Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense

Mycophenolic acid (MPA) is a potent inosine-5′-monophosphate dehydrogenase (IMPDH) inhibitor for immunosuppressive chemotherapy. Most importantly, as the 2-morpholinoethyl ester prodrug of MPA, mycophenolate mofetil (MMF) is a well-known immunosuppressant used to prevent rejection in organ...
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Gespeichert in:

Autor*in:	Qing Zhang [verfasserIn] Beiye Yang [verfasserIn] Fengli Li [verfasserIn] Mengting Liu [verfasserIn] Shuang Lin [verfasserIn] Jianping Wang [verfasserIn] Yongbo Xue [verfasserIn] Hucheng Zhu [verfasserIn] Weiguang Sun [verfasserIn] Zhengxi Hu [verfasserIn] Yonghui Zhang [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	coral-derived fungus Penicillium bialowiezense Mycophenolic acid derivatives immunosuppressive activity molecular docking

Übergeordnetes Werk:	In: Marine Drugs - MDPI AG, 2005, 16(2018), 7, p 230
Übergeordnetes Werk:	volume:16 ; year:2018 ; number:7, p 230

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/md16070230

Katalog-ID:	DOAJ08550940X

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allfields	10.3390/md16070230 doi (DE-627)DOAJ08550940X (DE-599)DOAJ3962e7278a3e4a42b912c65467133264 DE-627 ger DE-627 rakwb eng QH301-705.5 Qing Zhang verfasserin aut Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Mycophenolic acid (MPA) is a potent inosine-5′-monophosphate dehydrogenase (IMPDH) inhibitor for immunosuppressive chemotherapy. Most importantly, as the 2-morpholinoethyl ester prodrug of MPA, mycophenolate mofetil (MMF) is a well-known immunosuppressant used to prevent rejection in organ transplantations. Nevertheless, due to its frequently occurred side effects, searching for new therapeutic agents is ongoing. In our current work, by virtue of efficient bioassay-guided fractionation and purification, eleven mycophenolic acid derivatives, including five previously unreported metabolites (3–7) and six known compounds (1, 2, and 8–11), were obtained from the coral-derived fungus Penicillium bialowiezense. Their structures were elucidated by means of extensive spectroscopic analyses (including 1D and 2D NMR and HRESIMS data) and comparison of the NMR and other physical data with those reported in the literature in the case of the known compounds. All the isolates 1–11 were evaluated for the immunosuppressive activity, and 1–3 showed potent IMPDH2 inhibitory potency with IC50 values of 0.84–0.95 μM, which were comparable to that of MPA (the positive control), while 4–10 showed significant inhibitory potency with IC50 values of 3.27–24.68 μM. All the MPA derivatives showed promising immunosuppressive activity, endowing them as potential drug leads for organ transplantations and autoimmune related diseases. coral-derived fungus Penicillium bialowiezense Mycophenolic acid derivatives immunosuppressive activity molecular docking Biology (General) Beiye Yang verfasserin aut Fengli Li verfasserin aut Mengting Liu verfasserin aut Shuang Lin verfasserin aut Jianping Wang verfasserin aut Yongbo Xue verfasserin aut Hucheng Zhu verfasserin aut Weiguang Sun verfasserin aut Zhengxi Hu verfasserin aut Yonghui Zhang verfasserin aut In Marine Drugs MDPI AG, 2005 16(2018), 7, p 230 (DE-627)477992420 (DE-600)2175190-0 16603397 nnns volume:16 year:2018 number:7, p 230 https://doi.org/10.3390/md16070230 kostenfrei https://doaj.org/article/3962e7278a3e4a42b912c65467133264 kostenfrei http://www.mdpi.com/1660-3397/16/7/230 kostenfrei https://doaj.org/toc/1660-3397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_381 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 16 2018 7, p 230
spelling	10.3390/md16070230 doi (DE-627)DOAJ08550940X (DE-599)DOAJ3962e7278a3e4a42b912c65467133264 DE-627 ger DE-627 rakwb eng QH301-705.5 Qing Zhang verfasserin aut Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Mycophenolic acid (MPA) is a potent inosine-5′-monophosphate dehydrogenase (IMPDH) inhibitor for immunosuppressive chemotherapy. Most importantly, as the 2-morpholinoethyl ester prodrug of MPA, mycophenolate mofetil (MMF) is a well-known immunosuppressant used to prevent rejection in organ transplantations. Nevertheless, due to its frequently occurred side effects, searching for new therapeutic agents is ongoing. In our current work, by virtue of efficient bioassay-guided fractionation and purification, eleven mycophenolic acid derivatives, including five previously unreported metabolites (3–7) and six known compounds (1, 2, and 8–11), were obtained from the coral-derived fungus Penicillium bialowiezense. Their structures were elucidated by means of extensive spectroscopic analyses (including 1D and 2D NMR and HRESIMS data) and comparison of