Sclerotioloids A–C: Three New Alkaloids from the Marine-Derived Fungus Aspergillus sclerotiorum ST0501

Alkaloids, as one of the largest classes of natural products with diverse structures, are an important source of innovative medicines. Filamentous fungi, especially those derived from the marine environment, are one of the major producers of alkaloids. In this study, three new alkaloids, sclerotiolo...

Full description

Saved in:
Bibliographic Details
Published inMarine drugs Vol. 21; no. 4; p. 219
Main Authors Mao, Jun-Qiu, Zheng, Yao-Yao, Wang, Chang-Yun, Liu, Yang, Yao, Guang-Shan
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 29.03.2023
MDPI
Subjects
alkaloid
Alkaloids
Alkaloids - chemistry
Alkaloids - pharmacology
Alkynes
Aspergillus
Aspergillus sclerotiorum
Cytotoxicity
Data analysis
Dexamethasone
Fungi
Fungi - chemistry
Hydrocarbons
Lipopolysaccharides
Magnetic Resonance Spectroscopy
Marine environment
marine-derived fungus
Metabolites
Molecular Structure
Natural products
NMR
Nuclear magnetic resonance
sclerotioloids
secondary metabolite
Single crystals
South China Sea
spectral analysis
Tandem Mass Spectrometry
X-ray diffraction
South China Sea
Aspergillus sclerotiorum
sclerotioloids
alkaloid
marine-derived fungus
secondary metabolite
Online AccessGet full text

Cover

Abstract Alkaloids, as one of the largest classes of natural products with diverse structures, are an important source of innovative medicines. Filamentous fungi, especially those derived from the marine environment, are one of the major producers of alkaloids. In this study, three new alkaloids, sclerotioloids A–C (1–3), along with six known analogs (4–9), were obtained under the guidance of the MS/MS-based molecular networking from the marine-derived fungus, Aspergillus sclerotiorum ST0501, collected from the South China Sea. Their chemical structures were elucidated by comprehensive analysis of the spectroscopic data, including 1D and 2D NMR and HRESIMS. Additionally, the configuration of compound 2 was unambiguously determined by X-ray single crystal diffraction, and that of compound 3 was determined by the TDDFT-ECD approach. Sclerotioloid A (1) represents the first example of 2,5-diketopiperazine alkaloid with a rare terminal alkyne. Sclerotioloid B (2) showed the inhibition of NO production induced by lipopolysaccharide (LPS), with an inhibition rate of 28.92% higher than that of dexamethasone (25.87%). These results expanded the library of fungal-derived alkaloids and further prove the potential of marine fungi in the generation of alkaloids with new scaffolds.
AbstractList Alkaloids, as one of the largest classes of natural products with diverse structures, are an important source of innovative medicines. Filamentous fungi, especially those derived from the marine environment, are one of the major producers of alkaloids. In this study, three new alkaloids, sclerotioloids A–C ( 1 – 3 ), along with six known analogs ( 4 – 9 ), were obtained under the guidance of the MS/MS-based molecular networking from the marine-derived fungus, Aspergillus sclerotiorum ST0501, collected from the South China Sea. Their chemical structures were elucidated by comprehensive analysis of the spectroscopic data, including 1D and 2D NMR and HRESIMS. Additionally, the configuration of compound 2 was unambiguously determined by X-ray single crystal diffraction, and that of compound 3 was determined by the TDDFT-ECD approach. Sclerotioloid A ( 1 ) represents the first example of 2,5-diketopiperazine alkaloid with a rare terminal alkyne. Sclerotioloid B ( 2 ) showed the inhibition of NO production induced by lipopolysaccharide (LPS), with an inhibition rate of 28.92% higher than that of dexamethasone (25.87%). These results expanded the library of fungal-derived alkaloids and further prove the potential of marine fungi in the generation of alkaloids with new scaffolds.
Alkaloids, as one of the largest classes of natural products with diverse structures, are an important source of innovative medicines. Filamentous fungi, especially those derived from the marine environment, are one of the major producers of alkaloids. In this study, three new alkaloids, sclerotioloids A-C (1-3), along with six known analogs (4-9), were obtained under the guidance of the MS/MS-based molecular networking from the marine-derived fungus, Aspergillus sclerotiorum ST0501, collected from the South China Sea. Their chemical structures were elucidated by comprehensive analysis of the spectroscopic data, including 1D and 2D NMR and HRESIMS. Additionally, the configuration of compound 2 was unambiguously determined by X-ray single crystal diffraction, and that of compound 3 was determined by the TDDFT-ECD approach. Sclerotioloid A (1) represents the first example of 2,5-diketopiperazine alkaloid with a rare terminal alkyne. Sclerotioloid B (2) showed the inhibition of NO production induced by lipopolysaccharide (LPS), with an inhibition rate of 28.92% higher than that of dexamethasone (25.87%). These results expanded the library of fungal-derived alkaloids and further prove the potential of marine fungi in the generation of alkaloids with new scaffolds.Alkaloids, as one of the largest classes of natural products with diverse structures, are an important source of innovative medicines. Filamentous fungi, especially those derived from the marine environment, are one of the major producers of alkaloids. In this study, three new alkaloids, sclerotioloids A-C (1-3), along with six known analogs (4-9), were obtained under the guidance of the MS/MS-based molecular networking from the marine-derived fungus, Aspergillus sclerotiorum ST0501, collected from the South China Sea. Their chemical structures were elucidated by comprehensive analysis of the spectroscopic data, including 1D and 2D NMR and HRESIMS. Additionally, the configuration of compound 2 was unambiguously determined by X-ray single crystal diffraction, and that of compound 3 was determined by the TDDFT-ECD approach. Sclerotioloid A (1) represents the first example of 2,5-diketopiperazine alkaloid with a rare terminal alkyne. Sclerotioloid B (2) showed the inhibition of NO production induced by lipopolysaccharide (LPS), with an inhibition rate of 28.92% higher than that of dexamethasone (25.87%). These results expanded the library of fungal-derived alkaloids and further prove the potential of marine fungi in the generation of alkaloids with new scaffolds.
