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Phytochemical constituents of the roots of Heliotropium verdcourtii (Boraginaceae)

Yıl 2024, Cilt: 11 Sayı: 2, 211 - 219, 03.06.2024
https://doi.org/10.21448/ijsm.1301392

Öz

The medicinal value of medicinal plants lies in some bioactive constituents that produce a definite physiological action on the human body. Heliotropium verdcourtii is a deciduous shrub or small tree traditionally used in the treatment of various diseases including fever, dry cough, measles, convulsions, epilepsy, diarrhea, and other ailments. The chemical constituents of the roots of the plant were not investigated to date. The aim of the study was to investigate the phytochemicals present in the roots of Heliotropium verdcourtii. The freshly collected root of the plant was chopped and air dried under shade. The dried and finely grounded plant root was extracted through maceration with n-hexane, chloroform/methanol (v/v 1:1), and methanol successively. The extracts were subjected to qualitative phytochemical tests for screening the classes of secondary metabolites present in the plant. Compound isolation of the chloroform/methanol (v/v 1:1) extract was performed through silica gel chromatographic separation. The structures of all isolated compounds were determined by spectroscopic methods as well as comparison with previous reports in the literature. The yields of n-hexane, chloroform/methanol (v/v 1:1), and methanol extracts were 2.2 g (0.4%), 25 g (5.0%), and 19.8 g (4.0%), respectively. The qualitative phytochemical test of the extracts revealed the presence of flavonoids, terpenoids, phenolics, saponins, glycosides and alkaloids. Silica gel chromatographic separation afforded a mixture of three isomeric triterpenoids identified as α-amyrin, β-amyrin, and bauerenol. To the best of our knowledge these bioactive compounds were isolated from the root of this plant, for the first time.

