Table Of ContentJiajuZhou
HandbookofActiveMarineNaturalProducts
Handbook of Active Marine Natural Products
Jiaju Zhou
Volume:Terpenoids,Part
ISBN----,e-ISBN(PDF)----,
e-ISBN(EPUB)----
Volume:Terpenoids,Part
ISBN----,e-ISBN(PDF)----,
e-ISBN(EPUB)----
Volume:Alkaloids,Part
ISBN----,e-ISBN(PDF)----,
e-ISBN(EPUB)----
Volume:Alkaloids,Part
ISBN----,e-ISBN(PDF)----,
e-ISBN(EPUB)----
Volume:PolyketidesandSteroids
ISBN----,e-ISBN(PDF)----,
e-ISBN(EPUB)----
Volume:O-HeterocyclesandAromatics
ISBN----,e-ISBN(PDF)----,
e-ISBN(EPUB)----
Volume:PeptidesandOthers
ISBN----,e-ISBN(PDF)----,
e-ISBN(EPUB)----
Jiaju Zhou
Handbook
of Active Marine
Natural Products
Volume 6: Aliphatic Metabolites
Author
Prof.JiajuZhou
ChineseAcademyofSciences
1303Department,10Building
31ZhongGuanCunNanDajie
100081Beijing
China
[email protected]
ISBN978-3-11-065400-4
e-ISBN(PDF)978-3-11-065579-7
e-ISBN(EPUB)978-3-11-065414-1
LibraryofCongressControlNumber:2019941348
BibliographicinformationpublishedbytheDeutscheNationalbibliothek
TheDeutscheNationalbibliothekliststhispublicationintheDeutscheNationalbibliografie;
detailedbibliographicdataareavailableontheInternetathttp://dnb.dnb.de.
©2019WalterdeGruyterGmbH,Berlin/Boston
Typesetting:IntegraSoftwareServicesPvt.Ltd.
Printingandbinding:CPIbooksGmbH,Leck
Coverimage:SciencePhotoLibrary/Douwma,Georgette
www.degruyter.com
Preface
The English edition Handbook of Active Marine Natural Products (HAMNP) with 8
Volumes is a selective version of the Marine Natural Products Dataset. The whole
dataset was collected and developed by the Molecular Design Group, Institute of
Process Engineering, Chinese Academy of Sciences during 1998–2016. Totally, it
covers 19,722 entries of secondary metabolites from marine living things, where
8,350 compound entries have pharmacological activity data. The 8,350 compound
entrieswerearrangedintoeightvolumestoformthesetofhandbooksasfollows:
Volume1:Terpenoids,Part1
Volume2:Terpenoids,Part2
Volume3:Alkaloids,Part1
Volume4:Alkaloids,Part2
Volume5:PolyketidesandSteroids
Volume6:AliphaticMetabolites
Volume7:O-HeterocyclesandAromatics
Volume8:PeptidesandOthers
ThissetofeightHAMNPbooksgathersthestructure,origin,andbioactivity,aswell
as other relevant information, of 8,350 active marine natural products from 3,025
marineorganisms.
The HAMNP handbooks represent a largest collection of active secondary me-
tabolitesfrommarineorganisms,andallkindsofscientificdatahavebeenreorgan-
ized as well-formatted data so that the books became helpful to researchers as
aconvenientreference.Thematerialscoveredinthesebooksincludethosethrough
systematiccollectionupto2012,andfurtheraccompaniedwiththelatestdatapub-
lishedinseveralcorejournalsuntil2016.
TheworkcoveredintheseHAMNPbookswasaccomplishedintwophases.The
initialphaserangedfrom1998to2001andthemainphasefrom2011to2018.Inthe
original version of the dataset, more than 22,000 compounds have been collected,
including duplicated compounds from different authors. The comprehensive data
compilation process include data specification definition, cross-validation, assess-
mentconfirmation,identificationofduplicatedstructures,andmergingofrelevant
information,leadingtothefinalaccomplishmentofthecurrent19,722datasets.
In brief,the maincompilation processofthe HAMNPbooksisgiven asfollows.
First,collectthenamelist,origin,andstructureofchemicalcompoundsfromsucces-
siveannualreviews(seeCoreReferencesR01andR02inIntroduction)andliterature
reviews.Second,double-checkthedocumentstoverifyandcompleteotherinforma-
tion.Third,confirmthestructuralinformationandothertypesofdatausingorthogo-
nal information from other sources with cross-validation methods. Fourth, the
structuresofmorethan22,000compoundsarerecheckedandtheinformationisinte-
gratedbymanualidentificationandcomputerprograms.Finally,thecomprehensive
https://doi.org/10.1515/9783110655797-201
VI Preface
informationonthe19,722compoundsconstitutesthedataset.Here,8,350activesets
werepickedupfromthedatasettoformthecurrentHAMNPhandbook.
