Malaysian Journal of Analytical Sciences Vol 24 No 4 (2020): 530 - 537

 

 

 

 

IRIDOID GLYCOSIDES AND PHENYLPROPANOIDS FROM Asystasia gangetica (L) T. ANDERSON VAR. Micrantha (ACANTHACEAE)

 

(Iridoid Glikosida dan Fenilpropanoid daripada Asystasia gangetica (L) T. Anderson Var. Micrantha (Acanthaceae))

 

Isna Athirah Othman1, 2, Norizan Ahmat1, 2*, Amjad Ayad Qatran Al-Khdhairawi2

 

1Faculty of Applied Sciences,

Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia

2Atta-ur-Rahman Institute for Natural Product Discovery,

Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor, Malaysia

 

*Corresponding author:  noriz118@uitm.edu.my

 

 

Received: 20 November 2019; Accepted: 29 June 2020; Published:  11 August 2020

 

 

Abstract

Asystasia gangetica (L) T. Anderson var. micrantha (Acanthaceae) or commonly known as “Chinese Violet” or “rumput Israel” in Malaysia is a rapidly growing herb usually found among short grasses and along pathways. This plant is used traditionally to treat diabetes mellitus, ear disease and gonorrhea. Its anthelmintic activity helps to treat swelling and rheumatism. The present study was designed to isolate and elucidate chemical constituents from A. gangetica. The methanolic extract of the A. gangetica leaves was fractionated by using vacuum liquid chromatography (VLC) and preparative high-performance liquid chromatography (HPLC). Selected fractions were purified by recycling HPLC and monitored by using ultra high-performance liquid chromatography (UHPLC). The structures of isolated compounds were characterized by using various spectroscopic methods, mainly nuclear magnetic resonance (NMR) and comparisons with previously reported data. Five phytochemical constituents namely, salidroside (1), verbascoside (2), forsythiaside (3), 3’’-O-caffeoyl-6-O-rhamnopyranosyl catalpol (4), and 4’’-O-caffeoyl-6-O-rhamnopyranosyl catalpol (5) were purified using recycling HPLC. Compounds 2, 3 and 5 were identified for the first time from A. gangetica.

 

Keywords: acanthaceae, Asystasia gangetica, iridoid glycosides, phenylpropanoid, high-performance liquid chromatography, nuclear magnetic resonance

 

Abstrak

Asystasia gangetica (L) T. Anderson var. micrantha (Acanthaceae) yang juga dikenali sebagai “Chinese Violet” atau “rumput Israel” di Malaysia adalah herba yang mudah membiak, biasanya ditemui di kalangan rumput pendek dan sepanjang jalan. Tumbuhan ini secara traditionalnya digunakan untuk merawat diabetes mellitus, sakit telinga dan gonorea. Keupayaan antihemintiknya membantu merawat bengkak dan reumatik. Kajian ini diolah untuk memencilkan dan mengenalpasti sebatian aktif daripada A. Gangetica. Ekstrak metanol daripada daun A. Gangetica difraksi menggunakan kromatografi cecair vakum (VLC) dan penyediaan kromatografi cecair bertekanan tinggi (HPLC). Fraksi terpilih telah ditulenkan menggunakan HPLC kitar semula dan dipantau menggunakan kromatografi cecair bertekanan tinggi ultra (UHPLC). Struktur sebatian yang dipencilkan dikenalpasti menggunakan pelbagai teknik spektroskopi terutamanya resonan magnetik nuklear (NMR) dan perbandingan dengan data yang telah dilaporkan sebelumnya. Lima sebation kimia iaitu salidrosida (1), verbascosida (2), forsithiasida (3), 3’’-O-kafeoil-6-O-rhamnopiranosil katalpol (4) dan 4’’-O-kafeoil-6-O-rhamnopiranosil katalpol (5) telah dipencilkan menggunakan HPLC pengitaran semula. Sebatian 2, 3 dan 5 adalah dilaporkan buat pertama kali dari A. gangetica.

 

Kata kunci:   acanthaceae, Asystasia gangetica, iridoid glikosida, fenilpropanoid, kromatografi cecair bertekanan tinggi, resonan magnetik nuklear

 

References

1.      Gopal, T., K., Megha, G., Chamundeeswari, D. and Reddy, C., U. (2013). Phytochemical and pharmacological studies on the whole plant of Asystasia gangetica. Indian Journal of Research in Pharmacy and Biotechnology, 1(3): 365-370.

