Glycosylated stigmasterol from the rind of Napoleonaea imperialis

Gloria Ihuoma Ndukwe; Ibiba Reuben Jack; Rachael Elijah Ekong

doi:10.2478/auoc-2022-0001

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Glycosylated stigmasterol from the rind of Napoleonaea imperialis

Ovidius University Annals of Chemistry

Volume 33 (2022): Issue 1 (January 2022)

By: Gloria Ihuoma Ndukwe, Ibiba Reuben Jack and Rachael Elijah Ekong

Open Access

|Mar 2022

Abstract

Napoleonaea imperialis rinds were separated from the seeds and extracted via maceration using methanol. The crude methanol extract was partitioned with n-hexane and dichloromethane to yield n-hexane fraction (11.01 g), dichloromethane fraction (35.16 g) and methanol fraction (101.75 g). Dichloromethane fraction was chromatographed and purified to give a compound whose structure was elucidated using one-dimension and two-dimension nuclear magnetic resonance (NMR) experiments. The isolated compound was characterized as glycosylated stigmasterol.

References

[1]. L.A. Harvey, Natural products in drug discovery, Drug Discovery Today 13 (2008) 894-901.10.1016/j.drudis.2008.07.00418691670
Search in Google Scholar Back to article
[2]. K. Altmann, The merger of natural products synthesis and medicinal chemistry: on the chemistry and chemical biology of epothilones, Organic and Biomolecular Chemistry 2 (2004) 2137-2152.10.1039/b405839a15280945
Search in Google Scholar Back to article
[3]. E.F. Koehn, T. G. Carter, The evolving role of natural products in drug discovery, Nature Reviews 4 (2005) 206-220.
Search in Google Scholar Back to article
[4]. T. Hohlfeld, N. Zimmermann, A. Weber, G. Jessen, H. Weber, K. Schror, H.D. Holtje, R. Ebel, Pyrazolinone analgesics prevent the antiplatelet effect of aspirin and preserve human platelet thromboxane synthesis, Journal of Thrombosis and Haemostasis 6 (2008) 166-173.10.1111/j.1538-7836.2007.02800.x17944992
Search in Google Scholar Back to article
[5]. I. Bulduk, F. Taktak, Isolation and characterization of antitumor alkaloid from poppy capsules (Papver somniferum), Journal of Chemistry 1 (2013) 1-4.10.1155/2013/493870
Search in Google Scholar Back to article
[6]. M.J. Moshi, Current and future prospects of integrating traditional and alternative medicine in the management of diseases in Tanzania, Tanzania Journal of Health Research 7 (2005) 159-167.
Search in Google Scholar Back to article
[7]. O. James, E.A. Friday, E.G. Unekwuojo, Antihypertensive effect of methanol extract of Napoleonaea imperialis (P. Beauv) in adrenaline induced hypertensive albino rats, International Journal of Biochemistry Research and Review 1 (2011) 47-57.10.9734/IJBCRR/2011/274
Search in Google Scholar Back to article
[8]. G.I. Ndukwe, C. M. Ojinnaka, A.O. Oyedeji, N. Nxasana, T. Apalata, Antibacterial activity of the fruit of Napoleoneae imperialis, Journal of Innovation and Research Health Science and Biotechnology 1 (2015) 1-11.
Search in Google Scholar Back to article
[9]. M. Idu, A. Odaro, T. Umweni, L. Ojelede, Ethnobotanical plants used for oral healthcare among the Esan tribe of Edo state, Nigeria, Ethnobotanical Leaflets 13 (2009) 548-563.
Search in Google Scholar Back to article
[10]. C.M. Ojinnaka, D.C. Okpala, A Molluscicidal triterpenoid saponin from the fruits of Napoleonaea imperialis P. Beauv. (Lecythidacaea), Journal of Applied Science and Environmental Management 16 (2012) 213-216.
Search in Google Scholar Back to article
[11]. G.I. Ndukwe, C.M. Ojinnaka, A.O. Oyedeji, Novel bioactive triterpenoid saponin from the fruits of Napoleonaea imperialis P. Beauv. (Lecythidacaea), International Journal of Chemical Studies 4 (2016) 80-87.
