Diisoprenyl Cyclohexene-Type Meroterpenoids with Cytotoxic Activity from a Mangrove Endophytic Fungus <i>Aspergillus</i> sp. GXNU-Y85

Five new diisoprenyl cyclohexene-type meroterpenoids, aspergienynes J–N (<b>1</b>–<b>5</b>), along with three known analogues (<b>6</b>–<b>8</b>), were obtained from the mangrove endophytic fungal strain <i>Aspergillus</i> sp. GXNU-Y85. The...

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Main Authors: Feng Qin, Zi-Shuo Song, Li Luo, Xiang-Long Bo, Fu-Rong Wu, Mei-Jing Tan, Fan-Fan Wang, Xi-Shan Huang, Heng-Shan Wang
Format: Article
Language:English
Published: MDPI AG 2024-01-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/22/2/58
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author Feng Qin
Zi-Shuo Song
Li Luo
Xiang-Long Bo
Fu-Rong Wu
Mei-Jing Tan
Fan-Fan Wang
Xi-Shan Huang
Heng-Shan Wang
author_facet Feng Qin
Zi-Shuo Song
Li Luo
Xiang-Long Bo
Fu-Rong Wu
Mei-Jing Tan
Fan-Fan Wang
Xi-Shan Huang
Heng-Shan Wang
author_sort Feng Qin
collection DOAJ
description Five new diisoprenyl cyclohexene-type meroterpenoids, aspergienynes J–N (<b>1</b>–<b>5</b>), along with three known analogues (<b>6</b>–<b>8</b>), were obtained from the mangrove endophytic fungal strain <i>Aspergillus</i> sp. GXNU-Y85. The chemical structures, including their absolute configurations, were established via spectroscopic data and comparison of experimental and calculated ECD spectra. Cytotoxicity assay results indicated that compound <b>8</b> had strong cytotoxicity against HeLa cancer cells, and its IC<sub>50</sub> value was 11.8 μM. In addition, flow cytometry analysis revealed that the cytotoxicity of <b>8</b> was due to the induction of G1 cell cycle arrest and apoptosis in HeLa cells.
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spelling doaj.art-e942971e9fd94eb3ae5cf9145b391d0b2024-02-23T15:25:12ZengMDPI AGMarine Drugs1660-33972024-01-012225810.3390/md22020058Diisoprenyl Cyclohexene-Type Meroterpenoids with Cytotoxic Activity from a Mangrove Endophytic Fungus <i>Aspergillus</i> sp. GXNU-Y85Feng Qin0Zi-Shuo Song1Li Luo2Xiang-Long Bo3Fu-Rong Wu4Mei-Jing Tan5Fan-Fan Wang6Xi-Shan Huang7Heng-Shan Wang8State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, ChinaState Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, ChinaState Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, ChinaState Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, ChinaState Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, ChinaState Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, ChinaGuangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, Yulin 537000, ChinaState Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, ChinaState Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, ChinaFive new diisoprenyl cyclohexene-type meroterpenoids, aspergienynes J–N (<b>1</b>–<b>5</b>), along with three known analogues (<b>6</b>–<b>8</b>), were obtained from the mangrove endophytic fungal strain <i>Aspergillus</i> sp. GXNU-Y85. The chemical structures, including their absolute configurations, were established via spectroscopic data and comparison of experimental and calculated ECD spectra. Cytotoxicity assay results indicated that compound <b>8</b> had strong cytotoxicity against HeLa cancer cells, and its IC<sub>50</sub> value was 11.8 μM. In addition, flow cytometry analysis revealed that the cytotoxicity of <b>8</b> was due to the induction of G1 cell cycle arrest and apoptosis in HeLa cells.https://www.mdpi.com/1660-3397/22/2/58mangrove endophytic fungus<i>Aspergillus</i> sp.meroterpenoidsanti-cancer activity
spellingShingle Feng Qin
Zi-Shuo Song
Li Luo
Xiang-Long Bo
Fu-Rong Wu
Mei-Jing Tan
Fan-Fan Wang
Xi-Shan Huang
Heng-Shan Wang
Diisoprenyl Cyclohexene-Type Meroterpenoids with Cytotoxic Activity from a Mangrove Endophytic Fungus <i>Aspergillus</i> sp. GXNU-Y85
Marine Drugs
mangrove endophytic fungus
<i>Aspergillus</i> sp.
meroterpenoids
anti-cancer activity
title Diisoprenyl Cyclohexene-Type Meroterpenoids with Cytotoxic Activity from a Mangrove Endophytic Fungus <i>Aspergillus</i> sp. GXNU-Y85
title_full Diisoprenyl Cyclohexene-Type Meroterpenoids with Cytotoxic Activity from a Mangrove Endophytic Fungus <i>Aspergillus</i> sp. GXNU-Y85
title_fullStr Diisoprenyl Cyclohexene-Type Meroterpenoids with Cytotoxic Activity from a Mangrove Endophytic Fungus <i>Aspergillus</i> sp. GXNU-Y85
title_full_unstemmed Diisoprenyl Cyclohexene-Type Meroterpenoids with Cytotoxic Activity from a Mangrove Endophytic Fungus <i>Aspergillus</i> sp. GXNU-Y85
title_short Diisoprenyl Cyclohexene-Type Meroterpenoids with Cytotoxic Activity from a Mangrove Endophytic Fungus <i>Aspergillus</i> sp. GXNU-Y85
title_sort diisoprenyl cyclohexene type meroterpenoids with cytotoxic activity from a mangrove endophytic fungus i aspergillus i sp gxnu y85
topic mangrove endophytic fungus
<i>Aspergillus</i> sp.
meroterpenoids
anti-cancer activity
url https://www.mdpi.com/1660-3397/22/2/58
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