Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases

Wen, Xiaoan; Sun, Hongbin; Li, Jun; Wu, Guanzhong; Zhang, Luyong; Wu, Xiaoming; Ni, Pei-Zhou

doi:10.1016/j.bmcl.2005.08.026

Cited by 108 publications

(62 citation statements)

References 18 publications

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“…The activity of these drugs had been successfully tested against different protozoa (19,20,23,24,25,26) and maslinic acid has been found to be active against Acanthamoeba (22). In the present study, anti-Acanthamoeba activity of these drugs has been described using a range of Acanthamoeba strains.…”

Section: Discussionmentioning

confidence: 82%

“…Caffeine and maslinic acid are glycogen phosphorylase inhibitors (17,18) and maslinic acid inhibits the secreted proteases of a number of different parasites (19,23,24,25,26). The activity of these drugs had been successfully tested against different protozoa (19,20,23,24,25,26) and maslinic acid has been found to be active against Acanthamoeba (22).…”

Section: Discussionmentioning

confidence: 99%

“…Maslinic acid is a natural triterpene isolated from the olive tree (Olea europaea) with multiple biological properties, such as antimicrobial and antiparasitic activity (19,20,21,22). Maslinic acid has been reported to be a potent inhibitor of glycogen phosphorylase and extracellular proteases of parasites such as Toxoplasma gondii and serine proteases from Cryptosporidium (19,23,24,25,26).…”

mentioning

confidence: 99%

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Amoebicidal Activity of Caffeine and Maslinic Acid by the Induction of Programmed Cell Death in Acanthamoeba

Martín-Navarro

López-Arencibia

Sifaoui

et al. 2017

Antimicrob Agents Chemother

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Free-living amoebae of the genus Acanthamoeba are the causal agents of a sight-threatening ulceration of the cornea called Acanthamoeba keratitis, as well as the rare but usually fatal disease granulomatous amoebic encephalitis. Although there are many therapeutic options for the treatment of Acanthamoeba infections, they are generally lengthy and/or have limited efficacy. For the best clinical outcome, treatments should target both the trophozoite and the cyst stages, as cysts are known to confer resistance to treatment. In this study, we document the activities of caffeine and maslinic acid against both the trophozoite and the cyst stages of three clinical strains of Acanthamoeba. These drugs were chosen because they are reported to inhibit glycogen phosphorylase, which is required for encystation. Maslinic acid is also reported to be an inhibitor of extracellular proteases, which may be relevant since the protease activities of Acanthamoeba species are correlated with their pathogenicity. We also provide evidence for the first time that both drugs exert their anti-amoebal effects through programmed cell death.

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Section: Discussionmentioning

confidence: 82%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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Amoebicidal Activity of Caffeine and Maslinic Acid by the Induction of Programmed Cell Death in Acanthamoeba

Martín-Navarro

López-Arencibia

Sifaoui

et al. 2017

Antimicrob Agents Chemother

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“…-Twelve compounds were isolated from the AcOEt-and BuOH-soluble fractions of the whole plant of D. chrysantha, and were identified as ellagic acid (1) [20], ursolic acid [15], pomolic acid [21], tormentic acid [15], euscaphic acid [15], euscaphic acid 28-O-b-d-glucopyranoside [15], and maslinic acid [22] by physical and spectroscopic methods, as well as by comparison of their data with literature values. To the best of our knowledge, compounds 2 -6, pomolic acid, and maslinic acid were isolated for the first time from this plant.…”

mentioning

confidence: 99%

Aldose‐Reductase‐ and Protein‐Glycation‐Inhibitory Principles from the Whole Plant of Duchesnea chrysantha

Kim

Jang

Lee

et al. 2008

Chemistry & Biodiversity

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Ellagic acid (1), 3,3'-di-O-methylellagic acid (2), 3,3',4-tri-O-methylellagic acid (3), isovitexin (4), kaempferol 3-O-beta-D-glucuronide methyl ester (5), quercetin 3-O-alpha-L-arabinopyranosyl-(1-->6)-beta-D-galactopyranoside (6), ursolic acid, pomolic acid, tormentic acid, euscaphic acid, euscaphic acid 28-O-beta-D-glucopyranoside, and maslinic acid were isolated from the AcOEt- and BuOH-soluble MeOH extract of Duchesnea chrysantha (whole plant). The isolates were subjected to in vitro bioassays to evaluate their inhibitory activity on rat-lens aldose reductase (RLAR) and formation of advanced glycation end products (AGEs). The ellagic acids and flavonoids, compounds 1-6, exhibited moderate inhibitory effects on RLAR. However, compounds 1 and 4-6 showed excellent inhibitory activities towards the formation of AGEs. This is the first report that 4 and 6 exhibit inhibitory activity towards AR and AGEs formation.

