Anticholinesterase activity of 7-methoxyflavones isolated from Kaempferia parviflora
The rhizome of Kaempferia parviflora or kra-chai-dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory screening of this plant extract exhibited significant acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. Thirteen known...
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| Published in: | Phytotherapy research Vol. 23; no. 12; pp. 1792 - 1794 |
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| Format: | Journal Article |
| Language: | English |
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Chichester, UK
John Wiley & Sons, Ltd
01-12-2009
Wiley |
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| Abstract | The rhizome of Kaempferia parviflora or kra-chai-dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory screening of this plant extract exhibited significant acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. Thirteen known methoxyflavones (1-13) were isolated and their structures were completely elucidated based on NMR analysis and compared with literature reports. Minor compounds 12-13 were reported for the first time from this species. The cholinesterase inhibitory test results showed that the highest potential inhibitors toward AChE and BChE were 5,7,4'-trimethoxyflavone (6) and 5,7-dimethoxyflavone (7), respectively, with the percentage inhibitory activity varying over 43-85%. The structure-activity relationship study led to the conclusion that compounds bearing 5,7-dimethoxy groups and a free substituent at C-3 had a significant inhibitory effect at a concentration of 0.1 mg/mL, but those bearing a 5-hydroxyl group reduced the inhibitory potency. On the other hand, flavones bearing a 3'- or 5'-methoxy group did not influence the inhibitory effect. Interestingly, 5,7-dimethoxyflavone (7) exhibited strong selectivity for BChE over AChE which may be of great interest to modify as a treatment agent for Alzheimer's disease. Copyright © 2009 John Wiley & Sons, Ltd. |
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| AbstractList | The rhizome of Kaempferia parviflora or kra-chai-dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory screening of this plant extract exhibited significant acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. Thirteen known methoxyflavones (1-13) were isolated and their structures were completely elucidated based on NMR analysis and compared with literature reports. Minor compounds 12-13 were reported for the first time from this species. The cholinesterase inhibitory test results showed that the highest potential inhibitors toward AChE and BChE were 5,7,4'-trimethoxyflavone (6) and 5,7-dimethoxyflavone (7), respectively, with the percentage inhibitory activity varying over 43-85%. The structure-activity relationship study led to the conclusion that compounds bearing 5,7-dimethoxy groups and a free substituent at C-3 had a significant inhibitory effect at a concentration of 0.1 mg/mL, but those bearing a 5-hydroxyl group reduced the inhibitory potency. On the other hand, flavones bearing a 3'- or 5'-methoxy group did not influence the inhibitory effect. Interestingly, 5,7-dimethoxyflavone (7) exhibited strong selectivity for BChE over AChE which may be of great interest to modify as a treatment agent for Alzheimer's disease. Copyright © 2009 John Wiley & Sons, Ltd. The rhizome of Kaempferia parviflora or kra-chai-dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory screening of this plant extract exhibited significant acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. Thirteen known methoxyflavones (1-13) were isolated and their structures were completely elucidated based on NMR analysis and compared with literature reports. Minor compounds 12-13 were reported for the first time from this species. The cholinesterase inhibitory test results showed that the highest potential inhibitors toward AChE and BChE were 5,7,4'-trimethoxyflavone (6) and 5,7-dimethoxyflavone (7), respectively, with the percentage inhibitory activity varying over 43-85%. The structure-activity relationship study led to the conclusion that compounds bearing 5,7-dimethoxy groups and a free substituent at C-3 had a significant inhibitory effect at a concentration of 0.1 mg/mL, but those bearing a 5-hydroxyl group reduced the inhibitory potency. On the other hand, flavones bearing a 3'- or 5'-methoxy group did not influence the inhibitory effect. Interestingly, 5,7-dimethoxyflavone (7) exhibited strong selectivity for BChE over AChE which may be of great interest to modify as a treatment agent for Alzheimer's disease. Abstract The rhizome of Kaempferia parviflora or kra‐chai‐dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory screening of this plant extract exhibited significant acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. Thirteen known methoxyflavones (1–13) were isolated and their structures were completely elucidated based on NMR analysis and compared with literature reports. Minor compounds 12–13 were reported for the first time from this species. The cholinesterase inhibitory test results showed that the highest potential inhibitors toward AChE and BChE were 5,7,4′‐trimethoxyflavone (6) and 5,7‐dimethoxyflavone (7), respectively, with the percentage inhibitory activity varying over 43–85%. The structure‐activity relationship study led to the conclusion that compounds bearing 5,7‐dimethoxy groups and a free substituent at C‐3 had a significant inhibitory effect at a concentration of 0.1 mg/mL, but those bearing a 5‐hydroxyl group reduced the inhibitory potency. On the other hand, flavones bearing a 3′‐ or 5′‐methoxy group did not influence the inhibitory effect. Interestingly, 5,7‐dimethoxyflavone (7) exhibited strong selectivity for BChE over AChE which may be of great interest to modify as a treatment agent for Alzheimer's disease. Copyright © 2009 John Wiley & Sons, Ltd. |
