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Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound

Hericium erinaceus, a mushroom species commonly known as Yamabushitake in Japan, is known to have a stimulatory effect on neurotrophic factors, such as brain-derived neurotrophic factor (BDNF) and nerve growth factor (NGF). Hericenone C, a meroterpenoid with palmitic acid as the fatty acid side chai...

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Autores principales: Tamrakar, Sonam, Wang, Dongmei, Hiraki, Eri, Han, Chunguang, Ruan, Yang, Allam, Ahmed E., Amen, Yhiya, Katakura, Yoshinori, Shimizu, Kuniyoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254140/
https://www.ncbi.nlm.nih.gov/pubmed/37299024
http://dx.doi.org/10.3390/molecules28114549
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author Tamrakar, Sonam
Wang, Dongmei
Hiraki, Eri
Han, Chunguang
Ruan, Yang
Allam, Ahmed E.
Amen, Yhiya
Katakura, Yoshinori
Shimizu, Kuniyoshi
author_facet Tamrakar, Sonam
Wang, Dongmei
Hiraki, Eri
Han, Chunguang
Ruan, Yang
Allam, Ahmed E.
Amen, Yhiya
Katakura, Yoshinori
Shimizu, Kuniyoshi
author_sort Tamrakar, Sonam
collection PubMed
description Hericium erinaceus, a mushroom species commonly known as Yamabushitake in Japan, is known to have a stimulatory effect on neurotrophic factors, such as brain-derived neurotrophic factor (BDNF) and nerve growth factor (NGF). Hericenone C, a meroterpenoid with palmitic acid as the fatty acid side chain, is reported to be one such stimulant. However, according to the structure of the compound, the fatty acid side chain seems highly susceptible to lipase decomposition, under in vivo metabolic conditions. To study this phenomenon, hericenone C from the ethanol extract of the fruiting body was subjected to lipase enzyme treatment and observed for changes in the chemical structure. The compound formed after the lipase enzyme digestion was isolated and identified using LC-QTOF-MS combined with (1)H-NMR analysis. It was found to be a derivative of hericenone C without its fatty acid side chain and was named deacylhericenone. Interestingly, a comparative investigation of the neuroprotective properties of hericenone C and deacylhericenone showed that the BDNF mRNA expression in human astrocytoma cells (1321N1) and the protection against H(2)O(2-)induced oxidative stress was considerably higher in the case of deacylhericenone. These findings suggest that the stronger bioactive form of the hericenone C compound is in fact deacylhericenone.
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spelling pubmed-102541402023-06-10 Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound Tamrakar, Sonam Wang, Dongmei Hiraki, Eri Han, Chunguang Ruan, Yang Allam, Ahmed E. Amen, Yhiya Katakura, Yoshinori Shimizu, Kuniyoshi Molecules Article Hericium erinaceus, a mushroom species commonly known as Yamabushitake in Japan, is known to have a stimulatory effect on neurotrophic factors, such as brain-derived neurotrophic factor (BDNF) and nerve growth factor (NGF). Hericenone C, a meroterpenoid with palmitic acid as the fatty acid side chain, is reported to be one such stimulant. However, according to the structure of the compound, the fatty acid side chain seems highly susceptible to lipase decomposition, under in vivo metabolic conditions. To study this phenomenon, hericenone C from the ethanol extract of the fruiting body was subjected to lipase enzyme treatment and observed for changes in the chemical structure. The compound formed after the lipase enzyme digestion was isolated and identified using LC-QTOF-MS combined with (1)H-NMR analysis. It was found to be a derivative of hericenone C without its fatty acid side chain and was named deacylhericenone. Interestingly, a comparative investigation of the neuroprotective properties of hericenone C and deacylhericenone showed that the BDNF mRNA expression in human astrocytoma cells (1321N1) and the protection against H(2)O(2-)induced oxidative stress was considerably higher in the case of deacylhericenone. These findings suggest that the stronger bioactive form of the hericenone C compound is in fact deacylhericenone. MDPI 2023-06-05 /pmc/articles/PMC10254140/ /pubmed/37299024 http://dx.doi.org/10.3390/molecules28114549 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tamrakar, Sonam
Wang, Dongmei
Hiraki, Eri
Han, Chunguang
Ruan, Yang
Allam, Ahmed E.
Amen, Yhiya
Katakura, Yoshinori
Shimizu, Kuniyoshi
Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound
title Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound
title_full Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound
title_fullStr Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound
title_full_unstemmed Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound
title_short Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound
title_sort deacylated derivative of hericenone c treated by lipase shows enhanced neuroprotective properties compared to its parent compound
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254140/
https://www.ncbi.nlm.nih.gov/pubmed/37299024
http://dx.doi.org/10.3390/molecules28114549
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