A diterpenoid sugiol from &lt;i&gt;Metasequoia glyptostroboides&lt;/i&gt; with α-glucosidase and tyrosinase inhibitory potential

Bajpai, Vivek K.; Kang, Sun Chul

doi:10.3329/bjp.v9i3.19026

Cited by 6 publications

(5 citation statements)

References 16 publications

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“…Bajpai and Kang [ 57 ] evaluated sugiol for tyrosinase and α-glucosidase inhibitory activity in vitro, in terms of its antimelanogenesis and antidiabetic potential, respectively. The results showed that sugiol at the concentration range of 0.100 to 10 mg/mL presented efficacy on inhibiting α-glucosidase (12.34 to 63.47% of inhibition) similar to acarbose (19.2 to 65.5% of inhibition at same concentration range), while at concentration 0.020 to 0.50 mg/mL, sugiol inhibits 28.2 to 67.4% of tyrosinase activity, only a little less active than kojic acid used as reference (32.4 to 76.5% inhibition at the same concentration range).…”

Section: Bioactive Secondary Metabolites From Juniperus mentioning

confidence: 99%

The Current Status of the Pharmaceutical Potential of Juniperus L. Metabolites

Tavares

Seca

2018

Medicines

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Background: Plants and their derived natural compounds possess various biological and therapeutic properties, which turns them into an increasing topic of interest and research. Juniperus genus is diverse in species, with several traditional medicines reported, and rich in natural compounds with potential for development of new drugs. Methods: The research for this review were based in the Scopus and Web of Science databases using terms combining Juniperus, secondary metabolites names, and biological activities. This is not an exhaustive review of Juniperus compounds with biological activities, but rather a critical selection taking into account the following criteria: (i) studies involving the most recent methodologies for quantitative evaluation of biological activities; and (ii) the compounds with the highest number of studies published in the last four years. Results: From Juniperus species, several diterpenes, flavonoids, and one lignan were emphasized taking into account their level of activity against several targets. Antitumor activity is by far the most studied, being followed by antibacterial and antiviral activities. Deoxypodophyllotoxin and one dehydroabietic acid derivative appears to be the most promising lead compounds. Conclusions: This review demonstrates the Juniperus species value as a source of secondary metabolites with relevant pharmaceutical potential.

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Section: Bioactive Secondary Metabolites From Juniperus mentioning

confidence: 99%

The Current Status of the Pharmaceutical Potential of Juniperus L. Metabolites

Tavares

Seca

2018

Medicines

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“…Interestingly, gomisin is a lignin compound that can be isolated from plants of the Schisandraceae family [ 32 ]. It is also known to have anti-diabetic activity by increasing AMPK phosphorylation [ 33 ], anti-oxidant, anti-tumor, and anti-inflammatory [ 34 ]. On the other hand, Fig 1 also shows that the presence of sugiol was indicated by the proton signals at chemical shifts of 0.59 (s), 0.83 (m, 6H), 0.97 (m, 1H), 1.20 (m, 5H), 1.41 (s) 1.60 (s), 1.81 (s), 1.93 (s), 2.46 (p, J = 1.8 Hz, 2H), 2.58 (s), 6.88 (s), 7.5 (s, OH), 7.75 (s).…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…On the other hand, Fig 1 also shows that the presence of sugiol was indicated by the proton signals at chemical shifts of 0.59 (s), 0.83 (m, 6H), 0.97 (m, 1H), 1.20 (m, 5H), 1.41 (s) 1.60 (s), 1.81 (s), 1.93 (s), 2.46 (p, J = 1.8 Hz, 2H), 2.58 (s), 6.88 (s), 7.5 (s, OH), 7.75 (s). Sugiol is a diterpenoid compound that can be isolated from Metasequoia glyptostroboides and the compound exhibited a large number of inhibitory effects on the α-glucosidase and tyrosinase enzymes tested in vitro [34]. Besides, uvariamicin-I was detected at chemical shifts of 0.64 (m, 3H), 0.83 (m, 14H), 0.97 (d, J = 2.7 Hz, 1H), 1.20 (m, 11H), 1.26 (s), 1.41, 1.45 (s), 1.51 (s, 2H), 1.81 (s), 1.93 (d, J = 5.7 Hz, 3H), 2.12, 2.55 (s), 2.99 (s), 3.12 (d, J = 2.4 Hz, 6H), 4.09 (d, J = 5.2 Hz, 2H), and 5.27 (s) ppm.…”

Section: Lcms/ms and 1 H Nmr Analysis Of Propolis Methanolic Extractmentioning

confidence: 99%

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Synthesis of zinc oxide nanoparticles using methanol propolis extract (Pro-ZnO NPs) as antidiabetic and antioxidant