Destekleyen Kurum

Hawassa University

Proje Numarası

Private project

Kaynakça

  • Adamski, Z., Blythe, L.L., Milella, L., Bufo, S.A. (2020). Biological Activities of Alkaloids: From Toxicology to Pharmacology. Toxins (Basel), 12(4), 210-213.
  • Aziz, R.A., Sarmidi, M.R., Kumaresan, S. (2003). Phytocehemical processing: the next emerging field in chemical engineering aspects and opportunities. J. Kejurut. Kim. Malay., 3, 45-60.
  • Bezabih, B., Yadessa, M., Tegene, D. (2017). Chemical constituents and antibacterial activities of the Leaves of Ehretia cymosa. Asian J. Sci. Tech., 8, 4974-4977.
  • Carothers, S., Nyamwihura, R., Collins, J., Zhang, H., Park, H.P., Setzer, W.N., Ogungbe, I.V. (2018). Bauerenol Acetate, the Pentacyclic Triterpenoid from Tabernaemontana longipes, is an Antitrypanosomal Agent. Molecules, 23(2), 355-362.
  • Chaluma, S., Ruth, S., Gemechu, G., Hailemichael, T., Aman, D., Teshome, A., Yadessa, M. (2018). Antibacterial Triterpenoid from the Leaves Extract of Ehretia cymosa. Eth. J. Sci. Sustain. Dev. (EJSSD), 5, 42-53.
  • Chen, Y., Peng, J., Cao, S. (2022). Bauerenol inhibits proliferation, migration and invasion of retinoblastoma cells via induction of apoptosis, autophagy and cell cycle arrest. Trop. J. Pharm. Res., 21(7), 1377-1382.
  • Dhanani, T., Shah, S., Gajbhiye, N.A., Kumar, S. (2017). Effect of extraction methods on yield, phytochemical constituents and antioxidant activity of Withania somnifera. Arab. J. Chem., 10, S1193-S1199.
  • Gottschling, M., Hilger, H.H. (2004). The systematic position of Ehretia cortesia nom. nov. (≡ Cortesia cuneifolia: Ehretiaceae, Boraginales) inferred from molecular and morphological data. Taxon, 53(4), 919-923.
  • Harborne, J.B. (1973). Methods of plant analysis. In: Phytochemical Methods. Chapman and Hall, London.
  • Hayouni, E.A., Abedrabba, M., Bouix, M., Hamdi, M. (2007). The effects of solvents and extraction method on the phenolic contents and biological activities in vitro of Tunisian Quercus coccifera L. and Juniperus phoenica L. fruit extracts. Food Chem., 105(3), 1126-1134.
  • Ishida, B.K., Ma, J., Bock, C. (2001). A simple rapid method for HPLC analysis of lycopene isomers. Phytochem. Anal., 12, 194-198.
  • Jacob, R.A., Burri, B.J. (1996). Oxidative damage and defense. Am. J. Clin. Nutr., 63(6), 985S-990S.
  • Jeruto, P., Mutai, C., Lukhoba, C., Ouma, G. (2011). Phytochemical constituents of some medicinal plants used by the Nandis of South Nandi district, Kenya. J. Anim. Plant Sci., 9(3), 1201-1210.
  • Jeruto, P., Tooa, E., Mwamburia, L.A., Amuka, O. (2015). An inventory of medicinal plants used to treat gynaecological-obstetric-urino-genital disorders in South Nandi Sub Country in Kenya. J. Nat. Sci. Res., 5, 136-152.
  • Juang, Y.P., Liang, P.H. (2020). Biological and Pharmacological Effects of Synthetic Saponins. Molecules, 25(21), 4974.
  • Kimutai, N. (2017). In-vitro cytotoxicity of three selected medicinal plant extracts from Kenya. World J. Pharm. Pharm. Sci., 6(6), 144-152.
  • Kumar, S., Pandey, A.K. (2013). Chemistry and biological activities of flavonoids: an overview. Sci. World J., 2013, 1-16. https://doi.org/10.1155/2013/162750
  • Li, L., Peng, Y., Li-Jia, X., Min-Hui, L., Pei-Gen, X. (2008). Flavonoid glycosides and phenolic acids from Ehretia thyrsiflora. Biochem. Syst. Ecol., 36(12), 915-918.
  • Li, L., Li, M.H., Xu, L.J., Guo, N., Wu-Lan, T., Shi, R. (2010). Distribution of seven polyphenols in several medicinal plants of Boraginaceae in China. J. Med. Plants Res., 4, 1216-1221.
  • Liliana, H.V., Javier, P., Arturo, N.O. (2012). The pentacyclic triterpenes α, β-amyrins: a review of sources and biological activities. Chapter 23 in: Rao, Venketeshwer. Phytochemicals: A Global Perspective of Their Role in Nutrition and Health. IntechOpen. ISBN: 978-953-51-4317-8. pp: 487-502. https://doi.org/10.5772/1387
  • Maroyi, A. (2021). Evaluation of medicinal uses, phytochemistry and biological activities of Ehretia cymosa Thonn. (Ehretiaceae). Int. J. Pharm. Sci., 12(2), 1521–1528.
  • Maundu, P., Tengnäs, B. (2005). Useful trees and shrubs for Kenya. World Agroforestry Centre East and Central Africa Regional Programme (ICRAF-ECA), Technical Handbook 35, Nairobi, Kenya, pp. 484.
  • Mesfin, G. (2018). Chemical Studies of the Resin of Commiphora erlangeriana and Some Plants in Yayu Nature Reserve [Unpublished PhD dissertation]. Addis Ababa University.
  • Miller, J.S. (2003). Classification of Boraginaceae subfam. Ehretioideae: resurrection of the genus Hilsenbergia Tausch ex Meisn. Adansonia, 25(2), 151-89.
  • Ogundajo, A., Ashafa, A.T. (2017). Phytochemical compositions and In vitro assessments of antioxidant and antidiabetic potentials of fractions from Ehretia cymosa. Pharmacogn. Mag., 13, S470-480.
  • Oladunmoye, M.K., Kehinde, F.Y. (2011). Ethnobotanical survey of medicinal plants used in treating viral infections among Yoruba tribe of South Western Nigeria. Afr. J. Microbiol. Res., 5(19), 2991-3004.
  • Parekh, J., Chands, S. (2008). Phytochemical screening of some plants from Western regions of India. Plant Arch., 8(2), 657-662.
  • Prashant, T., Bimlesh, K., Mandeep, K., Gurpreet, K., Harleen, K. (2011). Phytochemical screening and extraction: A review. Int. J. Pharm. Sci., 1(1), 98-106.
  • Raga, D.D., Herrera, A.A., Shen, C.C., Ragasa, C.Y. (2013). Triterpenes from Ardisia squamulosa C. Presl (Myrsinaceae) limit angiogenesis and the expression of von willebrand factor in duck chorioallantoic membrane. J. Chem. Pharm. Res., 5(10), 230-239.
  • Retief, E., Van Wyk, A.E. (2001). The genus Ehretia (Boraginaceae: Ehretioideae) In Southern Africa. Bothalia, 31(1), 9-23.
  • Sathish, K.P., Viswanathan, M.B.G., Venkatesan, M., Balakrishna, K. (2017). Bauerenol, a triterpenoid from Indian Suregada angustifolia: Induces reactive oxygen species–mediated P38MAPK activation and apoptosis in human hepatocellular carcinoma (HepG2) cells. Tumor Biol., 39(4), 1-15.
  • Soto-Blanco, B. (2022). Chapter 12 - Herbal glycosides in healthcare, Editor(s): Subhash C.; Mandal, Amit Kumar Nayak; Amal Kumar Dhara, Herbal Biomolecules in Healthcare Applications, Academic Press, pp. 239-282.
  • Thirupathi, A., Silveira, P., Nesi, R., Pinho, R. (2017). β-Amyrin, a pentacyclic triterpene, exhibits anti-fibrotic, anti-inflammatory, and anti-apoptotic effects on dimethyl nitrosamine–induced hepatic fibrosis in male rats. Hum. Exp. Toxicol., 36(2), 113-122.
  • Tidke, Pranjal & Umekar, Milind & Sangode, Chetna (2021). A general appraisal of Ehretia laevis Roxb: An essential medicinal plant. Int. J. Pharm. Phytochem. Res., 2, 11-17.
  • Weigend, M., Selvi, F., Thomas, D., Hilger, H. (2016). Boraginaceae. Flowering Plants. Eudicots. pp.41-102.

