Soluble epoxide hydrolase inhibitory activity of anthraquinone components from Aloe

Sun, Ya Nan; Kim, Young Ho; Li, Wei; Jo, Ah Reum; Yan, Xi Tao; Yang, Seo Young

doi:10.1016/j.bmc.2015.09.003

Cited by 16 publications

(10 citation statements)

References 40 publications

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“…Natural products and related compounds are powerful alternatives for drug development. Phenolic and saponin constituents are important secondary metabolites in both medicinal plants and marine organisms that exhibit diverse pharmacological effects, such as anti-inflammatory [ 8 ], anti-cancer [ 19 ], anti-diabetic [ 20 ], anti-cardiovascular [ 21 ], and anti-oxidant activities [ 22 ]. Although there have been a few studies on the anti-inflammatory effects of P. tenuifolia [ 7 ], to the best of our knowledge, this is the first report on the inhibitory effects of individual constituents of P. tenuifolia roots on pro-inflammatory cytokine production in LPS-stimulated BMDCs.…”

Section: Resultsmentioning

confidence: 99%

Bioactive Compounds from Polygala tenuifolia and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Pro-inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

Vinh

Heo

Phong

et al. 2020

Plants

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The roots of Polygala tenuifolia Wild (Polygalaceae), which is among the most important components of traditional Chinese herbal medicine, have been widely used for over 1000 years to treat a variety of diseases. In the current investigation of secondary metabolites with anti-inflammatory properties from Korean medicinal plants, a phytochemical constituent study led to the isolation of 15 compounds (1–15) from the roots of P. tenuifolia via a combination of chromatographic methods. Their structures were determined by means of spectroscopic data such as nuclear magnetic resonance (NMR), 1D- and 2D-NMR, and liquid chromatography-mass spectrometry (LC-MS). As the obtained results, the isolated compounds were divided into two groups—phenolic glycosides (1–9) and triterpenoid saponins (10–15). The anti-inflammatory effects of crude extracts, fractions, and isolated compounds were investigated on the production of the pro-inflammatory cytokines interleukin (IL)-12 p40, IL-6, and tumour necrosis factor-α in lipopolysaccharide-stimulated bone marrow-derived dendritic cells. The IC50 values, ranging from 0.08 ± 0.01 to 21.05 ± 0.40 μM, indicated potent inhibitory effects of the isolated compounds on the production of all three pro-inflammatory cytokines. In particular, compounds 3–12, 14, and 15 showed promising anti-inflammatory activity. These results suggest that phenolic and triterpenoid saponins from P. tenuifolia may be excellent anti-inflammatory agents.

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Section: Resultsmentioning

confidence: 99%

Bioactive Compounds from Polygala tenuifolia and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Pro-inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

Vinh

Heo

Phong

et al. 2020

Plants

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“…The A. vera plant was first extracted with 95% methanol, and the extract was then fractionated into n -hexane, CHCl 3 , EtOAc and BuOH fractions. The CHCl 3 and EtOAc fractions were subjected to column chromatography over silica gel and C-18 to isolate one new compound 1 , along with known compounds 2–9 , which were identified as 9-dihydroxyl-2'- O -( Z )-cinnamoyl-7-methoxy-aloesin ( 1 ), aloe-emodin ( 2 ) 5 , aloin A ( 3 ) 5 , aloin B ( 4 ) 5 , elgonica dimer A ( 5 ) 5 , feralolide ( 6 ) 15 , isoaloeresin D ( 7 ) 16 , aloeresin E ( 8 ), 16 and, 7- O -methylaloeresin A ( 9 ) 17 ( Figure 1 , Figure S8?15 ). The structures were identified by 1D/2D nuclear magnetic resonance (NMR), high-resolution electrospray ionization mass spectrometry (HRESIMS), and by comparison with previous reports.…”

Section: Resultsmentioning

confidence: 99%

“…This plant gel has many biological activities, including anti-inflammatory 3 , 4 , anti-viral 4 , anti-bacterial 4 , anti-cancer 3 , 4 , anti-diabetic 4 and anti-allergy activities 4 ; it also provides protection against radiation 4 . The main phytochemicals in this gel are derivatives of anthraquinone and C-glucosylanthrone: aloin A and B, emodin, desoxyaloin, aloinoside B and C, and elgonica dimer A 1 , 5 . Aloesin, aloe emodin and aloin A have been reported to have antioxidant activities 6 , while aloinoside B and C are known to inhibit the activity of soluble epoxide hydrolase and phosphodiesterase-4D 5 , 7 .…”