D.¹,

Plashintania²,

Putri³

et al. 2023

PLoS ONE

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In recent times, the overall health of individuals has been declining due to unhealthy lifestyles, leading to various diseases, including diabetes. To address this issue, antidiabetic and antioxidant agents are required to back-up human well-being. Zinc oxide (ZnO) is one such substance known for its antidiabetic and antioxidant effects. To enhance its capability and effectiveness, propolis was utilized to synthesize zinc oxide nanoparticles (Pro-ZnO NPs). The objective of this study was to synthesize Pro-ZnO NPs and assess their performance by conducting inhibition assays against α-amylase and α-glucosidase enzymes, as well as a 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay. The results showed that Pro-ZnO NPs were formed in a hexagonal wurtzite structure, with particle sizes ranging from 30 to 50 nm and an absorption band observed at 341 nm. The stability, chemical properties, and crystallography of Pro-ZnO NPs were also thoroughly examined using appropriate methods. The Pro-ZnO NPs demonstrated significant inhibitory effects against α-amylase and α-glucosidase enzymes, with inhibition rates reaching 69.52% and 73.78%, respectively, whereas the antioxidant activity was as high as 70.76%. Consequently, with their high inhibition rates, the Pro-ZnO NPs demonstrate the potential to be employed as a natural agent for combating diabetes and promoting antioxidant effects.

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“…It is estimated that about 40% of the tested bioactive substances present problems related to low water solubility (Savjani et al, 2012), including natural products (Coimbra et al, 2011). This is the case of sugiol, a diterpenoid isolated from the bark of several trees from the Cupressaceae family, such as Cupressus sempervirens (Zhang et al, 2012) , Cupressus geovania (Jolad et al, 2005) , Cupressus lusitanica (Mohareb et al, 2010) , Calocedrus formosana (Chao et al, 2005) , Metasequoia glyptostroboides (Bajpai and Kang, 2014), and Pilgerodendron uviferum (Solís et al, 2004). Despite unsatisfactory water solubility previously reported (Sengupta et al, 1960), sugiol has already been shown to have anti-inflammatory, antibacterial, and anti-cancer properties during in vitro assays (Bajpai and Kang, 2011; Sengupta et al, 2011; Jung et al, 2015; D'yakonov et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Activity and Cell-Death Pathway in Leishmania infantum Induced by Sugiol: Vectorization Using Yeast Cell Wall Particles Obtained From Saccharomyces cerevisiae

Scariot

Volpato

Fernandes

et al. 2019

Front. Cell. Infect. Microbiol.

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Visceral leishmaniasis, caused by Leishmania infantum , is a neglected tropical disease, to which efforts in the innovation of effective and affordable treatments remain limited, despite the rising incidence in several regions of the world. In this work, the antileishmanial effects of sugiol were investigated in vitro . This compound was isolated from the bark of Cupressus lusitanica and showed promising activity against L. infantum . In spite of the positive results, it is known that the compound is a poorly water-soluble diterpene molecule, which hinders further investigation, especially in preclinical animal studies. Thus, in an alternative delivery method, sugiol was entrapped in glucan-rich particles obtained from Saccharomyces cerevisiae yeast cell walls (YCWPs). To evaluate the activity of sugiol, the experiments were divided into two parts: (i) the in vitro investigation of antileishmanial activity of free sugiol against L. infantum promastigotes after 24, 48, and 72 h of treatment and (ii) the evaluation of antileishmanial activity of sugiol entrapped in glucan-rich particles against intracellular L. infantum amastigotes. Free sugiol induced the cell-death process in promastigotes, which was triggered by enhancing cytosolic calcium level and promoting the autophagy up to the first 24 h. Over time, the presence of autophagic vacuoles became rarer, especially after treatment with lower concentrations of sugiol, but other cellular events intensified, like ROS production, cell shrinkage, and phosphatidylserine exposure. Hyperpolarization of mitochondrial membrane potential was found at 72 h, induced by the mitochondria calcium uptake, causing an increase in ROS production and lipid peroxidation as a consequence. These events resulted in the cell death of promastigotes by secondary necrosis. Sugiol entrapped in glucan-rich particles was specifically recognized by dectin-1 receptor on the plasma membrane of macrophages, the main host cell of Leishmania spp. Electron micrographs revealed particles containing sugiol within the infected macrophages and these particles were active against the intracellular L. infantum amastigotes without affecting the host cell. Therefore, the YCWPs act like a Trojan horse to successfully deliver sugiol into the macrophage, presenting an interesting strategy to deliver water-insoluble drugs to parasitized cells.

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A diterpenoid sugiol from <i>Metasequoia glyptostroboides</i> with α-glucosidase and tyrosinase inhibitory potential

Cited by 6 publications

References 16 publications

The Current Status of the Pharmaceutical Potential of Juniperus L. Metabolites

The Current Status of the Pharmaceutical Potential of Juniperus L. Metabolites

Synthesis of zinc oxide nanoparticles using methanol propolis extract (Pro-ZnO NPs) as antidiabetic and antioxidant

Activity and Cell-Death Pathway in Leishmania infantum Induced by Sugiol: Vectorization Using Yeast Cell Wall Particles Obtained From Saccharomyces cerevisiae

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