Phytochemical constituents of the roots of Heliotropium verdcourtii (Boraginaceae)

Yıl 2024, Cilt: 11 Sayı: 2, 211 - 219, 03.06.2024
https://doi.org/10.21448/ijsm.1301392

Öz

The medicinal value of medicinal plants lies in some bioactive constituents that produce a definite physiological action on the human body. Heliotropium verdcourtii is a deciduous shrub or small tree traditionally used in the treatment of various diseases including fever, dry cough, measles, convulsions, epilepsy, diarrhea, and other ailments. The chemical constituents of the roots of the plant were not investigated to date. The aim of the study was to investigate the phytochemicals present in the roots of Heliotropium verdcourtii. The freshly collected root of the plant was chopped and air dried under shade. The dried and finely grounded plant root was extracted through maceration with n-hexane, chloroform/methanol (v/v 1:1), and methanol successively. The extracts were subjected to qualitative phytochemical tests for screening the classes of secondary metabolites present in the plant. Compound isolation of the chloroform/methanol (v/v 1:1) extract was performed through silica gel chromatographic separation. The structures of all isolated compounds were determined by spectroscopic methods as well as comparison with previous reports in the literature. The yields of n-hexane, chloroform/methanol (v/v 1:1), and methanol extracts were 2.2 g (0.4%), 25 g (5.0%), and 19.8 g (4.0%), respectively. The qualitative phytochemical test of the extracts revealed the presence of flavonoids, terpenoids, phenolics, saponins, glycosides and alkaloids. Silica gel chromatographic separation afforded a mixture of three isomeric triterpenoids identified as α-amyrin, β-amyrin, and bauerenol. To the best of our knowledge these bioactive compounds were isolated from the root of this plant, for the first time.

