Malaysian Journal of Analytical Sciences Vol 23 No 4 (2019): 677 - 681

ISOLATION OF NEW ROTUNDONE FROM THE ROOTS OF Croton hirtus (EUPHORBIACEAE)

(Pemencilan Komponen Rotundona Terbaharu daripada Akar Croton hirtus (Euphorbiaceae))

Andi Rifki Rosandy ¹, Anis Asmi Azman¹, Rozida Khalid¹, Rizafizah Othaman¹, Azwan Mat Lazim¹, Iqbal M. Choudary², Yana Maulana Syah³, Jalifah Latip¹, Ikram M. Said¹, Muntaz Abu Bakar¹*

¹Faculty of Science and Technology,

Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia

²Hussain Ebrahim Jamal Research Institute of Chemistry,

University of Karachi, Karachi, 75270, Pakistan

³Organic Chemistry Division, Faculty of Mathematics and Natural Sciences,

Institut Teknologi Bandung, Jalan Ganesha 10, Bandung 40132, Indonesia

*Corresponding author: muntaz@ukm.edu.my

Received: 31 March 2018; Accepted: 17 April 2019

Abstract

Croton is a genus of Euphorbiaceae which consists of approximately 1,300 species and are widely distributed in Asia, Africa and South America. Phytochemical study on the root of Croton hirtus has been conducted. The powder of the root of C. hirtus was extracted using the methanol solvent at room temperature for 24 hours and repeated three times. The crude extracts obtained were analysed using thin layer chromatography (TLC) then fractionated via vacuum column chromatography (VLC) and proceed the isolation using radial chromatography (RC) to get the pure compounds. The pure compounds obtained were elucidated by nuclear magnetic resonance (NMR), Fourier transform infrared (FT-IR) and mass spectroscopy to confirm their structures and from that analysis, the compounds were identified as two new compounds naming (+)5,14-dihydroxyrotundone-9-(2’-methybut-2’-enoate) (1) and (-)5,14-dihydroxyrotundane-9-benzoate (2) with total weight 135 mg and 145 mg respectively. This two compound were reported for this time on this genus.

Keywords: rotundone, euphorbiaceae, Croton hirtus

Abstrak

Croton merupakan genus dalam famili Euphorbiaceae yang mengandungi kira-kira 1,300 spesies dan taburannya meliputi Asia, Afrika dan Amerika Selatan. Kajian fitokimia ke atas akar Croton hirtus telah dijalankan. Serbuk akar C. hirtus diekstrak dengan menggunakan pelarut metanol pada suhu bilik selama 24 jam dan pengesktrakan diulang sebanyak tiga kali. Ekstrak mentah yang diperoleh dianalisis dengan menggunakan kromatografi lapisan nipis (KLN) kemudian difraksikan melalui kromatografi cecair vakum (KCV) dan pengasingan diteruskan dengan menggunakan kromatografi radial (KR) untuk mendapatkan sebatian tulen. Sebatian tulen yang diperoleh ditentukan oleh resonan magnetik nuklear (RMN), Inframerah transformasi Fourier (TFI) dan spektroskopi jisim untuk mengesahkan struktur mereka dan dari analisis itu, sebatian telah dikenal pasti sebagai dua sebatian baru yang diberi nama (+)5,14-dihidroksirotundona-9-(2’-metibut-2’-enoat) (1) and (-)5,14-dihidroksirotundana-9-benzoat (2) dengan jumlah berat masing-masing sebanyak 135 mg dan 145 mg. Kedua-dua sebatian ini dilaporkan buat kali pertama bagi genus ini.

Kata kunci: rotundona, euphorbiaceae, Croton hirtus

References

1. Berry, P. E., Hipp, A. L., Wurdack, K. J., Van Ee, B. and Riina R. (2005). Molecular phylogenetics of the giant genus Croton and tribe Crotoneae (Euphorbiaceae sensu stricto) using ITS and trnL-trnF DNA sequence data. American Journal Botany, 92: 1520-1534.

2. Berry, P. E., Van Ee, B. and Haber Elizabeth, A. (2011). Resolving the tangled identity of Croton chrysodaphne baill (Euphorbiaceae) in Madagascar. Candollea, 66: 113-118.

3. Webster, G. L. and Gillespie, L. (1994). Synopsis of the genera and suprageneric taxa of euphorbiaceae. Annals Missouri Botanical Garden, 81: 33-144.

4. Peixoto, R. N. S., Guilhon, G. M. S. P., Das Graças, B., Zoghbi, M., Araújo, I. S., Uetanabaro, A. P. T., Lourivaldo, S. S. and Brasil, D. D. S. B. (2013). Volatiles, a glutarimide alkaloid and antimicrobial effects of Croton pullei (Euphorbiaceae). Molecules, 18: 195-3205.

5. Da, Costa, Filho, L. O., de Moura, Silva, M. H., de Almeida-Cortez, J. S., da Silva, S. I, and Morais de Oliveira, A. F. (2012). Foliar cuticular n-alkane of some Croton species from Brazilian semiarid vegetation. Biochemical Systematic Ecology, 41: 13-15.

6. Sidney, G., De, L., Antônia, M. G. L. C., José, A. D. L., José M. M. N, Mariana, H. C. and Edilberto R. S. (2010). Fixed and volatile constituents of genus croton plants: C. adenocalyx baill - euphorbiaceae. Review latinoamer química, 38:133-144.

7. Suárez, A. I., Oropeza, M., Vásquez, L., Tillett, S. and Compagnone, R. S. (2011). Chemical composition of the essential oil of Croton gossypiifolius from Venezuela. Natural Product Communications, 6(1): 97-99.

8. Rosandy, A. R., Azman, A. A., Khalid, R. M., Othaman, R., Lazim, A. M., Choudary, I. M., Syah, Y. M., Latip, J., Said. I. Md. and Bakar, M. A. (2018). New diterpenoids from the roots of Croton hirtus (Euphorbiaceae). Malaysian Journal of Analytical Sciences, 22(1): 64-71.

9. Nasib, A., Ali, K. and Khan, S. (2008). In vitro propagation of Croton (Codiaeum varlegatum). Journal Pakistan Botany, 40: 99-104.

10. Júnior, F. E. B., De, Oliveira, D. R., Bento, E. B., Leite, L. H. I., Souza, D. O., Siebra, A. L. A., Sampaio, R. S., Martisn, A. O. P. B., Ramos, A. G. B., Tintino, S. R., Lacerda-Neto, L. J., Figueiredo, P. R. L., Oliveira, L. R., Rodrigues, C. K. S., Sales, V. S., Figueiredo, R. S. D. N., Nascimento, E. P., Monteiro, A. B., Costa, J. G. M., Coutinho, H. D. M,, Amaro, E. N., De Menezes, I. R. A. and Kerntopf, M. R. (2013). Antiulcerogenic activity of the hydroalcoholic extract of leaves of Croton campestris A. St.-Hill in rodents. Evidence-based Complementary Alternative Medicine, 2013: 1-10.

11. Salatino, A., Salatino, M. L. F. and Negri, G. (2007). Traditional uses, chemistry and pharmacology of Croton species (Euphorbiaceae). Journal Brazil Chemistry Society, 18: 11-33.

12. De Lima, S. G., Medeiros, L. B. P. and Cunha, C. N. L. C. (2012). Chemical composition of essential oils of Croton hirtus L’Her from Piauí (Brazil). Journal Essential Oil Research, 24: 371-376.