A new arylnaphthalene type lignan from Cordia rufescens A. DC. (Boraginaceae)

Silva, Sâmia Andrícia Souza da; Souto, Augusto Lopes; Agra, Maria de Fátima; Cunha, Emídio Vasconcelos Leitão da; Barbosa-Filho, José Maria; Silva, Marcelo Sobral da; Braz‐Filho, Raimundo

doi:10.3998/ark.5550190.0005.607

Cited by 23 publications

(10 citation statements)

References 7 publications

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“…Aryl naphthalene lignans (ANLs) are widely distributed in dietary or medicinal plants and exhibit excellent biological activities, such as antibacterial, anti-inflammatory, antiviral and anticancer activities (26). In addition, some herbs with ANLs were used as folk medicine for adjuvant therapy of diabetes, such as Cordia rufescens (27,28). Researchers of Shionogi & Co., Ltd. reported that S-8921 and S-8921G, two synthetic ANLs, exhibited significant hypocholesterolemic effects in vivo, which expanded the application of lignans to metabolic diseases (29).…”

Section: Introductionmentioning

confidence: 99%

Diphyllin Improves High-Fat Diet-Induced Obesity in Mice Through Brown and Beige Adipocytes

Duan

Jiang

et al. 2020

Front. Endocrinol.

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Brown adipose tissue (BAT) and beige adipose tissue dissipate metabolic energy and mediate nonshivering thermogenesis, thereby boosting energy expenditure. Increasing the browning of BAT and beige adipose tissue is expected to be a promising strategy for combatting obesity. Through phenotype screening of C3H10-T1/2 mesenchymal stem cells, diphyllin was identified as a promising molecule in promoting brown adipocyte differentiation. In vitro studies revealed that diphyllin promoted C3H10-T1/2 cell and primary brown/beige preadipocyte differentiation and thermogenesis, which resulted increased energy consumption. We synthesized the compound and evaluated its effect on metabolism in vivo. Chronic experiments revealed that mice fed a high-fat diet (HFD) with 100 mg/kg diphyllin had ameliorated oral glucose tolerance and insulin sensitivity and decreased body weight and fat content ratio. Adaptive thermogenesis in HFD-fed mice under cold stimulation and whole-body energy expenditure were augmented after chronic diphyllin treatment. Diphyllin may be involved in regulating the development of brown and beige adipocytes by inhibiting V-ATPase and reducing intracellular autophagy. This study provides new clues for the discovery of anti-obesity molecules from natural products.

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Section: Introductionmentioning

confidence: 99%

Diphyllin Improves High-Fat Diet-Induced Obesity in Mice Through Brown and Beige Adipocytes

Duan

Jiang

et al. 2020

Front. Endocrinol.

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“…HMBC analysis aided in the identification of C1 00 (114.6 ppm) through its correlations to H3 00 and H8 00 , and C2 00 (152.8 ppm) through its correlation to H4 00 , where all aromatic protons were identified by COSY and HSQC. Comparison of these shifts to 2-naphthols with aryl amines or aryl ethers covalently linked to C1 suggested that 1a/ 1b has phenol carbons with chemical shifts that are consistent with an aryl amine attached at C1 00 of 1a/1b, 52,53 ruling out arylation of dOG at either O 6 or O 8 of the heterocyclic base. The remaining possible points of covalent attachment between C1 of 2-naphthol and dOG include the nitrogen atoms N1, N 2 , N3, and N7.…”

Section: ' Results and Discussionmentioning

confidence: 99%

Copper/H₂O₂-Mediated Oxidation of 2′-Deoxyguanosine in the Presence of 2-Naphthol Leads to the Formation of Two Distinct Isomeric Adducts

et al. 2011

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Exposure of cells to phenolic compounds through exogenous and endogenous sources can lead to deleterious effects via nucleobase modifications of DNA occurring under oxidative conditions. 2'-Deoxyguanosine (dG) is the most electron rich of the four canonical bases and includes many nucleophilic sites; it is also susceptible to oxidation with numerous reactive oxygen species. In these studies, dG was allowed to react with 2-naphthol in the presence of copper or iron salts yielding two principal isomeric products. Spectroscopic analysis and reactions with alkylated nucleosides support the assignment of compound 1a/1b as a pair of atropisomer N(2) adducts and compound 2a/2b as a diastereomeric mixture of tricyclic [4.3.3.0] adducts. Both products are the result of an overall four-electron oxidation process and consequently have the same masses, though drastically different structures, providing mechanistic insight into their formation. Thus, dG alkylation by 2-naphthol under oxidative conditions yields products whose structural properties are altered, leading to potentially mutagenic effects in genomic DNA.

