Phytochemical investigation of the n-hexane-soluble fraction of the aqueous ethanol extract of the aerial parts of Hypericum helianthemoides (Spach) Boiss. (Hypericaceae), furnished four undescribed polycylic polyprenylated benzoylphloroglucinols (PPBPs) 1-4, together with phytyl formate (5) and thirteen previously reported prenylated phloroglucinol derivatives, including yezo'otogirin C (6), hyperibrins A (7) and F (8), hyperibones G (9), J (10), La (11a)/Lb (11b), 7-epi-clusianone a (12a)/7-epi-clusianone b (12b), and hypermongones A (13), C (14), E (15), G (16), H (17), and sampsonione L (18). The structures of 1-4 were established by extensive 1D and 2D NMR spectral analysis as well as HREI-MS. The absolute configurations of the stereogenic carbons in 1 were established by X-ray crystallographic analysis, while the stereochemistry of 2 was assigned by quantum chemical calculation of its H and C NMR chemical shift values using DP4 probability analysis. The isolated compounds were assayed for antileishmanial activity on Leishmania tropica and L. major parasites. Compounds 9 and 16 displayed activities against L. tropica, with IC values of 17.7 and 31.5 μM, respectively. Moreover, 9 was only active against L. major, with IC value of 34.2 μM.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.phytochem.2025.114473 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Hyperhelianthemones A-D: Polycyclic polyprenylated benzoylphloroglucinols from Hypericum helianthemoides.
Phytochemistry
March 2025
Instituto de Ciências Biomédicas Abel Salazar and CIIMAR, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal. Electronic address:
Phytochemical investigation of the n-hexane-soluble fraction of the aqueous ethanol extract of the aerial parts of Hypericum helianthemoides (Spach) Boiss. (Hypericaceae), furnished four undescribed polycylic polyprenylated benzoylphloroglucinols (PPBPs) 1-4, together with phytyl formate (5) and thirteen previously reported prenylated phloroglucinol derivatives, including yezo'otogirin C (6), hyperibrins A (7) and F (8), hyperibones G (9), J (10), La (11a)/Lb (11b), 7-epi-clusianone a (12a)/7-epi-clusianone b (12b), and hypermongones A (13), C (14), E (15), G (16), H (17), and sampsonione L (18). The structures of 1-4 were established by extensive 1D and 2D NMR spectral analysis as well as HREI-MS.
View Article and Find Full Text PDFPolyprenylated Benzoylphloroglucinols Isolated from Species and Their Cytotoxic Effects on Cancer Cell Lines.
ACS Omega
October 2024
Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok (KMUTNB), Bangkok 10800, Thailand.
Polyprenylated benzoylphloroglucinols (PPBPs) make up a group of complex natural products with anticancer potentials that are mainly distributed in plants. As part of our intensive exploration on new bioactive substances from this genus, we report two undescribed PPBPs, picrorhizones I () and J (), along with four known analogues (-) from the stem bark of and . The new structures were elucidated on the basis of spectroscopic analysis, particularly 1D and 2D NMR and HRESIMS, whereas the absolute configurations were determined by a combination of ECD and NMR calculations coupled with a DP4+ probability analysis.
View Article and Find Full Text PDFGarcowacinols A-J, cytotoxic polyprenylated benzoylphloroglucinol derivatives from the twigs of Garcinia cowa.
Phytochemistry
May 2023
Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
Ten undescribed polyprenylated benzoylphloroglucinol derivatives named garcowacinols A‒J (1-10) and four known analogues (11-14) were isolated from the twigs of Garcinia cowa. Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and their absolute configurations were established based on NOESY and ECD data. All isolated compounds were evaluated for their cytotoxicity against five types of human cancer cells (KB, HeLa S3, MCF-7, Hep G2, and HT-29) as well as Vero cells by MTT colorimetric assay.
View Article and Find Full Text PDFCytotoxic Polyprenylated Benzoylphloroglucinol Derivatives from the Branches of Garcinia schomburgkiana.
Planta Med
April 2023
Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, Thailand.
Five undescribed polyprenylated benzoylphloroglucinol derivatives (1: - 5: ), named garschomcinols A - E, and five known analogues (6: - 10: ) were isolated from the branches of . Their structures were determined on the basis of 1D and 2D NMR and HRESIMS analyses. The absolute configuration of the bicyclo [3.
View Article and Find Full Text PDF-Glucosidase Inhibitory and Antimicrobial Benzoylphloroglucinols from Fruits: In Vitro and In Silico Studies.
Molecules
April 2022
Research Unit in Natural Products Chemistry and Bioactivities, Faculty of Science and Technology, Thammasat University Lampang Campus, Lampang 52190, Thailand.
α-Glucosidase plays a role in hydrolyzing complex carbohydrates into glucose, which is easily absorbed, causing postprandial hyperglycemia. Inhibition of α-glucosidase is therefore an ideal approach to preventing this condition. A novel polyprenylated benzoylphloroglucinol, which we named schomburgkianone I (), was isolated from the fruit of , along with an already-reported compound, guttiferone K ().
View Article and Find Full Text PDFWant 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!