2.      Worawittayanon, P., Ruadreo, J., Disadee, W., Sahakitpichan, P., Sitthimonchai, S., Thasana, N., Ruchirawat, S. and Kanchanapoom, T. (2012). Iridoid and flavone glycosides from Asystasia gangetica subsp. micrantha and Asystasia salicifolia and their antioxidant activities. Biochemical Systematics and Ecology, 40:38-42.

3.      Senthamilselvi, M. M., Kesavan, D. and Sulochana, N. (2011). A new biflavone glycoside from flowers of Asystasia gangetica. Chemistry of Natural Compounds, 47(3):360-362.

4.      Tilloo, S., K., Pande, V. B., Rasala, T., M. and Kale V., V. (2012). Asystasia gangetica: Review on multipotential application. International Research Journal of Pharmacy, 3(4):18-20.

5.      Mastihubová, M. and Poláková, M. (2016). A selective and mild glycosylation method of natural phenolic alcohols. Beilstein Journal of Organic Chemistry, 12: 524-530.

6.      Yoo, Y. M., Nam, J. H., Kim, M. Y., Choi, J., Lee, K. T. and Park, H. J., 2009. Analgesic and anti-gastropathic effects of salidroside isolated from Acer tegmentosum heartwood. The Open Bioactive Compounds Journal, 2: 1-7.

7.      López-Rodríguez, R., Herrera-Ruiz M., Trejo-Tapia, G., Domínguez-Mendoza, B. E., González-Cortazar M. and Zamilpa, A. (2019). In vivo gastroprotective and antidepressant effects of iridoids, verbascoside and tenuifloroside from Castilleja tenuiflora Benth. Molecules, 24: 1292.

8.      Pardo, F., Perich, F., Villarroel, L. and Torres, R., 1993. Isolation of verbascoside, an antimicrobial constituent of Buddleja globosa leaves. Journal of Ethnopharmacology, 39(3): 221-222.

9.      Nishibe, S., Okabe, K., Tsukamoto H., Sakushima A. and Hisada S. (1982). The structure of forsythiaside isolated from Forsythia suspensa. Chemical and Pharmaceutical Bulletin, 30(3): 1048-1050.

10.   Jia, J., Zhang, F., Li, Z., Qin, X. and Zhang, L. (2015). Comparison of fruit of Forsythia suspensa at two different maturation stages by NMR-based metabolomics. Molecules, 20: 10065-10081.

11.   Qu, H., Zhang, Y., Wang, Y., Li, B. and Sun, W., 2008. Antioxidant and antibacterial activity of two compounds (forsythiaside and forsythin) isolated from Forsythia suspensa. Journal of Pharmacy and Pharmacology, 60(2): 261-266.

12.   Kroll-Mřller, P., Pedersen, K. D., Gousiadou C., Kokubun, T., Albach D., Taskova, R., Garnock-Jones. P. J., Gotfredsen C. H. and Jensen S. R. (2017). Iridoid glucosides in the genus Veronica (Plantaginaceae) from New Zealand. Phytochemistry, 140: 174-180.

13.   Kupeli, E., Harput, U. S., Varel, M., Yesilada, E., Saracoglu, I. (2005). Bioassay-guided isolation of iridoid glucosides with antinociceptive and anti-inflammatory activities from Veronica anagallis-aquatica L. Journal of Ethnopharmacology, 102: 170-176.

14.   Oh, H., Pae, H. O., Oh, G. S., Lee, S. Y., Chai, K. Y., Song, C. E., Kwon, T. O., Chung, H. T., Lee, H. S. (2002). Inhibition of inducible nitric oxide synthesis by catalposide from Catalpa ovata. Planta Medica, 68: 685-689.

15.   Warashina, T., Miyase, T. and Ueno, A. (1991). Iridoid glycosides from Verbascum thapsus L. Chemical and Pharmaceutical Bulletin, 39(12): 3261-3264.

16.   Helfrich, E. and Rimpler, H., 1999. Iridoid glycosides and phenolic glycosides from Holmskioldia sanguinea. Phytochemistry, 50(4): 619-627.