Antioxidant epoxydon and benzolactone derivatives from the insect-associated fungus <i>Phoma</i> sp.

Li, Tianxiao; Meng, Dan-Dan; Guo, Yaxin; Bai, Bing; Xu, Gaigai; Yang, Yanan; Xie, Xinglong; Wang, Ying; Xu, Chunping

doi:10.1080/10286020.2019.1612380

Cited by 7 publications

(10 citation statements)

References 19 publications

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“…COSY and HMBC correlations allowed the straightforward assembly of the remaining subunit of the molecule as a 2-hydroxymethyl-4,5,6-trihydroxycyclohexenone unit. Coupling values for H-17′ with H-16′ ( J = 10.7 Hz) and H-18′ ( J = 3.9 Hz) and comparison with model compounds containing this unit indicated trans and cis relative orientations for the H16′–H17′ and H17′–H18′ relationships, respectively. − An HMBC correlation between H-16′ and carboxyl carbon C-1′ indicated that C-1′ was esterified to the C-16′ oxygen atom of this unit. Notably, H-16′ was the only oxymethine in the molecule with a significant downfield shift increment suggestive of acylation (δ H 5.94).…”

Section: Resultsmentioning

confidence: 99%

“…The relative configurations of the two stereogenic moieties in 1 could not be definitively correlated because of their distance from one another, but absolute configurations are proposed for them individually based on biogenetic precedents. The absolute configuration of the 2-hydroxymethyl-4,5,6-trihydroxycyclohexenone substructure is proposed as (16′ S , 17′ R , 18′ R ) based on its likely origin from the pathway leading to the known fungal metabolite epoxydon, as was judged to be the case for the structurally analogous fungal metabolites epoxydon 6-methylsalicylate ester, epoxydine B, epoxydon 3-chlorosalicylate ester, and 6 S -acetoxy-4 R ,5 R -dihydroxy-2-hydroxymethylcyclohex-2-en-1-one . The latter compound and epoxydine B differ from 1 by having much simpler acyl groups linked at the analogous position of the substituted cyclohexenone unit.…”

Section: Resultsmentioning

confidence: 99%

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Arenicolins: C-Glycosylated Depsides from Penicillium arenicola

Perlatti

Earp

et al. 2020

J. Nat. Prod.

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During investigation of the secondary metabolism of four strains of Penicillium arenicola, two new depsides, arenicolins A (1) and B (2), were isolated and characterized. Their structures were established mainly by analysis of NMR and HRMS data and by comparison with known compounds. These depsides incorporate intriguing structural features, including dual alkyl side chains and a C-glycosyl unit, with 1 also containing an acylated 2-hydroxymethyl-4,5,6-trihydroxycyclohexenone moiety. Although the arenicolins were produced by all strains tested, arenicolin A (1) was obtained using only one of five medium compositions employed, while arenicolin B (2) was produced in all media tested. Neither compound showed antibacterial or antifungal activity, but 1 exhibited cytotoxicity toward mammalian cell lines, including colorectal carcinoma (HCT-116), neuroblastoma (IMR-32), and ductal carcinoma (BT-474), with IC 50 values of 7.3, 6.0, and 9.7 μM, respectively.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Arenicolins: C-Glycosylated Depsides from Penicillium arenicola

Perlatti

Earp

et al. 2020

J. Nat. Prod.

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“…Mosher's reaction was performed in accordance with the previous method with slight modifications. 25 Compound 9a (the aglycone of compound 9) (1 mg) was dissolved in 500 μL of anhydrous tetrahydrofuran (THF), and then 2 equiv of 4-(dimethylamino) pyridine (4-DMAP), 2 equiv of DCC, and 2 equiv of (R)-MTPA chloride were added under vacuum. The mixture was dried and stirred at 25 °C for 24 h. Then, the solvent was removed, the mixture was purified using a Sephadex LH-20 column (MeOH), and the (R)-MTPA ester of 9aR was obtained.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…Unfortunately, in the 1 H NMR spectra, there was no difference in the chemical shifts between (R)-MTPA ester and (S)-MTPA ester; it might be due the influence of 9-OH. 25 Consequently, the structure of 9 was determined and named as 4-O-methylstroside B.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Antioxidant and Cytoprotective Effects of New Diarylheptanoids from Rhynchanthus beesianus

Zhu

Cheng

Zhao

et al. 2021

J. Agric. Food Chem.

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Rhynchanthus beesianus (Zingiberaceae) has been an important food spice and vegetable in southern China. Fifteen phenolic compounds (1–15) including three new diarylheptanoids, rhynchanines A–C (1–3) and one new phenylpropanoid, 4-O-methylstroside B (9), were isolated from R. beesianus rhizomes. The structures of new compounds were elucidated by comprehensive analyses through NMR, HRMS technique, acid hydrolysis, and Mosher’s reaction. Among them, compound 5 is the first isolated natural product and its NMR data are reported. Most of the isolated compounds, especially 3–6 and 8, showed significant antioxidant activities on DPPH, ABTS+ radical scavenging, and FRAP assays. Furthermore, the antioxidant phenolic compounds were evaluated for their cytoprotective capacity against H2O2-induced oxidative stress in HepG-2 cells. Compounds 3 and 5 could significantly inhibit reactive oxygen species production, and compounds 3, 5, and 6 could remarkably prevent the cell apoptosis. Then, the R. beesianus rhizome, which contained phenolic compounds, might serve as a functional food for potential application on preventing oxidative stress-connected diseases.

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“…Through ABTS and DPPH assays, the radical scavenging effects of MCPs and SCPs were tested (Li et al, 2020;Thomas and Bielski, 1989). Briefly, the ABTS solution and potassium persulfate solution were mixed equally and put in the dark for 18 h. Using 50% ethyl alcohol, the mixture was diluted to 0.70 ± 0.05 (A 734 nm ) and caramel product solutions (50.0-0.5 mg/mL) were also prepared.…”

Section: Antioxidant Assaysmentioning

confidence: 99%

Type I caramel products of maltose and sucrose with water and their antioxidant activities

Luo

Zhang

et al. 2022

Food Sci. Technol

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To study the caramel reactions of disaccharides with water, the type I maltose caramel products (MCPs) and sucrose caramel products (SCPs) at three reaction stages were yielded and their reaction rates, UV absorptions, flavor compounds, and antioxidant activities were also detected. It was found that the caramel reactions of sucrose were faster than those of maltose and their reaction rates quickly increased to a high level in the middle stage. UV absorption of SCP in the late stage at 305 nm was much stronger than those of MCPs. Both the MCP and SCP obtained at 180 °C and 4 min had the highest concentrations of 5-hydroxymethylfurfural and total flavor compounds. Moreover, the total flavor concentrations of SCPs were much larger than those of MCPs and the antioxidant effects of SCPs were also stronger. Thus, a preferred condition for both two disaccharide caramel reactions was suggested at 180 °C for 4 min and the sucrose caramels could give better flavors than maltose caramels.

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Antioxidant epoxydon and benzolactone derivatives from the insect-associated fungus Phoma sp.

Cited by 7 publications

References 19 publications

Arenicolins: C-Glycosylated Depsides from Penicillium arenicola

Arenicolins: C-Glycosylated Depsides from Penicillium arenicola

Antioxidant and Cytoprotective Effects of New Diarylheptanoids from Rhynchanthus beesianus

Type I caramel products of maltose and sucrose with water and their antioxidant activities

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