Structural Elucidation and Free Radical Scavenging Activity of a new o-Orsellinic Acid Derivative Isolated from the Lichen Cladonia rappii

Rappiidic acid, a new o-orsellinic acid derivative, was isolated from the lichen Cladonia rappii. Its capability to scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS) was investigated and compared with resveratrol and (+)-usnic acid. Usnic acid at 100 μM was the most efficien...

Full description

Saved in:
Bibliographic Details
Published inNatural product communications Vol. 11; no. 9; p. 1311
Main Authors Lage, Tiago C.A., Horta, Lívia P., Montanari, Ricardo M., Silva, Jefferson G., de Fátima, Ângelo, Fernandes, Sergio A., Modolo, Luzia V.
Format Journal Article
LanguageEnglish
Published Los Angeles, CA SAGE Publications 01.09.2016
Subjects
Online AccessGet full text

Cover

Loading…
Abstract Rappiidic acid, a new o-orsellinic acid derivative, was isolated from the lichen Cladonia rappii. Its capability to scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS) was investigated and compared with resveratrol and (+)-usnic acid. Usnic acid at 100 μM was the most efficient ROS scavenger, exhibiting activity 3-fold higher than that of resveratrol. At the same concentration, rappidic acid scavenged 23.1% of ROS formed, demonstrating that this compound is twice as active as resveratrol. Both compounds were shown to be poor RNS scavengers.
AbstractList Rappiidic acid, a new o-orsellinic acid derivative, was isolated from the lichen Cladonia rappii. Its capability to scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS) was investigated and compared with resveratrol and (+)-usnic acid. Usnic acid at 100 μM was the most efficient ROS scavenger, exhibiting activity 3-fold higher than that of resveratrol. At the same concentration, rappidic acid scavenged 23.1% of ROS formed, demonstrating that this compound is twice as active as resveratrol. Both compounds were shown to be poor RNS scavengers.
Rappiidic acid, a new o-orsellinic acid derivative, was isolated from the lichen Cladonia rappii. Its capability to scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS) was investigated and compared with resveratrol and (+)-usnic acid. Usnic acid at 100 μM was the most efficient ROS scavenger, exhibiting activity 3-fold higher than that of resveratrol. At the same concentration, rappidic acid scavenged 23.1% of ROS formed, demonstrating that this compound is twice as active as resveratrol. Both compounds were shown to be poor RNS scavengers.Rappiidic acid, a new o-orsellinic acid derivative, was isolated from the lichen Cladonia rappii. Its capability to scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS) was investigated and compared with resveratrol and (+)-usnic acid. Usnic acid at 100 μM was the most efficient ROS scavenger, exhibiting activity 3-fold higher than that of resveratrol. At the same concentration, rappidic acid scavenged 23.1% of ROS formed, demonstrating that this compound is twice as active as resveratrol. Both compounds were shown to be poor RNS scavengers.
Author Modolo, Luzia V.
Montanari, Ricardo M.
Fernandes, Sergio A.
Silva, Jefferson G.
Lage, Tiago C.A.
de Fátima, Ângelo
Horta, Lívia P.
Author_xml – sequence: 1
  givenname: Tiago C.A.
  surname: Lage
  fullname: Lage, Tiago C.A.
– sequence: 2
  givenname: Lívia P.
  surname: Horta
  fullname: Horta, Lívia P.
– sequence: 3
  givenname: Ricardo M.
  surname: Montanari
  fullname: Montanari, Ricardo M.
– sequence: 4
  givenname: Jefferson G.
  surname: Silva
  fullname: Silva, Jefferson G.
– sequence: 5
  givenname: Ângelo
  surname: de Fátima
  fullname: de Fátima, Ângelo
– sequence: 6
  givenname: Sergio A.
  surname: Fernandes
  fullname: Fernandes, Sergio A.
  email: sefernandes@gmail.com
– sequence: 7
  givenname: Luzia V.
  surname: Modolo
  fullname: Modolo, Luzia V.
