LBF20306CV01: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}
{{Lipid/Header}}


{{Metabolite
{{Metabolite
|LipidBank=XPR8040
|LipidBank=XPR8040
|LipidMaps=LMFA03120021
|LipidMaps=LMFA03120021
|SysName= (R) -4-{ (Z) -3- [ (1R,2S) -2- [ (Z) -2-octenyl ] -5-oxo-3-cyclopentenyl ] -1-propenyl}-4-butanolide
|SysName= 4R- {cis-3- [ (1R,2S) -2- (cis-2-Octenyl) -5-oxo-3-cyclopentenyl] -1-propenyl} -4-butanolide
|Common Name=&&preclavulone lactone I&&(R) -4-{ (Z) -3- [ (1R,2S) -2- [ (Z) -2-octenyl ] -5-oxo-3-cyclopentenyl ] -1-propenyl}-4-butanolide&&
|Common Name=&&Preclavulone lactone I&&4R- {3Z- [ (1R,2S) -2- (2Z-Octenyl) -5-oxo-3-cyclopentenyl] -1-propenyl} -4-butanolide&&
|Reflactive=[<FONT FACE="Symbol">a</FONT>]<SUB><FONT SIZE=-1>D</FONT></SUB> -168.0°[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Optical=[ alpha ]_D  -168.0°[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Mass Spectra=HRFABMS m/z 316.2028 for C<SUB><FONT SIZE=-1>2</FONT></SUB><SUB><FONT SIZE=-1>0</FONT></SUB>H<SUB><FONT SIZE=-1>2</FONT></SUB><SUB><FONT SIZE=-1>8</FONT></SUB>O<SUB><FONT SIZE=-1>3</FONT></SUB> (M<SUP><FONT SIZE=-1>+</FONT></SUP>), calcd 316.2038.[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Mass Spectra=HRFABMS m/z 316.2028 for C_{20}H_{28}O_3  (M^+ ), calcd 316.2038.[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|UV Spectra=<FONT FACE="Symbol">l</FONT><SUP><FONT SIZE=-1>C</FONT></SUP><SUP><FONT SIZE=-1>H</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP><SUP><FONT SIZE=-1>C</FONT></SUP><SUP><FONT SIZE=-1>N</FONT></SUP>&<SUB><FONT SIZE=-1>m</FONT></SUB><SUB><FONT SIZE=-1>a</FONT></SUB><SUB><FONT SIZE=-1>x</FONT></SUB> 215 nm(<FONT FACE="Symbol">e</FONT>5740)[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|UV Spectra= lambda ^{CH3CN}&_{max} 215 nm( epsilon 5740)[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|IR Spectra=<FONT FACE="Symbol">n</FONT> 1775 and 1706cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|IR Spectra= nu  1775 and 1706cm^{-1}[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(500MHz,CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>)<FONT FACE="Symbol">d</FONT>ppm0.89(3H,t,J=7.5Hz),1.2-1.4(6H,m),1.92(1H,dtd,8.4,9.7,12.9Hz),2.01(2H,brq,J=7.3Hz),2.11(1H,dt,J=2.3,5.9),2.27(1H,brtd,J=7.0,14.5Hz),2.32(1H,brtd,J=7.1,14.5Hz),2.41(1H,qd,J=6.6,12.9Hz),2.52(2H,m),2.57(2H,dd,J=6.6,9.7Hz),2.72(1H,qt,J=2.3,7.0Hz),5.27(1H,dt,J=6.6,8.4Hz),5.36(1H,brtd,J=7.1,10.8Hz),5.53(1H,dd,J=8.4,11.1Hz),5.54(1H,m),5.56(1H,td,J=7.2,11.1Hz),6.16(1H,dd,J=2.3,5.1Hz),7.60(1H,dd,J=2.3,5.8Hz).[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]] <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR(125MHz,CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>)<FONT FACE="Symbol">d</FONT>ppm14.0,22.5,27.3,27.5,28.9,29.1,29.2,31.3,31.5,46.3,50.3,76.0,125.2,129.9,130.9,133.1,133.4,167.2,177.0,210.6[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|NMR Spectra=^1 H-NMR(500MHz,CDCl_3 ) delta ppm0.89(3H,t,J=7.5Hz),1.2-1.4(6H,m),1.92(1H,dtd,8.4,9.7,12.9Hz),2.01(2H,brq,J=7.3Hz),2.11(1H,dt,J=2.3,5.9),2.27(1H,brtd,J=7.0,14.5Hz),2.32(1H,brtd,J=7.1,14.5Hz),2.41(1H,qd,J=6.6,12.9Hz),2.52(2H,m),2.57(2H,dd,J=6.6,9.7Hz),2.72(1H,qt,J=2.3,7.0Hz),5.27(1H,dt,J=6.6,8.4Hz),5.36(1H,brtd,J=7.1,10.8Hz),5.53(1H,dd,J=8.4,11.1Hz),5.54(1H,m),5.56(1H,td,J=7.2,11.1Hz),6.16(1H,dd,J=2.3,5.1Hz),7.60(1H,dd,J=2.3,5.8Hz).[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]] ^{13}C-NMR(125MHz,CDCl_3 ) delta ppm14.0,22.5,27.3,27.5,28.9,29.1,29.2,31.3,31.5,46.3,50.3,76.0,125.2,129.9,130.9,133.1,133.4,167.2,177.0,210.6[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Source=Preclavulone lactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Chemical Synthesis=Preclavulone lactone I was synthesized from (S)-(-)-malic acid.[[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
|Metabolism=Preclavulone lactone may possibly be biosynthesized from preclavulon A. Clavulones may be biosynthesized from preclavulone lactones via clavulolactones by oxygenation at C-12, dehydration between C-7 and C-8, and esterification at C-1 and C-4. [[Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Watanabe_K:Iguchi_K:,Tetrahedron Lett.,1997,38,8319}}]]
}}
}}


