Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H<sub>2</sub>O<sub>2</sub> Combined with Periodate Oxidation

Mecozzi, Francesco; Dong, Jianfei; Angelone, Davide; Browne, Wesley R.; Eisink, Niek N. H. M.

doi:10.1002/ejoc.201901380

Cited by 23 publications

(11 citation statements)

References 40 publications

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“…It is well known that alkenes can experience oxidation under a variety of conditions 17 , 18 , 19 , 20 . For example, oxidative cleavage is fostered by ozone treatment through the formation of an ozonide intermediate, which undergoes further decomposition using an appropriate reducing agent to produce carbonyl products.…”

Section: Resultsmentioning

confidence: 99%

Silica Gel-mediated Oxidation of Prenyl Motifs Generates Natural Product-Like Artifacts

et al. 2021

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Prenyl moieties are commonly encountered in the natural products of terpenoid and mixed biosynthetic origin. The reactivity of unsaturated prenyl motifs is less recognized and shown here to affect the acyclic Rhodiola rosea monoterpene glycoside, kenposide A (8), which oxidizes readily on silica gel when exposed to air. The major degradation product mediated under these conditions was a new aldehyde, 9. Exhibiting a shortened carbon skeleton formed through the breakdown of the terminal isopropenyl group, 9 is prone to acetalization in protic solvents. Further investigation of minor degradation products of both 8 and 8-prenylapigenin (8-PA, 12), a flavonoid with an ortho-prenyl substituent, revealed that the aldehyde formation was likely realized through epoxidation and subsequent cleavage at the prenyl olefinic bond. Employment of 1H NMR full spin analysis (HiFSA) achieved the assignment of all chemical shifts and coupling constants of the investigated terpenoids and facilitated the structural validation of the degradation product, 9. This study indicates that prenylated compounds are generally susceptible to oxidative degradation, particularly in the presence of catalytic mediators, but also under physiological conditions. Such oxidative artifact/metabolite formation leads to a series of compounds with prenyl-derived (cyclic) partial structures that are analogous to species formed during Phase I metabolism in vivo. Phytochemical and pharmacological studies should take precautions or at least consider the impact of (unavoidable) exposure of prenyl-containing compounds to catalytic and/or oxidative conditions.

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Section: Resultsmentioning

confidence: 99%

Silica Gel-mediated Oxidation of Prenyl Motifs Generates Natural Product-Like Artifacts

et al. 2021

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“…26 Oxidation after H 2 O 2 exposure is an early event preceding apoptosis, it can be activated by excessive ROS levels, viral infections, UV radiation or DNA damage. 27,28 During early stage AMD, ARPE-19…”

Section: Discussionmentioning

confidence: 99%

SS‐31 protect retinal pigment epithelial cells from H₂O₂‐induced cell injury by reducing apoptosis

Bai

Yang

et al. 2021

Clin Exp Pharma Physio

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Age-related macular degeneration (AMD) is a complex retinal degeneration disease associated with retinal pigment epithelium (RPE) cell dysfunction or degeneration. 1 Late-stage AMD has a substantial influence on vision, which combined with choroidal neovascularization (CNV) under the retina and results in acute or severe vision loss. 2,3 Retinal pigment epithelium cells located between retina photoreceptors and the choriocapillaris/Bruch's membrane complex supply the retina with essential cellular maintenance for photoreceptor nutrient transport. [4][5][6] Evidence has shown that effects from oxidative stress induced damage in the RPE/retina. 7 Damage by oxidative stress causes DNA cleavage and lipid peroxidation, resulting in irreversible damage to cells. 8,9 ARPE-19 cells are highly vulnerable to oxidative stress. Oxidative damage induced ARPE-19 cell death and chronic inflammation and is considered as a pathological cause in the progression of AMD. [10][11][12] In this study, we use hydrogen peroxide (H 2 O 2 ) as oxidative stress inducer to learn the possible antioxidant stress mechanism in ARPE-19 cells.Antioxidant supplementation is a plausible strategy to avoid oxidative stress and maintain the function of the retina. 13 To date, however, there has been no effective approach for suppressing oxidative stress-induced RPE cell injury without undesirable side effects. d-Arg-2,6-dimethyltyrosine-Lys-Phe-NH2 (SS-31) is a kind of cell-permeable mitochondria-targeting antioxidant peptide that could reduce oxidative stress, inhibit reactive oxygen species (ROS) regeneration and mitochondrial depolarization and protect multiple cell types against various external insults. 14,15 In this study, we studied the role of SS-31 in protecting RPE cells from the oxidative insults and explored the mechanisms underlying the antioxidant effect of SS-31.

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“…New synthetic Natural Product Reports Review methodologies using catalytic RuCl 3 or OsO 4 in combination with various oxidants could overcome several of the limitations imposed by ozonolysis, and they would be useful in the CtD strategy. 65…”

Section: Ring Expansionmentioning

confidence: 99%

Recent ring distortion reactions for diversifying complex natural products

et al. 2022

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Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H₂O₂ Combined with Periodate Oxidation

Cited by 23 publications

References 40 publications

Silica Gel-mediated Oxidation of Prenyl Motifs Generates Natural Product-Like Artifacts

Silica Gel-mediated Oxidation of Prenyl Motifs Generates Natural Product-Like Artifacts

SS‐31 protect retinal pigment epithelial cells from H₂O₂‐induced cell injury by reducing apoptosis

Recent ring distortion reactions for diversifying complex natural products

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Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H2O2 Combined with Periodate Oxidation

Cited by 23 publications

References 40 publications

Silica Gel-mediated Oxidation of Prenyl Motifs Generates Natural Product-Like Artifacts

Silica Gel-mediated Oxidation of Prenyl Motifs Generates Natural Product-Like Artifacts

SS‐31 protect retinal pigment epithelial cells from H2O2‐induced cell injury by reducing apoptosis

Recent ring distortion reactions for diversifying complex natural products

Contact Info

Product

Resources

About

Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H₂O₂ Combined with Periodate Oxidation

SS‐31 protect retinal pigment epithelial cells from H₂O₂‐induced cell injury by reducing apoptosis