BackLink https://www.ncbi.nlm.nih.gov/pubmed/30807031$$D View this record in MEDLINE/PubMed
BookMark eNp9kcFqHDEMhk1JadI0L9BD8bGXSawZz9g-hm3SBBYCTQu9DRpbs3GYtbf2zJa8Qp-6Dpv2UqguEuj7hfTrLTsKMRBj70GcAyh1AaaRrdLfoRMAQpimfsVOoG3bykjVHpW6ANUzcczOcn4UJbSWQpo37LgRWijRwAn7dT-nxc5LwolfTYv1DmcfA8fg-HUi4l_QeVua9xb3FDY-bPilnf3ez088jhx5oJ88Vncp0zT54G1pe8c_UfL7MmpP_DbHCWdyfExxy-cH4mtvHyjw1YQuBo884W7n_Tv2esQp09lLPmXfrq--rm6q9d3n29XlurK1kXOFHdIoLNpWYGd104l60IAAQw3CkSDpRmXkIMAAtUQknBq0Vo1RDmo5NKfs42HuLsUfC-W53_psy_YYKC65r0F3IE0xtaAfXtBl2JLrd8lvMT31f_wrQH0AbIo5Jxr_IiD65z_1__6piC4Ooowb6h_jkkK593-K30dRkvo
Cites_doi 10.1007/s00114-002-0305-3
10.1016/j.pupt.2013.07.002
10.1016/j.lwt.2014.04.047
10.56499/jppres14.042_2.5.138
10.1016/j.bmc.2012.02.036
10.1016/S0928-0987(97)00078-X
10.1021/np50047a033
10.1007/s11101-010-9201-1
10.1016/S0031-9422(02)00383-7
10.1590/S0102-33062011000200004
10.1021/np9803777
10.1039/B904541D
10.1016/j.femsec.2005.05.003
ContentType Journal Article
Copyright 2016 SAGE Publications Inc.
Copyright_xml – notice: 2016 SAGE Publications Inc.
DBID AAYXX
CITATION
NPM
7X8
DOI 10.1177/1934578X1601100932
DatabaseName CrossRef
PubMed
MEDLINE - Academic
DatabaseTitle CrossRef
PubMed
MEDLINE - Academic
DatabaseTitleList PubMed

CrossRef
MEDLINE - Academic
Database_xml – sequence: 1
  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
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1555-9475
ExternalDocumentID 30807031
10_1177_1934578X1601100932
10.1177_1934578X1601100932
Genre Journal Article
GroupedDBID ---
0R~
123
53G
54M
AADUE
AAFWJ
AARIX
AASGM
ABDBF
ABDNZ
ABKRH
ABQXT
ABRHV
ACLDX
ACOFE
ACROE
ADOGD
AENEX
AEWDL
AEXNY
AFCOW
AFKRG
AFPKN
AFRWT
AFUIA
AGNHF
AJUZI
ALMA_UNASSIGNED_HOLDINGS
BDDNI
CFDXU
DOPDO
EBS
EJD
F5P
GROUPED_DOAJ
H13
HZ~
J8X
O9-
OK1
ROL
SAFTQ
SAUOL
SCDPB
SCNPE
SFC
SJN
ZPPRI
ZRKOI
AAYXX
ACHEB
CITATION
NPM
7X8
ID FETCH-LOGICAL-c294t-a6aef0cac50a6c83602b81a11b210de0e4df794b0191e5eee0d7b887397d124b3
IEDL.DBID AFRWT
ISSN 1934-578X
IngestDate Fri Jul 11 09:07:45 EDT 2025
Thu Apr 03 07:07:41 EDT 2025
Tue Jul 01 05:27:32 EDT 2025
Tue Jun 17 22:49:24 EDT 2025
IsPeerReviewed true
IsScholarly true
Issue 9
Keywords Superoxide anion
DPPH
Rappiidic acid
Natural products
Cladonia rappii A. Evans
Free radical scavenging
Orsellinic acid
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c294t-a6aef0cac50a6c83602b81a11b210de0e4df794b0191e5eee0d7b887397d124b3
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
PMID 30807031
PQID 2186149100
PQPubID 23479
ParticipantIDs proquest_miscellaneous_2186149100
pubmed_primary_30807031
crossref_primary_10_1177_1934578X1601100932
sage_journals_10_1177_1934578X1601100932
ProviderPackageCode CITATION
AAYXX
PublicationCentury 2000
PublicationDate 20160900
2016-09-00
2016-Sep
20160901
PublicationDateYYYYMMDD 2016-09-01
PublicationDate_xml – month: 9
  year: 2016
  text: 20160900
PublicationDecade 2010
PublicationPlace Los Angeles, CA