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“…1), which recently has attracted attention for its biological properties. [1][2][3][4][5][6][7] It was shown that Banaba leaf extract (1% CRA) treatment for 2 weeks decreased blood glucose levels in humans. 8) In addition, CRA (10 mg) has been shown to reduce post challenge plasma glucose levels at 90 min in humans.…”

mentioning

confidence: 99%

Dietary Corosolic Acid Ameliorates Obesity and Hepatic Steatosis in KK-Ay Mice

Yamada

Hosokawa

Yamada

et al. 2008

Biological & Pharmaceutical Bulletin

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Banaba leaves (Lagerstroemia speciosa LINN.) have been used as a traditional medicine in Southeast Asia, and tea made from the leaves is used as a treatment for diabetes. The leaves contain large amounts of corosolic acid (CRA) (Fig. 1), which recently has attracted attention for its biological properties. [1][2][3][4][5][6][7] It was shown that Banaba leaf extract (1% CRA) treatment for 2 weeks decreased blood glucose levels in humans. 8) In addition, CRA (10 mg) has been shown to reduce post challenge plasma glucose levels at 90 min in humans. 7) We previously reported that CRA ameliorates hypertension and abnormal lipid metabolism as well as mitigating oxidative stress and the inflammatory state in SHR/NDmcrcp rats on a high fat diet, 9) that is an animal model of metabolic syndrome.10) We also found that the administration of CRA (10 mg/kg) in a normal diet for 2 weeks improved hyperglycemia by reducing insulin resistance in a KK-Ay mouse, an obese animal model that spontaneously develops hypertriglyceridemia, hyperglycemia, hyperinsulinemia, and diabetes. 11,12) However, the effects of CRA on the adipocytokines and transcription factors that play central roles in the development of obesity are unknown.Obesity and type 2 diabetes in both humans and animals are associated with insulin resistance.13) Adiponectin is an insulin-sensitizing hormone, and plasma levels of adiponectin have been reported to be significantly reduced in obese /diabetic mice and humans.14-16) It also was reported that adiponectin receptors, AdipoR1 and AdipoR2, are downregulated in adipose tissue and skeletal muscle in obese diabetic ob/ob mouse, which is correlated with decreased adiponectin sensitivity. 17)Abnormalities of lipid metabolism are frequently observed in obesity and type 2 diabetes. Peroxisome proliferator-activated receptor (PPAR)a is predominantly expressed in liver, and regulates the expression of genes involved in lipid metabolism. Activators of PPARa decrease circulating lipid levels and are commonly used to treat hypertriglyceridemia and other dyslipidemic states. Recent studies suggest that the activation of PPARa prevents high fat diet-induced obesity, 18) insulin resistance, 18,19) and hepatic steatosis. 20) It was also found that activation of PPARa increased AdipoR1 and AdipoR2 expression in adipocytes in vivo. 21)Growth and differentiation of adipocytes are regulated by PPARg, which is highly expressed in adipose tissue. Activation of PPARg by agonists such as thiazolidinediones increases the number of small adipocytes, which increases the amount of the insulin-sensitizing hormone adiponectin. 15,22) PPARg activation also stimulates lipid storage in adipocytes and reduces lipotoxicity in liver and skeletal muscle, thereby improving insulin sensitivity. 23)In the present study, we examined the inhibitory effects of CRA on the development of obesity and hepatic steatosis in Corosolic acid (CRA), a constituent of Banaba leaves, has been reported to exert anti-hypertension, anti-hyperinsulinemia, anti-hyperglycemi...

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Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases

Cited by 108 publications

References 18 publications

Amoebicidal Activity of Caffeine and Maslinic Acid by the Induction of Programmed Cell Death in Acanthamoeba

Amoebicidal Activity of Caffeine and Maslinic Acid by the Induction of Programmed Cell Death in Acanthamoeba

Aldose‐Reductase‐ and Protein‐Glycation‐Inhibitory Principles from the Whole Plant of Duchesnea chrysantha

Dietary Corosolic Acid Ameliorates Obesity and Hepatic Steatosis in KK-Ay Mice

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