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“…Benzo [k,l]xanthene lignans (BXLs) are a group of rare natural products belonging to the class of polyphenols. To date, only six naturally occurring BXLs have been discovered: rufescidride [1], mongolicumin A [2] and its dimethyl ester [3], yunnaneic acid H [4], chiliantin D [5], and dodegranoside [6]. Because of their limited availability in nature, the biological activities of natural BXLs have been almost unexplored for years.…”

Section: Introductionmentioning

confidence: 99%

Characterization and Interaction with Biomembrane Model of Benzo[k,l]xanthene Lignan Loaded Solid Lipid Nanoparticles

et al. 2022

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Benzo[k,l]xanthene lignans are a group of rare natural products belonging to the class of polyphenols with promising biological activities and are studied as potential chemotherapeutic agents. The lipophilic character of a xanthene core makes these molecules difficult to be used in an aqueous medium, limiting their employment in studies for pharmaceutical applications. To overcome this problem, a drug-delivery system which is able to improve the stability and bioavailability of the compound can be used. In this study, a bioactive benzoxanthene lignan (BXL) has been included in SLN. Unloaded and BXL-loaded SLN have been prepared using the Phase Inversion Temperature method and characterized in terms of size, zeta potential, entrapment efficiency and stability. Differential scanning calorimetry was used to evaluate the thermotropic behavior and ability of SLN to act as carriers for BXL. A biomembrane model, represented by multilamellar vesicles, was used to simulate the interaction of the SLN with the cellular membrane. Unloaded and loaded SLN were incubated with the MLV, and their interactions were evaluated through variations in their calorimetric curves. The results obtained suggest that SLN could be used as a delivery system for BXL.

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A new arylnaphthalene type lignan from Cordia rufescens A. DC. (Boraginaceae)

Abstract: A new arylnaphthalene type lignan named rufescidride, the first containing an unusual anhydride moiety, has been isolated from the stem and branches of Cordia rufescens. Its structure was elucidated on the basis of spectral data (IR, MS and NMR), mainly 1D and 2D NMR.

Cited by 23 publications

References 7 publications

Diphyllin Improves High-Fat Diet-Induced Obesity in Mice Through Brown and Beige Adipocytes

Diphyllin Improves High-Fat Diet-Induced Obesity in Mice Through Brown and Beige Adipocytes

Copper/H₂O₂-Mediated Oxidation of 2′-Deoxyguanosine in the Presence of 2-Naphthol Leads to the Formation of Two Distinct Isomeric Adducts

Characterization and Interaction with Biomembrane Model of Benzo[k,l]xanthene Lignan Loaded Solid Lipid Nanoparticles

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A new arylnaphthalene type lignan from Cordia rufescens A. DC. (Boraginaceae)

Abstract: A new arylnaphthalene type lignan named rufescidride, the first containing an unusual anhydride moiety, has been isolated from the stem and branches of Cordia rufescens. Its structure was elucidated on the basis of spectral data (IR, MS and NMR), mainly 1D and 2D NMR.

Cited by 23 publications

References 7 publications

Diphyllin Improves High-Fat Diet-Induced Obesity in Mice Through Brown and Beige Adipocytes

Diphyllin Improves High-Fat Diet-Induced Obesity in Mice Through Brown and Beige Adipocytes

Copper/H2O2-Mediated Oxidation of 2′-Deoxyguanosine in the Presence of 2-Naphthol Leads to the Formation of Two Distinct Isomeric Adducts

Characterization and Interaction with Biomembrane Model of Benzo[k,l]xanthene Lignan Loaded Solid Lipid Nanoparticles

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Copper/H₂O₂-Mediated Oxidation of 2′-Deoxyguanosine in the Presence of 2-Naphthol Leads to the Formation of Two Distinct Isomeric Adducts