Chlorogenic-acid
Chlorogenic acid is an ester of caffeic acid and quinic acid. Chlorogenic acid is the major polyphenolic compound in coffee, isolated from the leaves and fruits of dicotyledonous plants.It is an intermediate metabolite in the biosynthesis of lignin. It has a role as a plant metabolite and a food component. It is a cinnamate ester and a tannin. Antioxidant.
General
Type : Natural, Antioxidant, Dihydroxyphenyl, Hydroxycinnamic-ester
Chemical_Nomenclature : (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Canonical SMILES : C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
InChI : InChI=1S\/C16H18O9\/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21\/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)\/b4-2+\/t11-,12-,14-,16+\/m1\/s1
InChIKey : CWVRJTMFETXNAD-JUHZACGLSA-N
Other name(s) : CGA || Chlorogenic acid || 3-O-Caffeoylquinic acid || 3-(3,4-Dihydroxycinnamoyl)quinic acid || 3-Caffeoylquinic acid || CHEBI:16112 || CHEBI:95271 || CHEMBL284616 || ZINC2138728 || DB12029
MW : 354.31
Formula : C16H18O9
CAS_number : 327-97-9
PubChem : 1794427
UniChem : CWVRJTMFETXNAD-JUHZACGLSA-N
Target
Structures : No structure
Families : Fungal_carboxylesterase_lipase, AlphaBeta_hydrolase, Tannase, FaeC, Hormone-sensitive_lipase_like, Plant_carboxylesterase, Monoglyceridelipase_lysophospholip
References (12)
| Title : The effect of chlorogenic acid, a potential botanical insecticide, on gene transcription and protein expression of carboxylesterases in the armyworm (Mythimna separata) - Lin_2023_Pestic.Biochem.Physiol_195_105575 |
| Author(s) : Lin DJ , Zhang YX , Fang Y , Gao SJ , Wang R , Wang JD |
| Ref : Pestic Biochem Physiol , 195 :105575 , 2023 |
| Abstract : |
| PubMedSearch : Lin_2023_Pestic.Biochem.Physiol_195_105575 |
| PubMedID: 37666601 |
| Title : A highly active esterase from Lactobacillus helveticus hydrolyzes chlorogenic acid in sunflower meal to prevent chlorogenic acid induced greening in sunflower protein isolates - Lo Verde_2022_Food.Res.Int_162_111996 |
| Author(s) : Lo Verde C , Pepra-Ameyaw NB , Drucker CT , Okumura TLS , Lyon KA , Muniz JC , Sermet CS , Were Senger L , Owens CP |
| Ref : Food Res Int , 162 :111996 , 2022 |
| Abstract : |
| PubMedSearch : Lo Verde_2022_Food.Res.Int_162_111996 |
| PubMedID: 36461298 |
| Gene_locus related to this paper: lache-u6f2k7 |
| Title : Discovery and characterization of tannase genes in plants: roles in hydrolysis of tannins - Dai_2020_New.Phytol_226_1104 |
| Author(s) : Dai X , Liu Y , Zhuang J , Yao S , Liu L , Jiang X , Zhou K , Wang Y , Xie D , Bennetzen JL , Gao L , Xia T |
| Ref : New Phytol , 226 :1104 , 2020 |
| Abstract : |
| PubMedSearch : Dai_2020_New.Phytol_226_1104 |
| PubMedID: 32061142 |
| Gene_locus related to this paper: camsi-a0a5b9g8c2 , jugre-JrTA , fraan-FaTA , vitvi-VvTA , citcl-CcTA , dioka-DkTA , camsi-CsTA |
| Title : A novel feruloyl esterase with high rosmarinic acid hydrolysis activity from Bacillus pumilus W3 - Liang_2020_Int.J.Biol.Macromol_161_525 |
| Author(s) : Liang W , Xiong T , Wang X , Deng H , Bai Y , Fan TP , Zheng X , Cai Y |
| Ref : Int J Biol Macromol , 161 :525 , 2020 |
| Abstract : |
| PubMedSearch : Liang_2020_Int.J.Biol.Macromol_161_525 |
| PubMedID: 32531366 |
| Gene_locus related to this paper: 9baci-BpFae12 |
| Title : Hydrolysis of chlorogenic acid in apple juice using a p-coumaryl esterase of Rhizoctonia solani - Siebert_2019_J.Sci.Food.Agric_99_6644 |