| Author | Sawasdee, Pattara Kokpol, Udom Sabphon, Chalisa Sitthiwongwanit, Duangporn |
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| Cites_doi | 10.1016/j.fitote.2003.08.017 10.1016/j.jep.2005.03.035 10.1016/0006-2952(61)90145-9 10.1016/j.fitote.2007.11.017 10.1016/S0031-9422(98)00186-1 10.3390/12092130 10.1016/S0031-9422(98)00622-0 10.1016/j.chroma.2007.01.033 10.1016/j.jep.2007.10.042 10.1262/jrd.18092 10.1016/j.jep.2006.09.037 10.1016/j.ejphar.2007.04.001 10.1016/j.jep.2003.08.008 |
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| Keywords | Monocotyledones Pharmacognosy Flavonoid Medicinal plant methoxyflavone Polyphenol Folk medicine Angiospermae Plant origin Phenols Flavone derivatives Spermatophyta Kaempferia parviflora anticholinesterase activity Anticholinesterase agent Zingiberaceae |
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| References_xml | – volume: 16 start-page: 265 year: 2007 end-page: 269 article-title: Isolation of acetylcholinesterase inhibitors from the flowers of Linne publication-title: Food Sci Biotechnol – volume: 102 start-page: 120 year: 2005 end-page: 122 article-title: Anti‐gastric ulcer effect of publication-title: J Ethnopharmacol – volume: 110 start-page: 559 year: 2007 end-page: 562 article-title: ethanolic extract promoted nitric oxide production in human umbilical vein endothelial cells publication-title: J Ethnopharmacol – volume: 7 start-page: 88 year: 1961 end-page: 95 article-title: A new and rapid colorimetric determination of acetylcholinesterase activity publication-title: Biochem Pharmacol – volume: 49 start-page: 1549 year: 1998 end-page: 1553 article-title: Flavone aglycones in glandular hairs of × publication-title: Phytochemistry – start-page: 42 year: 2002 end-page: 43 – volume: 116 start-page: 191 year: 2008 end-page: 193 article-title: Anti‐allergic activity of compounds from publication-title: J Ethnopharmacol – volume: 79 start-page: 214 year: 2008 end-page: 216 article-title: Vasorelaxation and antispasmodic effects of ethanolic extract in isolated rat organ studies publication-title: Fitoterapia – volume: 89 start-page: 261 year: 2003 end-page: 264 article-title: Screening for acetylcholinesterase inhibitory activity in plants used in Thai traditional rejuvenating and neurotonic remedies publication-title: J Ethnopharmacol – volume: 1143 start-page: 227 year: 2007 end-page: 233 article-title: Simultaneous identification and quantitation of 11 flavonoid constituents in by gas chromatography publication-title: J Chromatogr A – volume: 566 start-page: 67 year: 2007 end-page: 74 article-title: Modulation of function of multidrug resistance associated‐proteins by extracts and their components publication-title: Eur J Pharmacol – volume: 12 start-page: 2130 year: 2007 end-page: 2139 article-title: Acetylcholinesterase inhibition by flavonoids from publication-title: Molecules – volume: 53 start-page: 351 year: 2007 end-page: 356 article-title: Effect of daily treatment with Thai herb, , in Hershberger assay using castrated immature rats publication-title: J Reprod Develop – volume: 50 start-page: 899 year: 1999 end-page: 902 article-title: Eicosenones and methylated flavonols from publication-title: Phytochemistry – volume: 75 start-page: 89 year: 2004 end-page: 92 article-title: Bioactive flavonoids from publication-title: Fitoterapia – ident: e_1_2_1_16_1 doi: 10.1016/j.fitote.2003.08.017 – volume: 16 start-page: 265 year: 2007 ident: e_1_2_1_7_1 article-title: Isolation of acetylcholinesterase inhibitors from the flowers of Chrysanthemum indicum Linne publication-title: Food Sci Biotechnol contributor: fullname: Lim SS – ident: e_1_2_1_10_1 doi: 10.1016/j.jep.2005.03.035 – ident: e_1_2_1_4_1 doi: 10.1016/0006-2952(61)90145-9 – ident: e_1_2_1_14_1 doi: 10.1016/j.fitote.2007.11.017 – ident: e_1_2_1_2_1 doi: 10.1016/S0031-9422(98)00186-1 – ident: e_1_2_1_6_1 doi: 10.3390/12092130 – ident: e_1_2_1_3_1 doi: 10.1016/S0031-9422(98)00622-0 – start-page: 42 volume-title: Technology Chao Barn year: 2002 ident: e_1_2_1_9_1 contributor: fullname: Pengcharoen O – ident: e_1_2_1_11_1 doi: 10.1016/j.chroma.2007.01.033 – ident: e_1_2_1_12_1 doi: 10.1016/j.jep.2007.10.042 – ident: e_1_2_1_13_1 doi: 10.1262/jrd.18092 – ident: e_1_2_1_15_1 doi: 10.1016/j.jep.2006.09.037 – ident: e_1_2_1_8_1 doi: 10.1016/j.ejphar.2007.04.001 – ident: e_1_2_1_5_1 doi: 10.1016/j.jep.2003.08.008 |
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| Snippet | The rhizome of Kaempferia parviflora or kra-chai-dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory screening of... The rhizome of Kaempferia parviflora or kra‐chai‐dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory screening of... Abstract The rhizome of Kaempferia parviflora or kra‐chai‐dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory... |
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| SubjectTerms | Acetylcholinesterase - metabolism anticholinesterase activity Apigenin - isolation & purification Apigenin - pharmacology Biological and medical sciences Butyrylcholinesterase - metabolism Cholinesterase Inhibitors - isolation & purification Cholinesterase Inhibitors - pharmacology Chromatography, High Pressure Liquid Flavonoids - isolation & purification Flavonoids - pharmacology General pharmacology Kaempferia parviflora Medical sciences Medicine, East Asian Traditional methoxyflavone Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Extracts - pharmacology Rhizome - chemistry Structure-Activity Relationship Zingiberaceae - chemistry |
| Title | Anticholinesterase activity of 7-methoxyflavones isolated from Kaempferia parviflora |
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