Leojaponin is a typical diterpene isolated and identified from the leaves of the traditional Chinese medicine Yimucao (Leonurus japonicus). It has a unique chemical structure bearing a furan moiety and a cross alpha, beta- unsaturated carbonyl, which is a pharmacophore for many drugs, and it can be chemically transformed into a series of derivatives. Also, some so called natural products isolated from L. japonicus might be artifacts transformed from leojaponin during the process of purification. Although leojaponin is not active against acetylcholinesterase, a similar compound isolated from the herb displayed moderate inhibitory activity on acetylcholinesterase. Therefore, establishment of the process of preparing leojaponin and derivation of this compound are of great importance in utilization of this medicinal plant. In this paper, the purification and chemical transformation of leojaponin are reported. The raw material was extracted with 95% ethyl alcohol, and then the solvent was evaporated to dryness by using a rotary evaporator. After that, the residue was dissolved in water and extracted with ethyl acetate, and fractionated by column chromatography on AB-8 macroporous resin. The collected fraction was separated and purified by semi-preparative HPLC. As a result, the purity of the product quantitated by HPLC normality was over 98%. And then three new derivatives have been synthesized by transformation of leojaponin through oxidation and Mannich reactions. All the chemical structures of the new compounds have been elucidated by using 1D and 2D NMR spectroscopic analysis. The in silica interactions between the four compounds and acetylcholinesterase have been performed, and the results showed that compound 2 had the best binding activity (-9.6 kcal/mol).
| Published in | Asia-Pacific Journal of Chemistry (Volume 3, Issue 1) |
| Page(s) | 1-6 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
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Copyright © The Author(s), 2024. Published by Science Publishing Group |
Leonurus japonicus, Leojaponin, Oxidation, Mannich Reaction
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APA Style
Hankui Wu, Yuanping Wang, Yuhua Su, Zhen Su, Kunpeng Zhang, et al. (2021). Purification and Chemical Transformation of Leojaponin, a Diterpene from Leonurus japonicus. Asia-Pacific Journal of Chemistry, 3(1), 1-6.
ACS Style
Hankui Wu; Yuanping Wang; Yuhua Su; Zhen Su; Kunpeng Zhang, et al. Purification and Chemical Transformation of Leojaponin, a Diterpene from Leonurus japonicus. Asia-Pac. J. Chem. 2021, 3(1), 1-6.
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Download@article{10060140,
author = {Hankui Wu and Yuanping Wang and Yuhua Su and Zhen Su and Kunpeng Zhang and Shanshan Sun and Shihan Cai and Linlin Hou},
title = {Purification and Chemical Transformation of Leojaponin, a Diterpene from Leonurus japonicus},
journal = {Asia-Pacific Journal of Chemistry},
volume = {3},
number = {1},
pages = {1-6},
url = {https://www.sciencepublishinggroup.com/article/10060140},
abstract = {Leojaponin is a typical diterpene isolated and identified from the leaves of the traditional Chinese medicine Yimucao (Leonurus japonicus). It has a unique chemical structure bearing a furan moiety and a cross alpha, beta- unsaturated carbonyl, which is a pharmacophore for many drugs, and it can be chemically transformed into a series of derivatives. Also, some so called natural products isolated from L. japonicus might be artifacts transformed from leojaponin during the process of purification. Although leojaponin is not active against acetylcholinesterase, a similar compound isolated from the herb displayed moderate inhibitory activity on acetylcholinesterase. Therefore, establishment of the process of preparing leojaponin and derivation of this compound are of great importance in utilization of this medicinal plant. In this paper, the purification and chemical transformation of leojaponin are reported. The raw material was extracted with 95% ethyl alcohol, and then the solvent was evaporated to dryness by using a rotary evaporator. After that, the residue was dissolved in water and extracted with ethyl acetate, and fractionated by column chromatography on AB-8 macroporous resin. The collected fraction was separated and purified by semi-preparative HPLC. As a result, the purity of the product quantitated by HPLC normality was over 98%. And then three new derivatives have been synthesized by transformation of leojaponin through oxidation and Mannich reactions. All the chemical structures of the new compounds have been elucidated by using 1D and 2D NMR spectroscopic analysis. The in silica interactions between the four compounds and acetylcholinesterase have been performed, and the results showed that compound 2 had the best binding activity (-9.6 kcal/mol).},
year = {2021}
}
TY - JOUR T1 - Purification and Chemical Transformation of Leojaponin, a Diterpene from Leonurus japonicus AU - Hankui Wu AU - Yuanping Wang AU - Yuhua Su AU - Zhen Su AU - Kunpeng Zhang AU - Shanshan Sun AU - Shihan Cai AU - Linlin Hou Y1 - 2021/08/26 PY - 2021 T2 - Asia-Pacific Journal of Chemistry JF - Asia-Pacific Journal of Chemistry JO - Asia-Pacific Journal of Chemistry SP - 1 EP - 6 PB - Science Publishing Group UR - http://www.sciencepg.com/article/10060140 AB - Leojaponin is a typical diterpene isolated and identified from the leaves of the traditional Chinese medicine Yimucao (Leonurus japonicus). It has a unique chemical structure bearing a furan moiety and a cross alpha, beta- unsaturated carbonyl, which is a pharmacophore for many drugs, and it can be chemically transformed into a series of derivatives. Also, some so called natural products isolated from L. japonicus might be artifacts transformed from leojaponin during the process of purification. Although leojaponin is not active against acetylcholinesterase, a similar compound isolated from the herb displayed moderate inhibitory activity on acetylcholinesterase. Therefore, establishment of the process of preparing leojaponin and derivation of this compound are of great importance in utilization of this medicinal plant. In this paper, the purification and chemical transformation of leojaponin are reported. The raw material was extracted with 95% ethyl alcohol, and then the solvent was evaporated to dryness by using a rotary evaporator. After that, the residue was dissolved in water and extracted with ethyl acetate, and fractionated by column chromatography on AB-8 macroporous resin. The collected fraction was separated and purified by semi-preparative HPLC. As a result, the purity of the product quantitated by HPLC normality was over 98%. And then three new derivatives have been synthesized by transformation of leojaponin through oxidation and Mannich reactions. All the chemical structures of the new compounds have been elucidated by using 1D and 2D NMR spectroscopic analysis. The in silica interactions between the four compounds and acetylcholinesterase have been performed, and the results showed that compound 2 had the best binding activity (-9.6 kcal/mol). VL - 3 IS - 1 ER -
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