Spectroscopic characterization of a derivative of naphthalene isolated from Hibiscus sabdariffa calyx

Authors

  • Adewumi Idowu Adeagbo
    Department of Chemistry, Emmanuel Alayande University of Education, Oyo, Nigeria
  • Adekunle Abeeb Azeez
    Department of Chemistry, University of Ibadan, Nigeria

Keywords:

Hibiscus sabdariffa, Naphthalene derivative, chromatographic separation, 1H and 13C NMR spectroscopy

Abstract

Hibiscus sabdariffa (Hs) is a nutritive and medicinal herb that belongs to the Malvaceae family. It is mainly composed of organic acids, anthocyanins, polysaccharides and flavonoids. Hibiscus sabdariffa, being a natural source of bioactive compounds made up of several reactive functional groups, could serve the purpose of a starting material in the production of other compounds. Acidified aqueous ethanol extract of Hs was subjected to column chromatographic fractionation that yielded a yellow liquid isolate, which was characterized by UV–Visible, Infrared spectroscopy, Nuclear Magnetic Resonance (NMR) and High Resolution Mass Spectrometry (HRMS). The NMR spectra displayed distinct signals of a naphthalene ring linked through a carbonyl carbon to a napht 2 –yl moiety. 1H and 13C NMR indicated the presence of five aromatic protons (dH 6.98 – 7.51) resonating with ten aromatic carbon atoms (dc100.0 – 177.9), (C 189.2, indicating the presence of a carbonyl carbon coupled with a hydrogenated naphthalene ring substituent. Absorptions at 304nm, 366 nm and 506nm are due to pi- pi∗ and n - pi∗ , respectively. IR peak at 2923 cm-1 is ascribed to C − H stretch, while the peak at 1732(s) cm-1, with shoulders at 1634(w) and 1794(w), affirmed the presence of carbonyl functional group conjugated to an unsaturated naphtalen-2yl ring system. The isolated naphthalene derivative is characterized as ‘3 methyl-1, 4, 4a, 5, 6, 7, 8, 8a, octahydronaphtalen-2-yl)(naphtalen-2yl)methanone.

Dimensions

[1] A. I. B. Abou-Sreea, M. H. Roby, H. A. Mahdy, N. M. Abdou, A. M. El-Tahan, M. T. El-Saadony, K. A. El-Tarabily & F. M. ElSaadony, “Improvement of selected morphological, physiological, and biochemical parameters of roselle (Hibiscus sabdariffa L.) grown under different salinity levels using potassium silicate and Aloe Saponaria extract”, Plants 11 (2022) 2. https://www.mdpi.com/2223-7747/11/4/497. DOI: https://doi.org/10.3390/plants11040497

[2] S. O. Salami & A. J. Afolayan, “Assessment of antimicrobial activities and toxicological effects of green and red cultivars of roselle – Hibiscus sabdarifa L.”, European Journal of Medicinal Plants 31 (2020) 1. https://scispace.com/pdf/assessment-of-antimicrobial-activities-and-toxicological-3nayvwrzmc.pdf. DOI: https://doi.org/10.9734/ejmp/2020/v31i1530320

[3] S. Yagi, A. I. Uba, K. I. Sinan, D. Piatti, G. Sagratini, G. Caprioli, S. M. Eltigani, I. Lazarova & G. Zengin, “Comparative study on the chemical profile, antioxidant activity and enzyme inhibition capacity of red and white Hibiscus sabdariffa variety calyces”, ACS Omega 8 (2023) 42511. https://pubs.acs.org/doi/10.1021/acsomega.3c05217. DOI: https://doi.org/10.1021/acsomega.3c05217

[4] N. Aryanti, A. Nafiunisa & D. H. Wardhani, “Conventional and ultrasound-assisted extraction of anthocyanin from red and purple roselle (Hibiscus sabdariffa L.) calyces and characterisation of its anthocyanin powder”, International Food Research Journal 26 (2019) 529. https://www.cabidigitallibrary.org/doi/pdf/10.5555/20193328822.

