. A. (2014). Effect of methanol extract of Dicranopteris linearis against carbon tetrachloride- induced acute liver injury in rats. BMC Complementary and Alternative Medicine, 14(1), Article 123. https://doi.org/10.1186/1472-6882-14-123
Kumar, A., Fernández, H., & Revilla, M. A. (Eds.). (2010). Working with Ferns: Issues and Applications. Springer New York. https://doi.org/10.1007/978-1-4419-7162-3
Li, X.-L., Tu, L., Zhao, Y., Peng, L.-Y., Xu, G., Cheng, X., & Zhao, Q.-S. (2008). Terpenoids from two Dicranopteris species. Helvetica Chimica Acta, 91(5), 856-861. https://doi.org/10.1002/hlca.200890089
Mar, W., Seo, E.-K., & Je, K.-H. (2001). Cytotoxic constituents of Psoralea corylifolia. Arch. Pharm. Res., 24(3), 211-213.
Ngoc Mai, T. T., Minh, P. N., Phat, N. T., Chi, M. T., Duong, T. H., Nhi Phan, N. H., Minh An, T. N., Dang, V.-S., Van Hue, N., Hong Anh, N. T., & Tri, M. D. (2024). In vitro and in silico docking and molecular dynamic of antimicrobial activities, alpha-glucosidase, and anti-inflammatory activity of compounds from the aerial parts of Mussaenda saigonensis. RSC Advances, 14(17), 12081-12095. https://doi.org/10.1039/D4RA01865F
Oboh, G., Agunloye, O. M., Adefegha, S. A., Akinyemi, A. J., & Ademiluyi, A. O. (2015). Caffeic and chlorogenic acids inhibit key enzymes linked to type 2 diabetes (in vitro): A comparative study. Journal of Basic and Clinical Physiology and Pharmacology, 26(2), 165-170. https://doi.org/10.1515/jbcpp-2013-0141
Ponnusamy, Y., Chear, N. J.-Y., Ramanathan, S., & Lai, C.-S. (2015). Polyphenols rich fraction of Dicranopteris linearis promotes fibroblast cell migration and proliferation in vitro. Journal of Ethnopharmacology, 168, 305-314. https://doi.org/10.1016/j.jep.2015.03.062
Raja, D. P., Manickam, V. S., De Britto, A. J., Gopalakrishnan, S., Ushioda, T., Satoh, M., Tanimura, A., Fuchino, H., & Tanaka, N. (1995). Chemical and chemotaxonomical studies on Dicranopteris species. Chem. Pharm. Bull., 43(10), 1800-1803. https://doi.org/10.1248/cpb.43.1800
Sarker, S. K., & Hossain, A. B. M. E. (1970). Pteridophytes of greater Mymensingh district of Bangladesh used as vegetables and medicines. Bangladesh Journal of Plant Taxonomy, 16(1), 47-56. https://doi.org/10.3329/bjpt.v16i1.2746
Sukandar, E. R., Kaennakam, S., Wongsuwan, S., Chatwichien, J., Krobthong, S., Yingchutrakul, Y., Mahatnirunkul, T., Mulya, F., Parasuk, V., Harding, D. J., Poldorn, P., Rungrotmongkol, T., Tip-pyang, S., Aonbangkhen, C., & Chavasiri, W. (2023). Schomburginones A‒J, geranylated benzophenones from the leaves of Garcinia schomburgkiana and their cytotoxic and anti-inflammatory activities. Phytochemistry, 211, Article 113701. https://doi.org/10.1016/j.phytochem.2023.113701
Zakaria, Z. A., Sahmat, A., Azmi, A. H., Nur Zainol, A. S., Omar, M. H., Balan, T., Sulistyorini, L., Azizah, R., & Abdullah, M. N. H. (2021). Polyphenolics and triterpenes presence in chloroform extract of Dicranopteris linearis leaves attenuated paracetamol-induced liver intoxication in rat. BMC Complementary Medicine and Therapies, 21(1), Article 35. https://doi.org/10.1186/s12906-020-03200-2
Tai, B. H., & Van Kiem, P. (2020). Phenolic compounds from Trigonostemon honbaensis and their cytotoxic activity. Vietnam Journal of Chemistry, 58(6), 759-764. https://doi.org/10.1002/vjch.202000068
Bochkov, D. V., Sysolyatin, S. V., Kalashnikov, A. I., & Surmacheva, I. A. (2011). Shikimic acid: Review of its analytical, isolation, and purification techniques from plant and microbial sources. Journal of Chemical Biology, 5(1), 5-17. https://doi.org/10.1007/s12154-011-0064-8
Cao, H., Chai, T.-T., Wang, X., Morais-Braga, M. F. B., Yang, J.-H., Wong, F.-C., Wang, R., Yao, H., Cao, J., Cornara, L., Burlando, B., Wang, Y., Xiao, J., & Coutinho, H. D. M. (2017). Phytochemicals from fern species: Potential for medicine applications. Phytochemistry Reviews, 16(3), 379-440. https://doi.org/10.1007/s11101-016-9488-7
Chen, J., Chen, J.-J., & Gao, K. (2014). Chemical constituents and biological activities of Dicranopteris linearis. Chemistry of Natural Compounds, 49(6), 1129-1131. https://doi.org/10.1007/s10600-014-0839-6
Duong, T.-H., Tran, T.-M.-D., To, P.-M., Phan, N.-H.-N., Nguyen, T.-P., Le, H. T., & Sichaem, J. (2024). Potential antioxidant compounds from the spores of Dicranopteris linearis and the branches of Averrhoa bilimbi. Antioxidants, 13, 1319-1333.
