Vibralactone is isolated from the basidiomycete fungus Boreostereum vibrans as one of the strongest lipase inhibitors. Its unusual beta-lactone-fused bicycle is derived from an aryl ring moiety via an oxidative ring-expansion prior to an intramolecular cyclization. VibC 9agam-VibC performs the carbocycle formation of an oxepinone to a fused bicyclic beta-lactone
Type : Natural,Lactone,Lipase inhibitor
Chemical_Nomenclature : (1R,5S)-3-(hydroxymethyl)-1-(3-methylbut-2-enyl)-6-oxabicyclo[3.2.0]hept-2-en-7-one
Canonical SMILES : CC(=CCC12C=C(CC1OC2=O)CO)C
InChI : InChI=1S\/C12H16O3\/c1-8(2)3-4-12-6-9(7-13)5-10(12)15-11(12)14\/h3,6,10,13H,4-5,7H2,1-2H3\/t10-,12+\/m0\/s1
InChIKey : UGNVBODTSYDQPO-CMPLNLGQSA-N
Other name(s) : CHEMBL3928292
MW : 208.25
Formula : C12H16O3
CAS_number :
PubChem : 16095274
UniChem : UGNVBODTSYDQPO-CMPLNLGQSA-N
IUPHAR :
Wikipedia :
Families :
Stucture :
Protein :
Title : Functional characterization of Vib-PT, an aromatic prenyltransferase involved in the biosynthesis of vibralactone from Stereum vibrans - Bai_2020_Appl.Environ.Microbiol__ |
Author(s) : Bai N , Li GH , Luo SL , Du L , Hu QY , Xu HK , Zhang KQ , Zhao PJ |
Ref : Applied Environmental Microbiology , : , 2020 |
Abstract : Bai_2020_Appl.Environ.Microbiol__ |
ESTHER : Bai_2020_Appl.Environ.Microbiol__ |
PubMedSearch : Bai_2020_Appl.Environ.Microbiol__ |
PubMedID: 32144102 |
Title : A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic beta-Lactone in Vibralactone - Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209 |
Author(s) : Feng KN , Yang YL , Xu YX , Zhang Y , Feng T , Huang SX , Liu JK , Zeng Y |
Ref : Angew Chem Int Ed Engl , 59 :7209 , 2020 |
Abstract : Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209 |
ESTHER : Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209 |
PubMedSearch : Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209 |
PubMedID: 32050043 |
Gene_locus related to this paper: 9agam-VibC , stehr-Sh.112560 |
Title : A Concise Total Synthesis of (+\/-)-Vibralactone - Nistanaki_2019_Angew.Chem.Int.Ed.Engl_58_1724 |
Author(s) : Nistanaki SK , Boralsky LA , Pan RD , Nelson HM |
Ref : Angew Chem Int Ed Engl , 58 :1724 , 2019 |
Abstract : Nistanaki_2019_Angew.Chem.Int.Ed.Engl_58_1724 |
ESTHER : Nistanaki_2019_Angew.Chem.Int.Ed.Engl_58_1724 |
PubMedSearch : Nistanaki_2019_Angew.Chem.Int.Ed.Engl_58_1724 |
PubMedID: 30548983 |
Title : Novel Natural Oximes and Oxime Esters with a Vibralactone Backbone from the Basidiomycete Boreostereum vibrans - Chen_2016_ChemistryOpen_5_142 |
Author(s) : Chen HP , Zhao ZZ , Li ZH , Dong ZJ , Wei K , Bai X , Zhang L , Wen CN , Feng T , Liu JK |
Ref : ChemistryOpen , 5 :142 , 2016 |
Abstract : Chen_2016_ChemistryOpen_5_142 |
ESTHER : Chen_2016_ChemistryOpen_5_142 |
PubMedSearch : Chen_2016_ChemistryOpen_5_142 |
PubMedID: 27308232 |
Title : Omuralide and vibralactone: differences in the proteasome- beta-lactone-gamma-lactam binding scaffold alter target preferences - List_2014_Angew.Chem.Int.Ed.Engl_53_571 |
Author(s) : List A , Zeiler E , Gallastegui N , Rusch M , Hedberg C , Sieber SA , Groll M |
Ref : Angew Chem Int Ed Engl , 53 :571 , 2014 |
Abstract : List_2014_Angew.Chem.Int.Ed.Engl_53_571 |
ESTHER : List_2014_Angew.Chem.Int.Ed.Engl_53_571 |
PubMedSearch : List_2014_Angew.Chem.Int.Ed.Engl_53_571 |
PubMedID: 24285701 |
Title : Three new vibralactone-related compounds from cultures of Basidiomycete Boreostereum vibrans - Wang_2014_J.Asian.Nat.Prod.Res_16_447 |
Author(s) : Wang GQ , Wei K , Zhang L , Li ZH , Wang QA , Liu JK |
Ref : J Asian Nat Prod Res , 16 :447 , 2014 |
Abstract : Wang_2014_J.Asian.Nat.Prod.Res_16_447 |
ESTHER : Wang_2014_J.Asian.Nat.Prod.Res_16_447 |
PubMedSearch : Wang_2014_J.Asian.Nat.Prod.Res_16_447 |
PubMedID: 24684503 |
Title : Derivatives of vibralactone from cultures of the basidiomycete Boreostereum vibrans - Jiang_2008_Chem.Pharm.Bull.(Tokyo)_56_1286 |
Author(s) : Jiang MY , Wang F , Yang XL , Fang LZ , Dong ZJ , Zhu HJ , Liu JK |
Ref : Chem Pharm Bull (Tokyo) , 56 :1286 , 2008 |
Abstract : Jiang_2008_Chem.Pharm.Bull.(Tokyo)_56_1286 |
ESTHER : Jiang_2008_Chem.Pharm.Bull.(Tokyo)_56_1286 |
PubMedSearch : Jiang_2008_Chem.Pharm.Bull.(Tokyo)_56_1286 |
PubMedID: 18758102 |
Title : Vibralactone: a lipase inhibitor with an unusual fused beta-lactone produced by cultures of the basidiomycete Boreostereum vibrans - Liu_2006_Org.Lett_8_5749 |
Author(s) : Liu DZ , Wang F , Liao TG , Tang JG , Steglich W , Zhu HJ , Liu JK |
Ref : Org Lett , 8 :5749 , 2006 |
Abstract : Liu_2006_Org.Lett_8_5749 |
ESTHER : Liu_2006_Org.Lett_8_5749 |
PubMedSearch : Liu_2006_Org.Lett_8_5749 |
PubMedID: 17134263 |