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. Compound 5 exhibited significant anti-proliferative effects on the three cell lines, with IC values ranging from 0.24-5.3 μM.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/cbdv.202401027 | DOI Listing |
Chem Biodivers
November 2024
College of Pharmacy, Shenzhen Technology University, Shenzhen, 518118, People's Republic of China.
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 PDFJ Org Chem
June 2023
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.
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 PDFBiosci 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 PDFPlanta Med
April 2023
Department of Chemistry, Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand.
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 PDFFitoterapia
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 PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!