Proje Numarası

Private project

Kaynakça

  • Adamski, Z., Blythe, L.L., Milella, L., Bufo, S.A. (2020). Biological Activities of Alkaloids: From Toxicology to Pharmacology. Toxins (Basel), 12(4), 210-213.
  • Aziz, R.A., Sarmidi, M.R., Kumaresan, S. (2003). Phytocehemical processing: the next emerging field in chemical engineering aspects and opportunities. J. Kejurut. Kim. Malay., 3, 45-60.
  • Bezabih, B., Yadessa, M., Tegene, D. (2017). Chemical constituents and antibacterial activities of the Leaves of Ehretia cymosa. Asian J. Sci. Tech., 8, 4974-4977.
  • Carothers, S., Nyamwihura, R., Collins, J., Zhang, H., Park, H.P., Setzer, W.N., Ogungbe, I.V. (2018). Bauerenol Acetate, the Pentacyclic Triterpenoid from Tabernaemontana longipes, is an Antitrypanosomal Agent. Molecules, 23(2), 355-362.
  • Chaluma, S., Ruth, S., Gemechu, G., Hailemichael, T., Aman, D., Teshome, A., Yadessa, M. (2018). Antibacterial Triterpenoid from the Leaves Extract of Ehretia cymosa. Eth. J. Sci. Sustain. Dev. (EJSSD), 5, 42-53.
  • Chen, Y., Peng, J., Cao, S. (2022). Bauerenol inhibits proliferation, migration and invasion of retinoblastoma cells via induction of apoptosis, autophagy and cell cycle arrest. Trop. J. Pharm. Res., 21(7), 1377-1382.
  • Dhanani, T., Shah, S., Gajbhiye, N.A., Kumar, S. (2017). Effect of extraction methods on yield, phytochemical constituents and antioxidant activity of Withania somnifera. Arab. J. Chem., 10, S1193-S1199.
  • Gottschling, M., Hilger, H.H. (2004). The systematic position of Ehretia cortesia nom. nov. (≡ Cortesia cuneifolia: Ehretiaceae, Boraginales) inferred from molecular and morphological data. Taxon, 53(4), 919-923.
  • Harborne, J.B. (1973). Methods of plant analysis. In: Phytochemical Methods. Chapman and Hall, London.
  • Hayouni, E.A., Abedrabba, M., Bouix, M., Hamdi, M. (2007). The effects of solvents and extraction method on the phenolic contents and biological activities in vitro of Tunisian Quercus coccifera L. and Juniperus phoenica L. fruit extracts. Food Chem., 105(3), 1126-1134.
  • Ishida, B.K., Ma, J., Bock, C. (2001). A simple rapid method for HPLC analysis of lycopene isomers. Phytochem. Anal., 12, 194-198.
  • Jacob, R.A., Burri, B.J. (1996). Oxidative damage and defense. Am. J. Clin. Nutr., 63(6), 985S-990S.
  • Jeruto, P., Mutai, C., Lukhoba, C., Ouma, G. (2011). Phytochemical constituents of some medicinal plants used by the Nandis of South Nandi district, Kenya. J. Anim. Plant Sci., 9(3), 1201-1210.
  • Jeruto, P., Tooa, E., Mwamburia, L.A., Amuka, O. (2015). An inventory of medicinal plants used to treat gynaecological-obstetric-urino-genital disorders in South Nandi Sub Country in Kenya. J. Nat. Sci. Res., 5, 136-152.
  • Juang, Y.P., Liang, P.H. (2020). Biological and Pharmacological Effects of Synthetic Saponins. Molecules, 25(21), 4974.
  • Kimutai, N. (2017). In-vitro cytotoxicity of three selected medicinal plant extracts from Kenya. World J. Pharm. Pharm. Sci., 6(6), 144-152.
  • Kumar, S., Pandey, A.K. (2013). Chemistry and biological activities of flavonoids: an overview. Sci. World J., 2013, 1-16. https://doi.org/10.1155/2013/162750
  • Li, L., Peng, Y., Li-Jia, X., Min-Hui, L., Pei-Gen, X. (2008). Flavonoid glycosides and phenolic acids from Ehretia thyrsiflora. Biochem. Syst. Ecol., 36(12), 915-918.
  • Li, L., Li, M.H., Xu, L.J., Guo, N., Wu-Lan, T., Shi, R. (2010). Distribution of seven polyphenols in several medicinal plants of Boraginaceae in China. J. Med. Plants Res., 4, 1216-1221.
  • Liliana, H.V., Javier, P., Arturo, N.O. (2012). The pentacyclic triterpenes α, β-amyrins: a review of sources and biological activities. Chapter 23 in: Rao, Venketeshwer. Phytochemicals: A Global Perspective of Their Role in Nutrition and Health. IntechOpen. ISBN: 978-953-51-4317-8. pp: 487-502. https://doi.org/10.5772/1387