{{Lipid/Footer}}
{{Lipid/Footer}}

Latest revision as of 05:43, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR8040
LipidMaps LMFA03120021
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20306CV01
Preclavulone lactone I
LBF20306CV01.png
Structural Information
4R- {cis-3- [ (1R,2S) -2- (cis-2-Octenyl) -5-oxo-3-cyclopentenyl] -1-propenyl} -4-butanolide
  • Preclavulone lactone I
  • 4R- {3Z- [ (1R,2S) -2- (2Z-Octenyl) -5-oxo-3-cyclopentenyl] -1-propenyl} -4-butanolide
Formula C20H28O3
Exact Mass 316.203844762
Average Mass 316.43452
SMILES C(CC=CC[C@@H]([C@@H]1CC=C[C@@H](C2)OC(=O)C2)C=CC(=O)1)CCC
Physicochemical Information
[ α ]D -168.0° IwashimaMet al.
Preclavulone lactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iwashima_M et al.
Preclavulone lactone I was synthesized from (S)-(-)-malic acid. Iwashima_M et al.
Preclavulone lactone may possibly be biosynthesized from preclavulon A. Clavulones may be biosynthesized from preclavulone lactones via clavulolactones by oxygenation at C-12, dehydration between C-7 and C-8, and esterification at C-1 and C-4. Iwashima_M et al.
Spectral Information
Mass Spectra HRFABMS m/z 316.2028 for C20}H_{28O3 (M+), calcd 316.2038. IwashimaMet al.
UV Spectra λ CH3CN&max 215 nm( ε 5740) IwashimaMet al.
IR Spectra ν 1775 and 1706cm-1 IwashimaMet al.
NMR Spectra 1H-NMR(500MHz,CDCl3) δ ppm0.89(3H,t,J=7.5Hz),1.2-1.4(6H,m),1.92(1H,dtd,8.4,9.7,12.9Hz),2.01(2H,brq,J=7.3Hz),2.11(1H,dt,J=2.3,5.9),2.27(1H,brtd,J=7.0,14.5Hz),2.32(1H,brtd,J=7.1,14.5Hz),2.41(1H,qd,J=6.6,12.9Hz),2.52(2H,m),2.57(2H,dd,J=6.6,9.7Hz),2.72(1H,qt,J=2.3,7.0Hz),5.27(1H,dt,J=6.6,8.4Hz),5.36(1H,brtd,J=7.1,10.8Hz),5.53(1H,dd,J=8.4,11.1Hz),5.54(1H,m),5.56(1H,td,J=7.2,11.1Hz),6.16(1H,dd,J=2.3,5.1Hz),7.60(1H,dd,J=2.3,5.8Hz). IwashimaMet al. 13C-NMR(125MHz,CDCl3) δ ppm14.0,22.5,27.3,27.5,28.9,29.1,29.2,31.3,31.5,46.3,50.3,76.0,125.2,129.9,130.9,133.1,133.4,167.2,177.0,210.6 IwashimaMet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20306CV01 See above. Iwashima_M et al. 1997


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