Pyrrole-2-carboxaldehyde is a pyrrole carrying a formyl substituent at the 2-position. It is a member of pyrroles and a 1,3-thiazole-2-carbaldehyde.
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A: Py-2-C derivatives from microorganisms exhibit a range of physiological activities. For example, Mycalazal 2 from Mycale micracanthoxea showed strong cytotoxic effects against various cancer cell lines. Compounds from Mycale cecilia demonstrated cytotoxic effects against several tumor cell lines. Additionally, Py-2-C derivatives from Jiangella gansuensis showed significant anti-inflammatory activity by inhibiting NO production in LPS-treated macrophages. These findings suggest that Py-2-C derivatives from microorganisms have potential applications in cancer therapy and anti-inflammatory treatments.
A: Py-2-C derivatives from plants exhibit diverse physiological activities. For instance, magnolamide from Magnolia coco showed significant inhibitory activity against Cu+-induced LDL oxidation, comparable to known antioxidants like probucol and resveratrol. Pyrrolezanthine-6-methyl ether from Ilex paraguariensis did not show significant HNE inhibitory activity. Compounds from Lycium chinense fruits demonstrated high hepatoprotective activity. These results indicate that Py-2-C derivatives from plants have potential applications in preventing oxidative stress-related diseases and promoting liver health.
A: Py-2-C derivatives from fungi exhibit a range of physiological activities. For example, a Py-2-C from Mycoleptodonoides aitchisonii showed strong NQO1-inducing activity. Compounds from Xylaria nigripes demonstrated antioxidant effects by inhibiting oxidative stress in vascular smooth muscle cells. Additionally, Py-2-C derivatives from Phlebopus portentosus exhibited neuroprotective effects against H2O2-induced oxidative stress. These findings suggest that Py-2-C derivatives from fungi have potential therapeutic applications in treating oxidative stress-related diseases and neurodegenerative conditions.
A: The chemical synthesis of Py-2-C involves the condensation of glucose with alkylamines under acidic conditions, such as acetic acid catalysis. This reaction produces N-substituted-5-methoxymethyl-2-formyl-pyrroles in low yields. The proposed mechanism includes the formation of 3-deoxy-D-glucose, followed by an attack of the alkylamine on the enol site, leading to the formation of a dihydropyrrole, which then undergoes dehydration to form the final Py-2-C product. This synthetic route suggests that similar reactions could occur under physiological conditions over time.
A: Py-2-C derivatives originate from multiple sources and exhibit a range of physiological activities. They can be chemically synthesized from glucose and amino acid derivatives under acidic conditions. Naturally, they are found in fungi, plants, and microorganisms. The physiological activities of Py-2-C derivatives include antioxidant effects, cytotoxicity against cancer cells, neuroprotective effects, and inhibition of various enzymes. For example, compounds like pyrrolezanthine and cordyrrole A have shown significant biological activities, including hepatoprotection and adipocyte differentiation inhibition. The study highlights the potential of Py-2-C derivatives for pharmaceutical applications, particularly as biomarkers and therapeutic agents.