Three problems need to be solved to compile a multidisciplinary reference
book.First,everydefinitionandconceptshouldbeexplicitwhenexpandingknowl-
edge, connotation, and extension included, without any research details. Second,
the reliability assessment is essential for all kinds of data, because the devil is in
thedetail.Third,itisessentialtosearch,identify,andintegratedataofduplicated
chemical compounds. Fortunately, well-developed software packages can help us
automaticallyidentifythemajorityofduplicatedchemicalcompounds.Theremain-
ingissuescanberesolvedalongwithmanualprocessing.
Itistheguidingprincipleoftheauthortomakethebooktobepithy,thorough,
precise, and intelligible. In fact, we always view ourselves as HAMNP’s readers,
with the exclusive objective to let readers gain the most useful knowledge in the
shortestpossibletime.
ThecorecontentsandhighlightsoftheHAMNPbooksarethe“threediversities,”
thatis,thediversityofchemicalstructures,thediversityofbiologicalresources,and
the diversity of pharmacological activities. In terms of chemical structure diversity,
we refer to the classification system from references, then further improve and ex-
pand it based on the latest research and development to define our classification
frameworkofstructures.Oncereadersbrowsethecontentsofthebooks,theclassifi-
cationsystemisstraightforward.Forthediversityofbiologicalresources,itisrecom-
mended to refer to Index 3 in each volume – Compound Marine Organism Source
Index,andIndex4ineachvolume–CompoundMarineSourceSamplingGeographic
LocationIndex.Forthediversityofpharmacologicalactivities,itisrecommendedto
refertoIndex5ineachvolume–CompoundPharmacologicalActivityIndex.
TheseHAMNPhandbooksareexpectedtohelpreaderswhoareengagedinre-
search, in teaching, and in the development of marine natural products. It should
alsobenefitcollegestudents,postgraduates,marineresourcemanagers,andthose
whoareinterestedinthechemistryandpharmacologyofmarinenaturalproducts.
Wewouldfeelfortunateifitworksasexpected.
JiajuZhou
InstituteofProcessEngineering(IPE),
ChineseAcademyofSciences(CAS)
February2019
Contents
Preface V
AbouttheAuthor IX
Introduction XI
HowtoUsetheHAMNPBooks XIX
ListofAbbreviationsandAcronyms XXIII
ListofCancerCellCodes XXXIII
1 AliphaticMetabolites 1
1.1 SaturatedAliphaticChainCompounds 1
1.2 AlkenicCompounds 8
1.3 AcetylenicCompounds 40
1.4 Miscellaneousacetylenes 97
1.5 MonocarbocyclicCompounds 101
1.6 PolycyclicAldehydesandKetones 119
1.7 Heteroalicyclic 125
1.8 Prostaglandins(Prostanoids) 170
1.9 Oxylipins(ExcludingEicosanoids) 172
1.10 Acylglycerols 199
1.11 Phospholipids 202
1.12 Glycolipids 220
1.13 Sphingolipids 230
1.14 PandangolideandSporiolideCyclicLactones 266
1.15 MacrosphelideCyclicTri-lactones 267
1.16 MacrolactinCyclicLactones 269
1.17 Long-chainAromaticSystems 274
1.18 MarineAcetogenins 278
Index1CompoundNameandSynonymIndex 283
Index2CompoundMolecularFormulaIndex 298
Index3CompoundOrganismSourceIndex 317
Index4CompoundSamplingGeographicLocalityIndex 323
Index5CompoundPharmacologicalActivityIndex 326
About the Author
Prof.JiajuZhouwasborninOctober1939inTianjin,China.Hegraduated
fromRareEarthInorganicChemistrySpecialty,ChemistryDepartment,
PekingUniversity,in1963underasix-yearprogram.Beforeheretiredin
2008,ZhouwastheleaderofMoleculeDesignGroup,IPE,CAS.Zhou’s
areasofresearchincluderareearthchemistry,mineralanalytical
chemistry,chemicalindustryprocesssimulation(inIPE,CASandUBC,
Canada),designofcrystalstructuraldatabase(inOSRD,NIST,
Gaithersburg,MD,USA),scientificdatabaseR&D,andcomputer-aidedand
artificialintelligencedrugdesign.ZhoudevelopedthefirstTCMdatabase
(TCMDB)with23,033entries.Since2008,hehasworkedonMarine
NaturalProductsprojectandhasdevelopedtheMarineNaturalProductsDatabase(MNPDB)with
19,722entries.
https://doi.org/10.1515/9783110655797-202