Section: Introductionmentioning

confidence: 99%

“…The main phytochemicals in this gel are derivatives of anthraquinone and C-glucosylanthrone: aloin A and B, emodin, desoxyaloin, aloinoside B and C, and elgonica dimer A 1 , 5 . Aloesin, aloe emodin and aloin A have been reported to have antioxidant activities 6 , while aloinoside B and C are known to inhibit the activity of soluble epoxide hydrolase and phosphodiesterase-4D 5 , 7 .…”

Section: Introductionmentioning

confidence: 99%

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Tyrosinase inhibitory components from Aloe vera and their antiviral activity

Kim

Yoon

Yang

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A new compound, 9-dihydroxyl-2'-O-(Z)-cinnamoyl-7-methoxy-aloesin (1), and eight known compounds (2–9) were isolated from Aloe vera. Their structures were elucidated using 1D/2D nuclear magnetic resonance and mass spectra. Compound 9 exhibited reversible competitive inhibitory activity against the enzyme tyrosinase, with an IC50 value of 9.8 ± 0.9 µM. A molecular simulation revealed that compound 9 interacts via hydrogen bonding with residues His244, Thr261, and Val283 of tyrosinase. Additionally, compounds 3 and 7 were shown by half-leaf assays to exhibit inhibitory activity towards Pepper mild mottle virus.

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“…Aloe vera ( A. vera ) is a perennial herbaceous plant of the Liliaceae family, distributed widely in Africa, Asia, Europe, and the southern parts of North America. It is popularly used in functional foods and nutraceuticals (Coelho, et al, ; Sun, et al, ). In A. vera , the chromones show perfect radical scavenging and anti‐inflammatory properties (Choodej, Sommit, & Pudhom, ; Lucini, Pellizzoni, Pellegrino, Molinaria, & Colla, ), and the anthraquinone derivatives show effective antioxidant and anticancer properties (Huang, et al, ; Lo, Nian, Chiu, Wang, & Wu, ; Nemmar, Al‐Salam, Yuvaraju, Beegam, & Ali, ).…”

Section: Introductionmentioning

confidence: 99%

Main anthraquinone components in Aloe vera and their inhibitory effects on the formation of advanced glycation end-products

Kang

Zhao

et al. 2016

Journal of Food Processing and Preservation

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Food heating process causes increased protein glycation and the formation of advanced glycation endproducts (AGEs) which related with diabetes and ageing. Aloe vera (A. vera) extract is a potent antioxidant with established effects attributed largely to a key ingredient anthraquinone. This study investigated the inhibitory ability of the three anthraquinones from A. vera on the formation of AGEs in a heated model system at 70°C. Anthraquinones, including aloe‐emodin (AED), emodin (ED), and chrysophanol (CSN), were extracted from A. vera and analyzed by ultra‐high performance liquid chromatography‐tandem mass spectrometry. Under optimal extraction conditions, the extraction yield of the anthraquinones was 4.377 mg/g. Anthraquinones showed good inhibition toward the formation of glycation products; the inhibition rates of AED, ED, and CSN on crosslinked AGEs were 46.48%, 66.38%, and 57.32% at 10 μM concentrations. Sodium dodecyl sulfate–polyacrylamide gel electrophoresis images also proved that the anthraquinones could significantly inhibit crosslinked AGE formation in a time‐dependent manner. ED showed higher inhibitory ability than AED and CSN on the formation of Nɛ‐(carboxymethyl)lysine and crosslinked AGEs. The results indicate that the antiglycation properties of these anthraquinones are likely related to the phenolic hydroxyl groups in their structures, but this ability is not related to their antioxidant activity, which probably depends on the whole structure of the quinone. Generally, the anthraquinones in A. vera, especially ED, can effectively inhibit AGE formation and reduce protein crosslinking during food processing, even at low concentration. Practical applications The inhibitory effects of three anthraquinones extracted from Aloe vera on the formation of AGEs were investigated in a heated model system. The results indicate Aloe can be used as an effective inhibitor of glycation products in food processing, moreover, this research can be useful for finding suitable nature inhibitors of AGEs for food processing.

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Soluble epoxide hydrolase inhibitory activity of anthraquinone components from Aloe

Cited by 16 publications

References 40 publications

Bioactive Compounds from Polygala tenuifolia and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Pro-inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

Bioactive Compounds from Polygala tenuifolia and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Pro-inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

Tyrosinase inhibitory components from Aloe vera and their antiviral activity

Main anthraquinone components in Aloe vera and their inhibitory effects on the formation of advanced glycation end-products

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