1.0 2010-04-08 22:11:29 UTC 2019-11-26 03:10:47 UTC FDB014812 Capsidiol Phytoalexin of infected sweet pepper fruits (Capsicum annuum) Capsidiol is a bicyclic terpene that is biosynthetically derived from the mevalonate pathway via farnesyl pyrophosphate (FPP). The E,E-farnesyl cation is first created by the loss of pyrophosphate. Kinetic studies have indicated that turnover appears to be limited by a chemical step after the initial loss of pyrophosphate. Crystal structures of recombinant tobacco 5-epi-aristolochene synthase (TEAS), alone and also complexed with two FPP analogues have been reported and analyzed to suggest the following mechanism of biosynthesis. The E,E-farnesyl cation undergoes cyclization to form the germacryl cation. The second ring closure gives the bicyclic eudesmyl cation, which is stabilized by various dipole interactions, then H-2 migrates to C-3 producing a tertiary cation at C-2 (farnesyl numbering). Production of 5-epi-aristolochene from FPP by 5-epi-aristolochene 3-hydroxylase, a sesquiterpene cyclase, is considered the critical step in capsidiol biosynthesis. Aristolochene synthase enzymes from Penicillium roqueforti, Nicotiana tabacum have been purified and their crystal structures have been reported suggesting different steriochemistries for aristolochene. Penicillium roqueforti's enzyme appears to synthesizes aristolochene by way of (S)-germacrene A , however, the Nicotiana tabacum enzyme 5-epi-aristolochene synthase produces the diastereoisomeric product by way of (R)-germacrene A.; Capsidiol is a phytoalexin, a natural fungicide present in pepper. (PMID: 10335386); Capsidiol shows bacteriostatic properties in vitro against Helicobacter pylori with a minimum inhibitory concentration (MIC) of 200 microg/mL. (PMID: 17002415); Capsidiol is a bicyclic, dihydroxylated sesquiterpene produced by several solanaceous species in response to a variety of environmental stimuli. It is the primary antimicrobial compound produced by Nicotiana tabacum in response to fungal elicitation, and it is formed via the isoprenoid pathway from 5-epi-aristolochene. (PMID: 11556809); Capsidiol is a terpenoid compound that accumulates in tobacco Nicotiana tabacum and chili pepper Capsicum annuum in response to fungal infection. Capsidiol is categorized under the broad term of phytoalexin, a class of low molecular weight plant secondary metabolites that are produced during infection. Phytoalexins are also characterized as a part of a two pronged response to infection which involves a short term response consisting of production of free radicals near the site of infection and a long term response involving the production of hormones and an increase in enzymes to biosynthesize phyoalexins such as capsidiol. Capsidiol is found in many foods, some of which are orange bell pepper, red bell pepper, green vegetables, and pepper (c. annuum). (1R,3R,4S,4AR,6R)-6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol 1beta,3alpha,4betaH-eremophila-9,11-diene-1,3-diol Capsidiol C15H24O2 236.3499 236.177630012 4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol 4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,5,6,7-hexahydro-1H-naphthalene-1,3-diol 37208-05-2 CC1C(O)CC(O)C2=CCC(CC12C)C(C)=C InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3 BXXSHQYDJWZXPB-UHFFFAOYSA-N belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Cyclic alcohol Eremophilane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol a sesquiterpenoid Solid logp 2.70 ALOGPS logs -2.45 ALOGPS solubility 8.47e-01 g/l ALOGPS melting_point Mp 152-153° logp 1.91 ChemAxon pka_strongest_acidic 14.35 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol ChemAxon average_mass 236.3499 ChemAxon mono_mass 236.177630012 ChemAxon smiles CC1C(O)CC(O)C2=CCC(CC12C)C(C)=C ChemAxon formula C15H24O2 ChemAxon inchi InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3 ChemAxon inchikey BXXSHQYDJWZXPB-UHFFFAOYSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 70.52 ChemAxon polarizability 27.98 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 57246 Specdb::MsMs 57247 Specdb::MsMs 57248 Specdb::MsMs 112866 Specdb::MsMs 112867 Specdb::MsMs 112868 HMDB02352 28283 #<Reference:0x0000561271bc0708> #<Reference:0x0000561271bc0500> #<Reference:0x0000561271bc02f8> Green bell pepper Type 1 specific Capsicum annuum 4072 2.9 2.9 2.9 mg/100 g Green vegetables Unknown generic Italian sweet red pepper Type 1 specific Capsicum annuum 4072 Orange bell pepper Type 1 specific Capsicum annuum 4072 2.9 2.9 2.9 mg/100 g Pepper Type 1 specific Capsicum annuum 4072 2.9 2.9 2.9 mg/100 g Pepper (C. frutescens) Type 1 specific Capsicum annuum var. annuum 40321 Red bell pepper Type 1 specific Capsicum annuum 4072 2.9 2.9 2.9 mg/100 g Yellow bell pepper Type 1 specific Capsicum annuum 4072 2.9 2.9 2.9 mg/100 g fungicide 940 A substance used to destroy fungal pests. pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. phytoalexin 1223 A toxin made by a plant that acts against an organism attacking it.