Isolation of Ethyl  p -Methoxycinnamate from  Azadirachta indica  Root Bark as Hong Kong Caterpillar ( Tenebrio molitor ) Antifeedant

Rosnani Nasution; Cut Nyak Candein; Nurdin Saidi; Muhammad Bahi; Marianne Marianne

doi:10.22146/ijc.64487

Isolation of Ethyl p-Methoxycinnamate from Azadirachta indica Root Bark as Hong Kong Caterpillar (Tenebrio molitor) Antifeedant

https://doi.org/10.22146/ijc.64487

Rosnani Nasution^(1*), Cut Nyak Candein⁽²⁾, Nurdin Saidi⁽³⁾, Muhammad Bahi⁽⁴⁾, Marianne Marianne⁽⁵⁾

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Syiah Kuala, Banda Aceh 23111, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Syiah Kuala, Banda Aceh 23111, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Syiah Kuala, Banda Aceh 23111, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Syiah Kuala, Banda Aceh 23111, Indonesia
(5) Department of Pharmacology, Faculty of Pharmacy, Universitas Sumatera Utara, Medan, 20155, Indonesia
(*) Corresponding Author

Abstract

This study aims to identify the antifeedant activity of Azadirachta indica A. Juss root bark against Hong Kong caterpillar (Tenebrio molitor). A. indica A. root was macerated in n-hexane, ethyl acetate, and methanol. The investigation of antifeedant activity was conducted by using the no choice leaf disk method. The antifeedant activity (%AI) tests showed that the extracts of n-hexane, ethyl acetate, and methanol with each concentration of 0.5% were 6.71, 71.78, and 40.14%, respectively. The ethyl acetate extract demonstrated the most active antifeedant activity. Ethyl acetate extract was fractionated to obtain five subfractions (A-E). Each subfraction with each concentration of 0.5% showed the %AI of 70.55, 85.29; 67.40, 82.70 and 82.22%, respectively. Furthermore, GC-MS results demonstrated that ethyl acetate extract contained 19 compounds. The main compounds are methyl hexadecanoate and methyl 8-octadecenoate. Further purification of fraction A, which has the highest amount, was then carried out. The obtained isolate, i.e., A3₂, was determined as ethyl p-methoxycinnamate confirmed by ¹³C- and ¹H-NMR, FTIR, and MS spectra. The presence of ethyl p-methoxycinnamate makes A. indica A. root is potential as T. molitor antifeedant. The implication of these findings is to reference herbal antifeedants and reduce the use of synthetic pesticides.

Keywords

Azadirachta indica A. Juss root bark, Antifeedant, Ethyl p-methoxycinnamate, Tenebrio molitor.

Full Text:

Full Text PDF

References

[1] Nasution, R., Barus, T., Nasution, P., and Saidi, N., 2014, Isolation and structure elucidation of steroid from leaves of Artocarpus camansi (Kulu) as antidiabetic, Int. J. PharmTech Res., 6 (4), 1279–1285.

[2] Nasution, R., Fitrah, C.N., Helwati, H., Murniana, Arifin, B., Cutchamzurni, C., Rizal, Y., and Marianne, 2018, Antidiabetes activities extract hexane from the peels of Artocarpus camansi Blanco fruit, Asian J. Pharm. Clin. Res., 11 (1), 12–17.

[3] Nasution, R., Mariane, Mustanir, and Roswita, M., 2015, Anti-obesity compounds from the leaves of plants Morus alba (moraceae), Int. J. ChemTech. Res., 8 (10), 228–234.

[4] Nasution, R., Marianne, and Nur, H., 2015, β-Amyrin acetate of ethyl acetate extract of the bark plant Artocarpus camansi and its antidiabetic activity, Pharma Chem., 7 (6), 71–78.

[5] Nasution, R., Mustanir, Marianne, and Marzuki, I., 2016, Isolation compound anti-obesity from the bark ara (Ficus racemosa) of Aceh, Orient. J. Chem., 32 (5), 2693–2699.

[6] Arifin, B., Nasution, R., Saidi, N., Marianne, and Aprilia, S., 2014, Vitex trifolia plant control of mice environmentally friendly, Int. J. Chemtech. Res., 6 (11), 4595–4600.

[7] Kardinan, A., 2011, Penggunaan pestisida nabati sebagai kearifan local dalam pengendalian hama tanaman menuju system pertanian organik, Pengembangan Inovasi Pertanian, 4 (4), 262–278.

[8] Kumar, V.S., and Navaratnam, V., 2013, Neem (Azadirachta indica): Prehistory to contemporary medicinal uses to humankind, Asian Pac. J. Trop. Biomed., 3 (7), 505–514.

[9] Adam, R.P., 2001, Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, Allured Publishing Corporation, Carol Stream, USA.

[10] Mondal, E., and Chakraborty, K., 2016, Azadirachta indica- A tree with multifaceted applications: An overview, J. Pharm. Sci. Res., 8 (5), 299–306.

[11] Hossain, M.A., and Nagooru, M.R., 2011, Biochemical profiling and total flavonoids contents of leaves crude extract of endemic medicinal plant Corydyline terminalis L. Kunth, Pharmacogn. J., 3 (24), 25–30.

[12] Shah, B., and Seth, A., 2012, Textbook of Pharmacognosy and Phytochemistry, Elsevier Health Sciences, New York, USA.

[13] Gokhale, S.B., Kokate, C., and Purohit, A.P., 2019, Pharmacognosy-IV, Nikali Prakashan, India.

