Computed Regioselectivity and Conjectured Biological Activity of Ene Reactions of Singlet Oxygen with the Natural Product Hyperforin

© 2017 The American Society of Photobiology..

Hyperforin is a constituent of St. John's wort and coexists with the singlet oxygen sensitizer hypericin. Density functional theory, molecular mechanics and Connolly surface calculations show that accessibility in the singlet oxygen "ene" reaction favors the hyperforin "southwest" and "southeast" prenyl (2-methyl-2-butenyl) groups over the northern prenyl groups. While the southern part of hyperforin is initially more susceptible to oxidation, up to 4 "ene" reactions of singlet oxygen can take place. Computational results assist in predicting the fate of adjacent hydroperoxides in hyperforin, where the loss of hydrogen atoms may lead to the formation of a hydrotrioxide and a carbonyl instead of a Russell reaction.

Medienart:

E-Artikel

Erscheinungsjahr:

2017

Erschienen:

2017

Enthalten in:

Zur Gesamtaufnahme - volume:93

Enthalten in:

Photochemistry and photobiology - 93(2017), 2 vom: 15. März, Seite 626-631

Sprache:

Englisch

Beteiligte Personen:

Abramova, Inna [VerfasserIn]
Rudshteyn, Benjamin [VerfasserIn]
Liebman, Joel F [VerfasserIn]
Greer, Alexander [VerfasserIn]

Links:

Volltext

Themen:

17778-80-2
BBX060AN9V
Biological Products
DHD7FFG6YS
Hydrogen Peroxide
Hyperforin
Journal Article
Phloroglucinol
Photosensitizing Agents
RM741E34FP
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Singlet Oxygen
Terpenes

Anmerkungen:

Date Completed 11.10.2018

Date Revised 11.10.2018

published: Print-Electronic

Citation Status MEDLINE

doi:

10.1111/php.12706

funding:

Förderinstitution / Projekttitel:

PPN (Katalog-ID):

NLM267678878