Formation of Previously Undescribed Δ7-Phytosterol Oxidation Products and Tocopherylquinone Adducts in Pumpkin Seed Oil during Roasting, Screw-Pressing, and Simulated Culinary Processing at Elevated Temperatures
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F26784246%3A_____%2F22%3AN0000056" target="_blank" >RIV/26784246:_____/22:N0000056 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22330/22:43924010 RIV/60076658:12220/22:43905895
Result on the web
<a href="https://pubs.acs.org/doi/10.1021/acs.jafc.2c03292" target="_blank" >https://pubs.acs.org/doi/10.1021/acs.jafc.2c03292</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.jafc.2c03292" target="_blank" >10.1021/acs.jafc.2c03292</a>
Alternative languages
Result language
angličtina
Original language name
Formation of Previously Undescribed Δ7-Phytosterol Oxidation Products and Tocopherylquinone Adducts in Pumpkin Seed Oil during Roasting, Screw-Pressing, and Simulated Culinary Processing at Elevated Temperatures
Original language description
The influence of pumpkin seed roasting conditions (110–140 °C) and screw-pressing on the formation of previously undescribed Δ7-phytosterol oxidation products and tocopherylquinone adducts with nucleophilic phosphatidylethanolamine species was investigated. The roasting process of pumpkin seed paste at a temperature above 120 °C for 30 min considerably enhanced the formation of Δ7-oxysterols. Targeted analysis [electron impact mass spectrometry (MS), 1D-nuclear magnetic resonance] led to the identification of five novel markers of pumpkin paste roasting, among which (3β,5α,22E,24S)-stigmasta-7,22-dien-6-one-3-ol (6-oxo-α-spinasterol), stereoisomers of (3β,5α,22E)-7,8-epoxystigmast-22-en-3-ol (7,8-epoxy-α-spinasterol), and (3β,5α)-22,23-epoxystigmast-7-en-3-ol (7,8-epoxy-α-spinasterol) were reported in edible oils for the first time. Simulated culinary processing provided novel stereoisomers of (3β,5α,22E)-stigmasta-7,22-dien-3,6-diol, unusual (3β,5α,22E)-stigmasta-7,22-dien-6,15-dione-3-ol, and (5α,22E)-stigmasta-7,22-dien-3-one accompanied by minor stereoisomers of (3β,5α)-7,8;22,23-diepoxystigmastan-3-ol. Moreover, a clear relationship between the pumpkin seed oil stability index and synergistic effect of glycerophospholipids with present tocochromanols was found. High-resolution atmospheric pressure chemical ionization–MS experiments clearly demonstrated the formation of various γ-tocopherylquinone adducts with primary amines, namely, octylamine. The mitigation strategy of potentially detrimental oxysterols from pumpkin seed oil included optimization of processing parameters while maintaining the formation of desirable sensory-active compounds.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/QK1910302" target="_blank" >QK1910302: Processing of waste products obtained during oil extraction from oil crop seeds on new commodities with nutritional and health benefits</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Agricultural and Food Chemistry
ISSN
0021-8561
e-ISSN
1520-5118
Volume of the periodical
70
Issue of the periodical within the volume
37
Country of publishing house
US - UNITED STATES
Number of pages
14
Pages from-to
11689–11703
UT code for WoS article
000877010700001
EID of the result in the Scopus database
2-s2.0-85138459178