Alkaloids, as one of the largest classes of natural products with diverse structures, are an important source of innovative medicines. Filamentous fungi, especially those derived from the marine environment, are one of the major producers of alkaloids. In this study, three new alkaloids, sclerotioloids A–C (1–3), along with six known analogs (4–9), were obtained under the guidance of the MS/MS-based molecular networking from the marine-derived fungus, Aspergillus sclerotiorum ST0501, collected from the South China Sea. Their chemical structures were elucidated by comprehensive analysis of the spectroscopic data, including 1D and 2D NMR and HRESIMS. Additionally, the configuration of compound 2 was unambiguously determined by X-ray single crystal diffraction, and that of compound 3 was determined by the TDDFT-ECD approach. Sclerotioloid A (1) represents the first example of 2,5-diketopiperazine alkaloid with a rare terminal alkyne. Sclerotioloid B (2) showed the inhibition of NO production induced by lipopolysaccharide (LPS), with an inhibition rate of 28.92% higher than that of dexamethasone (25.87%). These results expanded the library of fungal-derived alkaloids and further prove the potential of marine fungi in the generation of alkaloids with new scaffolds.
Alkaloids, as one of the largest classes of natural products with diverse structures, are an important source of innovative medicines. Filamentous fungi, especially those derived from the marine environment, are one of the major producers of alkaloids. In this study, three new alkaloids, sclerotioloids A-C ( - ), along with six known analogs ( - ), were obtained under the guidance of the MS/MS-based molecular networking from the marine-derived fungus, ST0501, collected from the South China Sea. Their chemical structures were elucidated by comprehensive analysis of the spectroscopic data, including 1D and 2D NMR and HRESIMS. Additionally, the configuration of compound was unambiguously determined by X-ray single crystal diffraction, and that of compound was determined by the TDDFT-ECD approach. Sclerotioloid A ( ) represents the first example of 2,5-diketopiperazine alkaloid with a rare terminal alkyne. Sclerotioloid B ( ) showed the inhibition of NO production induced by lipopolysaccharide (LPS), with an inhibition rate of 28.92% higher than that of dexamethasone (25.87%). These results expanded the library of fungal-derived alkaloids and further prove the potential of marine fungi in the generation of alkaloids with new scaffolds.
Author Wang, Chang-Yun
Liu, Yang
Mao, Jun-Qiu
Zheng, Yao-Yao
Yao, Guang-Shan
AuthorAffiliation 3 Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China
4 Institute for Insect Biotechnology, Justus-Liebig-University of Giessen, 35392 Giessen, Germany
5 Department of Bioresources of the Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), 35392 Giessen, Germany
2 Fujian Key Laboratory on Conservation and Sustainable Utilization of Marine Biodiversity, Institute of Oceanography, Minjiang University, Fuzhou 350108, China
1 Key Laboratory of Marine Drugs, The Ministry of Education of China, Institute of Evolution & Marine Biodiversity, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
AuthorAffiliation_xml – name: 2 Fujian Key Laboratory on Conservation and Sustainable Utilization of Marine Biodiversity, Institute of Oceanography, Minjiang University, Fuzhou 350108, China
– name: 4 Institute for Insect Biotechnology, Justus-Liebig-University of Giessen, 35392 Giessen, Germany
– name: 5 Department of Bioresources of the Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), 35392 Giessen, Germany
– name: 3 Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China
– name: 1 Key Laboratory of Marine Drugs, The Ministry of Education of China, Institute of Evolution & Marine Biodiversity, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
Author_xml – sequence: 1
  givenname: Jun-Qiu
  surname: Mao
  fullname: Mao, Jun-Qiu
– sequence: 2
  givenname: Yao-Yao
  surname: Zheng
  fullname: Zheng, Yao-Yao
– sequence: 3
  givenname: Chang-Yun
  surname: Wang
  fullname: Wang, Chang-Yun
– sequence: 4
  givenname: Yang
  surname: Liu
  fullname: Liu, Yang
– sequence: 5
  givenname: Guang-Shan
  surname: Yao
  fullname: Yao, Guang-Shan
BackLink https://www.ncbi.nlm.nih.gov/pubmed/37103358$$D View this record in MEDLINE/PubMed