the NMR and other physical data with those reported in the literature in the case of the known compounds. All the isolates 1–11 were evaluated for the immunosuppressive activity, and 1–3 showed potent IMPDH2 inhibitory potency with IC50 values of 0.84–0.95 μM, which were comparable to that of MPA (the positive control), while 4–10 showed significant inhibitory potency with IC50 values of 3.27–24.68 μM. All the MPA derivatives showed promising immunosuppressive activity, endowing them as potential drug leads for organ transplantations and autoimmune related diseases. coral-derived fungus Penicillium bialowiezense Mycophenolic acid derivatives immunosuppressive activity molecular docking Biology (General) Beiye Yang verfasserin aut Fengli Li verfasserin aut Mengting Liu verfasserin aut Shuang Lin verfasserin aut Jianping Wang verfasserin aut Yongbo Xue verfasserin aut Hucheng Zhu verfasserin aut Weiguang Sun verfasserin aut Zhengxi Hu verfasserin aut Yonghui Zhang verfasserin aut In Marine Drugs MDPI AG, 2005 16(2018), 7, p 230 (DE-627)477992420 (DE-600)2175190-0 16603397 nnns volume:16 year:2018 number:7, p 230 https://doi.org/10.3390/md16070230 kostenfrei https://doaj.org/article/3962e7278a3e4a42b912c65467133264 kostenfrei http://www.mdpi.com/1660-3397/16/7/230 kostenfrei https://doaj.org/toc/1660-3397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_381 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 16 2018 7, p 230
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authorswithroles_txt_mv	Qing Zhang @@aut@@ Beiye Yang @@aut@@ Fengli Li @@aut@@ Mengting Liu @@aut@@ Shuang Lin @@aut@@ Jianping Wang @@aut@@ Yongbo Xue @@aut@@ Hucheng Zhu @@aut@@ Weiguang Sun @@aut@@ Zhengxi Hu @@aut@@ Yonghui Zhang @@aut@@
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callnumber-first	Q - Science
author	Qing Zhang
spellingShingle	Qing Zhang misc QH301-705.5 misc coral-derived fungus misc Penicillium bialowiezense misc Mycophenolic acid derivatives misc immunosuppressive activity misc molecular docking misc Biology (General) Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense
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topic_title	QH301-705.5 Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense coral-derived fungus Penicillium bialowiezense Mycophenolic acid derivatives immunosuppressive activity molecular docking
topic	misc QH301-705.5 misc coral-derived fungus misc Penicillium bialowiezense misc Mycophenolic acid derivatives misc immunosuppressive activity misc molecular docking misc Biology (General)
topic_unstemmed	misc QH301-705.5 misc coral-derived fungus misc Penicillium bialowiezense misc Mycophenolic acid derivatives misc immunosuppressive activity misc molecular docking misc Biology (General)
topic_browse	misc QH301-705.5 misc coral-derived fungus misc Penicillium bialowiezense misc Mycophenolic acid derivatives misc immunosuppressive activity misc molecular docking misc Biology (General)
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title	Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense
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title_full	Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense
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title_sort	mycophenolic acid derivatives with immunosuppressive activity from the coral-derived fungus penicillium bialowiezense
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title_auth	Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense
abstract	Mycophenolic acid (MPA) is a potent inosine-5′-monophosphate dehydrogenase (IMPDH) inhibitor for immunosuppressive chemotherapy. Most importantly, as the 2-morpholinoethyl ester prodrug of MPA, mycophenolate mofetil (MMF) is a well-known immunosuppressant used to prevent rejection in organ transplantations. Nevertheless, due to its frequently occurred side effects, searching for new therapeutic agents is ongoing. In our current work, by virtue of efficient bioassay-guided fractionation and purification, eleven mycophenolic acid derivatives, including five previously unreported metabolites (3–7) and six known compounds (1, 2, and 8–11), were obtained from the coral-derived fungus Penicillium bialowiezense. Their structures were elucidated by means of extensive spectroscopic analyses (including 1D and 2D NMR and HRESIMS data) and comparison of the NMR and other physical data with those reported in the literature in the case of the known compounds. All the isolates 1–11 were evaluated for the immunosuppressive activity, and 1–3 showed potent IMPDH2 inhibitory potency with IC50 values of 0.84–0.95 μM, which were comparable to that of MPA (the positive control), while 4–10 showed significant inhibitory potency with IC50 values of 3.27–24.68 μM. All the MPA derivatives showed promising immunosuppressive activity, endowing them as potential drug leads for organ transplantations and autoimmune related diseases.
