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Anti-inflammatory steroidal sapogenins and a conjugated chalcone-stilbene from Dracaena usambarensis Engl.
Fitoterapia ( IF 2.5 ) Pub Date : 2020-08-31 , DOI: 10.1016/j.fitote.2020.104717
Vaderament-A Nchiozem-Ngnitedem 1 , Leonidah Kerubo Omosa 2 , Kibrom Gebreheiwot Bedane 3 , Solomon Derese 2 , Lukas Brieger 4 , Carsten Strohmann 4 , Michael Spiteller 5
Affiliation  

Four new steroidal sapogenins, dracaenogenins Csingle bondF (14), a new conjugated chalcone-stilbene, 3′′-methoxycochinchinenene H (5) together with eight known compounds namely, (25S)-spirosta-1,4-dien-3-one (6), trans-resveratrol (7), 4,4′-dihydroxy-3′-methoxychalcone (8), N-trans-coumaroyltyramine (9), N-trans-p-coumaroyloctopamine (10), N-trans-feruloyloctopamine (11), 7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N2,N3-bis(4-hydroxyphenethyl)-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxamide (12) and grossamide (13) were isolated from the stems of Dracaena usambarensis Engl. from Kenya. It is important to note that compounds 12 and 13 are being reported from this genus for the first time. Structural elucidation of the isolated compounds was done using spectroscopic (NMR, UV, IR, optical rotation) and spectrometric (HRESIMS) techniques. The absolute and relative configurations of the isolated compounds were determined by employing single crystal X-ray crystallography analysis, NOESY correlations and coupling constants. The anti-inflammatory potencies of the isolated compounds were evaluated by measuring the levels of four cytokines (IL-1β, IL-2, GM-CSF and TNF-α) in the supernatant media of human peripheral blood mononuclear cells (PBMCs) stimulated by lipopolysaccharide (LPS). At the tested concentration of 100 μM, the new conjugated chalcone-stilbene 5, the dihydrochalcone, 8 and the lignanamide, 13 were substantially more potent than the standard drug, ibuprofen, inhibiting the release of all the cytokines, IL-1β, IL-2, GM-CSF and TNF-α from 0.06–58.04% compared to LPS control. These compounds should therefore be considered for development into anti-inflammatory drug candidates. Compound 7 significantly decreased the release of GM-CSF (6.11% of LPS control) and TNF-α (18.35% of LPS control). The cytokine TNF-α was sensitive to all the tested compounds 1-13.



中文翻译:

来自Dracaena usambarensis Engl的抗炎类固醇皂苷元和缀合的查尔酮-二苯乙烯。

四个新的甾体皂苷元,dracaenogeninsÇ 单键F(1 - 4),一个新的共轭查耳酮-二苯乙烯,3'' - methoxycochinchinenene H(5)与即8种已知化合物一起,(25小号)-spirosta -1,4- dien- -3-酮(6),反式-白藜芦醇(7),4,4'-二羟基-3'-甲氧基查(8),ñ -反式-coumaroyltyramine(9),ñ -反式- p -coumaroyloctopamine(10),ñ -反式-feruloyloctopamine(11),7-羟基-1-(4-羟基-3-甲氧基苯基) - ñ 2Ñ 3 -(4-羟基苯乙基)-6-甲氧基-1,2-二氢萘-2,3-二甲酰胺(12)和从美国龙血树(Dracaena usambarensis Engl )的茎中分离出了总酰胺(13)。来自肯尼亚。重要的是要注意化合物1213首次被报道为该属。使用光谱学(NMR,UV,IR,旋光)和光谱学(HRESIMS)技术对分离出的化合物进行结构解析。分离出的化合物的绝对构型和相对构型通过单晶X射线晶体学分析,NOESY相关性和耦合常数确定。通过测量经刺激的人外周血单核细胞(PBMC)上清液中四种细胞因子(IL-1β,IL-2,GM-CSF和TNF-α)的水平来评估分离化合物的抗炎能力。脂多糖(LPS)。在100μM的测试浓度下,新的共轭查尔酮-二苯乙烯5,二氢查耳酮8和木脂酰胺13与LPS对照相比,它们比标准药物布洛芬更有效,可抑制所有细胞因子IL-1β IL-2,GM-CSF和TNF-α的释放,范围为0.06-58.04%。因此,应考虑将这些化合物开发成抗炎药候选物。化合物7显着降低了GM-CSF(LPS对照的6.11%)和TNF-α(LPS对照的18.35%)的释放。细胞因子TNF-α是所有敏感测试化合物1 - 13

更新日期:2020-09-12
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