Concise Synthesis of Both Enantiomers of Pilocarpine

Schmidt, Theresa; Heise, Niels V.; Merzweiler, Kurt; Deigner, Hans‐Peter; Al‐Harrasi, Ahmed; Csuk, René

doi:10.3390/molecules26123676

Cited by 4 publications

(4 citation statements)

References 64 publications

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“…It was previously shown that 2-furoic acid was served as a starting material for the synthesis of the enantiomers of pilocarpine, which is used against glaucoma. 27 Furoic acid, a potential compound to alleviate obesity, could strongly reduce lipase activity by a noncompetitive mechanism. 28 The structurally related compound 5-(tetradecyloxy)-2-furoic acid (TOFA), which was a novel inhibitor of acetyl-CoA carboxylase, exhibited the strongest growth suppression of human pancreatic cancer cells.…”

Section: ■ Discussionmentioning

confidence: 99%

“…2-Furoic acid and structurally related compounds, as an important renewable building block platform, have already become a research hotspot in the field of pharmaceutical synthesis. It was previously shown that 2-furoic acid was served as a starting material for the synthesis of the enantiomers of pilocarpine, which is used against glaucoma . Furoic acid, a potential compound to alleviate obesity, could strongly reduce lipase activity by a noncompetitive mechanism .…”

Section: Discussionmentioning

confidence: 99%

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Novel Lead Compound Discovery from Aspergillus fumigatus 1T-2 against Meloidogyne incognita Based on a Chemical Ecology Study

Wang

Qin

Fan

et al. 2022

J. Agric. Food Chem.

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To replace biohazardous nematicides, there is an ever-increasing need to identify natural product-based agents to contain root-knot nematodes (RKNs) in agriculture. In this chemical ecology study, an antagonistic fungus Aspergillus fumigatus 1T-2, which could cause the formation of withering of the gut and vacuole-like structures in the nematode body, was isolated based on the gradually increased antagonistic interactions between the soil fungi and RKNs. Based on these typical morphological characteristics, a potent nematode-antagonistic compound 2-furoic acid, which had a simple structure, was successfully identified from 1T-2 fermentation broth by liquid chromatography−mass spectrometry (LC−MS). 2-Furoic acid showed effective mortality activity in vitro, of which the LC 50 value to Megalaima incognita at 24 h was 37.75 μg/mL. 2-Furoic acid had similar mortality activity to the positive control fosthiazate at 30 μg/mL. Continuous 2-furoic acid exposure had obvious negative influences on both nematode vitality and egg hatchability. Notably, significant variations were observed in nematodes and eggs with 2-furoic acid treatment, which might be induced by novel nematocidal mechanisms. Furthermore, the 1T-2 fermentation broth and 2-furoic acid had significant control efficacy on M. incognita under the greenhouse test-tube assay. Overall, these findings provide valuable insights into the use of 2-furoic acid with biocontrol potential as a preferable lead structure for the development of innovative nematicides.

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Section: ■ Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Novel Lead Compound Discovery from Aspergillus fumigatus 1T-2 against Meloidogyne incognita Based on a Chemical Ecology Study

Wang

Qin

Fan

et al. 2022

J. Agric. Food Chem.

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“…The structures of isolated compounds were characterized using various spectroscopic techniques, such as high-resolution electrospray ionization mass spectroscopy (HRESIMS), nuclear magnetic resonance (NMR), and so on. These isolated compounds were determined as glutinol (1) [13], friedelin (2) [14], betulin (3) [15], 2α,19α-dihydroxyursolic acid (4) [16], 2α-hydroxyursolic acid (5) [17], 1-hentriacontanol (6) [18], confusoside (7) [19], 2 ,3,4,4 -tetrahydroxydihydrochalcone (8) [20], 2 ,4,4 -trihydroxydihydrochalcone (9) [21], fragranone C (10) [22], 1-[4-(β-D-glucopyranosyloxy)-2-hydroxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)-1-propanone (11) [9], butein-4 -O-β-Dglucoside (12) [23], kaempferol 6-C-β-D-glucopyranoside (13) [24], quercetin-3-Orhamnopyranoside ( 14) [25], quercetin-3-O-β-D-galactoside (15) [26], sulfuretin (16) [27], paeonoside (17) [28], and acernikol (18) [29]. According to the structural skeletons, the isolated compounds could be classified as triterpenoids (1)(2)(3)(4)(5), aliphatic alcohol (6), dihydrochalcones (7)(8)(9)(10)(11), chalcone (12), flavanols (13)(14)(15), aurone (16), phenolic glycosi...…”

