Flavonoid glycosides from leaves and straw of Oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination

Ill-Min Chung; Sung-Kyu Park; Mohd Ali; Mayakrishnan Prabakaran; Young-Tek Oh; Seung-Hyun Kim; Nasir Ali Siddiqui; Ateeque Ahmad

doi:10.1016/j.jsps.2018.01.003

Flavonoid glycosides from leaves and straw of Oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination

Saudi Pharm J. 2018 Mar;26(3):375-387. doi: 10.1016/j.jsps.2018.01.003. Epub 2018 Jan 12.

Authors

Ill-Min Chung¹, Sung-Kyu Park¹, Mohd Ali², Mayakrishnan Prabakaran¹, Young-Tek Oh¹, Seung-Hyun Kim¹, Nasir Ali Siddiqui³, Ateeque Ahmad^{4

5}

Affiliations

¹ Department of Applied Bioscience, College of Life and Environmental Science, Konkuk University, Seoul 05029, South Korea.
² Department of Pharmacognosy and Phytochemistry, Hamdard University, New Delhi 110062, India.
³ Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, P.O. Box 2457, Saudi Arabia.
⁴ Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India.
⁵ Department of Applied Bioscience, Konkuk University, Seoul 143-701, South Korea.

Abstract

Five new flavonoids namely, 5-hydroxy-6-isoprenyl-7,4'-dimethoxyflavonol-3-O-β-d-arabinofuranoside (1), 5,7-dihydroxy-4'-methoxyflavone-7-O-β-d-arabinopyranosyl-2''-n-decan-1'''-oate (2), 3-butanoyl-5,6,8-trihydroxy-7,4'-dimethoxyflavonol--5-O-β-d-glucopyranoside (3), 7, 4'-dimethoxy-5-hydroxyflavone-5-O-α-d-arabinopyranosyl-(2'' → 1''')-O-α-d-arabinopyranoside (4), and 5,6-dihydroxy-7, 4'-dimethoxyflavone-5-O-α-d-glucopyranoside (5), together with two known compounds, were isolated from the methanol extract of Oryza sativa leaves and straw. Their structures of new compounds were elucidated by 1D and 2D NMR spectral methods, viz: COSY, HMBC and HSQC aided by mass techniques and IR spectroscopy. The cytotoxicity of these compounds (1-7) were assessed by using (RAW 264.7) mouse macrophages cell line, and allelopathic effects of compounds (1-7) on the germination characteristics of barnyardgrass (Echinochloa oryzicola) and pigweed (Chenopodium album L.) were also evaluated. The compounds 1, 6 and 7 showed cytotoxicity and compounds 1-7 exhibited significant inhibitory activity on the seed germination of two weed species.

Keywords: Allelopathic effect; Barnyardgrass; Cytotoxicity test; Gramineae; New chemical constituents; Oryza sativa L.; Pigweed; Rice leaves and straw.