PublicationPlace_xml – name: Los Angeles, CA
– name: United States
PublicationTitle Natural product communications
PublicationTitleAlternate Nat Prod Commun
PublicationYear 2016
Publisher SAGE Publications
Publisher_xml – name: SAGE Publications
References Cocchietto, Skert, Nimis, Sava 2002; 89
Coll, Bowden 1986; 49
Boustie, Tomasi, Grube 2011; 10
Alves, Maia, Franco, Galvão, Silva, Gomes, Martins, Falcão, de Castro, da Silva 2014; 27
Ingólfsdóttir 2002; 61
Martins, Käffer, Alves, Pereira 2011; 25
Sanchez, Chiang, Szewczyk, Davidson, Manmeet, Oakley, Bok, Keller, Oakley, Wang 2010; 6
Ingólfsdóttir, Chung, Skúlason, Gissurarson, Vilhelmsdóttir 1998; 6
Plaza, Torres, Lücking, Vizcaya, Medina 2014; 2
2006; 18
Cordeiro, Reis, Cruz, Stocker-Wörgötter, Grube, Iacomini 2005; 54
da Silva, Reis, Muniz, Ruiz, de Carvalho, Sabino, Modolo, de Fátima 2012; 20
Kumar, Müller 1999; 62
Kosanić, Ranković, Stanojković, Rancić, Manojlović 2014; 59
bibr8-1934578X1601100932
Plaza CM (bibr9-1934578X1601100932) 2014; 2
bibr13-1934578X1601100932
bibr14-1934578X1601100932
(bibr6-1934578X1601100932) 2006; 18
bibr12-1934578X1601100932
bibr7-1934578X1601100932
bibr11-1934578X1601100932
bibr10-1934578X1601100932
bibr2-1934578X1601100932
bibr3-1934578X1601100932
bibr4-1934578X1601100932
bibr5-1934578X1601100932
bibr1-1934578X1601100932
References_xml – volume: 10
  start-page: 287
  year: 2011
  end-page: 307
  article-title: Bioactive lichen metabolites: alpine habitats as an untapped source
  publication-title: Phytochemistry Reviews
– volume: 61
  start-page: 729
  year: 2002
  end-page: 736
  article-title: Usnic acid
  publication-title: Phytochemistry
– volume: 18
  start-page: 7
  year: 2006
  end-page: 215
  article-title: Checklist of lichens and lichenicolous fungi of Rio Grande do Sul (Brazil)
  publication-title: Caderno de Pesquisa Série Biologia
– volume: 25
  start-page: 286
  year: 2011
  end-page: 292
  article-title: Fungos liquenizados da mata atlântica, no sul do Brasil
  publication-title: Acta Botanica Brasilica
– volume: 59
  start-page: 518
  year: 2014
  end-page: 525
  article-title: lichens and their major metabolites as possible natural antioxidant, antimicrobial and anticancer agents
  publication-title: LWT-Food Science and Technology
– volume: 89
  start-page: 137
  year: 2002
  end-page: 146
  article-title: A review on usnic acid, an interesting natural compound
  publication-title: Naturwissenschaften
– volume: 6
  start-page: 141
  year: 1998
  end-page: 144
  article-title: Antimycobacterial activity of lichen metabolites
  publication-title: European Journal of Pharmaceutical Sciences
– volume: 6
  start-page: 587
  year: 2010
  end-page: 593
  article-title: Molecular genetic analysis of the orsellinic acid/F9775 gene cluster of
  publication-title: Molecular BioSystems
– volume: 27
  start-page: 139
  year: 2014
  end-page: 143