Search in Google Scholar Back to article
[12]. G.I. Ndukwe, R.E. Ekong, I.R. Jack, Two new oleanane-type glycosides from Napoleonaea imperialis P. Beauv rind, Nigerian Journal of Chemical Research 26 (2021) 70-81.
Search in Google Scholar Back to article
[13]. I.R. Jack, R.E. Ekong, G.I. Ndukwe, Phytochemical constituents of dichloromethane fraction and essential oil of Napoleonaea imperialis rind, Journal of Pharmacognosy and Phytochemistry 9 (2020) 56-66.
Search in Google Scholar Back to article
[14]. G.I. Ndukwe, A. Oluah, G.K. Fekarurhobo, Isolation of an isoflavonoid and a terpenoid from the heartwood of Baphia nitida Lodd. (camwood), Ovidius University Annals of Chemistry 31 (2020) 5-8.10.2478/auoc-2020-0002
Search in Google Scholar Back to article
[15]. V. Kandati, P. Govardhan, C.S. Reddy, A.R. Nath, R.R. Reddy, In-vitro and in-vitro anti-inflammatory activity of Andrographis serpyllifolia (Rottl.Ex Vahl.), International Current Pharmaceutical Journal 1 (2012) 199-204.10.3329/icpj.v1i8.11250
Search in Google Scholar Back to article
[16]. V.H. Raju, S. Ganapaty, S.S. Prasanna, G.J. Vijaya, P.S. Kishore, A.K. Asif, phytochemical and pharmacological evaluation of Tragia cannabina for anti-inflammatory activity, International Current Pharmaceutical Journal 1 (2012) 213-216.10.3329/icpj.v1i8.11253
Search in Google Scholar Back to article
[17]. P.S. Jain, B.S. Bari, Isolation of lupeol, sigmasterol and campesterol from petroleum ether extract of woody stem of Wrightia tinctoria, Asian Journal of Plant Sciences 9 (2010) 163-167.10.3923/ajps.2010.163.167
Search in Google Scholar Back to article
[18]. P. Kiranmayee, K. Anitha, R. Usha, Phytochemical investigation of Caralluma attenutata (Wright) roots, International Journal of Pharmacognosy and Phytochemical Research 7 (2015) 1120-1024.
Search in Google Scholar Back to article
[19]. Y. Isah, I. Ndukwe, O.J. Amupitan, Isolation of stigmasterol from aerial plant part of Spillanthes acmella Murr, World Journal of Life Science and Medical Research 2 (2012) 78-86.
Search in Google Scholar Back to article
[20]. L.L. Pierre, N.M. Moses, Isolation and characterization of stigmasterol and B-sitosterol from Odontonema strictum (Acanthaceae), Journal of Innovations in Pharmaceuticals and Biological Sciences 2 (2015) 88-96.
Search in Google Scholar Back to article
[21]. P.V. Chaturvedula, I. Prakash, Isolation of stigmasterol and sitosterol from the dichloromethane extract of Rubus suavissimus, International Current Pharmaceutical Journal 1 (2012) 239-242.10.3329/icpj.v1i9.11613
Search in Google Scholar Back to article
[22]. A.J. Yusuf, M.I. Abdullahi, A.K. Haruna, A.Y. Idris, A.M. Musa, Isolation and characterization of stigmasterol and bis-(5,7-diacetyl-catechin-4’-α-rhamnopyranoside) from the stem bark of Neocarya macrophylla (Sabine) Prance (Chrysobalanaceae) Nigerian Journal of Basic and Applied Science 23 (2015) 15-22.
Search in Google Scholar Back to article
[23]. C.J. Cayme, Y.C. Ragasa, Structure elucidation of β-stigmasterol and β-sitosterol from Sesbania grandiflora (Linn) Pers. and β-carotene from Heliotropium indicum Linn. by NMR spectroscopy, Chemical Society of the Philippines 20 (2004) 5-14.
Search in Google Scholar Back to article
[24]. M. Dong, X.Z. Feng, X.B. Wang, T. Ikejima, J.L. Wu, Steroidal saponnins from Dioscorea panthaica and their cytotoxic activity, An International Journal of Pharmaceutical Sciences 59 (2004) 294-298.
Search in Google Scholar Back to article