Section: Identification Of Phytochemicals From a Fragransmentioning

confidence: 99%

Phytochemicals from Anneslea fragrans Wall. and Their Hepatoprotective and Anti-Inflammatory Activities

et al. 2023

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Anneslea fragrans Wall., popularly known as “Pangpo tea”, is an edible, medicinal, and ornamental plant of the Family Theaceae. The leaves of A. fragrans were historically applied for the treatment of liver and intestinal inflammatory diseases in China. This study aimed to explore the hepatoprotective agents from A. fragrans leaves through hepatoprotective and anti-inflammatory assessment. The phytochemical investigation of the leaves of A. fragrans resulted in the isolation and identification of a total of 18 chemical compounds, including triterpenoids, aliphatic alcohol, dihydrochalcones, chalcones, flavanols, phenolic glycoside, and lignans. Compounds 1–2, 4–6, 11–12, and 16–18 were identified from A. fragrans for the first time. Compounds 7 and 14 could significantly alleviate hepatocellular damage by decreasing the contents of aspartate aminotransferase (AST) and alanine aminotransferase (ALT) and inhibit the hepatocellular apoptosis in the HepG2 cells induced by N-acetyl-p-aminophenol (APAP). In addition, compounds 7 and 14 inhibited reactive oxygen species (ROS) and malondialdehyde (MDA) contents and increased the catalase (CAT) superoxide dismutase (SOD), and glutathione (GSH) levels for suppressing APAP-induced oxidative stress. Additionally, compounds 7, 13, and 14 also had significant anti-inflammatory effects by inhibiting interleukin-6 (IL-6), interleukin-1β (IL-1β), and tumor necrosis factor-α (TNF-α) productions on LPS-induced RAW246.7 cells.

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“…Pilocarpine is a parasympathomimetic agent that acts primarily as a non-specific muscarinic acetylcholine receptor agonist with mild beta-adrenergic activity. It is a tertiary alkaloid extracted from plants of the genus Pilocarpus and, specifically, it is found in the leaves of Pilocarpus microphyllus and Pilocarpus jaborandi [23][24][25]. Pilocarpine's IUPAC name is (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl) methyl]oxolan-2-one and its chemical structure is presented in Figure 2 [26].…”

Section: General Information On Pilocarpinementioning

confidence: 99%

A Review on the Role of Pilocarpine on the Management of Xerostomia and the Importance of the Topical Administration Systems Development

2022

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Xerostomia is linked to an increased risk of dental caries, oral fungal infections, and speaking/swallowing difficulties, factors that may significantly degrade patients’ life, socially- or emotionally-wise. Consequently, there is an increasing interest in developing management approaches for confronting this oral condition, at which pilocarpine, a parasympathomimetic agent, plays a vital role. Although the therapeutic effects of orally administrated pilocarpine on the salivary gland flow and the symptoms of xerostomia have been proved by numerous studies, the systemic administration of this drug is affiliated with various adverse effects. Some of the typical adverse effects include sweating, nausea, vomiting, diarrhea, rhinitis, dizziness and increased urinary frequency. In this vein, new strategies to develop novel and effective dosage forms for topical (i.e., in the oral cavity) pilocarpine administration, in order for the salivary flow to be enhanced with minimal systemic manifestations, have emerged. Therefore, the purpose of the current review is to survey the literature concerning the performance of topical pilocarpine delivery systems. According to the findings, the topical delivery of pilocarpine can be regarded as the equivalent to systemic delivery of the drug, efficacy-wise, but with improved patient tolerance and less adverse effects.

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Concise Synthesis of Both Enantiomers of Pilocarpine

Cited by 4 publications

References 64 publications

Novel Lead Compound Discovery from Aspergillus fumigatus 1T-2 against Meloidogyne incognita Based on a Chemical Ecology Study

Novel Lead Compound Discovery from Aspergillus fumigatus 1T-2 against Meloidogyne incognita Based on a Chemical Ecology Study

Phytochemicals from Anneslea fragrans Wall. and Their Hepatoprotective and Anti-Inflammatory Activities

A Review on the Role of Pilocarpine on the Management of Xerostomia and the Importance of the Topical Administration Systems Development

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