[14] Patel, S.M., Venkata, K.C.N., Bhattacharyya, P., Sethi, G., and Bishayee, A., 2016, Potential of neem (Azadirachta indica L.) for prevention and treatment of oncologic diseases, Semin. Cancer Biol.,40-41, 100–115.

[15] Wang, H.W., Liu, J.Q., Chen, J.X., Yang, Y.F., Yan, Y.X., Li, Z.R., and Qiu, M.H., 2013, New triterpenoids from the kernels of Azadirachta indica, Nat. Prod. Bioprospect., 3 (1), 33–37.

[16] Liu, L., Zhao, Y.L., Chen, G.G., Chen, Y.Y., Qin, X.J., Song, C.W., Yang, X.W., Liu, Y.P., and Luo, X.D., 2014, Limonoid and steroidal saponin from Azadirachta indica, Nat. Prod. Bioprospect., 4 (6), 335–340.

[17] Diabaté, D., Gnago, J.A., and Tano, Y., 2014, Toxicity, antifeedant and repellent, effect of Azadirachta indica A. Juss and Jatropacarcus L. aqueous extracts against Plutellaxylostella (Lepidoptera: Plutellidae), J. Basic Appl. Sci. Res., 4 (11), 51–60.

[18] Kurniati, R., Saidi, N., and Nasution, R., 2018, Antifeedant activity from neem leaf extract (Azadirachta indica A Juss), J. Nat., 18 (1), 7–10.

[19] Khan, N., Kennedy, A., Cotton, J., and Brumby, S., 2019, A pest to mental health? Exploring the link between exposure to agrichemicals in farmers and mental health, Int. J. Environ. Res. Public Health, 16 (8), 1327.

[20] Harborne, J.B., 2012, Phytochemical Methods: A Guide to Modern Techniques of Plant Analysis, Springer Science & Business Media, Netherlands.

[21] Jeyasankar, A., and Gokilamani, D., 2016, Biology and eco-friendly control of Amaranths pests, Hymenia recurvalis Fabricius and Psara basalis Walker (Lepidoptera: Crambidae), Int. J. Acad. Stud., 2 (4), 218–230.

[22] Alzohairy, M.A., 2016, Therapeutics role of Azadirachta indica (neem) and their active constituents in diseases prevention and treatment, Evidence-Based Complementary Altern. Med., 2016, 7382506.

[23] Hong, T.K., Kim, S.I., Heo, J.W., Lee, J.K., Choi, D.R., and Ahn, Y.J., 2011, Toxicity of Kaempferia galanga rhizome constituents to Meloidogyne incognita juveniles and eggs, Nematology, 13 (2), 235–244.

[24] Umar, M.I., Asmawi, M.Z., Sadikun, A., Abdul Majid, A.M.S., Al-Suede, F.S.R., Hassan, L.E., Altaf, R., and Ahamed, M.B.K., 2014, Ethyl-p-methoxycinnamate isolated from Kaempferia galanga inhibits inflammation by suppressing interleukin-1, tumor necrosis factor-a, and angiogenesis by blocking endothelial functions, Clinics, 69 (2), 134–144.

[25] Chowdhury, M.Z., Al Mahmud, Z., Ali, M.S., and Bachar, S.C., 2014, Phytochemical and pharmacological investigations of rhizome extracts of Kaempferia galanga, Int. J. Pharmacogn., 1 (3), 185–192.

[26] Elya, B., Kusuma I.K., Jufri, M., and Handayani, R., 2016, Antibacterial test against acne in vitro, the physical stability and patch test using cream containing ethyl p-methoxycinnamate extracted from Kaempferia galanga L., Rhizoma, Res. J. Med. Plants, 10 (8), 426–434.

[27] Umar, M.I., Asmawi, M.Z., Sadikun, A., Abdul Majid, A.M.S., Atangwho, I.J., Ahamed, M.B.K., Altaf, R., and Ahmad, A., 2014, Multi-constituent synergism is responsible for anti-inflammatory effect of Azadirachta indica leaf extract, Pharm. Biol., 52 (11), 1411–1422.

[28] Hakim, A., Andayani, Y., and Rahayuan, B.D., 2018, Isolation of ethyl p-methoxy cinnamate from Kaemferia galanga L, J. Phys.: Conf. Ser., 1095, 012039.

[29] Manitto, P., and Sammes, P.G., 1981, Biosynthesis of Natural Products, Ellis Horwood, Chichester, New York.

[30] Raphael, E., 2012, Phytochemical constituents of some leaves extract of Aloe vera and Azadirachta indica plant species, Glob. Adv. Res. J. Environ. Sci. Toxicol., 1(2), 14–17.

[31] Kiranmai, M., Usha Sri, B., Ibrahim, M., and Mahendra Kumar, C.B., 2012, Antioxidant activity and total flavonoids content of different extracts of Azadirachta indica A. Juss, J. Med. Plants Res., 6(46), 5737–5742.

[32] Hussain, M., Debnath, B., Qasim, M., Bamisile, B.S., Islam, W., Hameed, M.S., Wang, L., and Qiu, D., 2019, Role of saponins in plant defense against specialist herbivores, Molecules, 24 (11), 2067

[33] Rahman, M.M., Ahmad, S.H., Mohamed, M.T.M., and Ab Rahman, M.Z., 2014, Antimicrobial compounds from leaf extracts of Jatropha curcas, Psidium guajava, and Andrographis paniculata, Sci. World J., 2014, 635240.

[34] Abdel-Hady, H., El-Wakil, E.A., and Abdel-Gawad, M., 2018, GC-MS analysis, antioxidant and cytotoxic activities of Mentha spicata, Eur. J. Med. Plants, 26(1), 1–12.

DOI: https://doi.org/10.22146/ijc.64487