Spectroscopic Elucidation and Anticancer Potential of 7-methoxy-2-(4-methoxyphenyl)-5-O-glycosyl chromenone Isolated from Haplanthodes tentaculatus (L.) R. B. Majumdar

Authors

  • Parth B Trivedi Department of Chemistry, Ramnarain Ruia Autonomous College, Matunga, Mumbai, Maharashtra, India
  • Madhavi R Badole Department of Chemistry, Ramnarain Ruia Autonomous College, Matunga, Mumbai, Maharashtra, India

Abstract

In this research, we report on the isolation and structural elucidation of a new flavonoid glycoside called 7-methoxy-2-(4-methoxyphenyl)-5-O-glycosyl chromenone. This flavonoid glycoside was obtained from Haplanthodes tentaculatus, a plant that is native to the Western Ghats of India. The molecule was purified via the use of chromatographic procedures, and its structure was validated by the use of spectroscopic investigations, which included HRMS, 1H NMR, 13C NMR, FTIR, and UV-Visive technologies. With the use of HRMS analysis, the chemical formula C₂₃H₂₄O₁₀ was verified. The isolated molecule demonstrated anticancer activity in vitro against the MDA-MB-231 breast cancer cell line, with an IC₅₀ value of 58.99 ± 0.495 µg/ml. This indicates that the drug is very effective in curing cancer. The natural origin of 7-methoxy-2-(4-methoxyphenyl)-5-O-glycosyl chromenone and the possibility that it has a reduced toxicity level imply that it has the potential to be a lead molecule for the creation of anticancer drugs, despite the fact that it is less effective than the conventional medicine Cisplatin. The findings of this research add to the increasing body of evidence that bioactive chemicals derived from natural sources have the potential to be used in therapeutic medicine.

Keywords:

7-methoxy-2-(4-methoxyphenyl)-5-O-glycosyl chromenone, Haplanthodes tentaculatus, Flavonoid glycoside, Anticancer activity, MDA-MB-231 cells, Natural product chemistry, Spectroscopic characterization

DOI

https://doi.org/10.25004/IJPSDR.2024.160608

References

Panigrahi G DG. A Revision of Haplanthodes O. kuntze (Acanthaceae). Nelumbo-The Bulletin of the Botanical Survey of India. 1981;23(3&4):197–203. Available from: https://ischolar.sscldl.in/index.php/JONBSI/article/download/76557/66863

Deshmukh PV, Surveswaran S, Gore RY, Lekhak MM. Taxonomic studies in the genus Haplanthodes (Acanthaceae). Phytotaxa. 2021 Aug 26;516(3):201-222–201–222. Available from: https://www.biotaxa.org/Phytotaxa/article/view/phytotaxa.516.3.1

Parth B Trivedi MB. Unveiling the Phytochemical Profile and Medicinal Potential of Haplanthodes tentaculatus (L.) R. B. Majumdar. In: Proceedings for Interdisciplinary National E-conference on “Scientific Approaches for Sustainable Environment.” 2023. p. 58.

Sonawane P, Khairnar S, Shinde D, Aher H. A Review On Haplanthodes Verticillata. World Journal of Pharmaceutical Research. 2024;13(12):388–97. Available from: https://doi.org/10.20959/wjpr202412-32825

Deshmukh PV, Surveswaran S, Gore RY, Lekhak MM. Taxonomic studies in the genus Haplanthodes (Acanthaceae). Phytotaxa. 2021 Aug 26;516(3):201–22. Available from: https://doi.org/10.11646/phytotaxa.516.3.1

Carocho M, Ferreira ICFR. Anti-Cancer Agents in Medicinal Chemistry. 2013;13:1236–58.

