LBF20406CV01: Difference between revisions

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


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|LipidBank=XPR8035
|LipidBank=XPR8035
|LipidMaps=LMFA03120016
|LipidMaps=LMFA03120016
|SysName= (R) -4-{ (1E,3E) -3- [ (S) -2-acetoxy-2- [ (Z) -2-octenyl ] -5-oxo-3-cyclopentenylidene ] -1-propenyl}-4-butanolide
|SysName=4R- { (trans-1,trans-3) -3- [2S-Acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -1-propenyl} -4-butanolide
|Common Name=&&clavulolactone II&&(R) -4-{ (1E,3E) -3- [ (S) -2-acetoxy-2- [ (Z) -2-octenyl ] -5-oxo-3-cyclopentenylidene ] -1-propenyl}-4-butanolide&&
|Common Name=&&Clavulolactone II&&4R- { (1E,3E) -3- [2S-Acetoxy-2- (2Z-octenyl-5-oxo-3-cyclopentenylidene] -1-propenyl} -4-butanolide&&
|Reflactive=[<FONT FACE="Symbol">a</FONT>]<SUB><FONT SIZE=-1>D</FONT></SUB> -25.6°(C 0.26, CHCl<SUB><FONT SIZE=-1>3</FONT></SUB>)[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|Optical=[ alpha ]_D  -25.6°(C 0.26, CHCl_3 )[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|Mass Spectra=EIMS m/z 372 (M<SUP><FONT SIZE=-1>+</FONT></SUP>). HREIMS m/z 372.1920 for C<SUB><FONT SIZE=-1>2</FONT></SUB><SUB><FONT SIZE=-1>2</FONT></SUB>H<SUB><FONT SIZE=-1>2</FONT></SUB><SUB><FONT SIZE=-1>8</FONT></SUB>O<SUB><FONT SIZE=-1>5</FONT></SUB>, calcd 372.1937.[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|Mass Spectra=EIMS m/z 372 (M^+ ). HREIMS m/z 372.1920 for C_{22}H_{28}O_5 , calcd 372.1937.[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|UV Spectra=<FONT FACE="Symbol">l</FONT><SUP><FONT SIZE=-1>E</FONT></SUP><SUP><FONT SIZE=-1>t</FONT></SUP><SUP><FONT SIZE=-1>O</FONT></SUP><SUP><FONT SIZE=-1>H</FONT></SUP><SUB><FONT SIZE=-1>m</FONT></SUB><SUB><FONT SIZE=-1>a</FONT></SUB><SUB><FONT SIZE=-1>x</FONT></SUB> 292 nm(<FONT FACE="Symbol">e</FONT>16500),231 nm(<FONT FACE="Symbol">e</FONT>12500)[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|UV Spectra= lambda ^{EtOH}_{max} 292 nm( epsilon 16500),231 nm( epsilon 12500)[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|IR Spectra=<FONT FACE="Symbol">n</FONT><SUP><FONT SIZE=-1>f</FONT></SUP><SUP><FONT SIZE=-1>i</FONT></SUP><SUP><FONT SIZE=-1>l</FONT></SUP><SUP><FONT SIZE=-1>m</FONT></SUP><SUB><FONT SIZE=-1>m</FONT></SUB><SUB><FONT SIZE=-1>a</FONT></SUB><SUB><FONT SIZE=-1>x</FONT></SUB>1778,1745, 1704, 1644, and 1231cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|IR Spectra= nu ^{film}_{max}1778,1745, 1704, 1644, and 1231cm^{-1}[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(400MHz,CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>)<FONT FACE="Symbol">d</FONT>ppm0.87(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,brq,J=6.3Hz),2.02(3H,s),2.04(1H,m),2.52(1H,m),2.55(2H,m),2.71(1H,brdd,J=8.1,14.2Hz),2.91(1H,brdd,J=7.1,14.2Hz),5.15(1H,m),5.15(1H,m),5.52(1H,m),6.17(1H,dd,J=4.9,14.7Hz),6.42(1H,d,J=6.1Hz),6.82(1H,ddd,J=1.5,12.0,14.7Hz),6.91(1H,brd,J=12.0Hz),7.50(1H,brd,J=6.1Hz).[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]] <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR(100MHz,CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>)<FONT FACE="Symbol">d</FONT>ppm14.0,21.2,22.5,27.4,27.7,28.2,29.0,31.5,35.8,78.6,85.2,121.0,124.9,128.9,135.06,135.14,137.2,140.8,158.0,169.3,176.2,193.3.[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|NMR Spectra=^1 H-NMR(400MHz,CDCl_3 ) delta ppm0.87(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,brq,J=6.3Hz),2.02(3H,s),2.04(1H,m),2.52(1H,m),2.55(2H,m),2.71(1H,brdd,J=8.1,14.2Hz),2.91(1H,brdd,J=7.1,14.2Hz),5.15(1H,m),5.15(1H,m),5.52(1H,m),6.17(1H,dd,J=4.9,14.7Hz),6.42(1H,d,J=6.1Hz),6.82(1H,ddd,J=1.5,12.0,14.7Hz),6.91(1H,brd,J=12.0Hz),7.50(1H,brd,J=6.1Hz).[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]] ^{13}C-NMR(100MHz,CDCl_3 ) delta ppm14.0,21.2,22.5,27.4,27.7,28.2,29.0,31.5,35.8,78.6,85.2,121.0,124.9,128.9,135.06,135.14,137.2,140.8,158.0,169.3,176.2,193.3.[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|Source=Clavulolactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.[[Reference:Iwashima_M:Okamoto_K:Konno_F:Iguchi_K:,J. Nat. Prod.,1999,62,352|{{RelationTable/GetFirstAuthor|Reference:Iwashima_M:Okamoto_K:Konno_F:Iguchi_K:,J. Nat. Prod.,1999,62,352}}]][[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|Chemical Synthesis=Clavulolactone II was converted from clavulone II.[[Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Iwashima_M:Watanabe_K:,J. Nat. Prod.,1995,58,790}}]]
|Metabolism=
}}
}}
{{Lipid/Footer}}