| Author(s) : Siebert M , Berger RG , Pfeiffer F |
| Ref : J Sci Food Agric , 99 :6644 , 2019 |
| Abstract : |
| PubMedSearch : Siebert_2019_J.Sci.Food.Agric_99_6644 |
| PubMedID: 31325326 |
| Title : Evaluation of butyrylcholinesterase inhibitory activity by chlorogenic acids and coffee extracts assed in ITC and docking simulation models - Budryn_2018_Food.Res.Int_109_268 |
| Author(s) : Budryn G , Grzelczyk J , Jaskiewicz A , Zyzelewicz D , Perez-Sanchez H , Ceron-Carrasco JP |
| Ref : Food Res Int , 109 :268 , 2018 |
| Abstract : |
| PubMedSearch : Budryn_2018_Food.Res.Int_109_268 |
| PubMedID: 29803450 |
| Title : Characterization of a feruloyl esterase from Aspergillus terreus facilitates the division of fungal enzymes from Carbohydrate Esterase family 1 of the carbohydrate-active enzymes (CAZy) database - Makela_2018_Microb.Biotechnol_11_869 |
| Author(s) : Makela MR , Dilokpimol A , Koskela SM , Kuuskeri J , de Vries RP , Hilden K |
| Ref : Microb Biotechnol , 11 :869 , 2018 |
| Abstract : |
| PubMedSearch : Makela_2018_Microb.Biotechnol_11_869 |
| PubMedID: 29697197 |
| Gene_locus related to this paper: asptn-q0ci40 |
| Title : A p-coumaroyl esterase from Rhizoctonia solani with a pronounced chlorogenic acid esterase activity - Nieter_2017_N.Biotechnol_37_153 |
| Author(s) : Nieter A , Kelle S , Linke D , Berger RG |
| Ref : N Biotechnol , 37 :153 , 2017 |
| Abstract : |
| PubMedSearch : Nieter_2017_N.Biotechnol_37_153 |
| PubMedID: 28159727 |
| Gene_locus related to this paper: 9agam-x8iza2 |
| Title : Characterization of Cinnamoyl Esterases from Different Lactobacilli and Bifidobacteria - Fritsch_2017_Curr.Microbiol_74_247 |
| Author(s) : Fritsch C , Jansch A , Ehrmann MA , Toelstede S , Vogel RF |
| Ref : Curr Microbiol , 74 :247 , 2017 |
| Abstract : |
| PubMedSearch : Fritsch_2017_Curr.Microbiol_74_247 |
| PubMedID: 27999938 |
| Gene_locus related to this paper: limf3-b2gdc2 , lache-u6f2k7 , bifa0-b8du06 , lacac-q5fi30 , lacga-q040s2 , lacpl-LP.2953 , lacre-q2bvr2 |
| Title : Role of bifidobacteria in the hydrolysis of chlorogenic acid - Raimondi_2015_Microbiolopen_4_41 |
| Author(s) : Raimondi S , Anighoro A , Quartieri A , Amaretti A , Tomas-Barberan FA , Rastelli G , Rossi M |
| Ref : Microbiologyopen , 4 :41 , 2015 |
| Abstract : |
| PubMedSearch : Raimondi_2015_Microbiolopen_4_41 |
| PubMedID: 25515139 |
| Gene_locus related to this paper: bifa0-b8du06 |
| Title : A Chlorogenic Acid Esterase with a Unique Substrate Specificity from Ustilago maydis - Nieter_2015_Appl.Environ.Microbiol_81_1679 |
| Author(s) : Nieter A , Haase-Aschoff P , Kelle S , Linke D , Krings U , Popper L , Berger RG |
| Ref : Applied Environmental Microbiology , 81 :1679 , 2015 |
| Abstract : |
| PubMedSearch : Nieter_2015_Appl.Environ.Microbiol_81_1679 |
| PubMedID: 25548041 |
| Gene_locus related to this paper: ustma-A0A0D1CFG4 |
| Title : Feruloyl esterases as a tool for the release of phenolic compounds from agro-industrial by-products - Benoit_2006_Carbohydr.Res_341_1820 |
| Author(s) : Benoit I , Navarro D , Marnet N , Rakotomanomana N , Lesage-Meessen L , Sigoillot JC , Asther M |
| Ref : Carbohydr Res , 341 :1820 , 2006 |
| Abstract : |
| PubMedSearch : Benoit_2006_Carbohydr.Res_341_1820 |
| PubMedID: 16697997 |
| Gene_locus related to this paper: aspng-faeb , aspni-FAEA |