abstractGer	Mycophenolic acid (MPA) is a potent inosine-5′-monophosphate dehydrogenase (IMPDH) inhibitor for immunosuppressive chemotherapy. Most importantly, as the 2-morpholinoethyl ester prodrug of MPA, mycophenolate mofetil (MMF) is a well-known immunosuppressant used to prevent rejection in organ transplantations. Nevertheless, due to its frequently occurred side effects, searching for new therapeutic agents is ongoing. In our current work, by virtue of efficient bioassay-guided fractionation and purification, eleven mycophenolic acid derivatives, including five previously unreported metabolites (3–7) and six known compounds (1, 2, and 8–11), were obtained from the coral-derived fungus Penicillium bialowiezense. Their structures were elucidated by means of extensive spectroscopic analyses (including 1D and 2D NMR and HRESIMS data) and comparison of the NMR and other physical data with those reported in the literature in the case of the known compounds. All the isolates 1–11 were evaluated for the immunosuppressive activity, and 1–3 showed potent IMPDH2 inhibitory potency with IC50 values of 0.84–0.95 μM, which were comparable to that of MPA (the positive control), while 4–10 showed significant inhibitory potency with IC50 values of 3.27–24.68 μM. All the MPA derivatives showed promising immunosuppressive activity, endowing them as potential drug leads for organ transplantations and autoimmune related diseases.
abstract_unstemmed	Mycophenolic acid (MPA) is a potent inosine-5′-monophosphate dehydrogenase (IMPDH) inhibitor for immunosuppressive chemotherapy. Most importantly, as the 2-morpholinoethyl ester prodrug of MPA, mycophenolate mofetil (MMF) is a well-known immunosuppressant used to prevent rejection in organ transplantations. Nevertheless, due to its frequently occurred side effects, searching for new therapeutic agents is ongoing. In our current work, by virtue of efficient bioassay-guided fractionation and purification, eleven mycophenolic acid derivatives, including five previously unreported metabolites (3–7) and six known compounds (1, 2, and 8–11), were obtained from the coral-derived fungus Penicillium bialowiezense. Their structures were elucidated by means of extensive spectroscopic analyses (including 1D and 2D NMR and HRESIMS data) and comparison of the NMR and other physical data with those reported in the literature in the case of the known compounds. All the isolates 1–11 were evaluated for the immunosuppressive activity, and 1–3 showed potent IMPDH2 inhibitory potency with IC50 values of 0.84–0.95 μM, which were comparable to that of MPA (the positive control), while 4–10 showed significant inhibitory potency with IC50 values of 3.27–24.68 μM. All the MPA derivatives showed promising immunosuppressive activity, endowing them as potential drug leads for organ transplantations and autoimmune related diseases.
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title_short	Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense
url	https://doi.org/10.3390/md16070230 https://doaj.org/article/3962e7278a3e4a42b912c65467133264 http://www.mdpi.com/1660-3397/16/7/230 https://doaj.org/toc/1660-3397
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Most importantly, as the 2-morpholinoethyl ester prodrug of MPA, mycophenolate mofetil (MMF) is a well-known immunosuppressant used to prevent rejection in organ transplantations. Nevertheless, due to its frequently occurred side effects, searching for new therapeutic agents is ongoing. In our current work, by virtue of efficient bioassay-guided fractionation and purification, eleven mycophenolic acid derivatives, including five previously unreported metabolites (3&ndash;7) and six known compounds (1, 2, and 8&ndash;11), were obtained from the coral-derived fungus Penicillium bialowiezense. Their structures were elucidated by means of extensive spectroscopic analyses (including 1D and 2D NMR and HRESIMS data) and comparison of the NMR and other physical data with those reported in the literature in the case of the known compounds. All the isolates 1&ndash;11 were evaluated for the immunosuppressive activity, and 1&ndash;3 showed potent IMPDH2 inhibitory potency with IC50 values of 0.84&ndash;0.95 &mu;M, which were comparable to that of MPA (the positive control), while 4&ndash;10 showed significant inhibitory potency with IC50 values of 3.27&ndash;24.68 &mu;M. 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Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense

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