Synthetic and Biosynthetic Approaches to Marine Natural Products

184 Pages·2020·18.098 MB·English

by  Asunción Barbero

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Edited by
Asunción Barbero
Printed Edition of the Special Issue Published in Marine Drugs
www.mdpi.com/journal/marinedrugs
Synthetic and Biosynthetic Approaches
to Marine Natural Products

Synthetic and Biosynthetic Approaches
to Marine Natural Products
SpecialIssueEditor
Asuncio´nBarbero
MDPI•Basel•Beijing•Wuhan•Barcelona•Belgrade•Manchester•Tokyo•Cluj•Tianjin
SpecialIssueEditor
Asuncio´nBarbero
UniversidaddeValladolid
Spain
EditorialOffice
MDPI
St.Alban-Anlage66
4052Basel,Switzerland
This is a reprint of articles from the Special Issue published online in the open access journal
MarineDrugs (ISSN 1660-3397) (available at: https://www.mdpi.com/journal/marinedrugs/
specialissues/synthetic-biosynthetic).
Forcitationpurposes,citeeacharticleindependentlyasindicatedonthearticlepageonlineandas
indicatedbelow:
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PageRange.
ISBN978-3-03928-466-5(Pbk)
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(cid:2)c 2020bytheauthors. ArticlesinthisbookareOpenAccessanddistributedundertheCreative
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disseminationandawiderimpactofourpublications.
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licenseCCBY-NC-ND.
Contents
AbouttheSpecialIssueEditor . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . vii
Prefaceto”SyntheticandBiosyntheticApproachestoMarineNaturalProducts” . . . . . . . . ix
StefanoSerra
AGeneralStrategyfortheStereoselectiveSynthesisoftheFuranosesquiterpenesStructurally
RelatedtoPallescensins1–2
Reprintedfrom:Materials2019,17,245,doi:10.3390/md17040245 . . . . . . . . . . . . . . . . . . 1
QinghaoJin,ZhiyangFu,LipingGuanandHaiyingJiang
Syntheses of Benzo[d]Thiazol-2(3H)-One Derivatives and Their Antidepressant and
AnticonvulsantEffects
Reprintedfrom:Materials2019,17,430,doi:10.3390/md17070430 . . . . . . . . . . . . . . . . . . 15
DanqiongHuang,WenfuLiu,AnguoLi,ChaogangWangandZhangliHu
Discovery of Geranylgeranyl Pyrophosphate Synthase (GGPPS) Paralogs from
Haematococcus pluvialis Based on Iso-Seq Analysis and Their Function on
AstaxanthinBiosynthesis
Reprintedfrom:Materials2019,17,696,doi:10.3390/md17120696 . . . . . . . . . . . . . . . . . . 25
CarlosD´ıez-Poza,PatriciaVal,FranciscoJ.PulidoandAsuncio´nBarbero
Synthesisof PolysubstitutedTetrahydropyrans byStereoselective Hydroalkoxylationof Silyl
Alkenols:EnRoutetoTetrahydropyranylMarineAnalogues
Reprintedfrom:Materials2018,16,421,doi:10.3390/md16110421 . . . . . . . . . . . . . . . . . . 39
Hao-yunShi,YangXie,PeiHu,Zi-qiongGuo,Yi-hongLu,YuGaoandCheng-gangHuang
Asymmetric Synthesis of the C15–C32 Fragment of Alotamide and Determination of the
RelativeStereochemistry
Reprintedfrom:Materials2018,16,414,doi:10.3390/md16110414 . . . . . . . . . . . . . . . . . . 51
Alessia Caso, Ilaria Laurenzana, Daniela Lamorte, Stefania Trino, Germana Esposito,
VincenzoPiccialliandValeriaCostantino
