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. inhibit pancreatic lipase with an IC50 of 0.4 microg/mL
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
Families : Vibralactone ligand of proteins in family
Pancreatic_lipase
Protein :
human-PNLIP
References (33)
| Title : Synthetic study toward vibralactone - Shi_2025_Beilstein.J.Org.Chem_21_2376 |
| Author(s) : Shi L , Song J , Li Y , Li JC , Li S , Ren L , Liu ZY , Hao HD |
| Ref : Beilstein J Org Chem , 21 :2376 , 2025 |
| Abstract : |
| PubMedSearch : Shi_2025_Beilstein.J.Org.Chem_21_2376 |
| PubMedID: 41220833 |
| Gene_locus related to this paper: human-PNLIP |
| Title : Synthetic study toward vibralactone - Shi_2025_Beilstein.J.Org.Chem_21_2376 |
| Author(s) : Shi L , Song J , Li Y , Li JC , Li S , Ren L , Liu ZY , Hao HD |
| Ref : Beilstein J Org Chem , 21 :2376 , 2025 |
| Abstract : |
| PubMedSearch : Shi_2025_Beilstein.J.Org.Chem_21_2376 |
| PubMedID: 41220833 |
| Gene_locus related to this paper: human-PNLIP |
| Title : Synthetic study toward vibralactone - Shi_2025_Beilstein.J.Org.Chem_21_2376 |
| Author(s) : Shi L , Song J , Li Y , Li JC , Li S , Ren L , Liu ZY , Hao HD |
| Ref : Beilstein J Org Chem , 21 :2376 , 2025 |
| Abstract : |
| PubMedSearch : Shi_2025_Beilstein.J.Org.Chem_21_2376 |
| PubMedID: 41220833 |
| Gene_locus related to this paper: human-PNLIP |
| 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 : |
| PubMedSearch : Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209 |
| 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 |
| Abstract : |
| 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 : |
| PubMedSearch : Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209 |
| 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 |
| Abstract : |
| PubMedSearch : Bai_2020_Appl.Environ.Microbiol__ |
| PubMedID: 32144102 |
| 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 : |
| 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 : |
| 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 : |
| PubMedSearch : Nistanaki_2019_Angew.Chem.Int.Ed.Engl_58_1724 |
| PubMedID: 30548983 |
| 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 : |
| PubMedSearch : Nistanaki_2019_Angew.Chem.Int.Ed.Engl_58_1724 |
| PubMedID: 30548983 |
| 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 : |
| 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 : |
| PubMedSearch : Chen_2016_ChemistryOpen_5_142 |
| PubMedID: 27308232 |
| 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 : |
| PubMedSearch : Chen_2016_ChemistryOpen_5_142 |
| PubMedID: 27308232 |
| 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 : |
| PubMedSearch : Chen_2016_ChemistryOpen_5_142 |
| PubMedID: 27308232 |
| Title : Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents - Wei_2015_Nat.Prod.Bioprospect_5_129 |
| Author(s) : Wei K , Wang GQ , Bai X , Niu YF , Chen HP , Wen CN , Li ZH , Dong ZJ , Zuo ZL , Xiong WY , Liu JK |
| Ref : Nat Prod Bioprospect , 5 :129 , 2015 |
| Abstract : |
| PubMedSearch : Wei_2015_Nat.Prod.Bioprospect_5_129 |
| PubMedID: 26085282 |
| Gene_locus related to this paper: human-PNLIP |
| Title : Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents - Wei_2015_Nat.Prod.Bioprospect_5_129 |
| Author(s) : Wei K , Wang GQ , Bai X , Niu YF , Chen HP , Wen CN , Li ZH , Dong ZJ , Zuo ZL , Xiong WY , Liu JK |
| Ref : Nat Prod Bioprospect , 5 :129 , 2015 |
| Abstract : |
| PubMedSearch : Wei_2015_Nat.Prod.Bioprospect_5_129 |
| PubMedID: 26085282 |
| Gene_locus related to this paper: human-PNLIP |
| Title : Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents - Wei_2015_Nat.Prod.Bioprospect_5_129 |
| Author(s) : Wei K , Wang GQ , Bai X , Niu YF , Chen HP , Wen CN , Li ZH , Dong ZJ , Zuo ZL , Xiong WY , Liu JK |
| Ref : Nat Prod Bioprospect , 5 :129 , 2015 |
| Abstract : |
| PubMedSearch : Wei_2015_Nat.Prod.Bioprospect_5_129 |
| PubMedID: 26085282 |
| Gene_locus related to this paper: human-PNLIP |
| 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 : |
| 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 : |
| PubMedSearch : Wang_2014_J.Asian.Nat.Prod.Res_16_447 |
| PubMedID: 24684503 |
| 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 : |
| 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 : |
| PubMedSearch : Wang_2014_J.Asian.Nat.Prod.Res_16_447 |
| PubMedID: 24684503 |
| 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 : |
| 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 : |
| 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 : |
| PubMedSearch : Jiang_2008_Chem.Pharm.Bull.(Tokyo)_56_1286 |
| PubMedID: 18758102 |
| 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 : |
| PubMedSearch : Jiang_2008_Chem.Pharm.Bull.(Tokyo)_56_1286 |
| PubMedID: 18758102 |
| 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 : |
| 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 : |
| PubMedSearch : Liu_2006_Org.Lett_8_5749 |
| PubMedID: 17134263 |
| Gene_locus related to this paper: human-PNLIP |
| 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 : |
| PubMedSearch : Liu_2006_Org.Lett_8_5749 |
| PubMedID: 17134263 |
| Gene_locus related to this paper: human-PNLIP |
| 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 : |
| PubMedSearch : Liu_2006_Org.Lett_8_5749 |
| PubMedID: 17134263 |
| Gene_locus related to this paper: human-PNLIP |