BookMark eNqFks1uEzEQxy1URD_gwgOglbggpMDYXq_XXFAUKFRq4dBwthx_JA7edWrvFnHjHXhDngS36beQsA8ez_zmr7Fn9tFOH3uL0HMMbygV8LYzBEMNBItHaA83DUyKm-_csXfRfs5rAMpaUT9Bu5RjoOWyh1anOtgUBx9D9CZX0z-_fs_eVfNVsrb6Yn9U0_BdbUMuxa4aVrY6Ucn3dvLBJn9uTXU49suxZOaNTUsfQrHztWgau-p0DgzwU_TYqZDts6vzAH07_DiffZ4cf_10NJseTzSDZpjULcVlEa1VgwUzLbQcqNPEqEa3jinbUtcQ4rTQ2lkKmmvBhOCCwYJrSg_Q0VbXRLWWm-Q7lX7KqLy8dMS0lCoNvhQogQhiG8pVSa0dFy0DZwzjmFBqFoIXrfdbrc246KzRth-SCvdE70d6v5LLeC4x4Jq0ghWFV1cKKZ6NNg-y81nbEFRv45glEXXpHaO8-T_aQiNEzSgp6MsH6DqOqS_fekmxsqko1Iu71d-Ufd38ArzeAjrFnJN1NwgGeTFZ8nayCgwPYO0HVVp88XIf_pXyF-9Ozo0
CitedBy_id crossref_primary_10_3390_ph17070922
crossref_primary_10_3390_md22070321
crossref_primary_10_3390_md21100510
crossref_primary_10_1016_j_aquaculture_2024_741653
crossref_primary_10_1039_D4NP00067F
crossref_primary_10_1039_D3NP90029K
crossref_primary_10_3390_md22100433
Cites_doi 10.1038/nprot.2008.141
10.3390/md18030132
10.3389/fonc.2021.644608
10.1021/acs.jnatprod.5b00337
10.1071/CH9851785
10.1007/s11557-022-01856-3
10.1007/s42995-019-00021-2
10.1002/anie.200604381
10.1038/nbt.3597
10.1023/A:1008364727071
10.1021/np300707x
10.3389/fmicb.2020.00085
10.1021/np200597m
10.1039/C9NP00069K
10.1021/np0101245
10.3389/fmicb.2022.808532
10.1016/j.bbagen.2007.11.016
10.3987/R-1980-11-1767
10.1071/CH9890349
10.3390/md14040076
10.1039/D1NP00076D
10.1021/np960607m
10.3390/md17100559
10.1021/ja028538n
10.1039/c0np00061b
10.3390/md17090514
10.1039/D0NP00089B
10.1038/ja.2011.63
10.1021/acs.jafc.9b04254
10.1021/acs.jnatprod.1c01194
10.1021/acschemneuro.8b00243
10.1021/acs.jnatprod.0c00804
ContentType Journal Article
Copyright 2023 by the authors. 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/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
2023 by the authors. 2023
Copyright_xml – notice: 2023 by the authors. 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/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
– notice: 2023 by the authors. 2023
DBID AAYXX
CITATION
CGR
CUY
CVF
ECM
EIF
NPM
3V.
7T7
7TN
7X7
7XB
88E
8FD
8FE
8FH
8FI
8FJ
8FK
ABUWG
AEUYN
AFKRA
AZQEC
BBNVY
BENPR
BHPHI
BKSAR
C1K
CCPQU
DWQXO
F1W
FR3
FYUFA
GHDGH
GNUQQ
H95
H99
HCIFZ
K9.
L.F
L.G
LK8
M0S
M1P
M7P
P64
PCBAR
PHGZM
PHGZT
PIMPY
PJZUB
PKEHL
PPXIY
PQEST
PQGLB
PQQKQ
PQUKI
PRINS
7X8
7S9
L.6
5PM
DOA
DOI 10.3390/md21040219
DatabaseName CrossRef
Medline
MEDLINE
MEDLINE (Ovid)
MEDLINE
MEDLINE
PubMed
ProQuest Central (Corporate)
Industrial and Applied Microbiology Abstracts (Microbiology A)
Oceanic Abstracts
Health & Medical Collection
ProQuest Central (purchase pre-March 2016)
Medical Database (Alumni Edition)
Technology Research Database
ProQuest SciTech Collection
ProQuest Natural Science Collection
Hospital Premium Collection
Hospital Premium Collection (Alumni Edition)
ProQuest Central (Alumni) (purchase pre-March 2016)
ProQuest Central (Alumni Edition)
ProQuest One Sustainability
ProQuest Central UK/Ireland
ProQuest Central Essentials
Biological Science Collection
ProQuest Central
Natural Science Collection
Earth, Atmospheric & Aquatic Science Collection
Environmental Sciences and Pollution Management
ProQuest One Community College
ProQuest Central Korea
ASFA: Aquatic Sciences and Fisheries Abstracts
Engineering Research Database
Health Research Premium Collection
Health Research Premium Collection (Alumni)
ProQuest Central Student
Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources
ASFA: Marine Biotechnology Abstracts
SciTech Premium Collection
ProQuest Health & Medical Complete (Alumni)
Aquatic Science & Fisheries Abstracts (ASFA) Marine Biotechnology Abstracts
Aquatic Science & Fisheries Abstracts (ASFA) Professional
ProQuest Biological Science Collection
Health & Medical Collection (Alumni Edition)
Medical Database
Biological Science Database
Biotechnology and BioEngineering Abstracts
Earth, Atmospheric & Aquatic Science Database
ProQuest Central Premium
ProQuest One Academic (New)
Publicly Available Content Database
ProQuest Health & Medical Research Collection
ProQuest One Academic Middle East (New)
ProQuest One Health & Nursing
ProQuest One Academic Eastern Edition (DO NOT USE)
ProQuest One Applied & Life Sciences
ProQuest One Academic
ProQuest One Academic UKI Edition
ProQuest Central China
MEDLINE - Academic
AGRICOLA
AGRICOLA - Academic
PubMed Central (Full Participant titles)
DOAJ Directory of Open Access Journals
DatabaseTitle CrossRef
MEDLINE
Medline Complete
MEDLINE with Full Text
PubMed
MEDLINE (Ovid)
Publicly Available Content Database
Aquatic Science & Fisheries Abstracts (ASFA) Professional
ProQuest Central Student
Technology Research Database
