| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2010-04-08 22:11:29 UTC |
|---|
| Update date | 2019-11-26 03:10:47 UTC |
|---|
| Primary ID | FDB014812 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | Capsidiol |
|---|
| Description | 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). |
|---|
| CAS Number | 37208-05-2 |
|---|
| Structure | |
|---|
| Synonyms | | Synonym | Source |
|---|
| Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C15H24O2 |
|---|
| IUPAC name | 4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol |
|---|
| InChI Identifier | 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 |
|---|
| InChI Key | BXXSHQYDJWZXPB-UHFFFAOYSA-N |
|---|
| Isomeric SMILES | CC1C(O)CC(O)C2=CCC(CC12C)C(C)=C |
|---|
| Average Molecular Weight | 236.3499 |
|---|
| Monoisotopic Molecular Weight | 236.177630012 |
|---|
| Classification |
|---|
| Description | 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Prenol lipids |
|---|
| Sub Class | Sesquiterpenoids |
|---|
| Direct Parent | Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids |
|---|
| Alternative Parents | |
|---|
| Substituents | - Eremophilane sesquiterpenoid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
|
|---|
| Molecular Framework | Aliphatic homopolycyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Ontology | No ontology term |
|---|
| Physico-Chemical Properties |
|---|
| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
|---|
| Physical state | Solid | |
|---|
| Physical Description | Not Available | |
|---|
| Mass Composition | C 76.23%; H 10.23%; O 13.54% | DFC |
|---|
| Melting Point | Mp 152-153° | DFC |
|---|
| Boiling Point | Not Available | |
|---|
| Experimental Water Solubility | Not Available | |
|---|
| Experimental logP | Not Available | |
|---|
| Experimental pKa | Not Available | |
|---|
| Isoelectric point | Not Available | |
|---|
| Charge | Not Available | |
|---|
| Optical Rotation | [a]22D +21 (c, 2.1 in CHCl3) | DFC |
|---|
| Spectroscopic UV Data | Not Available | |
|---|
| Density | Not Available | |
|---|
| Refractive Index | Not Available | |
|---|
|
|---|
| Spectra |
|---|
| Spectra | |
|---|
| EI-MS/GC-MS | Not Available |
|---|
| MS/MS | | Type | Description | Splash Key | View |
|---|
| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0190000000-4f408854a045f002ce8c | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gbi-2690000000-f2e94dce44ae9b9ac2df | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxr-9710000000-4e4ebb2003b289f81d11 | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-e1fa0089980b18e8a422 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00kr-0190000000-5cc78cd709d6e3a58815 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0i09-2960000000-4d5021b41dbcabf76b87 | 2016-08-03 | View Spectrum |
|
|---|
| NMR | Not Available |
|---|
| External Links |
|---|
| ChemSpider ID | 142224 |
|---|
| ChEMBL ID | Not Available |
|---|
| KEGG Compound ID | C09627 |
|---|
| Pubchem Compound ID | 161937 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | 28283 |
|---|
| Phenol-Explorer ID | Not Available |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB02352 |
|---|
| CRC / DFC (Dictionary of Food Compounds) ID | JWH26-L:JWH27-M |
|---|
| EAFUS ID | Not Available |
|---|
| Dr. Duke ID | CAPSIDIOL |
|---|
| BIGG ID | Not Available |
|---|
| KNApSAcK ID | C00003108 |
|---|
| HET ID | Not Available |
|---|
| Food Biomarker Ontology | Not Available |
|---|
| VMH ID | Not Available |
|---|
| Flavornet ID | Not Available |
|---|
| GoodScent ID | Not Available |
|---|
| SuperScent ID | Not Available |
|---|
| Wikipedia ID | Capsidiol |
|---|
| Phenol-Explorer Metabolite ID | Not Available |
|---|
| Duplicate IDS | Not Available |
|---|
| Old DFC IDS | Not Available |
|---|
| Associated Foods |
|---|
| Food | Content Range | Average | Reference |
|---|
| Food | | | Reference |
|---|
|
| Biological Effects and Interactions |
|---|
| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
|---|
| fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | | phytoalexin | 26115 | A toxin made by a plant that acts against an organism attacking it. | DUKE |
|
|---|
| Enzymes | Not Available |
|---|
| Pathways | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Biosynthesis | Not Available |
|---|
| Organoleptic Properties |
|---|
| Flavours | Not Available |
|---|
| Files |
|---|
| MSDS | Not Available |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| General Reference | Not Available |
|---|
| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
|
|---|
