Vibralactone

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

General

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

Target

References (9)

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
PubMedID: 32050043
Gene_locus related to this paper: 9agam-VibC , stehr-Sh.112560

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
PubMedID: 32144102

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
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
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
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
PubMedID: 24684503

Title : Elucidating the biosynthetic pathway for vibralactone: a pancreatic lipase inhibitor with a fused bicyclic beta-lactone -
Author(s) : Zhao PJ , Yang YL , Du L , Liu JK , Zeng Y
Ref : Angew Chem Int Ed Engl , 52 :2298 , 2013
PubMedID: 23339115

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
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
PubMedID: 17134263