Anti-inflammatory, antimicrobial and acetylcholinesterase inhibitory activities of friedelanes from Maytenus robusta branches and isolation of further triterpenoids

Vulvovaginal candidiasis (VVC) is the second most common vaginal infection that affects women of reproductive age. Its increased occurrence and associated treatment cost coupled to the rise in resistance of the causative pathogen to current antifungal therapies has necessitated the need for the discovery and development of novel effective antifungal agents for the treatment of the disease. We report in this study the anti-Candida albicans activity of Solanum torvum 70% ethanol fruit extract (STF), fractions and some isolated compounds against four (4) fluconazole-resistant strains of C. albicans. We further report on the effect of the isolated compounds on the antifungal activity of fluconazole and voriconazole in the resistant isolates as well as their inhibitory effect on C. albicans biofilm formation. STF was fractionated using n-hexane, chloroform (CHCl3) and ethyl acetate (EtOAc) to obtain four respective major fractions, which were then evaluated for anti-C. albicans activity using the microbroth dilution method. The whole extract and fractions recorded MICs that ranged from 0.25 to 16.00 mg/mL. From the most active fraction, STF- CHCl3 (MIC = 0.25–1.00 mg/mL), four (4) known compounds were isolated as Betulinic acid, 3-oxo-friedelan-20α-oic acid, Sitosterol-3-β-D-glucopyranoside and Oleanolic acid. The compounds demonstrated considerably higher antifungal activity (0.016 to 0.512 mg/mL) than the extract and fractions and caused a concentration-dependent anti-biofilm formation activity. They also increased the sensitivity of the C. albicans isolates to fluconazole. This is the first report of 3-oxo-friedelan-20α-oic acid in the plant as well as the first report of betulinic acid, sitosterol-3-β-D-glucopyranoside and oleanolic acid from the fruits of S. torvum. The present study has demonstrated the anti-C. albicans activity of the constituents of S. torvum ethanol fruit extract and also shown that the constituents possess anti-biofilm formation and resistance modulatory activities against fluconazole-resistant clinical C. albicans isolates.

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“…albicans isolates lending credence to the anti- C . albicans activity of friedelane-type triterpenoids [ 53 ].…”

Section: Discussionmentioning

confidence: 99%

Bioactive triterpenoids from Solanum torvum fruits with antifungal, resistance modulatory and anti-biofilm formation activities against fluconazole-resistant candida albicans strains

et al. 2021

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“…at the dose of 20 mg/kg (68, 77, and 61%, respectively). Indomethacin, used as the positive control, showed 79% inhibition at a dose of 10 mg/kg (Sousa et al, 2017).…”

Section: Friedelanes-compounds 198-204mentioning

confidence: 98%

“…After 4 hr, compounds 199 , 200 , and 201 showed activities at the dose of 10 mg/kg (71, 75, and 59%, respectively) and at the dose of 20 mg/kg (68, 77, and 61%, respectively). Indomethacin, used as the positive control, showed 79% inhibition at a dose of 10 mg/kg (Sousa et al, 2017).…”

Section: Antiinflammatory Activity Of Natural Triterpenesmentioning

confidence: 99%

Antiinflammatory activity of natural triterpenes—An overview from 2006 to 2021

Miranda

Jesus

Luiz

et al. 2022

Phytotherapy Research

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Terpenes are one of the most abundant classes of secondary metabolites produced by plants and can be divided based on the number of isoprene units (C5) in monoterpenes (2 units—C10), sesquiterpenes (3 units—C15), diterpenes (4 units—C20), triterpenes (6 units—C30), etc. Chemically, triterpenes are classified based on their structural skeleton including lanostanes, euphanes, cycloartanes, ursanes, oleananes, lupanes, tirucallanes, cucurbitanes, dammaranes, baccharanes, friedelanes, hopanes, serratanes etc. Additionally, glycosylated (saponins) or highly oxidated/degraded (limonoids) triterpenes could be found in nature. The antiinflammatory effect and action as immunomodulators of these secondary metabolites have been demonstrated in different studies. This review reports an overview of articles published in the last 15 years (from 2006 to 2021 using PubMed and SciFinder database) describing the antiinflammatory effects of different triterpenes with their presumed mechanism of action, suggesting that triterpenes could be appointed as natural products with future pharmaceutical applicability.

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“…GC-MS was applied to detect the unsaponifiable matter in four mushroom oils, which were quantified by internal standard 5α-cholestane. According to the data in lupeol and friedelan-3-one (7.85-29.67 mg/kg) benefited four tested oils with antimicrobial, anti-inflammatory, and anticonvulsant activities (Gallo & Sarachine, 2009;Ichiko et al, 2016;Jordan et al, 2020;Sousa et al, 2017).…”

Section: Unsaponifiable Mattersmentioning

confidence: 99%

Superior component compositions and antioxidant activity of Volvariella volvacea oil compared to those of Agrocybe cylindracea and two Lentinula edodes oils

Kang,

Yue,

Wei

et al. 2023

Food Science & Nutrition

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The biological activity of an oil not only depends on its fatty acid composition but also the lipid composition and trace components. In this paper, to select the optimal mushroom oil, the component compositions (fatty acids, lipids, polyphenols, flavones, tocopherols, and unsaponifiable matters) and antioxidant activities in vitro of four mushroom oils (Agrocybe cylindracea, two Lentinula edodes, and Volvariella volvacea) were investigated and compared. The results showed that the four tested oils had the same fatty acid composition in different amounts, but the lipid component, minor components, and free radical scavenging activity in the tested oils varied widely depending on the type of mushroom. Overall, Volvariella volvacea oil was considered superior to the other three tested oils, as it had the largest contents of polar lipids, diglycerides, polyunsaturated fatty acids (74.38%), unsaponifiable matter (319.09 mg/kg), total phenols (124.08 mg/100 g), tocopherols (139.86 mg/100 g), as well as the highest ABTS and FRAP values (349.45 and 3801.70 μmol Trolox/100 g). This finding suggests that Volvariella volvacea oil is a promising resource that should be further researched.

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Anti-inflammatory, antimicrobial and acetylcholinesterase inhibitory activities of friedelanes from Maytenus robusta branches and isolation of further triterpenoids

Cited by 10 publications

References 16 publications

Bioactive triterpenoids from Solanum torvum fruits with antifungal, resistance modulatory and anti-biofilm formation activities against fluconazole-resistant candida albicans strains

Bioactive triterpenoids from Solanum torvum fruits with antifungal, resistance modulatory and anti-biofilm formation activities against fluconazole-resistant candida albicans strains

Antiinflammatory activity of natural triterpenes—An overview from 2006 to 2021

Superior component compositions and antioxidant activity of Volvariella volvacea oil compared to those of Agrocybe cylindracea and two Lentinula edodes oils

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