Prenylated acetophenones from the roots of Calendula officinalis and their anti-inflammatory activity.

Biosci Biotechnol Biochem

Graduate School of Integrated Pharmaceutical and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan.

Published: June 2023

Calendula officinalis is a medicinal plant in the Asteraceae family, and it has a broad range of biological activities. In this study, we focused on the roots of C. officinalis, which have remarkable anti-inflammatory properties. By using a bioassay-guided fractionation approach, prenylated acetophenones 1 and 2-of which 1 was previously unknown-were isolated, and their structures were determined by spectroscopic analysis. Both compounds decreased lipopolysaccharide-stimulated NO production in J774.1 cells. This study could lead to the use of the Calendula roots as a natural source of inflammatory mediators.

Download full-text PDF

Source
http://dx.doi.org/10.1093/bbb/zbad042DOI Listing

Publication Analysis

Top Keywords

prenylated acetophenones
8
calendula officinalis
8
acetophenones roots
4
roots calendula
4
officinalis anti-inflammatory
4
anti-inflammatory activity
4
activity calendula
4
officinalis medicinal
4
medicinal plant
4
plant asteraceae
4

Similar Publications

Four new prenylated acetophenone derivatives, including one acetophenone dimer [acronyrone D (1)] and three acetophenone monomers [acronyrones E-G (2-4)], along with seven known analogues (5-11) were obtained from the leaves of Acronychia pedunculata. Their structures and absolute configurations were established by analysis of HRMS and NMR data, single crystal X-ray diffraction studies and quantum chemical calculations. In addition, the isolates were tested for their anti-proliferative acivity against HCT-116, RKO and SW480 cancer cell lines.

View Article and Find Full Text PDF

We report an improved synthetic protocol for hydroxy methyl-derived polysubstituted furans employing Bi(III)-catalyzed dehydrative cycloisomerization of α-hydroxy oxetanyl ketones. This procedure provides rapid access (within 5 min) to highly substituted furans with exceptional functional group diversity, excellent yields, generality, scalability, and operationally simple reaction conditions. Further, it demonstrated the utility of this method in the first enantioselective total synthesis of furyl-hydroquinone-derived biologically potent natural products shikonofurans J, D, E, and C in seven linear steps, starting from readily available building blocks of 2,5-dihydroxy acetophenone and 3-oxetanone employing chiral-phosphoric acid (TRIP)-catalyzed asymmetric prenylation as a key step to induce the chirality.

View Article and Find Full Text PDF

Prenylated acetophenones from the roots of Calendula officinalis and their anti-inflammatory activity.

Biosci Biotechnol Biochem

June 2023

Graduate School of Integrated Pharmaceutical and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan.

Calendula officinalis is a medicinal plant in the Asteraceae family, and it has a broad range of biological activities. In this study, we focused on the roots of C. officinalis, which have remarkable anti-inflammatory properties.

View Article and Find Full Text PDF

A new prenylated xanthenoid with a highly oxidized core, acrotrione B (1: ), together with six previously reported acetophenones (2:  - 7: ), were isolated from the roots of . The structures of the isolated compounds were elucidated by thorough analysis of their 1D and 2D NMR spectroscopic data. The relative and absolute configurations of acrotrione B were determined by electronic circular dichroism (ECD) calculations.

View Article and Find Full Text PDF

Acronyrones A-C, unusual prenylated acetophenones from Acronychia pedunculata.

Fitoterapia

November 2022

Science and Technology Innovation Center, Guangzhou University of Chinese Medicine, Guangzhou 510405, People's Republic of China. Electronic address:

Two novel prenylated acetophenones with new carbon skeletons, acronyrones A and B (1 and 2), and a new analogue, acronyrone C (3), together with two known compounds (4 and 5) were isolated from the leaves of Acronychia pedunculata. Their structures with absolute configurations were identified by interpretation of spectroscopic data, single crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 represent the first example of prenylated acetophenones possessed a C (1) and a C (2) side chain, forming a 4-isobutylchroman-2-one unit and a 3-(2-methylpropylidene)benzofuran-2(3H)-one moiety with the acetophenone core, respectively.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!