  • Maroyi, A. (2021). Evaluation of medicinal uses, phytochemistry and biological activities of Ehretia cymosa Thonn. (Ehretiaceae). Int. J. Pharm. Sci., 12(2), 1521–1528.
  • Maundu, P., Tengnäs, B. (2005). Useful trees and shrubs for Kenya. World Agroforestry Centre East and Central Africa Regional Programme (ICRAF-ECA), Technical Handbook 35, Nairobi, Kenya, pp. 484.
  • Mesfin, G. (2018). Chemical Studies of the Resin of Commiphora erlangeriana and Some Plants in Yayu Nature Reserve [Unpublished PhD dissertation]. Addis Ababa University.
  • Miller, J.S. (2003). Classification of Boraginaceae subfam. Ehretioideae: resurrection of the genus Hilsenbergia Tausch ex Meisn. Adansonia, 25(2), 151-89.
  • Ogundajo, A., Ashafa, A.T. (2017). Phytochemical compositions and In vitro assessments of antioxidant and antidiabetic potentials of fractions from Ehretia cymosa. Pharmacogn. Mag., 13, S470-480.
  • Oladunmoye, M.K., Kehinde, F.Y. (2011). Ethnobotanical survey of medicinal plants used in treating viral infections among Yoruba tribe of South Western Nigeria. Afr. J. Microbiol. Res., 5(19), 2991-3004.
  • Parekh, J., Chands, S. (2008). Phytochemical screening of some plants from Western regions of India. Plant Arch., 8(2), 657-662.
  • Prashant, T., Bimlesh, K., Mandeep, K., Gurpreet, K., Harleen, K. (2011). Phytochemical screening and extraction: A review. Int. J. Pharm. Sci., 1(1), 98-106.
  • Raga, D.D., Herrera, A.A., Shen, C.C., Ragasa, C.Y. (2013). Triterpenes from Ardisia squamulosa C. Presl (Myrsinaceae) limit angiogenesis and the expression of von willebrand factor in duck chorioallantoic membrane. J. Chem. Pharm. Res., 5(10), 230-239.
  • Retief, E., Van Wyk, A.E. (2001). The genus Ehretia (Boraginaceae: Ehretioideae) In Southern Africa. Bothalia, 31(1), 9-23.
  • Sathish, K.P., Viswanathan, M.B.G., Venkatesan, M., Balakrishna, K. (2017). Bauerenol, a triterpenoid from Indian Suregada angustifolia: Induces reactive oxygen species–mediated P38MAPK activation and apoptosis in human hepatocellular carcinoma (HepG2) cells. Tumor Biol., 39(4), 1-15.
  • Soto-Blanco, B. (2022). Chapter 12 - Herbal glycosides in healthcare, Editor(s): Subhash C.; Mandal, Amit Kumar Nayak; Amal Kumar Dhara, Herbal Biomolecules in Healthcare Applications, Academic Press, pp. 239-282.
  • Thirupathi, A., Silveira, P., Nesi, R., Pinho, R. (2017). β-Amyrin, a pentacyclic triterpene, exhibits anti-fibrotic, anti-inflammatory, and anti-apoptotic effects on dimethyl nitrosamine–induced hepatic fibrosis in male rats. Hum. Exp. Toxicol., 36(2), 113-122.
  • Tidke, Pranjal & Umekar, Milind & Sangode, Chetna (2021). A general appraisal of Ehretia laevis Roxb: An essential medicinal plant. Int. J. Pharm. Phytochem. Res., 2, 11-17.
  • Weigend, M., Selvi, F., Thomas, D., Hilger, H. (2016). Boraginaceae. Flowering Plants. Eudicots. pp.41-102.
Toplam 35 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Organik Kimya
Bölüm Makaleler
Yazarlar

Tegene Tesfaye Tole 0000-0002-5858-9239

Habtamu Hailu Feso Bu kişi benim 0009-0005-9718-4065

Legesse Adane 0000-0001-5153-6946

Proje Numarası Private project
Erken Görünüm Tarihi 22 Nisan 2024
Yayımlanma Tarihi 3 Haziran 2024
Gönderilme Tarihi 23 Mayıs 2023
Yayımlandığı Sayı Yıl 2024 Cilt: 11 Sayı: 2

Kaynak Göster

APA Tole, T. T., Feso, H. H., & Adane, L. (2024). Phytochemical constituents of the roots of Heliotropium verdcourtii (Boraginaceae). International Journal of Secondary Metabolite, 11(2), 211-219. https://doi.org/10.21448/ijsm.1301392
International Journal of Secondary Metabolite
e-ISSN: 2148-6905