ProQuest One Academic Middle East (New)
ProQuest Central Essentials
ProQuest Health & Medical Complete (Alumni)
ProQuest Central (Alumni Edition)
SciTech Premium Collection
ProQuest One Community College
ProQuest One Health & Nursing
ProQuest Natural Science Collection
ProQuest Central China
Environmental Sciences and Pollution Management
ProQuest Central
Earth, Atmospheric & Aquatic Science Collection
ProQuest One Applied & Life Sciences
ProQuest One Sustainability
ProQuest Health & Medical Research Collection
Health Research Premium Collection
Oceanic Abstracts
Health and Medicine Complete (Alumni Edition)
Natural Science Collection
ProQuest Central Korea
Health & Medical Research Collection
Biological Science Collection
Aquatic Science & Fisheries Abstracts (ASFA) Marine Biotechnology Abstracts
Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources
Industrial and Applied Microbiology Abstracts (Microbiology A)
ProQuest Central (New)
ProQuest Medical Library (Alumni)
ProQuest Biological Science Collection
ProQuest One Academic Eastern Edition
Earth, Atmospheric & Aquatic Science Database
ProQuest Hospital Collection
Health Research Premium Collection (Alumni)
Biological Science Database
ProQuest SciTech Collection
ProQuest Hospital Collection (Alumni)
Biotechnology and BioEngineering Abstracts
ProQuest Health & Medical Complete
ProQuest Medical Library
ProQuest One Academic UKI Edition
ASFA: Aquatic Sciences and Fisheries Abstracts
Engineering Research Database
ProQuest One Academic
ProQuest One Academic (New)
ProQuest Central (Alumni)
MEDLINE - Academic
AGRICOLA
AGRICOLA - Academic
DatabaseTitleList
MEDLINE - Academic

AGRICOLA
CrossRef
MEDLINE
Publicly Available Content Database
Database_xml – sequence: 1
  dbid: DOA
  name: Acceso a contenido Full Text - Doaj
  url: https://www.doaj.org/
  sourceTypes: Open Website
– sequence: 2
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
– sequence: 3
  dbid: EIF
  name: MEDLINE
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search
  sourceTypes: Index Database
– sequence: 4
  dbid: BENPR
  name: ProQuest Central
  url: https://www.proquest.com/central
  sourceTypes: Aggregation Database
DeliveryMethod fulltext_linktorsrc
Discipline Pharmacy, Therapeutics, & Pharmacology
EISSN 1660-3397
ExternalDocumentID oai_doaj_org_article_0292e637a50b4f79850fdd571233db97
PMC10142895
37103358
10_3390_md21040219
Genre Journal Article
GeographicLocations South China Sea
GeographicLocations_xml – name: South China Sea
GrantInformation_xml – fundername: Natural Science Foundation of Fujian Province
  grantid: 2021J011043
– fundername: National Natural Science Foundation of China
  grantid: 81874300 and41830535
– fundername: Shandong Provincial Natural Science Foundation (Major Basic Research Projects)
  grantid: ZR2019ZD18
– fundername: Minjiang University
  grantid: NOs. MYK19011; JAT190622
– fundername: Taishan Scholars Program
– fundername: Program of Open Studio for Druggability Research of Marine Natural Products
– fundername: Minjiang University
  grantid: MYK19011; JAT190622
– fundername: National Natural Science Foundation of China
  grantid: 81874300; 41830535
– fundername: National Laboratory for Marine Science and Technology
GroupedDBID ---
29M
2WC
53G
5GY
5VS
7X7
88E
8CJ
8FE
8FH
8FI
8FJ
AADQD
AAHBH
AAYXX
ABUWG
ACGFO
ACIHN
ACPRK
ADBBV
AEAQA
AENEX
AEUYN
AFKRA
AFRAH
AFZYC
AHMBA
ALIPV
ALMA_UNASSIGNED_HOLDINGS
AOIJS
BAWUL
BBNVY
BCNDV
BENPR
BHPHI
BKSAR
BPHCQ
BVXVI
CCPQU
CITATION
CS3
D1J
DIK
DU5
E3Z
EBD
EDH
F5P
FYUFA
GROUPED_DOAJ
GX1
HCIFZ
HH5
HMCUK
HYE
IAO
IHR
ITC
KQ8
LK5
LK8
M1P
M48
M7P
M7R
MK0
MODMG
M~E
O5R
O5S
OK1
OVT
P2P
PCBAR
PGMZT
PHGZM
PHGZT
PIMPY
PQQKQ
PROAC
PSQYO
RNS
RPM
TR2
UKHRP
XSB
3V.
CGR
CUY
CVF
ECM
EIF
NPM
7T7
7TN
7XB
8FD
8FK
AZQEC
C1K
DWQXO
F1W
FR3
GNUQQ
H95
H99
K9.
L.F
L.G
P64
PJZUB
PKEHL
PPXIY
PQEST
PQGLB
PQUKI
PRINS
7X8
7S9
L.6
5PM
PUEGO
ID FETCH-LOGICAL-c506t-48311112cca6195d808703fc2da6c8f5ae83f622fc9ccfe30c7c95997950b7c33
IEDL.DBID M48
ISSN 1660-3397
IngestDate Wed Aug 27 00:20:32 EDT 2025
Thu Aug 21 18:37:48 EDT 2025
Fri Jul 11 15:09:24 EDT 2025
Fri Jul 11 02:29:01 EDT 2025
Fri Jul 25 10:34:44 EDT 2025
Thu Jan 02 22:53:12 EST 2025
Thu Apr 24 22:52:07 EDT 2025
Tue Jul 01 03:19:55 EDT 2025
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 4
Keywords Aspergillus sclerotiorum
sclerotioloids
alkaloid
marine-derived fungus
secondary metabolite
Language English
License 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/).