Duong, T.-H., Vu, Y. T., Long, N. P., Phan, N.-H.-N., Pham, N.-K.-T., Sichaem, J., Kieu, N.-K.-D., Duong, C.-B., Nguyen, T.-T., Dang, V.-S., & Nguyen, H. T. (2023). Bioactive-guided phytochemical investigations, in vitro and in silico alpha-glucosidase inhibition of two vietnamese medicinal plants Dicranopteris linearis and Psychotria adenophylla. Pharmaceuticals, 16(9), Article 1253. https://doi.org/10.3390/ph16091253
Kamisan, F. H., Yahya, F., Mamat, S. S., Kamarolzaman, M. F. F., Mohtarrudin, N., Kek, T. L., Salleh, M. Z., Hussain, M. K., & Zakaria, Z. A. (2014). Effect of methanol extract of Dicranopteris linearis against carbon tetrachloride- induced acute liver injury in rats. BMC Complementary and Alternative Medicine, 14(1), Article 123. https://doi.org/10.1186/1472-6882-14-123
Kumar, A., Fernández, H., & Revilla, M. A. (Eds.). (2010). Working with Ferns: Issues and Applications. Springer New York. https://doi.org/10.1007/978-1-4419-7162-3
Li, X.-L., Tu, L., Zhao, Y., Peng, L.-Y., Xu, G., Cheng, X., & Zhao, Q.-S. (2008). Terpenoids from two Dicranopteris species. Helvetica Chimica Acta, 91(5), 856-861. https://doi.org/10.1002/hlca.200890089
Mar, W., Seo, E.-K., & Je, K.-H. (2001). Cytotoxic constituents of Psoralea corylifolia. Arch. Pharm. Res., 24(3), 211-213.
Ngoc Mai, T. T., Minh, P. N., Phat, N. T., Chi, M. T., Duong, T. H., Nhi Phan, N. H., Minh An, T. N., Dang, V.-S., Van Hue, N., Hong Anh, N. T., & Tri, M. D. (2024). In vitro and in silico docking and molecular dynamic of antimicrobial activities, alpha-glucosidase, and anti-inflammatory activity of compounds from the aerial parts of Mussaenda saigonensis. RSC Advances, 14(17), 12081-12095. https://doi.org/10.1039/D4RA01865F
Oboh, G., Agunloye, O. M., Adefegha, S. A., Akinyemi, A. J., & Ademiluyi, A. O. (2015). Caffeic and chlorogenic acids inhibit key enzymes linked to type 2 diabetes (in vitro): A comparative study. Journal of Basic and Clinical Physiology and Pharmacology, 26(2), 165-170. https://doi.org/10.1515/jbcpp-2013-0141
Ponnusamy, Y., Chear, N. J.-Y., Ramanathan, S., & Lai, C.-S. (2015). Polyphenols rich fraction of Dicranopteris linearis promotes fibroblast cell migration and proliferation in vitro. Journal of Ethnopharmacology, 168, 305-314. https://doi.org/10.1016/j.jep.2015.03.062
Raja, D. P., Manickam, V. S., De Britto, A. J., Gopalakrishnan, S., Ushioda, T., Satoh, M., Tanimura, A., Fuchino, H., & Tanaka, N. (1995). Chemical and chemotaxonomical studies on Dicranopteris species. Chem. Pharm. Bull., 43(10), 1800-1803. https://doi.org/10.1248/cpb.43.1800
Sarker, S. K., & Hossain, A. B. M. E. (1970). Pteridophytes of greater Mymensingh district of Bangladesh used as vegetables and medicines. Bangladesh Journal of Plant Taxonomy, 16(1), 47-56. https://doi.org/10.3329/bjpt.v16i1.2746
Sukandar, E. R., Kaennakam, S., Wongsuwan, S., Chatwichien, J., Krobthong, S., Yingchutrakul, Y., Mahatnirunkul, T., Mulya, F., Parasuk, V., Harding, D. J., Poldorn, P., Rungrotmongkol, T., Tip-pyang, S., Aonbangkhen, C., & Chavasiri, W. (2023). Schomburginones A‒J, geranylated benzophenones from the leaves of Garcinia schomburgkiana and their cytotoxic and anti-inflammatory activities. Phytochemistry, 211, Article 113701. https://doi.org/10.1016/j.phytochem.2023.113701
Zakaria, Z. A., Sahmat, A., Azmi, A. H., Nur Zainol, A. S., Omar, M. H., Balan, T., Sulistyorini, L., Azizah, R., & Abdullah, M. N. H. (2021). Polyphenolics and triterpenes presence in chloroform extract of Dicranopteris linearis leaves attenuated paracetamol-induced liver intoxication in rat. BMC Complementary Medicine and Therapies, 21(1), Article 35. https://doi.org/10.1186/s12906-020-03200-2