Gnanasekaran G, Murthy GVS, Deng YF. Resurrection of the genus Haplanthus (Acanthaceae: Andrographinae). Blumea: Journal of Plant Taxonomy and Plant Geography. 2016;61(3):165–9. Available from: https://doi.org/10.3767/000651916X693185

Brusotti G, Cesari I, Dentamaro A, Caccialanza G, Massolini G. Isolation and characterization of bioactive compounds from plant resources: The role of analysis in the ethnopharmacological approach. Journal of Pharmaceutical and Biomedical Analysis. 2014 Jan 18;87:218–28. Available from: https://doi.org/10.1016/j.jpba.2013.03.007

Hou X, Cheng Z, Wang J. Preparative purification of corilagin from Phyllanthus by combining ionic liquid extraction, prep-HPLC, and precipitation. Analytical Methods. 2020 Jul 9;12(26):3382–9. Available from: https://pubs.rsc.org/en/content/articlehtml/2020/ay/d0ay00860e

Latif Z, Sarker SD. Isolation of Natural Products by Preparative High Performance Liquid Chromatography (Prep-HPLC). Methods in Molecular Biology. 2012;864:255–74. Available from: https://link.springer.com/protocol/10.1007/978-1-61779-624-1_10

Singh R, Dhiman M, Saklani A, Immanuel Selvaraj C, Kate AS. Isolation and characterization of a novel flavanone glycoside from an endemic plant Haplanthodes neilgherryensis. Journal of Asian Natural Products Research. 2022;24(1):96–101. Available from: https://www.tandfonline.com/doi/abs/10.1080/10286020.2021.1880394

Kumar R, Kumar V, Sharma A, Kumar R, Mahey S, Kumar V, et al. A Review On Antiproliferative Activity Of Plant Extracts Against Breast Cancer Cell Lines. Article in International Journal of Pharmaceutical Sciences and Research. 2019;10(7):3144. Available from: http://dx.doi.org/10.13040/IJPSR.0975-8232.10

Bhanot A, Sharma R, Noolvi MN. Natural sources as potential anti-cancer agents: A review. International Journal of Phytomedicine. 2011;3:9–26. Available from: http://www.arjournals.org/index.php/ijpm/index

Yayli N, Baltaci C, Genç H, Terzioǧlu S. Phenolic and Flavone C-Glycosides from Scleranthus uncinatus. Pharmaceutical Biology. 2002;40(5):369–73. Available from: https://doi.org/10.1076/phbi.40.5.369.8450

Sasidharan S, Chen Y, Saravanan D, Sundram KM, Yoga Latha L. Extraction, isolation and characterization of bioactive compounds from plants’ extracts. African Journal of Traditional, Complementary and Alternative Medicines. 2011;8(1):1–10. Available from: https://doi.org/10.4314/ajtcam.v8i1.60483

Xia PF, Feng ZM, Yang YN, Zhang PC. Two flavonoid glycosides and a phenylpropanoid glucose ester from the leaves of Sterculia foetida. Journal of Asian Natural Products Research. 2009;11(8):766–71. Available from: https://doi.org/10.1080/10286020903055103

Chopin J, Dellamonica G. C-glycosylflavonoids. The Flavonoids. 1988;63–97. Available from: https://doi.org/10.1007/978-1-4899-2913-6_3

Singh AK, Yadav S, Chauhan BS, Nandy N, Singh R, Neogi K, et al. Classification of clinical isolates of klebsiella pneumoniae based on their in vitro biofilm forming capabilities and elucidation of the biofilm matrix chemistry with special reference to the protein content. Frontiers in Microbiology. 2019;10(APR):415385. Available from: https://doi.org/10.3389/fmicb.2019.00669

Published

30-11-2024
Statistics
Abstract Display: 96
PDF Downloads: 69
Dimension Badge

How to Cite

“Spectroscopic Elucidation and Anticancer Potential of 7-Methoxy-2-(4-Methoxyphenyl)-5-O-Glycosyl Chromenone Isolated from Haplanthodes Tentaculatus (L.) R. B. Majumdar”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 16, no. 6, Nov. 2024, pp. 983-9, https://doi.org/10.25004/IJPSDR.2024.160608.

Issue

Section

Research Article

How to Cite

“Spectroscopic Elucidation and Anticancer Potential of 7-Methoxy-2-(4-Methoxyphenyl)-5-O-Glycosyl Chromenone Isolated from Haplanthodes Tentaculatus (L.) R. B. Majumdar”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 16, no. 6, Nov. 2024, pp. 983-9, https://doi.org/10.25004/IJPSDR.2024.160608.

Similar Articles

1-10 of 693

You may also start an advanced similarity search for this article.