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c506t-48311112cca6195d808703fc2da6c8f5ae83f622fc9ccfe30c7c95997950b7c33
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
OpenAccessLink http://journals.scholarsportal.info/openUrl.xqy?doi=10.3390/md21040219
PMID 37103358
PQID 2806565639
PQPubID 2032365
ParticipantIDs doaj_primary_oai_doaj_org_article_0292e637a50b4f79850fdd571233db97
pubmedcentral_primary_oai_pubmedcentral_nih_gov_10142895
proquest_miscellaneous_2942105376
proquest_miscellaneous_2806994532
proquest_journals_2806565639
pubmed_primary_37103358
crossref_primary_10_3390_md21040219
crossref_citationtrail_10_3390_md21040219
ProviderPackageCode CITATION
AAYXX
PublicationCentury 2000
PublicationDate 20230329
PublicationDateYYYYMMDD 2023-03-29
PublicationDate_xml – month: 3
  year: 2023
  text: 20230329
  day: 29
PublicationDecade 2020
PublicationPlace Switzerland
PublicationPlace_xml – name: Switzerland
– name: Basel
PublicationTitle Marine drugs
PublicationTitleAlternate Mar Drugs
PublicationYear 2023
Publisher MDPI AG
MDPI
Publisher_xml – name: MDPI AG
– name: MDPI
References Natoli (ref_7) 2021; 11
He (ref_21) 2019; 67
Wu (ref_15) 2020; 11
Carroll (ref_3) 2020; 37
Hendriks (ref_8) 1999; 10
Marcuccio (ref_26) 1985; 38
Wang (ref_18) 2022; 13
Kunwar (ref_29) 2008; 1780
Wang (ref_19) 2015; 78
Fu (ref_24) 2011; 74
Carroll (ref_1) 2022; 39
Chen (ref_13) 2013; 76
Xia (ref_32) 2019; 10
ref_17
ref_16
Wang (ref_28) 2016; 34
Shin (ref_25) 1980; 14
Pierce (ref_30) 2008; 3
Wang (ref_11) 2011; 64
Guo (ref_10) 2022; 85
Aquino (ref_31) 2001; 64
Ibrahim (ref_9) 2022; 22
Sterns (ref_27) 1989; 42
Huang (ref_22) 2002; 124
Kato (ref_23) 2007; 46
Liu (ref_14) 2019; 1
Rateb (ref_4) 2011; 28
ref_5
Whyte (ref_20) 1996; 59
Carroll (ref_2) 2021; 38
Chao (ref_12) 2021; 84
ref_6
References_xml – volume: 3
  start-page: 1494
  year: 2008
  ident: ref_30
  article-title: A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing
  publication-title: Nat. Protoc.
  doi: 10.1038/nprot.2008.141
– ident: ref_16
  doi: 10.3390/md18030132
– volume: 11
  start-page: 644608
  year: 2021
  ident: ref_7
  article-title: Plinabulin, a Distinct Microtubule-Targeting Chemotherapy, Promotes M1-Like Macrophage Polarization and Anti-tumor Immunity
  publication-title: Front. Oncol.
  doi: 10.3389/fonc.2021.644608
– volume: 78
  start-page: 1415
  year: 2015
  ident: ref_19
  article-title: Transferring Fungi to a Deuterium-Enriched Medium Results in Assorted, Conditional Changes in Secondary Metabolite Production
  publication-title: J. Nat. Prod.
  doi: 10.1021/acs.jnatprod.5b00337
– volume: 38
  start-page: 1785
  year: 1985
  ident: ref_26
  article-title: Pyrazine chemistry. V. Synthesis of methylanhydropicroroccellin and dimethylpicroroccellin
  publication-title: Aust. J. Chem.
  doi: 10.1071/CH9851785
– volume: 22
  start-page: 8
  year: 2022
  ident: ref_9
  article-title: Exploring Potential of Aspergillus sclerotiorum: Secondary Metabolites and Biotechnological Relevance
  publication-title: Mycol. Prog.
  doi: 10.1007/s11557-022-01856-3
– volume: 1
  start-page: 60
  year: 2019
  ident: ref_14
  article-title: Metabolites from marine invertebrates and their symbiotic microorganisms: Molecular diversity discovery, mining, and application
  publication-title: Mar. Life Sci. Technol.
  doi: 10.1007/s42995-019-00021-2
– volume: 46
  start-page: 2254
  year: 2007
  ident: ref_23
  article-title: Notoamides A-D: Prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp.
  publication-title: Angew. Chem. Int. Ed.
  doi: 10.1002/anie.200604381
– volume: 34
  start-page: 828
  year: 2016
  ident: ref_28
  article-title: Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking
  publication-title: Nat. Biotechnol.
  doi: 10.1038/nbt.3597
– volume: 10
  start-page: 1233
  year: 1999
  ident: ref_8
  article-title: High antitumour activity of ET743 against human tumour xenografts from melanoma, non-small-cell lung and ovarian cancer
  publication-title: Ann. Oncol.
  doi: 10.1023/A:1008364727071
– volume: 76
  start-page: 547
  year: 2013
  ident: ref_13
  article-title: Bioactive indole alkaloids and phenyl ether derivatives from a marine-derived Aspergillus sp. Fungus
  publication-title: J. Nat. Prod.
