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

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-hydroxyflavon...

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Main Authors: Ill-Min Chung, Sung-Kyu Park, Mohd Ali, Mayakrishnan Prabakaran, Young-Tek Oh, Seung-Hyun Kim, Nasir Ali Siddiqui, Ateeque Ahmad
Format: Article
Language:English
Published: Springer 2018-03-01
Series:Saudi Pharmaceutical Journal
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Online Access:http://www.sciencedirect.com/science/article/pii/S1319016418300033
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author Ill-Min Chung
Sung-Kyu Park
Mohd Ali
Mayakrishnan Prabakaran
Young-Tek Oh
Seung-Hyun Kim
Nasir Ali Siddiqui
Ateeque Ahmad
author_facet Ill-Min Chung
Sung-Kyu Park
Mohd Ali
Mayakrishnan Prabakaran
Young-Tek Oh
Seung-Hyun Kim
Nasir Ali Siddiqui
Ateeque Ahmad
author_sort Ill-Min Chung
collection DOAJ
description 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.
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spelling doaj-art-127d72e44b7847b89a2fca7b4dcd7d372025-08-20T03:55:44ZengSpringerSaudi Pharmaceutical Journal1319-01642018-03-0126337538710.1016/j.jsps.2018.01.003Flavonoid glycosides from leaves and straw of Oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germinationIll-Min Chung0Sung-Kyu Park1Mohd Ali2Mayakrishnan Prabakaran3Young-Tek Oh4Seung-Hyun Kim5Nasir Ali Siddiqui6Ateeque Ahmad7Department of Applied Bioscience, College of Life and Environmental Science, Konkuk University, Seoul 05029, South KoreaDepartment of Applied Bioscience, College of Life and Environmental Science, Konkuk University, Seoul 05029, South KoreaDepartment of Pharmacognosy and Phytochemistry, Hamdard University, New Delhi 110062, IndiaDepartment of Applied Bioscience, College of Life and Environmental Science, Konkuk University, Seoul 05029, South KoreaDepartment of Applied Bioscience, College of Life and Environmental Science, Konkuk University, Seoul 05029, South KoreaDepartment of Applied Bioscience, College of Life and Environmental Science, Konkuk University, Seoul 05029, South KoreaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, P.O. Box 2457, Saudi ArabiaProcess Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India; Department of Applied Bioscience, Konkuk University, Seoul 143-701, South Korea; Corresponding author at: Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India.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.http://www.sciencedirect.com/science/article/pii/S1319016418300033Oryza sativa L.GramineaeRice leaves and strawNew chemical constituentsCytotoxicity testAllelopathic effect
spellingShingle Ill-Min Chung
Sung-Kyu Park
Mohd Ali
Mayakrishnan Prabakaran
Young-Tek Oh
Seung-Hyun Kim
Nasir Ali Siddiqui
Ateeque Ahmad
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 Pharmaceutical Journal
Oryza sativa L.
Gramineae
Rice leaves and straw
New chemical constituents
Cytotoxicity test
Allelopathic effect
title Flavonoid glycosides from leaves and straw of Oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination
title_full Flavonoid glycosides from leaves and straw of Oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination
title_fullStr Flavonoid glycosides from leaves and straw of Oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination
title_full_unstemmed Flavonoid glycosides from leaves and straw of Oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination
title_short Flavonoid glycosides from leaves and straw of Oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination
title_sort flavonoid glycosides from leaves and straw of oryza sativa and their effects of cytotoxicity on a macrophage cell line and allelopathic on weed germination
topic Oryza sativa L.
Gramineae
Rice leaves and straw
New chemical constituents
Cytotoxicity test
Allelopathic effect
url http://www.sciencedirect.com/science/article/pii/S1319016418300033
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