Abstract
A new lignan (3a → 9′:6a → 9-[(7′S,8′R )-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-2,7′-cycloligna-7-en-9,9′dicarbonyl]-6b-(p-coumaroyl) sucrose) was isolated from Heliotropium angiospermum Murray, Boraginaceae, along with four known substances: trigonotin A, rosmarinic acid, narcissin, and ethyl lithospermate. Their structures were deduced based on spectroscopic data analysis (MS and NMR of 1H and 13C) and a comparison with the published data. The absolute configuration for the undescribed lignan was determined using electronic circular dichroism analysis. In addition, the anti-inflammatory activity of this aryldihydronaphthalene was investigated by measuring its ability to inhibit the production of cytokines and nitric oxide by stimulated J774 macrophages. The glycosylated lignan, in a range of non-cytotoxic concentrations, reduced the production/release of pro-inflammatory mediators by stimulated macrophages, showing efficacy like that of dexamethasone, a glucocorticoid medication used as a control drug.
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Funding
This work was supported by Instituto Nacional de Ciência e Tecnologia, Rede Norte Nordeste de Fitoprodutos/Conselho Nacional de Desenvolvimento Científico e Tecnológico (INCT-RENNOFITO/CNPQ).
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GLDS was responsible for collecting the plant material, performing the laboratory work, interpreting the experimental data, and writing the manuscript first draft. JPRS, DIAF, YMN, and TAS assisted in HPLC method development, MS, and NMR analysis. CFV and LCFO carried out biological activity analysis. JIMM collected and identified the plant material. LSA and FMSJ performed ECD analyses and assisted in data interpretation. JFT, IMF, and MSS critically revised the paper and coordinated the project. All authors read the final manuscript and approved the submission.
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dos Santos, G.L.D., de Araújo, D.I.A.F., Raimundo e Silva, J.P. et al. Sucrose Diester of Aryldihydronaphthalene-Type Lignan with Anti-inflammatory Activity from Heliotropium angiospermum. Rev. Bras. Farmacogn. 32, 734–740 (2022). https://doi.org/10.1007/s43450-022-00295-1
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DOI: https://doi.org/10.1007/s43450-022-00295-1