  doi: 10.1021/np300707x
– volume: 11
  start-page: 85
  year: 2020
  ident: ref_15
  article-title: Epigenetic Agents Trigger the Production of Bioactive Nucleoside Derivatives and Bisabolane Sesquiterpenes from the Marine-Derived Fungus Aspergillus versicolor
  publication-title: Front. Microbiol.
  doi: 10.3389/fmicb.2020.00085
– volume: 74
  start-page: 2219
  year: 2011
  ident: ref_24
  article-title: α-Pyrones and diketopiperazine derivatives from the marine-derived actinomycete Nocardiopsis dassonvillei HR10-5
  publication-title: J. Nat. Prod.
  doi: 10.1021/np200597m
– volume: 37
  start-page: 175
  year: 2020
  ident: ref_3
  article-title: Marine natural products
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/C9NP00069K
– volume: 64
  start-page: 1019
  year: 2001
  ident: ref_31
  article-title: Phenolic constituents and antioxidant activity of an extract of Anthurium versicolor leaves
  publication-title: J. Nat. Prod.
  doi: 10.1021/np0101245
– volume: 13
  start-page: 808532
  year: 2022
  ident: ref_18
  article-title: 2,5-Diketopiperazines from a Sponge-Derived Fungus Aspergillus sclerotiorum
  publication-title: Front. Microbiol.
  doi: 10.3389/fmicb.2022.808532
– volume: 1780
  start-page: 673
  year: 2008
  ident: ref_29
  article-title: Quantitative cellular uptake, localization and cytotoxicity of curcumin in normal and tumor cells
  publication-title: Biochim. Biophys. Acta Gen. Subj.
  doi: 10.1016/j.bbagen.2007.11.016
– volume: 14
  start-page: 1767
  year: 1980
  ident: ref_25
  article-title: Synthesis and structural assignment of naturally occurring 3-benzyl-6-benzylidene-2,5-piperazinedione
  publication-title: Heterocycles
  doi: 10.3987/R-1980-11-1767
– volume: 42
  start-page: 349
  year: 1989
  ident: ref_27
  article-title: Conformational studies of some piperazine-2,5-diones: Crystal structures of three isomeric forms of methylanhydropicroroccellin (derivative of a lichen diketopiperazine) and a derivative bromohydrin
  publication-title: Aust. J. Chem.
  doi: 10.1071/CH9890349
– ident: ref_5
  doi: 10.3390/md14040076
– volume: 39
  start-page: 1122
  year: 2022
  ident: ref_1
  article-title: Marine natural products
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/D1NP00076D
– volume: 59
  start-page: 1093
  year: 1996
  ident: ref_20
  article-title: Sclerotiamide: A new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum
  publication-title: J. Nat. Prod.
  doi: 10.1021/np960607m
– ident: ref_6
  doi: 10.3390/md17100559
– volume: 124
  start-page: 14556
  year: 2002
  ident: ref_22
  article-title: Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja028538n
– volume: 28
  start-page: 290
  year: 2011
  ident: ref_4
  article-title: Secondary metabolites of fungi from marine habitats
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/c0np00061b
– ident: ref_17
  doi: 10.3390/md17090514
– volume: 38
  start-page: 362
  year: 2021
  ident: ref_2
  article-title: Marine natural products
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/D0NP00089B
– volume: 64
  start-page: 679
  year: 2011
  ident: ref_11
  article-title: A new cytotoxic indole-3-ethenamide from the halotolerant fungus Aspergillus sclerotiorum PT06-1
  publication-title: J. Antibiot.
  doi: 10.1038/ja.2011.63
– volume: 67
  start-page: 10660
  year: 2019
  ident: ref_21
  article-title: Cytotoxic Indolyl Diketopiperazines from the Aspergillus sp. GZWMJZ-258, Endophytic with the Medicinal and Edible Plant Garcinia multiflora
  publication-title: J. Agric. Food Chem.
  doi: 10.1021/acs.jafc.9b04254
– volume: 85
  start-page: 1067
  year: 2022
  ident: ref_10
  article-title: Sclerotiamides C-H, Notoamides from a Marine Gorgonian-Derived Fungus with Cytotoxic Activities
  publication-title: J. Nat. Prod.
  doi: 10.1021/acs.jnatprod.1c01194
– volume: 10
  start-page: 295
  year: 2019
  ident: ref_32
  article-title: Discovery of a New Pterocarpan-Type Antineuroinflammatory Compound from Sophora tonkinensis through Suppression of the TLR4/NFκB/MAPK Signaling Pathway with PU.1 as a Potential Target
  publication-title: ACS Chem. Neurosci.
  doi: 10.1021/acschemneuro.8b00243
– volume: 84
  start-page: 11
  year: 2021
  ident: ref_12
  article-title: Targeted Isolation of Asperheptatides from a Coral-Derived Fungus Using LC-MS/MS-Based Molecular Networking and Antitubercular Activities of Modified Cinnamate Derivatives
  publication-title: J. Nat. Prod.
  doi: 10.1021/acs.jnatprod.0c00804
SSID ssj0035894
Score 2.4006433
Snippet Alkaloids, as one of the largest classes of natural products with diverse structures, are an important source of innovative medicines. Filamentous fungi,...
