Wheldone revisited: structure revision via DFT-GIAO chemical shift calculations, 1,1-HD-ADEQUATE NMR spectroscopy, and X‑ray crystallography studies

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F24%3A00597766" target="_blank" >RIV/68378271:_____/24:00597766 - isvavai.cz</a>

Výsledek na webu

<a href="https://hdl.handle.net/11104/0355621" target="_blank" >https://hdl.handle.net/11104/0355621</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.jnatprod.4c00649" target="_blank" >10.1021/acs.jnatprod.4c00649</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Wheldone revisited: structure revision via DFT-GIAO chemical shift calculations, 1,1-HD-ADEQUATE NMR spectroscopy, and X‑ray crystallography studies

Popis výsledku v původním jazyce

Wheldone is a fungal metabolite isolated from the coculture of Aspergillus fischeri and Xylaria flabelliformis, displaying cytotoxic activity against breast, melanoma, and ovarian cancer cell lines. Initially, its structure was characterized as an unusual 5-methylbicyclo[5.4.0]undeca-3,5-diene scaffold with a 2-hydroxy-1-propanone side chain and a 3-(2-(1-hydroxyethyl)-2-methyl-2,5-dihydrofuran-3-yl)acrylic acid moiety. Upon further examination, minor inconsistencies in the data suggested the need for the structure to be revisited. Thus, the structure of wheldone has been revised using an orthogonal experimental-computational approach, which combines 1,1-HD-ADEQUATE NMR experiments, DFT-GIAO chemical shift calculations, and single-crystal X-ray diffraction (SCXRD) analysis of a semisynthetic p-bromobenzylamide derivative, formed via a Steglich-type reaction.

Název v anglickém jazyce

Wheldone revisited: structure revision via DFT-GIAO chemical shift calculations, 1,1-HD-ADEQUATE NMR spectroscopy, and X‑ray crystallography studies

Popis výsledku anglicky

Wheldone is a fungal metabolite isolated from the coculture of Aspergillus fischeri and Xylaria flabelliformis, displaying cytotoxic activity against breast, melanoma, and ovarian cancer cell lines. Initially, its structure was characterized as an unusual 5-methylbicyclo[5.4.0]undeca-3,5-diene scaffold with a 2-hydroxy-1-propanone side chain and a 3-(2-(1-hydroxyethyl)-2-methyl-2,5-dihydrofuran-3-yl)acrylic acid moiety. Upon further examination, minor inconsistencies in the data suggested the need for the structure to be revisited. Thus, the structure of wheldone has been revised using an orthogonal experimental-computational approach, which combines 1,1-HD-ADEQUATE NMR experiments, DFT-GIAO chemical shift calculations, and single-crystal X-ray diffraction (SCXRD) analysis of a semisynthetic p-bromobenzylamide derivative, formed via a Steglich-type reaction.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Natural Products

ISSN

0163-3864

e-ISSN

1520-6025

Svazek periodika

87

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

2095-2100

Kód UT WoS článku

001275484400001

EID výsledku v databázi Scopus

2-s2.0-85199264286