Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

New Polyprenylated Acylphloroglucinol Derivatives and Xanthones From Hypericum wilsonii.

ABSTRACT: Four new polyprenylated acylphloroglucinol derivatives, hyperwilone A-D (1-4), and two new xanthones, wilsonxanthone A (5) and wilsonxanthone B (6), together with eight known compounds were isolated from the aerial parts of Hypericum wilsonii. Their structures were expounded by comprehensive analysis of the 1D and 2D NMR spectra and HRESIMS. The relative configurations and absolute configurations of 1-6 were determined by NMR calculations and comparing their experimental and computed ECD data. All compounds were evaluated for GLUT4 translocation effects in L6 myotubes. Compound 5 showed the strongest GLUT4 translocation effects with 2.57 folds at a concentration of 30 μg/ml.

SUBMITTER: Hao J

PROVIDER: S-EPMC8497742 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

New Polyprenylated Acylphloroglucinol Derivatives and Xanthones From Hypericum wilsonii.

Hao Ji J Zhou Tongxi T Ma Yuanren Y Deng Jingtong J Cheng Haitao H Wang Qiang Q Lin Qinxiong Q Yang Xinzhou X Choi Hoyoung H

Frontiers in chemistry 20210924

Four new polyprenylated acylphloroglucinol derivatives, hyperwilone A-D (1-4), and two new xanthones, wilsonxanthone A (5) and wilsonxanthone B (6), together with eight known compounds were isolated from the aerial parts of Hypericum wilsonii. Their structures were expounded by comprehensive analysis of the 1D and 2D NMR spectra and HRESIMS. The relative configurations and absolute configurations of 1-6 were determined by NMR calculations and comparing their ex ...[more]

PMID: 34631657

Similar Datasets

Polycyclic Polyprenylated Acylphloroglucinol Derivatives from Hypericum acmosepalum.

Project description:Hypericum acmosepalum belongs to the Hypericum genus of the Guttiferae family. The characteristic components in Hypericum are mainly a series of polycyclic polyprenylated acylphloroglucinols (PPAPs), flavonoids, and xanthones. Among them, the PPAPs have received much attention due to their novel structures and diverse pharmacological activities and have become hot spots in organic chemistry and medicinal chemistry. However, there are few reports about the chemical constituents of Hypericum acmosepalum at present, especially the PPAPs. This research is dedicated to the study of the air-dried aerial parts of Hypericum acmosepalum, which were extracted with 95% EtOH under reflux, then suspended and successively partitioned with petroleum ether and ethyl acetate. Five PPAP derivatives were obtained using various chromatographic techniques, and their structures were determined by NMR spectroscopic data, including two new phloroglucinol derivatives, hyperacmosin A (1) and hyperacmosin B (2). Those compounds were evaluated for their neuroprotective effect using two models.

| S-EPMC6337531 | biostudies-literature

Hypercohones D-G, New Polycyclic Polyprenylated Acylphloroglucinol Type Natural Products from Hypericum cohaerens.

Project description:AbstractFour new polycyclic polyprenylated acylphloroglucinol type metabolites, hypercohones D-G (1-4), along with four known analogues (5-8), were isolated from the aerial parts of Hypericum cohaerens. The structures of these isolates were elucidated by extensive spectroscopic methods. The inhibitory activities of these isolates against five human cancer cell lines in vitro were also tested.

| S-EPMC4004852 | biostudies-literature

Dearomatized Isoprenylated Acylphloroglucinol Derivatives with Potential Antitumor Activities from Hypericum henryi.

Project description:A series of dearomatized isoprenylated acylphloroglucinols derivatives, hyperhenols A-E (1-5), as well as seven known analogues (6-12), were characterized from Hypericum henryi. Their structures were determined by combination of NMR, ECD spectroscopy, and X-ray diffraction analysis. Compounds 1 and 6-8 were tested to exhibit potential antitumor properties, of which 6 and 7 inhibited cell growth through inducing apoptosis and cell cycle arrest. In addition, these compounds could induce autophagy and PINK1/Parkin-mediated mitophagy in cancer cell lines, as well as suppress lung cancer A549 cells metastasis in vitro.

| S-EPMC7046846 | biostudies-literature

Hypercohones A–C, acylphloroglucinol derivatives with homo-adamantane cores from Hypericum cohaerens

Project description:Three new homo-adamantanyl type natural products were derived from polyprenylated polycyclic acylphloroglucinol. Hypercohones A-C (1–3), along with five other known hypercohones (4–8), were isolated from the aerial parts of Hypericum cohaerens. The structures of 1–3 were elucidated on the basis of comprehensive spectroscopic analysis. The inhibitory activities of these isolates against five human cancer cell lines in vitro were tested. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-013-0032-9 and is accessible for authorized users.

| S-EPMC4131619 | biostudies-literature

Hyperacmosins K-M, three new polycyclic polyprenylated acylphloroglucinols from Hypericum acmosepalum.

