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519:-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.
24:
459:. In pepper or tobacco fields, the oomycete is soil-borne and initially infects roots, collars and lower leaves. Sporangia are moved within fields by contact with field equipment, clothing, gloves, tools etc. and initial infections spread
118:
507:. 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-
585:
Maldonado-Bonilla LD, Betancourt-Jiménez M, Lozoya-Gloria E (2008) "Local and systemic gene expression of sesquiterpene phytoalexin biosynthetic enzymes in plant leaves".
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near the site of infection and a long term response involving the production of hormones and an increase in enzymes to biosynthesize phytoalexins such as capsidiol.
511:
synthase (TEAS), alone and also complexed with two FPP analogues have been reported and analyzed to suggest the following mechanism of biosynthesis. The
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463:
through splashing of water from irrigation or rain. Initial responses to infection include production of radical oxygen species, including H
687:
Starks C.M.; Back K.; Chappell J.; Noel J.P.; (1997) Structural Basis for Cyclic
Terpene Biosynthesis by Tobacco 5-Epi-Aristolochene Synthase.
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alone has been shown to induce capsidiol production. Capsidiol production is then increased in response to radical oxygen species production.
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are also characterized as a part of a two pronged response to infection which involves a short term response consisting of production of
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535:
have been purified and their crystal structures have been reported suggesting different stereochemistries for aristolochene.
311:
InChI=1/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/t10-,11-,13-,14-,15-/m1/s1
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Arreola-Cortes A.; Castro-Mercado E.; Lozoya-Gloria E.; Garcia-Pineda E. (2007). "Capsidiol production in pepper fruits (
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422:, a class of low molecular weight plant secondary metabolites that are produced during infection.
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in response to fungal infection. Capsidiol is categorized under the broad term of
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enzyme 5-epi-aristolochene synthase produces the diastereoisomeric product by way of (
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520:
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423:
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71:)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol
419:
618:
Uchida J.Y.; Aragaki M. (1980). "Chemical
Stimulation of oospore formation in
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Hammerschmidt R. (1999). "Phytoalexins: What have we learned after 60 years?"
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549:
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Capsidiol is a bicyclic terpene that is biosynthetically derived from the
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23:
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Dewick P.M. (2002)."The biosynthesis of C5-C25 terpenoid compounds".
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Except where otherwise noted, data are given for materials in their
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s enzyme appears to synthesizes aristolochene by way of (
503:-farnesyl cation is first created by the loss of
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453:after infection by the oomycete water-mold
438:Capsidiol is produced in the pepper fruit
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410:compound that accumulates in tobacco
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314:Key: BXXSHQYDJWZXPB-OKNSCYNVBL
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40:4α-Eremophila-9,11-diene-1β,3α-diol
471:. Exogenous treatment with H
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22:
388:(at 25 °C , 100 kPa).
335:O2/C1=C/C(\C(=C)C)C1((C)(O)C2)C
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731:Terpenes found in Solanaceae
647:Physiol. Mol. Plant Pathol.
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378:236.35 g/mol
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587:European J. Plant Path.
434:Mechanism of production
603:Anni. Rev. Phytopathol
538:Penicillium roqueforti
526:Penicillium roqueforti
523:synthase enzymes from
493:farnesyl pyrophosphate
47:Systematic IUPAC name
456:Phytophthora capsici
620:Phytophthoracapsici
131:Beilstein Reference
18:
489:mevalonate pathway
392:Infobox references
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555:Nicotiana tabacum
532:Nicotiana tabacum
495:(FPP). The
450:Nicotiana tabacum
414:and chili pepper
412:Nicotiana tabacum
400:Chemical compound
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267:CompTox Dashboard
119:Interactive image
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711:Phytoalexins
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629:, 1103-1108.
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78:Identifiers
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694:, 1815-1820
420:phytoalexin
344:Properties
189:100.247.709
151:CHEBI:28283
705:Categories
609:, 285-306.
592:, 439-449.
570:References
564:germacrene
550:germacrene
374:Molar mass
255:1O869T5P54
162:ChemSpider
106:3D model (
95:37208-05-2
85:CAS Number
37:IUPAC name
17:Capsidiol
624:Mycologia
461:zoospores
408:terpenoid
404:Capsidiol
721:Decalins
675:, 97-130
652:: 69-76.
136:2331764
689:Science
650:70(1-3)
446:tobacco
368:
222:PubChem
590:121(4)
328:SMILES
235:161937
210:C09627
171:142224
31:Names
716:Diols
542:'
406:is a
303:InChI
142:ChEBI
108:JSmol
491:via
246:UNII
201:KEGG
692:277
622:".
566:A.
444:or
272:EPA
225:CID
63:,4a
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529:,
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560:R
546:S
517:E
515:,
513:E
501:E
499:,
497:E
477:2
475:O
473:2
469:2
467:O
465:2
366:2
364:O
360:H
356:C
274:)
270:(
110:)
69:R
65:R
61:S
57:R
53:R
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