Bioactive drimane sesquiterpenoids and aromatic glycosides from Cinnamosma fragrans
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The authors declare no competing financial interest.
Acknowledgements
This work was supported by the Public Health Prepardness for Infectious Diseases (PHPID) New Investigator Grant (To L.H.R) of The Ohio State University, U.S., Public Health Preparedness for Infectious Diseases (PHPID) New Investigator Grant (to L.H.R). We thank the instrumentation facility of the College of Pharmacy and the Campus Chemical Instrument Center (CCIC) of The Ohio State University for the acquisition of the NMR, Mass, UV, and IR spectroscopic data.
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2022, PhytochemistryCitation Excerpt :On the basis of above-mentioned evidence, the absolute configuration of imperlignanoside D (10) was clarified to be 7S,7′S,8S,8′R. By comparing the spectroscopic data with those reported in literatures, the structures of known compounds 11–47 were identified as 4-hydroxy-3-methoxy phenyl-β-d-xylopyranosyl (1 → 6)-O-β-d-glucopyranoside (11) (Lin et al., 2010), cuneataside D (12) (Jin et al., 2015), 3,4-dimethoxyphenyl-β-d-glucopyranoside (13) (Xuan et al., 2006), 3,4-dimethoxyphenyl-1-O-β-d-apiofuranosyl (1 → 6)-β-d-glucopyranoside (14) (He et al., 2017), 3,4-dimethoxyphenyl-6-O-(α-l-rhamnopyranosyl)-β-d-glucopyranoside (15) (Jin et al., 2015), 3,4,5-trimethoxyphenyl 1-O-β-apiofuranosyl (1''→6′)-β-glucopyranoside (16) (Kanchanapoom et al., 2002), salicin (17) (Mizuno et al., 1991), 2′-O-(E)-p-coumaroylsalicin (18) (Dagvadorj et al., 2010), poliothrysoside (19) (Shaari and Waterman, 1994), salireposide (20) (Belyanin et al., 2012), 4′-hydroxybenzyl-2-hydroxybenzoate-1′-O-β-d-glucopyranoside (21) (Hou et al., 2021), p-hydroxybenzaldehyde (22) (Kim et al., 2003), p-hydroxybenzoic acid (23) (Demmak et al., 2019), 3,4-dihydroxybenzoic acid (24) (Song et al., 2007), 3-methoxy-4-hydroxybenzoic acid (25) (Kong et al., 1996), 4-hydroxy-3,5-dimethoxybenzaldehyde (26) (Wang et al., 2017), syringic acid (27) (Hu et al., 2006), glucosyringic acid (28) (Ma et al., 2020), echipuroside A (29) (Li et al., 2002), 4-hydroxy cinnamic acid (30) (Yang et al., 2014), caffeic acid (31) (Zhang et al., 2006), ethyl caffeate (32) (Shen et al., 2010), coniferaldehyde (33) (Song et al., 2008), ferulic acid (34) (Yang et al., 2001), (+)-(7S,8S)-guaiacylglycerol (35) (Gan et al., 2010; Tian et al., 2014; Wang et al., 2014; Warashina et al., 2005), (+)-(7S,8S)-guaiacylglycerol 8-O-β-d-glucopyranoside (36) (Gan et al., 2010; Qu et al., 2014), (7S,8S)-syringoylglycerol (37) (Gan et al., 2010; Matsuura et al., 2004; Wang et al., 2014), (7R,8R)-4-O-methylsyringoylglycerol (38) (Gan et al., 2010; Liu et al., 2012; Matsuura et al., 2004; Wang et al., 2014), 1,2′,4′,6′-tetraacetyl-3,6-diferuloyl-sucrose (39) (Li et al., 2013), sucrose diester of 4,4′-dihydroxy-3,3′-dimethoxy-β-truxinic acid (40) (Dinberg et al., 2001; Xu et al., 2016; Zhang et al., 2016), (−)-syringaresinol-4-O-β-d-glucopyranoside (41) (Shao et al., 2018; Yan et al., 2009), (6R,7S,8S)-7α-[(β-glucopyranosyl)oxy]lyoniresinol (42) (Ohashi et al., 1994; Ono et al., 2009), 5-methoxyflavone (43) (Fu et al., 2010), 6-hydroxy 5-methoxyflavone (44) (Awaad et al., 2006), 5,2′-dimethoxyflavone (45) (Lee et al., 2008), tricin 4′-O-(erythro-β-guaiacylglyceryl) ether (46) (Nakajima et al., 2003), tricin 4′-O-(erythro-β-4-hydroxyphenylglyceryl) ether (47) (Chang et al., 2010), respectively. The effects of compounds 1–47 on lipopolysaccharides (LPS)-stimulated nitric oxide (NO) release in RAW264.7 cells were measured through the Griess reaction at the concentration without significant cytotoxicity (Fig. S70) to clarify their potentical anti-inflammatory effects (Chen et al., 2020).
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2020, Tetrahedron LettersCitation Excerpt :Its 1H NMR spectrum displayed characteristic signals for one oxymethylene (δH 4.52 and 4.20) and three methyls (δH 0.93, 0.92, 0.73). The NMR and HRESIMS data mentioned above suggested that 3 is an analogue of 1α-hydroxyconfertifolin (8) and cinnamolide [29] with two hydroxy moieties. The HMBC correlations (Fig. 5) of H-1 (δH 3.84, br t, 2.5 Hz) with C-3 (δC 33.8) and C-5 (δC 36.5), H-7 (δH 6.86, t, 4.1 Hz) with C-5, C-6 (δC 25.0), C-9 (δC 78.3), and C-12 (δC 168.6), H-15 (δH 0.73, 3H, s) with C-1, C-9, and C-10 (δC 39.5), and all of H-5 (δH 2.38, dd, 11.1, 5.6 Hz), H-11a (δH 4.52, d, 10.1 Hz), and H-11b (δH 4.20, d, 10.1 Hz) with C-9 demonstrated the presences of a C7-8 double bond and the two hydroxy moieties at C-1 and C-9 in 3.