SourceID doaj
pubmedcentral
proquest
pubmed
crossref
SourceType Open Website
Open Access Repository
Aggregation Database
Index Database
Enrichment Source
StartPage 219
SubjectTerms alkaloid
Alkaloids
Alkaloids - chemistry
Alkaloids - pharmacology
Alkynes
Aspergillus
Aspergillus sclerotiorum
Cytotoxicity
Data analysis
Dexamethasone
Fungi
Fungi - chemistry
Hydrocarbons
Lipopolysaccharides
Magnetic Resonance Spectroscopy
Marine environment
marine-derived fungus
Metabolites
Molecular Structure
Natural products
NMR
Nuclear magnetic resonance
sclerotioloids
secondary metabolite
Single crystals
South China Sea
spectral analysis
Tandem Mass Spectrometry
X-ray diffraction
SummonAdditionalLinks – databaseName: DOAJ Directory of Open Access Journals
  dbid: DOA
  link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1LaxsxEBYlp15K0keyqVNUWgKBLJGl1a7Um5vWhEJKIA7ktmi1UmKyXRc_ArnlP-Qf9pd0ZrV-ldBcgi_GGnllzWg0n6X5hpDPsGcYo7SNUzCXOJGZiwsnbYwnYo577VWTPnb6Mz25SH5cysuVUl94JyzQA4eJO2Jcc5eKzEhWJD7TSjJfljIDjyvKQjd55LDnzcFU8MFCKp0EMlIBoB7APSAbQErIp7Oy_TQs_Y-Flv_ekFzZcvqb5FUbK9JeGOMWeeHq12T_LJBN3x3SwTJ3anJI9-nZkob67g25PodOYyzSU42G5YT2_tw_HH-BTmPnKPg22qtuTGjCHBMKkSA9NZgMGH8Ds7x1Je2DJ5hBT2QTvxpWFbyfzL90PPtFzwdMsu5bctH_Pjg-idu6CrGVLJ3i_4foKDkoD-CTLBWDRSu85aVJrfLSOCV8yrm32lrvBLOZ1VLrTIMOMivEO7JRj2q3Qyjv2kyW0gvXFQC0jUq9wcNfA6KssCwiB_Ppzm1LOo61L6ocwAeqJl-qJiKfFrK_A9XGo1JfUWsLCaTHbj4Ao8lbo8mfMpqIdOY6z9s1O8mbM2Z4CXjGx0UzrDY8QjG1G82CjNaJFPw_MjqBwSJNTkS2gxktRisgoBNgnRFRawa29nPWW-rhdcP6jUWVAR3L3eeYgPfkJYdoDS_Tcd0hG9PxzO1BdDUtPjQL6S_w_iJb
  priority: 102
  providerName: Directory of Open Access Journals
– databaseName: Health & Medical Collection
  dbid: 7X7
  link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3NbtQwELagXLggKH-BFhmBKiE1wmvHccwFbQurCqmoUrfS3iLHsdsVISnJLlJvvANvyJN0Jslmu6iqconiceRkfjzjsb8h5D3MGcYk2oYxiEsYSeXCzEkbYkbMca990h4fO_4eH51F32Zy1i-4Nf22ypVNbA11XllcI__YZgDhEvrz5a8Qq0ZhdrUvoXGfPEDoMpRqNRsCLiETHXWQpAJCewjxIb6BeAlRdW5MQi1W_20O5v_7JG9MPJPH5FHvMdJxx-In5J4rt8neSQc5fbVPp-sTVM0-3aMnazDqq6fk4hQ61Viqp6jmeUPH__78PfwEnWrnKFg4Oi5-mK4JT5pQ8AfpscEjgeEXEM7fLqcTsAdL6ImY4ufzooD7ZvXSevmTnk6ZZKNn5GzydXp4FPbVFUIrWbzAVUQ0lxxYCEGUzBMGqiu85bmJbeKlcYnwMefeamu9E8wqC79YKy1ZpqwQz8lWWZXuJaF8ZJXMpRduJCDcNknsDaaADZCyzLKAfFj97tT20ONYAaNIIQRB1qRr1gTk3UB72QFu3Ep1gFwbKBAku31Q1edpr3Mp45q7WCgDA4680olkPs-lgsla5JlWAdlZ8TztNbdJ13IWkLdDM-gcJlJM6aplR6N1JAW_g0ZHMFgEywnIi06MhtEKcOsESGdAkg0B2_iczZZyftFif2NpZYiR5au7x_6aPOTgjeFmOa53yNaiXrpd8J4W2ZtWRa4BKHYa5w
  priority: 102
  providerName: ProQuest
Title Sclerotioloids A–C: Three New Alkaloids from the Marine-Derived Fungus Aspergillus sclerotiorum ST0501
URI https://www.ncbi.nlm.nih.gov/pubmed/37103358
https://www.proquest.com/docview/2806565639
https://www.proquest.com/docview/2806994532
https://www.proquest.com/docview/2942105376
https://pubmed.ncbi.nlm.nih.gov/PMC10142895
https://doaj.org/article/0292e637a50b4f79850fdd571233db97
Volume 21