SmenamideAAnalogues.SynthesisandBiologicalActivityonMultipleMyelomaCells
Reprintedfrom:Materials2018,16,206,doi:10.3390/md16060206 . . . . . . . . . . . . . . . . . . 71
Iva´n Cheng-Sa´nchez, Jose´ A. Torres-Vargas, Beatriz Mart´ınez-Poveda, Guillermo A.
Guerrero-Va´squez,MiguelA´ngelMedina,FranciscoSarabiaandAnaR.Quesada
SynthesisandAntitumorActivityEvaluationofCompoundsBasedonToluquinol
Reprintedfrom:Materials2019,17,492,doi:10.3390/md17090492 . . . . . . . . . . . . . . . . . . 85
SeoungRakLee, DahaeLee, HeeJeongEom, MajaRischer, Yoon-JooKo, KiSungKang,
ChungSubKim,ChristineBeemelmannsandKiHyunKim
Hybrid Polyketides from a Hydractinia-Associated Cladosporium sphaerospermum SW67 and
TheirPutativeBiosyntheticOrigin
Reprintedfrom:Materials2019,17,606,doi:10.3390/md17110606 . . . . . . . . . . . . . . . . . . 101
YiGongandXiaolingMiao
ShortChainFattyAcidBiosynthesisinMicroalgaeSynechococcussp.PCC7942
Reprintedfrom:Materials2019,17,255,doi:10.3390/md17050255 . . . . . . . . . . . . . . . . . . 117
v
ChamilaniNikapitiya,S.H.S.Dananjaya,H.P.S.U.Chandrarathna,MahanamaDeZoysaand
IlsonWhang
Octominin: A Novel Synthetic Anticandidal Peptide Derived from Defense Protein of
Octopusminor
Reprintedfrom:Materials2020,18,56,doi:10.3390/md18010056 . . . . . . . . . . . . . . . . . . . 133
QinxueJing, XuHu, YanziMa, JiahuiMu, WeiweiLiu, FanxingXu, ZhanlinLi, JiaoBai,
HuimingHuaandDahongLi
Marine-DerivedNaturalLeadCompoundDisulfide-LinkedDimerPsammaplinA:Biological
ActivityandStructuralModification
Reprintedfrom:Materials2019,17,384,doi:10.3390/md17070384 . . . . . . . . . . . . . . . . . . 149
vi
About the Special Issue Editor
Asuncio´n Barbero was born in Burgos, Spain. She studied Chemistry at the University of
ValladolidandreceivedherPh.D.degreeatthesameuniversity, workingwithProf. Pulido. She
joined Prof. Ian Fleming’s group at the University of Cambridge as a Marie Curie fellow for
twoyearsworkinginthestudyofstereocontrolinorganicsynthesisusingsiliconchemistry. She
returnedtoValladolidasAssistantProfessor,waspromotedtoAssociateProfessorin2001,andto
fullProfessorin2019. Since2013, shehasbeentheCoordinatoroftheGradeofChemistryatthe
UniversityofValladolid.Shehasco-authoredaround60internationalscientificpublicationsandhas
deliveredseveralinvitedandplenarylectures.Hercurrentinterestsincludetheuseoforganosilicon
compoundsinthesynthesisofheterocycles.
vii

Preface to ”Synthetic and Biosynthetic Approaches to
Marine Natural Products”
Theoceanisthenaturalhabitatforabundantmulticellularplantsoranimalsandunicellular
bacteria. These organisms are excellent producers of secondary metabolites that have important
biologicalproperties. Agroupofmarinenaturalproductsofspecialinterestistheheterocycles. The
chemicalstructuresandbiologicalpropertiesofthiscompoundtypehaveattractedtheattentionof
thescientificcommunity,whichhasattemptedtosynthesizeandbiosynthesizethisclassofmolecules.
ThisSpecialIssueofMarineDrugscollectsaseriesofpapersdescribingsyntheticorbiosynthetic
approachestomarinenaturalproductsoranalogsthatcontainaheterocyclicmoietyintheirstructure.
Asuncio´nBarbero
SpecialIssueEditor
ix