  article-title: Expectorant and antioxidant activities of purified fumarprotocetraric acid from Cladonia verticillaris lichen in mice
  publication-title: Pulmonary Pharmacology & Therapeutics
– volume: 54
  start-page: 381
  year: 2005
  end-page: 390
  article-title: Molecular studies of photobionts of selected lichens from the coastal vegetation of Brazil
  publication-title: FEMS Microbiology Ecology
– volume: 62
  start-page: 817
  year: 1999
  end-page: 820
  article-title: Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism
  publication-title: Journal of Natural Products
– volume: 20
  start-page: 2645
  year: 2012
  end-page: 2650
  article-title: Free radical scavenging and antiproliferative properties of Biginelli adducts
  publication-title: Bioorganic & Medicinal Chemistry
– volume: 2
  start-page: 138
  year: 2014
  end-page: 147
  article-title: Antioxidant activity, total phenols and flavonoids of lichens from Venezuelan Andes
  publication-title: Journal of Pharmacy & Pharmacognosy Research
– volume: 49
  start-page: 934
  year: 1986
  end-page: 936
  article-title: The application of vacuum liquid chromatography to the separation of terpene mixtures
  publication-title: Journal of Natural Products
– ident: bibr4-1934578X1601100932
  doi: 10.1007/s00114-002-0305-3
– volume: 18
  start-page: 7
  year: 2006
  ident: bibr6-1934578X1601100932
  publication-title: Caderno de Pesquisa Série Biologia
– ident: bibr11-1934578X1601100932
  doi: 10.1016/j.pupt.2013.07.002
– ident: bibr10-1934578X1601100932
  doi: 10.1016/j.lwt.2014.04.047
– volume: 2
  start-page: 138
  year: 2014
  ident: bibr9-1934578X1601100932
  publication-title: Journal of Pharmacy & Pharmacognosy Research
  doi: 10.56499/jppres14.042_2.5.138
– ident: bibr14-1934578X1601100932
  doi: 10.1016/j.bmc.2012.02.036
– ident: bibr2-1934578X1601100932
  doi: 10.1016/S0928-0987(97)00078-X
– ident: bibr13-1934578X1601100932
  doi: 10.1021/np50047a033
– ident: bibr1-1934578X1601100932
  doi: 10.1007/s11101-010-9201-1
– ident: bibr3-1934578X1601100932
  doi: 10.1016/S0031-9422(02)00383-7
– ident: bibr7-1934578X1601100932
  doi: 10.1590/S0102-33062011000200004
– ident: bibr12-1934578X1601100932
  doi: 10.1021/np9803777
– ident: bibr8-1934578X1601100932
  doi: 10.1039/B904541D
– ident: bibr5-1934578X1601100932
  doi: 10.1016/j.femsec.2005.05.003
SSID ssj0000884049
Score 2.0451946
Snippet Rappiidic acid, a new o-orsellinic acid derivative, was isolated from the lichen Cladonia rappii. Its capability to scavenge reactive oxygen species (ROS) and...
SourceID proquest
pubmed
crossref
sage
SourceType Aggregation Database
Index Database
Publisher
StartPage 1311
Title Structural Elucidation and Free Radical Scavenging Activity of a new o-Orsellinic Acid Derivative Isolated from the Lichen Cladonia rappii
URI https://journals.sagepub.com/doi/full/10.1177/1934578X1601100932
https://www.ncbi.nlm.nih.gov/pubmed/30807031