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1fb9MwELfG9sIL4j-BURmBJiEtKLXjOEZCqBurJqROFWulvkWuY28VIYW0RfSN78A35JNwl3-lU8UT6ktUn1PXd_bdLxf_jpBX4DO0jpXxIzAXPxTS-lMrjI8ZMcuccnF5fGxwEZ2Pw48TMdkjTf3OegIXO6Ed1pMaF9mbH9_W72HBv0PECZAdoDvgFsBByP55AB5JYiWDQdhmE7iIVVhRk96Q33JGJWf_rkDz5vuSfzmg_l1yp44caa9S9T2yZ_P75GhYUU-vj-loc5JqcUyP6HBDSr1-QK4voVOBJXuy-Sxd0N7vn79O30KnwloKOx3tZZ911YQnTijEhXSg8Wig_wGM9LtNaR_2hRX0RG7xq1mWwfWiuWmx-kIvR4EIug_JuH82Oj336yoLvhFBtMSnibhtMlAlgCmRxgEsYe4MS3VkYie0jbmLGHNGGeMsD4w0SigllQim0nD-iOzn89w-IZR1jRSpcNx2OcBuHUdOYypYg2gwNYFHXjfTnZiaghwrYWQJQBFUTbJRjUdetrJfK-KNnVInqLVWAsmyyy_mxVVSr70kYIrZiEsNAw6dVLEIXJoKCU6bp1MlPXLY6DxpDDApM87w4fAbL9pmWHuYUNG5na8qGaVCwdk_ZFQIg0XSHI88rsyoHS2H8I6DdXok3jKwrb-z3ZLPrksOcCyxDFhZPP0fE_CM3GYQu-GrdUwdkv1lsbLPIdZaTjvklpzIDjk4ObsYfuqUTyw65eL6A2_ULI4
linkProvider Scholars Portal
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV1fb9MwELem8QAviP-EDTACJiEtmmvHSYyEUNmoOrZOk9ZJfcscx96qZc3oH1Df-A58Dz4Un4S7pGlXNO1t6ktVn6tL7ny-8_l-R8g72DO0jpXxQ1AXP5CR9VMrjY8ZMcudcnFZPtY5CNvHwbee7K2QP3UtDF6rrG1iaaizwuAZ-VaZAYSPUJ8vv_vYNQqzq3ULjUot9uz0J4Rso0-7OyDf95y3vna32_6sq4BvJAvHeHqGZoID6xA8yCxmoLLCGZ7p0MROahsLF3LujDLGWcFMZJRUKlKSpZHBA1Aw-Xdg42UY7EW9eYAnZKyCCgJVCMW2LjKIpyA-QxSfK5te2RvgOof2_3uZVza61gNyf-ah0malUg_Jih08IhuHFcT1dJN2FxVbo026QQ8X4NfTx-TsCCYNsTVQXvSzEW3-_fV7-yNMGlpLwaLSZn6uqyGsbKHgf9KOxhJEfwcWww-b0RbYnwnMRAzz036ew_dR_afDyQU96jLJGk_I8a2896dkdVAM7HNCecNEMpNO2IaA8F7HodOYctZAylLDPPKhft2JmUGdY8eNPIGQB0WTLETjkbdz2ssK4ONaqi8otTkFgnKXPxTD02S2xhPGFbehiDQwHLhIxZK5LJMROAciS1XkkfVa5snMUoyShV575M18GNY4Jm70wBaTikapQAp-A40KgFkE5_HIs0qN5twKcCMFaKdH4iUFW3qc5ZFB_6zEGsdWzhCTyxc38_6a3G13O_vJ_u7B3hq5x8ETxIt6XK2T1fFwYl-C5zZOX5XLhZKT216f_wDScldA
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV3bbhMxELWqVEK8IO4sFDACKiF1Fcde766REEqbRi2lUURTqW-L12u3EWlScgHljX_gb_gcvoSZvSQNqvpW5SWKx5F35-IZj-cMIW9gz9A6VsYPQVz8QEbWT600PmbELHfKxXn52GEn3DsOPp3IkzXyp6qFwWuVlU3MDXU2MnhGXs8zgPARqu7KaxHdVvvjxXcfO0hhprVqp1GIyIGd_4TwbfJhvwW8fst5e7e3s-eXHQZ8I1k4xZM0NBkcHgMCCZnFDMRXOMMzHZrYSW1j4ULOnVHGOCuYiYySSkVKsjQyeBgK5n89wqioRta3dzvdL9U-IGSsggIQVQjF6ucZRFcQrSGmz6UtMO8UcJV7-_8tzUvbXvsuuVP6q7RZCNg9smaH98lmtwC8nm_R3rJ-a7JFN2l3CYU9f0DOjmDSGBsFDUb9bEKbf3_93nkPk8bWUrCvtDn4poshrHOh4I3SQ40FiX4LVOOHzWgbrNEMZiKi-Wl_MIDvk-pPx7NzetRjkjUekuMbefOPSG04GtonhPKGiWQmnbANAcG-jkOnMQGtgZSlhnnkXfW6E1MCn2P_jUECARCyJlmyxiOvF7QXBdzHlVTbyLUFBUJ05z-MxqdJqfEJ44rbUEQaFhy4SMWSuSyTEbgKIktV5JGNiudJaTcmyVLKPfJqMQwaj2kcPbSjWUGjVCAFv4ZGBbBYhOrxyONCjBarFeBUCpBOj8QrArbyOKsjw_5ZjjyOjZ0hQpdPr1_7S3ILdDP5vN85eEZuc3AL8dYeVxukNh3P7HNw46bpi1JfKPl60yr6D5HyXNs
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Sclerotioloids+A%E2%80%93C%3A+Three+New+Alkaloids+from+the+Marine-Derived+Fungus+Aspergillus+sclerotiorum+ST0501&rft.jtitle=Marine+drugs&rft.au=Jun-Qiu+Mao&rft.au=Yao-Yao+Zheng&rft.au=Chang-Yun+Wang&rft.au=Yang+Liu&rft.date=2023-03-29&rft.pub=MDPI+AG&rft.eissn=1660-3397&rft.volume=21&rft.issue=4&rft.spage=219&rft_id=info:doi/10.3390%2Fmd21040219&rft.externalDBID=DOA&rft.externalDocID=oai_doaj_org_article_0292e637a50b4f79850fdd571233db97
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1660-3397&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1660-3397&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1660-3397&client=summon