[5] H. A. Almahy, H. H. Abdel-Razik, Y. A. El-Badry & A. M. Ibrahim, “Ultrasound-assisted extraction of anthocyanin pigments from Hibiscus sabdariffa (Rosella) and its phytochemical activity in the Kingdom of Saudi Arabia”, International Journal of Chemical Sciences 15 (2017) 196. https://www.semanticscholar.org/reader/d3d72c005af76efcd2d56caef381a642dcb1c32e.

[6] G. J. Okore, E. E. Oguzie, C. E. Ogukwe & C. O. Akalezi, “GC-MS analysis of phytochemicals from the extract of Hibiscus sabdariffa grown in northern Nigeria”, Journal of Chemical Society of Nigeria 46 (2021) 0417. https://doi.org/10.46602/jcsn.v46i2.613. DOI: https://doi.org/10.46602/jcsn.v46i2.613

[7] N. M. N. Jauah, M. A. Nafiah, M. H. H. Hasnan & S. P. Tan, “Anti-diabetic activity and nuclear magnetic resonance (NMR) characterisation of natural esters from hexane and dichloromethane crude extracts from calyces of Hibiscus sabdariffa Linn”, International Journal of Recent Technology and Engineering 35 (2019) 102. https://www.ijrte.org/wp-content/uploads/papers/v8i2S7/B10220782S719.pdf. DOI: https://doi.org/10.35940/ijrte.B1022.0782S719

[8] T. V. N. Thien, L. T. M. Do, P. H. Dang, N. V. Huynh, H. P. Dang, T. T. Nguyen, K. T. Tran, H. D. M. N. & Q. T. That, “A new lignan from the flowers of Hibiscus sabdariffa L. (Malvaceae)”, Natural Product Research 35 (2019) 2218. https://www.tandfonline.com/doi/full/10.1080/14786419.2019.1667354. DOI: https://doi.org/10.1080/14786419.2019.1667354

[9] E. Sehim, B. H. Amin, M. Yosri, M. A. Alwaili, R. Y. Abd Elghaffar, H. M. Salama & D. H. Alkhalifah, “GC-MS analysis, antibacterial, and anticancer activities of Hibiscus sabdariffa L. methanolic extract: in vitro and in silico studies” Microorganisms 11 (2023) 16011. https://www.mdpi.com/2076-2607/11/6/1601. DOI: https://doi.org/10.3390/microorganisms11061601

[10] M. P. Sobantu, B. I. Okeleye, V. I. Okudoh, M. Meyerd & Y. G. Abouae, “In vitro antioxidant mechanism of action of Hibiscus sabdariffa in the induction of apoptosis against breast cancer”, Journal of Herbs, Spices & Medicinal Plants 29 (2023) 213. https://www.tandfonline.com/doi/epdf/10.1080/10496475.2022.2135661?needAccess=true. DOI: https://doi.org/10.1080/10496475.2022.2135661

[11] D. Anago, J. A. G. Segbo, F. Gnangnon, C. D. Akpovi & C. Agbangla, “Some medicinal plants with anti-breast cancer activity and the input of phytotherapy in the treatment of breast cancer”, European Scientific Journal 19 (2023) 66. https://doi.org/10.19044/esj.2023.v19n18p66. DOI: https://doi.org/10.19044/esj.2023.v19n18p66

[12] R. Yasmin, S. Gogoi, J. Bora, A. Chakraborty, S. Dey, G. Ghaziri, S. Bhattacharjee & L. H. Singh, “Novel insight into the cellular and molecular signalling pathways on cancer preventing effects of Hibiscus sabdariffa”, A Review. Journal of Cancer Preview 28 (2023) 77. https://doi.org/10.15430/JCP.2023.28.3.77. DOI: https://doi.org/10.15430/JCP.2023.28.3.77

[13] N. Elkattan, S. S. El-Saadany, A. L. ElSayed, A. M. Gomaa & J. Abdalmuneim, “Anticancer effects of two traditional drinks hibiscus (Hibiscus Sabdariffa Linn) and liquorice (Glycyrrhizaglabra)”, Zagazig J. Agric. Res. 46 (2019) 115. https://zjar.journals.ekb.eg/article_40329_8e8a60494c927cdb9875501cf8c5f929.pdf. DOI: https://doi.org/10.21608/zjar.2019.40329