Project description:Hyperacmosins K-M (1-3), three new polycyclic polyprenylated acylphloroglucinol (PPAPs) derivatives, were isolated from the air-dried aerial parts of Hypericum asmosepalum. Compounds 1 and 2 both possessed a rare 5,5-spiroketal subunit with the loss of C-2' carbonyl in the phloroglucinal ring, while compound 3 featured an unusual 1,2-seco-bicyclo[3.3.1] PPAP skeleton. Their structures were confirmed by NMR, HRESIMS, and CD spectra. The plausible biogenetic pathways of 1-3 were proposed, which gave an insight for future biomimetic synthesis of the novel compounds.

| S-EPMC9034054 | biostudies-literature

Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.

Project description:Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).

| S-EPMC4140454 | biostudies-literature

Antimicrobial Evaluation of Two Polycyclic Polyprenylated Acylphloroglucinol Compounds: PPAP23 and PPAP53.

Project description:Polycyclic polyprenylated acylphloroglucinols (PPAPs) comprise a large group of compounds of mostly plant origin. The best-known compound is hyperforin from St. John's wort with its antidepressant, antitumor and antimicrobial properties. The chemical synthesis of PPAP variants allows the generation of compounds with improved activity and compatibility. Here, we studied the antimicrobial activity of two synthetic PPAP-derivatives, the water-insoluble PPAP23 and the water-soluble sodium salt PPAP53. In vitro, both compounds exhibited good activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium. Both compounds had no adverse effects on Galleria mellonella wax moth larvae. However, they were unable to protect the larvae from infection with S. aureus because components of the larval coelom neutralized the antimicrobial activity; a similar effect was also seen with serum albumin. In silico docking studies with PPAP53 revealed that it binds to the F1 pocket of human serum albumin with a binding energy of -7.5 kcal/mol. In an infection model of septic arthritis, PPAP23 decreased the formation of abscesses and S. aureus load in kidneys; in a mouse skin abscess model, topical treatment with PPAP53 reduced S. aureus counts. Both PPAPs were active against anaerobic Gram-positive gut bacteria such as neurotransmitter-producing Clostridium, Enterococcus or Ruminococcus species. Based on these results, we foresee possible applications in the decolonization of pathogens.

| S-EPMC11312133 | biostudies-literature

Hyperisampsins H-M, Cytotoxic Polycyclic Polyprenylated Acylphloroglucinols from Hypericum sampsonii.

Project description:Six new polycyclic polyprenylated acylphloroglucinols (PPAPs), named hyperisampsins H-M (1-6), were isolated from the aerial parts of Hypericum sampsonii, together with five known analogs (7-11). The structures of 1-6 were established by extensive spectroscopic analyses, including HRESIMS and NMR. In addition, the absolute configurations of these new compounds were determined by electronic circular dichroism (ECD) calculations. Compounds 1 and 2 represent the first examples of PPAPs possessing a unique γ-lactone ring at C-23, while 3-6 differed from normal PPAPs with an unprecedented 1,2-dioxane ring. Compounds 1-7 were evaluated for their cytotoxic activities against a panel of human cancer cell lines in vitro, of which 3, 4, and 6 exhibited significant cytotoxic activities with IC50 values ranging from 0.56 to 3.00 μM. Moreover, compound 3 induces leukemia cell apoptotic death, evidenced by activation of caspase-3, degradation of PARP, up-regulation of Bax, and down-regulation of Bcl-2 and Bcl-xl.

| S-EPMC4594001 | biostudies-literature

Cytotoxic Xanthones from Hypericum stellatum, an Ethnomedicine in Southwest China.

Project description:Hypericum stellatum, a species endemic to China, is used to treat hepatitis by several ethnic groups in Guizhou Province. This research was inspired by the traditional medicinal usage of H. stellatum, and aims to explore the phytochemistry and bioactivity of H. stellatum to explain why local people in Guizhou widely apply H. stellatum for liver protection. In this study, two new prenylated xanthones, hypxanthones A (8) and B (9), together with seven known compounds, were isolated from the aerial parts of the plant. Spectroscopic data as well as experimental and calculated ECD spectra were used to establish the structures of these compounds. Six xanthones isolated in this study, together with four xanthones previously isolated from H. stellatum, were evaluated for their growth-inhibitory activities against five human liver carcinoma cell lines to analyze the bioactivity and structure-activity relationship of xanthones from H. stellatum. Isojacareubin (6) showed significant cytotoxicity against five human liver carcinoma cell lines, with an IC50 value ranging from 1.41 to 11.83 μM, which was stronger than the positive control cisplatin (IC50 = 4.47-20.62 μM). Hypxanthone B (9) showed moderate cytotoxicity to three of the five cell lines. Finally, structure-activity analysis revealed that the prenyl and pyrano substituent groups of these xanthones contributed to their cytotoxicity.

| S-EPMC6804229 | biostudies-literature

Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus.

Project description:Callisalignenes G-I (1-3), three new meroterpenoids of β-triketone and monoterpene, along with two known analogues (4 and 5), were isolated from Callistemon salignus. Their structures and absolute configurations were unambiguously established by a combination of NMR and MS analysis and electronic circular dichroism (ECD) evidence. Callisalignenes H (2) and I (3) have a rare sec-butyl moiety at C-7. Meroterpenoids 1-3 exhibited cytotoxicity against HCT116 cells with IC50 values of 8.51 ± 1.8, 9.12 ± 0.3, and 16.33 ± 3.3 μM, respectively. Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus.

| S-EPMC5507812 | biostudies-literature