Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)

Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)

Six new sorbicillinoids, trichoreeseione A (1) and B (2), trichodermolide B (3), 13-hydroxy-trichodermolide (4), 24-hydroxy-trichodimerol (5), 15-hydroxy-bisvertinol (7), together with three known analogs, trichodimerol (6), 24-hydroxy-bisvertinol (8), and bisvertinol (9), were isolated from the spo...

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Main Authors: Saif Ur Rehman, Lu-Jia Yang, Ya-Hui Zhang, Jing-Shuai Wu, Ting Shi, Waqas Haider, Chang-Lun Shao, Chang-Yun Wang
Format: Article
Language:English
Published: Frontiers Media S.A. 2020-06-01
Series:Frontiers in Microbiology
Subjects:
sponge-derived fungus
Trichoderma reesei
sorbicillinoid
naphthalene-trione
cytotoxic activity
Online Access:https://www.frontiersin.org/article/10.3389/fmicb.2020.01334/full
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language English
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author Saif Ur Rehman
Saif Ur Rehman
Saif Ur Rehman
Saif Ur Rehman
Lu-Jia Yang
Lu-Jia Yang
Lu-Jia Yang
Ya-Hui Zhang
Ya-Hui Zhang
Ya-Hui Zhang
Jing-Shuai Wu
Jing-Shuai Wu
Jing-Shuai Wu
Ting Shi
Ting Shi
Ting Shi
Waqas Haider
Waqas Haider
Waqas Haider
Chang-Lun Shao
Chang-Lun Shao
Chang-Lun Shao
Chang-Yun Wang
Chang-Yun Wang
Chang-Yun Wang
spellingShingle Saif Ur Rehman
Saif Ur Rehman
Saif Ur Rehman
Saif Ur Rehman
Lu-Jia Yang
Lu-Jia Yang
Lu-Jia Yang
Ya-Hui Zhang
Ya-Hui Zhang
Ya-Hui Zhang
Jing-Shuai Wu
Jing-Shuai Wu
Jing-Shuai Wu
Ting Shi
Ting Shi
Ting Shi
Waqas Haider
Waqas Haider
Waqas Haider
Chang-Lun Shao
Chang-Lun Shao
Chang-Lun Shao
Chang-Yun Wang
Chang-Yun Wang
Chang-Yun Wang
Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)
Frontiers in Microbiology
sponge-derived fungus
Trichoderma reesei
sorbicillinoid
naphthalene-trione
cytotoxic activity
author_facet Saif Ur Rehman
Saif Ur Rehman
Saif Ur Rehman
Saif Ur Rehman
Lu-Jia Yang
Lu-Jia Yang
Lu-Jia Yang
Ya-Hui Zhang
Ya-Hui Zhang
Ya-Hui Zhang
Jing-Shuai Wu
Jing-Shuai Wu
Jing-Shuai Wu
Ting Shi
Ting Shi
Ting Shi
Waqas Haider
Waqas Haider
Waqas Haider
Chang-Lun Shao
Chang-Lun Shao
Chang-Lun Shao
Chang-Yun Wang
Chang-Yun Wang
Chang-Yun Wang
author_sort Saif Ur Rehman
title Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)
title_short Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)
title_full Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)
title_fullStr Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)
title_full_unstemmed Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)
title_sort sorbicillinoid derivatives from sponge-derived fungus trichoderma reesei (hn-2016-018)
publisher Frontiers Media S.A.
series Frontiers in Microbiology
issn 1664-302X
publishDate 2020-06-01
description Six new sorbicillinoids, trichoreeseione A (1) and B (2), trichodermolide B (3), 13-hydroxy-trichodermolide (4), 24-hydroxy-trichodimerol (5), 15-hydroxy-bisvertinol (7), together with three known analogs, trichodimerol (6), 24-hydroxy-bisvertinol (8), and bisvertinol (9), were isolated from the sponge-derived fungus Trichoderma reesei (HN-2016-018). Their structures including absolute configurations were elucidated by analysis of NMR, MS data, and calculated ECD spectra. Compounds 1 and 2 with a characteristic naphthalene-trione ring were firstly reported in sorbicillinoid family. Compounds 3 and 4 were two rare sorbicillinoids containing a unique bicycle [3.2.1] lactone skeleton, while 3 with a propan-2-one moiety was also recorded first time in this family. Compound 5 displayed cytotoxic activity against A549, MCF-7, and HCT116 cell lines with the IC50 values of 5.1, 9.5, and 13.7 μM, respectively.
topic sponge-derived fungus
Trichoderma reesei
sorbicillinoid
naphthalene-trione
cytotoxic activity
url https://www.frontiersin.org/article/10.3389/fmicb.2020.01334/full
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spelling doaj-92a7099e76f94bd78f091c0691110b692020-11-25T03:29:26ZengFrontiers Media S.A.Frontiers in Microbiology1664-302X2020-06-011110.3389/fmicb.2020.01334544086Sorbicillinoid Derivatives From Sponge-Derived Fungus Trichoderma reesei (HN-2016-018)Saif Ur Rehman0Saif Ur Rehman1Saif Ur Rehman2Saif Ur Rehman3Lu-Jia Yang4Lu-Jia Yang5Lu-Jia Yang6Ya-Hui Zhang7Ya-Hui Zhang8Ya-Hui Zhang9Jing-Shuai Wu10Jing-Shuai Wu11Jing-Shuai Wu12Ting Shi13Ting Shi14Ting Shi15Waqas Haider16Waqas Haider17Waqas Haider18Chang-Lun Shao19Chang-Lun Shao20Chang-Lun Shao21Chang-Yun Wang22Chang-Yun Wang23Chang-Yun Wang24Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaInstitute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, ChinaLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, ChinaDepartment of Pharmacy, Faculty of Medical and Health Sciences, University of Poonch Rawalakot, Rawalakot, PakistanKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaInstitute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, ChinaLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaInstitute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, ChinaLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaInstitute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, ChinaLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaInstitute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, ChinaLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaInstitute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, ChinaLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaInstitute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, ChinaLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaInstitute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, ChinaLaboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, ChinaSix new sorbicillinoids, trichoreeseione A (1) and B (2), trichodermolide B (3), 13-hydroxy-trichodermolide (4), 24-hydroxy-trichodimerol (5), 15-hydroxy-bisvertinol (7), together with three known analogs, trichodimerol (6), 24-hydroxy-bisvertinol (8), and bisvertinol (9), were isolated from the sponge-derived fungus Trichoderma reesei (HN-2016-018). Their structures including absolute configurations were elucidated by analysis of NMR, MS data, and calculated ECD spectra. Compounds 1 and 2 with a characteristic naphthalene-trione ring were firstly reported in sorbicillinoid family. Compounds 3 and 4 were two rare sorbicillinoids containing a unique bicycle [3.2.1] lactone skeleton, while 3 with a propan-2-one moiety was also recorded first time in this family. Compound 5 displayed cytotoxic activity against A549, MCF-7, and HCT116 cell lines with the IC50 values of 5.1, 9.5, and 13.7 μM, respectively.https://www.frontiersin.org/article/10.3389/fmicb.2020.01334/fullsponge-derived fungusTrichoderma reeseisorbicillinoidnaphthalene-trionecytotoxic activity

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