Latest revision as of 05:49, 21 October 2010

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Upper classes: LB LBF



Clavulolactone II
LBF20406CV01.png
Structural Information
4R- { (trans-1,trans-3) -3- [2S-Acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -1-propenyl} -4-butanolide
  • Clavulolactone II
  • 4R- { (1E,3E) -3- [2S-Acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -1-propenyl} -4-butanolide
Formula C22H28O5
Exact Mass 372.193674006
Average Mass 372.45472000000007
SMILES CC(=O)O[C@@](CC=CCCCCC)(C=2)C(C(C2)=O)=CC=C[C@H](O1)CCC(=O)1
Physicochemical Information
[ α ]D -25.6°(C 0.26, CHCl3) IguchiKet al.
Clavulolactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iwashima_M et al. Iguchi_K et al.
Clavulolactone II was converted from clavulone II. Iguchi_K et al.
Spectral Information
Mass Spectra EIMS m/z 372 (M+). HREIMS m/z 372.1920 for C22}H_{28O5, calcd 372.1937. IguchiKet al.
UV Spectra λ EtOH
max
     292 nm( ε 16500),231 nm( ε 12500) IguchiKet al.
IR Spectra ν film
max
    1778,1745, 1704, 1644, and 1231cm-1 IguchiKet al.
NMR Spectra 1H-NMR(400MHz,CDCl3) δ ppm0.87(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,brq,J=6.3Hz),2.02(3H,s),2.04(1H,m),2.52(1H,m),2.55(2H,m),2.71(1H,brdd,J=8.1,14.2Hz),2.91(1H,brdd,J=7.1,14.2Hz),5.15(1H,m),5.15(1H,m),5.52(1H,m),6.17(1H,dd,J=4.9,14.7Hz),6.42(1H,d,J=6.1Hz),6.82(1H,ddd,J=1.5,12.0,14.7Hz),6.91(1H,brd,J=12.0Hz),7.50(1H,brd,J=6.1Hz). IguchiKet al. 13C-NMR(100MHz,CDCl3) δ ppm14.0,21.2,22.5,27.4,27.7,28.2,29.0,31.5,35.8,78.6,85.2,121.0,124.9,128.9,135.06,135.14,137.2,140.8,158.0,169.3,176.2,193.3. IguchiKet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV01 See above. Iguchi_K et al. 1995
n.a. LBF20406CV01 See above. Iwashima_M et al. 1999