Natural Secondary Metabolites: From Nature, Through Science, to Industry

960 Pages·2023·32.189 MB·English

by  Márcio Carocho, Sandrina A. Heleno, Lillian Barros

Márcio Carocho
Sandrina A. Heleno
Lillian Barros   Editors
Natural
Secondary
Metabolites
From Nature, Through Science,
to Industry
Natural Secondary Metabolites
á (cid:129) (cid:129)
M rcio Carocho Sandrina A. Heleno
Lillian Barros
Editors
Natural Secondary
Metabolites
From Nature, Through Science, to Industry
Editors
MárcioCarocho SandrinaA.Heleno
CentrodeInvestigaçãodeMontanha CentrodeInvestigaçãodeMontanha(CIMO)
(CIMO) InstitutoPolitécnicodeBragança
InstitutoPolitécnicodeBragança Bragança,Portugal
Bragança,Portugal
LillianBarros
CentrodeInvestigaçãodeMontanha
(CIMO)
InstitutoPolitécnicodeBragança
Bragança,Portugal
ISBN978-3-031-18586-1 ISBN978-3-031-18587-8 (eBook)
https://doi.org/10.1007/978-3-031-18587-8
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Preface
Secondary metabolites are also known as specialized molecules; they are not
involvedintheessentialfunctionsofanorganism.Thesemetabolitescanbefound
inmostlivingorganisms,suchasplants,fungi,animals,andbacteria.
Their importance for human activities is vast, especially given their chemical
diversity and specific roles they play in the organisms that produce them, making
them unique. Research around the world has been doing a remarkable, but never
never-endingefforttoidentify,categorize,understand,andobtainsecondarymetab-
olites from several organisms. Beyond scientific curiosity, this endeavor has been
drivenby potential applications ofthese molecules inseveralindustries, especially
thefood,cosmetic,textile,andpharmaceuticalindustries.
Muchofourworkisdevotedtosecondarymetabolites;thus,wefelttheneedto
compilemostoftheknowledgeonsecondarymetabolitesintoabookwhichincludes
thePlantandFungiKingdoms,butalsoknownapplicationsofthesemarvelmetab-
olites. To provide context, we added a historical perspective of how the study of
these molecules shaped human communities, and a final chapter focusing on the
futureofsecondarymetabolism.
Ourintentionisforthisbooktobeusedbystudentsandscientists,studyingthe
severalgroupsofplantandfungalmetabolites,butalsobytheindustriesthatobtain,
transform,andsellthesemoleculesorproductscontainingthem.Withthisbook,we
expect tohighlighttheirversatilityandapplicability,butalso toboost theirexploi-
tationandexposethestateoftheartoftheircontinuousstudy.
Bragança,Portugal MárcioCarocho
SandrinaA.Heleno
LillianBarros
v
Contents
PartI HistoryofSecondaryMetabolites
1 HistoryofSecondaryMetabolites:FromAncientMyths
toModernScientificValidation. . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
MarianaC.Pedrosa,LaíresLima,JoséIgnacioAloso-Esteban,
CustódioLoboRoriz,LillianBarros,IsabelC.F.R.Ferreira,
andMárcioCarocho
PartII PlantSecondaryMetabolites
2 BiochemistryofSecondaryMetabolisminPlants. . . . . . . . . . . . . . 21
NemanjaRajčević,DankaBukvički,DejanStojković,
andMarinaSoković
3 PhenolicAcidsandDerivatives:Description,Sources,
Properties,andApplications. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37
CelestinoSantos-Buelga,AnaM.González-Paramás,
andSusanaGonzález-Manzano
4 Flavonoids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
TâniaBragançaRibeiro,AdmaMelo,AnaA.Vilas-Boas,
andManuelaPintado
5 Terpenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 107
VirginieXavier,RafaelSpréa,TianeC.Finimundy,
SandrinaA.Heleno,JoanaS.Amaral,LillianBarros,
andIsabelC.F.R.Ferreira
6 PlantAlkaloids:Production,Extraction,andPotential
TherapeuticProperties. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 157
AntiaG.Pereira,LucíaCassani,PaulaGarcia-Oliveira,PazOtero,
SepidarMansoor,JavierEchave,JianboXiao,J.Simal-Gándara,
andM.A.Prieto
vii
viii Contents
7 Polyketides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 201
BorhaneEddineCherifZiani,AbidiMohamed,ChaimaZiani,
andLizaSaher
8 PlantTocopherolsandPhytosterolsandTheirBioactive
Properties. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 285
