Cyclofarnesoids and methylhexanoids produced from ß-carotene in Phycomyces blakesleeanus (Record no. 50323)

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fixed length control field 02700nam a2200313Ia 4500
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control field MX-MdCICY
005 - DATE AND TIME OF LATEST TRANSACTION
control field 20250625160146.0
040 ## - CATALOGING SOURCE
Transcribing agency CICY
090 ## - LOCALLY ASSIGNED LC-TYPE CALL NUMBER (OCLC); LOCAL CALL NUMBER (RLIN)
Classification number (OCLC) (R) ; Classification number, CALL (RLIN) (NR) B-16149
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245 10 - TITLE STATEMENT
Title Cyclofarnesoids and methylhexanoids produced from ß-carotene in Phycomyces blakesleeanus
490 0# - SERIES STATEMENT
Volume/sequential designation PhytoChemistry, 124, p.38-45, 2016
520 3# - SUMMARY, ETC.
Summary, etc. The oxidative cleavage of ß-carotene in the Mucorales produces three fragments of 18, 15, and 7 carbons, respective heads of three families of apocarotenoids: The methylhexanoids, the trisporoids, and the cyclofarnesoids (named after their 1,6-cyclofarnesane skeleton). The apocarotenoids are easily recognized because they are absent in white mutants unable to produce ß-carotene. In cultures of Phycomyces blakesleeanus we detected thirty-two apocarotenoids by LC, UV absorbance, and MS. With additional IR and NMR we identified two methylhexanoids and the eight most abundant cyclofarnesoids. Four of them were previously-unknown natural compounds, including 4-dihydrocyclofarnesine S, the most abundant cyclofarnesoid in young cultures. We arranged the apocarotenoids of the Mucorales in a scheme that helps classifying and naming them and suggests possible metabolites and biosynthetic pathways. We propose specific biosynthetic pathways for cyclofarnesoids and methylhexanoids based on structural comparisons, the time course of appearance of individual compounds, and the bioconversion of ß-apo-12-carotenol, an early precursor, to three more oxygenated cyclofarnesoids by the white mutants. Some of the reactions occur spontaneously in the increasingly acidic culture media. Mating increased the contents of methylhexanoids and cyclofarnesoids by ca. threefold in young cultures and ca. twelvefold in old ones (five days); cyclofarnesine S, the most abundant cyclofarnesoid in old cultures, increased over one hundredfold. We found no differences between the sexes and no activity as sexual pheromones, but we suggest that methylhexanoids and cyclofarnesoids could mediate species-specific physiology and behavior.
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element APOCAROTENOIDS
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element BIOCONVERSION
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element CYCLOFARNESOIDS
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element METHYLHEXANOIDS
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element MUCORALES
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element PHYCOMYCES BLAKESLEEANUS
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element PHYCOMYCETACEAE
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element B-CAROTENE
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Alcalde, E.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Medina, H.R.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Herrador, M.M.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Barrero, A.F.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Cerdá-Olmedo, E.
856 40 - ELECTRONIC LOCATION AND ACCESS
Uniform Resource Identifier <a href="https://drive.google.com/file/d/1MBz90Kut2qXtNOQaqHXOQ06bW8_l24t4/view?usp=drivesdk">https://drive.google.com/file/d/1MBz90Kut2qXtNOQaqHXOQ06bW8_l24t4/view?usp=drivesdk</a>
Public note Para ver el documento ingresa a Google con tu cuenta: @cicy.edu.mx
942 ## - ADDED ENTRY ELEMENTS (KOHA)
Source of classification or shelving scheme Clasificación local
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  Clasificación local     Ref1 CICY CICY Documento préstamo interbibliotecario 25.06.2025   B-16149 25.06.2025 25.06.2025 Documentos solicitados