https://www.proquest.com/docview/2186149100
Volume 11
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1ZS8NAEB60fdAX8bZejOCDIKtJuk3rk5RqqeIBHti3sFcgUNPSQ_Av-KudySGIIr4mSybszOx-uzPzDcChZ-JYS9-JVkxHFBl4TmhySCFdPZTKykBmlPm3d2HvWV73G_05GJW1MMUMTk44rYr-KFus2bv5Nvq0CDKeEuqQZGp9P8wozwiDnM-mr1F-31221eAnHKCevXJs23BG5Lso69vmoRo0w0ZQgWq7-_Dy9HUvQ14nc9TMQgRLKWttfhX8fT_7AVK_JYhle1Z3GZYKsInt3DpWYM6lq7DQKXu8rcHHY0Yfy9QbeDmYmSTvsIQqtdgdO4cPKovj4KPhtvPc0AjbJm84gcMYFRIqx6G4H0-Y2DNNDL1OLF6QXb9llOJ4RcZNeNYiF7IgwU284ezTFDsDZWlBUThWo1GSrMNz9_Kp0xNFdwZhgjM5FSpULvaMMg1PhYZrQQLd8pXvazpFWuc5aWNydk0Y0ncN55xnm5qWNAJAlkCFrm9AJR2mbguQaf9iGwdNrTnMZ5SnyXToMEh4UDdVqwbH5RxHo5yEI_ILnvKfGqnBQamGiKaTAyAqdcPZJOL-W3QipGE12Mz18_W9OkFn5vKvwRErLCoN8Q9B2_8fugOLhLTCPDltFyqkXLdHaGaq9wsD_ATnLOzh
linkProvider SAGE Publications
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LS8NAEB5qPdSL-LY-R_AgSCRJt2mLp1ItVWsFW7G3sK9AQNLSWn-Ev9qZPAqiiOfsbsLOY7_JznwDcO7qKFLCs04zohBF-K51FBmkI2wtENIIX6SU-Y-DoPci7sf1cQmui1qYfAfnV5xWRV-UOuuldXOdeKsmSMvGXpCynRH8WIFVUSdXXIbVdvf5dbT8xUIGJDIAzJMcnlWUzfy60Pej6Qfe_JbrlR4_3Q1Yz3EjtjNBb0LJJltQ6RTt2rbhc5gywTKLBt6-LXScNUtCmRjszqzFZ5leyeBQcwd57k2EbZ31jsBJhBIJYOPEeZrNmaMziTU9jg3ekIp-pOzgeEd6StDUINekICFH7HMiaYKdN2nIN0icyek0jnfgpXs76vScvNGCo_2WeHdkIG3kaqnrrgw0l3X4qulJz1MUEBrrWmEisltFcNCzdWutaxqKvBNhGUP4QNV2oZxMErsPyAx-kYn8hlJ8Y6elq0gLKK4jaKcaslmFy2KPw2nGpxF6OeX4T4lU4awQQ0jbyXcZMrGTxTzkVloU3NGwKuxl8lmuVyMUzLT8VbhggYWFTv3xooP_Dz2FSm_02A_7d4OHQ1gjABVkOWdHUCZB22MCKe_qJFfGLy2n2kE
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1ZS8NAEB60gvoi3tZzBB8EiSbpNq2PpRrqLR7Yt7AnBCQtrfoj_NXO5BCKIj5ndxN2Zna_ycx8A3Dga-eUCKzXduSiiNC3niKD9IRtREIaEYqcMv_mNuo9i8t-s1_2OeVamHIHx8ecVkVflB_WbN1D407KGOMJgQ5BmtYPopzxjCDINMwIQV5eDWY68cPL0_dvFjIiUYBgnuTxrKp05teFJq-nH5hzIt8rv4LiRVgosSN2CmEvwZTNlmGuW7VsW4HPx5wNlpk08Pz1XadFwySUmcF4ZC0-yDwsg4-au8hzfyLs6KJ_BA4cSiSQjQPvbjRmns4s1fQ4NXhGavqRM4TjBekqwVODXJeChB7xmpNJM-y-SkPng8SRHA7TdBWe4_Onbs8rmy14OjwVb56MpHW-lrrpy0hzaUeo2oEMAkVOobG-FcaR7SqChIFtWmt901J0QhGeMYQRVGMNatkgsxuAzOLnjAtbSnHUTktfkSaQb0fwTrVkuw5H1R4nw4JTIwlK2vGfEqnDfiWGhLaT4xkys4P3ccLttMjBo2F1WC_k871eg5AwU_PX4ZAFllR69ceLNv8_dA9m78_i5Pri9moL5glDRUXa2TbUSM52h3DKm9otdfELqBjbWg
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=Structural+Elucidation+and+Free+Radical+Scavenging+Activity+of+a+new+o-Orsellinic+Acid+Derivative+Isolated+from+the+Lichen+Cladonia+rappii&rft.jtitle=Natural+product+communications&rft.au=Lage%2C+Tiago+C+A&rft.au=Horta%2C+Livia+P&rft.au=Montanari%2C+Ricardo+M&rft.au=Silva%2C+Jefferson+G&rft.date=2016-09-01&rft.issn=1934-578X&rft.volume=11&rft.issue=9&rft.spage=1311&rft_id=info:doi/10.1177%2F1934578X1601100932&rft_id=info%3Apmid%2F30807031&rft.externalDocID=30807031
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1934-578X&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1934-578X&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1934-578X&client=summon