PradipPoudel,SpyridonA.Petropoulos,andFrancescoDiGioia
9 Anthra-,Benzo-,andNaphthoquinones. . . . . . . . . . . . . . . . . . .. . . 321
AlessandraDurazzo,PaoloGabrielli,andMassimoLucarini
10 Non-AlkaloidNitrogenContainingCompounds. . . . . . . . . . . . . . . 331
ElianaPereira,FilipaA.Fernandes,FilipaMandim,ManuelAyuso,
IsabelC.F.R.Ferreira,CristinaCaleja,andLillianBarros
11 Sulfur-ContainingCompoundsfromPlants. . . . . . . . . . . . . . . . . . 363
VeraCastro,M.Carpena,M.Fraga-Corral,A.Lopez-Soria,
P.Garcia-Perez,M.Barral-Martinez,R.Perez-Gregorio,HuiCao,
J.Simal-Gandara,andM.A.Prieto
12 InfluenceofGeneticsontheSecondaryMetabolitesofPlants. . . . . 403
JyotiSinghJadaun,RiteshYadav,NishaYadav,ShilpiBansal,
andNeelamS.Sangwan
PartIII FungiSecondaryMetabolites
13 BiochemistryofSecondaryMetabolismofFungi. . . . . . . . . . . . . . . 437
LiegeA.Pascoalino,TâniaC.S.P.Pires,OludemiTaofiq,
IsabelC.F.R.Ferreira,LillianBarros,andFilipaS.Reis
14 PhenolicAcidsfromFungi. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 475
ÂngelaLiberal,RossanaV.C.Cardoso,SandrinaA.Heleno,
ÂngelaFernandes,LillianBarros,andAnabelaMartins
15 TerpenesfromFungi. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 497
AnaF.Vinha,MarleneMachado,andM.BeatrizP.P.Oliveira
16 AlkaloidsfromFungi. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 529
JaniSilva,JulianaGarcia,RafaelaGuimarães,CátiaPalito,
AndréLemos,LillianBarros,andMariaJoséAlves
17 PolyketidesfromFungi. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 555
ChristianeContigli,MarceloSiqueiraValle,
SílviaCatarinaSalgadoOloris,LúciaPinheiroSantosPimenta,
andJacquelineAparecidaTakahashi
18 FungalQuinones:Benzo-,Naphtho-,andAnthraquinones. . . . . . . 607
VíctorLópezandFranciscoLes
Contents ix
19 Non-AlkaloidNitrogen-ContainingCompoundsfromFungi. . . . . . 627
HanineHached,LucíaCassani,YosraZbiss,M.Fraga-Corral,
IzamaraOliveira,Antia.G.Pereira,M.A.Prieto,SandrinaA.Heleno,
andMarcioCarocho
20 Sulfur-ContainingCompoundsfromFungi. . . . . . . . . . . . . . . . . . . 647
JulianaGarcia,JaniSilva,IreneGouvinhas,RafaelaGuimarães,
AntónioBovolini,MariaJoséSaavedra,andMariaJoséAlves
21 Mycosterols. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 673
ThaísMarquesUber,EmanueliBackes,
RúbiaCarvalhoGomesCorrêa,VanesaGesserCorrêa,
AdelarBracht,andRosaneMarinaPeralta
22 InfluenceofGeneticsontheSecondaryMetabolismofFungi. . . . . 687
DeboraLuizaCostaBarreto,CamilaRodriguesdeCarvalho,
TâniaMariadeAlmeidaAlves,CarlosLeomarZani,
CharlesLowellCantrell,StephenOscarDuke,
andLuizHenriqueRosa
PartIV FoodIndustry
23 ApplicationsofPlantSecondaryMetabolitesinthe
FoodIndustry. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 707
SpyridonA.Petropoulos
24 ApplicationsofFungiSecondaryMetabolitesinthe
FoodIndustry. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 739
MaríliaAparecidaFideliseMoura,DhionneCorreiaGomes,
andJacquelineAparecidaTakahashi
PartV PharmaceuticalIndustry
25 NewTrendsfromPlantSecondaryMetabolisminthe
PharmaceuticalIndustry. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 779
H.Oliveira,R.Pérez-Gregorio,I.Fernandes,S.Soares,V.Freitas,
andR.Dias
26 NewTrendsfromFungiSecondaryMetabolisminthe
PharmaceuticalIndustry. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 823
RicardoC.Calhelha,CarlosS.H.Shiraishi,LúciaRibeiro,
MárcioCarocho,RuiAbreu,PaulaCoutinho,LillianBarros,
JosianaVaz,andIsabelC.F.R.Ferreira
x Contents
PartVI OtherIndustries
27 CosmeticIndustry:NaturalSecondaryMetabolites
forBeautyandAging. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 853
SofiaM.Saraiva,SóniaP.Miguel,AndréR.T.S.Araujo,
MárcioRodrigues,MaximianoP.Ribeiro,andPaulaCoutinho
28 Biodyes:ASustainableApproachforTextileDyeing. . . . . . . . . . . 893
NunoBelino,JesusRodilla,andRoshanPaul
PartVII FutureofSecondaryMetabolites
29 NewChallengesandOpportunitiesfromSecondaryMetabolites. . . 925
IzamaradeOliveira,BiancaAlbuquerque,JonataM.Ueda,
MariaJoséAlves,IsabelC.F.R.Ferreira,LillianBarros,
andSandrinaA.Heleno
Part I
History of Secondary Metabolites