[14] D. Prabhakaran, M. M. Senthamilselvi & A. Rajeshkanna, “Anticancer activity of Hibiscus sabdariffa. L(Flowers) against human liver cancer (Hepg2) cell line”, International Journal of ChemTech Research 10 (2017) 351. https://www.sphinxsai.com/2017/ch_vol10_no12/3/(351-356)V10N12CT.pdf.

[15] I. O. Abdulsalami, S. Banjo, I. A. O. Bello, H. S. Bolarinwa & I. A. Egunjobi, “Fabrication of dye-sensitised solar cells using anthocyanidins from the extract of roselle (Hibiscus sabdariffa)”, Fountain Journal of Natural and Applied Science 5 (2016) 25. https://fountainjournals.com/index.php/FUJNAS/article/view/88/49. DOI: https://doi.org/10.53704/fujnas.v5i1.88

[16] Bako, E. E., Etim, J. P. Shinggu, S. S. Humphrey, L. J. Moses & M. E. Khan, “Quantum chemical calculations of lupeol (C30 H50 O) isolated from the ethyl acetate leaf extracts of Justicia secunda”, Journal of the Nigerian Society of Physical Sciences 6 (2024) 1. https://doi.org/10.46481/jnsps 2024.1995. DOI: https://doi.org/10.46481/jnsps.2024.1995

[17] T. K. Erick, J. J. Kiplimo & J. Matasyoh, “New naphthalene derivative isolated from Diaporthe sp. host to Syzygium cordatum Hochst, ex Krauss plant”, Journal of Medicinal Plants Research 15 (2021) 196. https://academicjournals.org/journal/JMPR/article-full-text-pdf/57AF74166845. DOI: https://doi.org/10.5897/JMPR2020.6910

[18] S. W. Yeon, H. Y. Kwon, J. I. Nam, J. H. Ahn, Y. H. Jo, A. Turk, Y. J. Lee, D. H. Shin, B. Y. Hwang & M. K. Lee, “Three new naphthalenes from the roots of Hibiscus syriacus”, Phytochemistry Letters 33 (2019)110. https://www.sciencedirect.com/science/article/abs/pii/S1874390019302587?via%3Dihub. DOI: https://doi.org/10.1016/j.phytol.2019.08.012

[19] O. Z. Esezobor, B. A. Maikasuwa, T. A. Tor-Anyiin & J. O. Igoli, “Synthesis of 4-phenylazo phenol from anthocyanins of Delonix regia and Hibiscus sabdariffa flowers”, American Chemical Science Journal 11 (2016) 1. https://journalcsij.com/index.php/CSIJ/article/view/266/531. DOI: https://doi.org/10.9734/ACSJ/2016/22393

[20] C. Parlak & P. Ramasami, “Theoretical and experimental study of infrared spectral data of 2-bromo-4-chlorobenzaldehyde”, Springer Nature Applied Sciences 2 (2020) 1148. https://doi.org/10.1007/s42452-020-2935-5. DOI: https://doi.org/10.1007/s42452-020-2935-5

Published

2025-12-31

How to Cite

Spectroscopic characterization of a derivative of naphthalene isolated from Hibiscus sabdariffa calyx. (2025). Recent Advances in Natural Sciences, 3(2), 232. https://doi.org/10.61298/rans.2025.3.2.232

Issue

Volume 3, Issue 2, December 2025

Section

Articles
Copyright & Licensing

Copyright (c) 2026 Adewumi Idowu Adeagbo, Adekunle Abeeb Azeez

Creative Commons License

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

How to Cite

Spectroscopic characterization of a derivative of naphthalene isolated from Hibiscus sabdariffa calyx. (2025). Recent Advances in Natural Sciences, 3(2), 232. https://doi.org/10.61298/rans.2025.3.2.232