[25]. M.R. Habib, F. Nikkon, M. Rahman, M.E. Haque, M.R. Karim, Isolation of stigmasterol and beta sitosterol from methanolic extract of root of bark of Calotropis gigantean (Linn), Pakistan Journal of Biological Science 10 (2007) 4174-4176.10.3923/pjbs.2007.4174.417619090304
Search in Google Scholar Back to article
[26]. O. Gabay, C. Sanchez, C. Salvat, F. Chevy, M. Breton, G. Nourissat, Stigmasterol: A phytosterol with potential antiosteoarthritic properties, Osteoarthritis Cartilage 18 (2010) 106-116.10.1016/j.joca.2009.08.01919786147
Search in Google Scholar Back to article
[27]. A.K. Batta, G. Xuab, A. Honda, T. Miyazaki, G. Salen, Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat, Journal of Pharmaceutical Sciences 55 (2006) 292-299.
Search in Google Scholar Back to article
[28]. L. Jae-Chul, H.P. Jong, B. Milos, K. Alexander, H. Yeong-Hwan, K. Byung-Soo, Antimutagenic constituents from the thorns of Gleditsia sinensis, Chemical and Pharmaceutical Bulletin 53 (2005) 561-564.10.1248/cpb.53.56115863930
Search in Google Scholar Back to article
[29]. S. Panda, M. Jafri, A. Kar, B.K. Meheta, Thyroid inhibitory, antiperoxidative and hypoglycemic effects of stigmasterol isolated from Butea monosperma, Fitoterapia 80 (2009) 123-126.10.1016/j.fitote.2008.12.00219105977
Search in Google Scholar Back to article
[30]. M. Afzai, G. Gupta, I. Kazmi, M. Rahman, O. Afzal, J. Alam, Anti-inflammatory and analgesic potential of a novel steroidal derivatives from Bryophyllum pinnatum, Fitoterapia 83 (2012) 853-858.10.1016/j.fitote.2012.03.01322465504
Search in Google Scholar Back to article
[31]. G. Wang, D. Jiang, J. Li, J. Han, Y. Liu, X. Li, Anthelmintic activity of steroidal saponins from Dioscorea zingiberensis, C. H. Wright against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus), Parasitology Research 107 (2010) 1365-1371.10.1007/s00436-010-2010-z20689967
Search in Google Scholar Back to article
[32]. U. Sharma, N. Kumar, B. Singh, K.R. Munshi, S. Bhalearao, Immunomodulatory active steroidal saponins from Asparagus racemosus, Medicinal Chemistry Research 22 (2013) 573-579.10.1007/s00044-012-0048-4
Search in Google Scholar Back to article
[33]. N. Antonio, D.L.H. Beatriz, V. Angel, Anti-inflammatory and immunomodulating properties of a sterol fraction from Sideritis foetens CLEM, Biological and Pharmaceutical Bulletin 24 (2001) 470-473.10.1248/bpb.24.47011379762
Search in Google Scholar Back to article
[34]. T. Kawabata, M. Cui, T. Hasegawa, F. Takano, T. Ohta, Anti-inflammatory and anti-melanogenic steroidal saponin glycosides from Fenugreek (Trigonella foenum-graecum L.) seeds, Planta Medica 77 (2011) 705-710.10.1055/s-0030-125047720979021
Search in Google Scholar Back to article
[35]. A. Li, W. Huang, Y. Wen, G. Gong, Q. Zhao, G. Yu, Anti-thrombotic activity and chemical characterization of steroidal saponins from Dioscorea zingiberensis CH, Fitoterapia 81 (2010) 1147-1156.10.1016/j.fitote.2010.07.01620659537
Search in Google Scholar Back to article

Articles in this issue

DOI: https://doi.org/10.2478/auoc-2022-0001 | Journal eISSN: 2286-038X | Journal ISSN: 1583-2430

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Language: English

Page range: 1 - 6

Submitted on: Dec 11, 2021

Accepted on: Feb 11, 2022

Published on: Mar 3, 2022

Published by: Ovidius University of Constanta

In partnership with: Paradigm Publishing Services

Publication frequency: 2 issues per year

Keywords:

rind,

chromatography,

saponins,

glycosylated stigmasterol

Related subjects:

Chemistry,

Chemistry, other

© 2022 Gloria Ihuoma Ndukwe, Ibiba Reuben Jack, Rachael Elijah Ekong, published by Ovidius University of Constanta
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Volume 33 (2022): Issue 1 (January 2022)