Chemical constituents from Bletilla striata and their NO production suppression in RAW 264.7 macrophage cells

Abstract

A novel glucoside bletilloside A (1) was isolated from the tubers of Bletilla striata, together with seven known compounds (2-8). Their structures were determined on the basis of extensive spectroscopic analyses. All compounds were evaluated for the inhibition on NO production effects in RAW 264.7 macrophage cells, while militarine (4) and dactylorhin A (5) exhibited moderate inhibitory effects.

Lung protective effects of dietary malate esters derivatives from Bletilla striata against SiO2 nanoparticles through activation of Nrf2 pathway

“…1 ) by means of chromatographic methods and recrystallization, including one new glucosyloxybenzyl 2-isobutylmalate, seven known glucosyloxybenzyl 2-isobutylmalates and other compounds. Finally, their structures were determined as follow: ( Z )-2-(2-methylpropyl) butenedioic acid-4- β- d -glucopyranosyloxybenzyl ester ( 1 ), gymnoside I ( 2 ) ( Yue et al, 2010 ), gymnoside II ( 3 ) ( Yue et al, 2010 ), 1-(4- O -glucopyranosyloxybenzyl) 4-methyl (2 R )-2-isobutylmalate ( 4 ) ( Huang et al, 2002 ), ( Z )-2-(2-methylpropyl) butenedioic acid bis(4- β - d -glucopyranosyloxybenzyl) ester ( 5 ) ( Huang et al, 2002 ), dactylorhin A ( 6 ) ( Huang et al, 2002 ), gymnoside III ( 7 ) ( Yue et al, 2010 ), militarine ( 8 ) ( Yue et al, 2010 ), tortoside A ( 9 ) ( Cai et al, 2004 ), 4-allyl-2, 6-dimethoxyphenol glucoside ( 10 ) ( Guan et al, 2009 ), bletilloside A ( 11 ) ( Zhao et al, 2018 ), shancigusin I ( 12 ) ( Morikawa et al, 2006 ), bleformin J ( 13 ) ( Lin et al, 2016 ), 4-hydroxy- trans -cinnamomic acid 4- β - d -glucopyranosyloxybenzyl ester ( 14 ) ( Zidorn et al, 2001 ), trans - p -hydroxycinnamic acid ( 15 ) ( Miao et al, 2008 ), p -hydroxybenzaldehyde ( 16 ) ( Ying et al, 2009 ), 4-methoxybenzyl alcohol ( 17 ) ( Xiang et al, 2017 ), p -hydroxyphenylacetic acid methyl ester ( 18 ) ( Feng et al, 2009 ), 4-methoxy catechol ( 19 ) ( Zhou et al, 2010 ), p -methoxyphenyl-propionic acid ( 20 ) ( Pcolinski et al, 1995 ), p -hydroxybenzoic acid ( 21 ) ( Gouvêa et al, 2016 ), vanillin ( 22 ) ( Duan et al, 2013 ), 4-(methoxymethyl)phenol ( 23 ) ( Wang et al, 2012 ), phenyl- β - d -glucopyranoside ( 24 ) ( Chen et al, 2008 ), 4-[(acetyloxy)methyl]phenyl- β - d -glucopyranoside ( 25 ) ( Li et al, 2006 ), p -methylphenyl-1- O - β - d -glucopyranoside ( 26 ) ( Duan et al, 2013 ), arbutin ( 27 ) ( Jiang et al, 2017 ), gastrodin ( 28 ) ( Han et al, 2015 ), n ...…”

“…Furthermore, 2-isobutylmalates can improve the activity of cytochrome C oxidase in HaCaT cells, showing a potential to be developed into anti-aging agents. For example, militarine exerts anti-inflammatory activity by inhibiting the release of NO in LPS-induced RAW264.7 cells ( Zhao et al, 2018 ). Despite these advances, the underlying mechanism regarding the lung cancer chemopreventive activity of militarine remains poorly understood.…”

Chemical Characterization and Metabolic Profiling of the Compounds in the Chinese Herbal Formula Li Chang Decoction by UPLC-QTOF/MS

“…A total of 5 characteristic compounds were detected in Bletillae Rhizoma. P47 dactylorhin A [ 16 ], P56 gymnoside III, and P61 militarine [ 17 ] were structurally similar to that contained two molecules of gastrodin (P22). Neutral loss of Glc (162 Da), H 2 O (18 Da), and gastrodin (268 Da) was used for identification.…”

Advances in militarine: Pharmacology, synthesis, molecular regulation and regulatory mechanisms

“…Studies by researchers have highlighted the significance of Militarine in pharmacology. For example, it induces apoptosis in cancer cell lines, protection of lung [ 19 ], anti-tumor properties [ 20 , 21 ], whitens in skin [ 6 ], reduces inflammatory [ 3 , 22 ], and exhibits anti-bacterial [ 23 ] and hemostasis [ 12 ] properties ( Table 1 ).…”