Two New Stereoisomers of Tetrahydrofuranoid Lignans from the Flower Buds of &lt;i&gt;Magnolia fargesii&lt;/i&gt;

Lee, Jun; Lee, Dong‐Ho; Jang, Dae Sik; Nam, Joo Won; Kim, Jong Pyung; Park, Ki Hun; Yang, Min; Seo, Eun Kyoung

doi:10.1248/cpb.55.137

Cited by 32 publications

(15 citation statements)

References 19 publications

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“…On the other hand, the trans configuration between C-8 and C-8′ was determined by the NOESY correlations between H-8′ and H-9, H-7′ and H-8 (Figure 4). The absolute configuration of 6 was determined by comparing the CD spectrum of 6 with those of tanegool and analogues [36,37]. The CD spectrum of 6 showed positive absorption peaks at 235 and 278 nm, which were identical with the known compound tanegool.…”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents from the Roots and Rhizomes of Asarum heterotropoides var. mandshuricum and the In Vitro Anti-Inflammatory Activity

et al. 2017

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Anti-inflammatory compounds were investigated from the ethanol extract of the roots and rhizomes of Asarum heterotropoides var. mandshuricum, a traditional Chinese medicine called Xixin and used for pain and inflammatory. Nine new compounds were isolated, including six new lignans, neoasarinin A–C (1–3), neoasarininoside A and B (4 and 5), and asarinin B (7), and one new monoterpene, asarincin A (8), two new amides, asaramid II and III (10 and 11), and one new natural monoterpene, asaricin B (9), along with 37 known compounds (6, 12–47). Their structures and absolute configurations were elucidated on the basis of spectroscopic methods and chemical analyses. This is the first report of the absolute configuration of asarinin A (6). The 8-O-4′ neolignans (1–5) were reported in the genus Asarum for the first time. The 15 compounds 17, 19, 22–25, 28, 31, 36, 40, 42, 43, 45–47 were isolated from the genus Asarum, and compounds 16, 32, 33, 37 and 39 were isolated from A. heterotropoides var. mandshuricum for the first time. Thirty-seven of the isolates were evaluated for anti-inflammatory activity against the release of β-glucuronidase in polymorphonuclear leukocytes (PMNs) induced by the platelet-activating factor (PAF), and compounds 1, 4, 7, 8, 14, 17–19, 22, 24, 25, 29, 30, 32, 33, 40–43, 45, and 46 showed potent anti-inflammatory activities in vitro, with 27.9%–72.6% inhibitions at 10−5 mol/L. The results of anti-inflammatory assay suggested that lignans obtained from the CHCl3 extract might be the main active components of Xixin.

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Section: Resultsmentioning

confidence: 99%

Chemical Constituents from the Roots and Rhizomes of Asarum heterotropoides var. mandshuricum and the In Vitro Anti-Inflammatory Activity

et al. 2017

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“…All trans orientation of H-7/H-8/H-8′ was determined by the cross-peak of H-7/H-9, H-7/H-8′, H-8/H-7′, H-9/H-8′ in the NOESY spectrum. There were no definitive conclusions on the relationships between the absolute configuration and circular dichroism (CD) in this series of tetrahydrofuranoid lignans [11,12]. Although the CD spectrum of 1 showed the positive absorption peaks at 228 and 284 nm, the absolute configuration was not determined.…”

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confidence: 89%

Four New Cytotoxic Tetrahydrofuranoid Lignans fromSinopodophyllum emodi

Sun¹,

Li²,

Chen³

et al. 2012

Planta Med

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Four new tetrahydrofuranoid lignans, (-)-tanegool-7'-methyl ether ( 1), (+)-7'-methoxylariciresinol (2), sinolignan C (3), and epipinoresinol-4,4'-di- O- β- D-glucopyranoside (4), were isolated from the roots and rhizomes of SINOPODOPHYLLUM EMODI together with one known lignan (5). Their structures and stereochemistry were elucidated on the basis of spectroscopic and mass spectrometric evidence. The isolation of compounds 1- 5 represents the first report of tetrahydrofuran lignans from the genus SINOPODOPHYLLUM. The cytotoxic activities of all isolated compounds were evaluated against HeLa and KB cell lines, and compound 1 showed the most potent cytotoxicity with IC₅₀ values of 9.7 µM and 4.7 µM, respectively.

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“…In particular, the dried flower buds of M. fargesii , or Xinyi, exhibit efficacy in treating airway inflammatory diseases including asthma, bronchitis, and emphysema ( Park et al, 2012 ; Oh et al, 2016 ). Xinyi contains several components with promising biological activity, such as essential oils ( Fang et al, 2004 ), lignans ( Lee et al, 2007 ), neolignans ( Schuhly et al, 2009 ), and sesquiterpenes ( Jung et al, 1998 ). Of these, lignans are an important class of naturally occurring plant compounds exhibiting potent anti-inflammatory properties ( Bastos et al, 2001 ).…”

Section: Introductionmentioning

confidence: 99%

Lignans Isolated From Flower Buds of Magnolia fargesii Attenuate Airway Inflammation Induced by Cigarette Smoke in vitro and in vivo

et al. 2018

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The flower buds of Magnolia fargesii, known traditionally as Xinyi, exert anti-inflammatory effects against inflammatory lung diseases such as COPD. Lignans isolated from Xinyi are an important group of plant-derived anti-inflammatory compounds. However, the mechanisms of action underlying their protective effects against COPD are not yet fully understood. Here, we showed that seven lignans (lignans 1–7) obtained from a CHCl3 fraction of Xinyi effectively suppress the inflammatory response in CSC-stimulated airway epithelial cells (in vitro) and in a mouse model of COPD established by exposure to CS and LPS. The CHCl3 fraction was found to inhibit CSC-induced IL-6 expression in human airway epithelial cells and to suppress the infiltration of inflammatory cells (neutrophils and macrophages) and secretion of inflammatory cytokines, such as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in the mouse model. Similarly, each of the seven lignans isolated from the CHCl3 fraction also suppressed the infiltration of inflammatory cells (neutrophils and macrophages) and secretion of inflammatory mediators such as reactive oxygen species (ROS), TNF-α, and IL-6 in vivo. Notably, all lignan compounds significantly suppressed both extracellular signal-related kinase (ERK) and Akt phosphorylation levels in CSC-stimulated human lung mucoepidermoid carcinoma (NCI-H292) cells. Of these, lignan 1 (dimethylpinoresinol) inhibited the expression of CSC-induced inflammatory cytokines (IL-1β, -6, and -8) in vitro in a dose-dependent manner by suppressing the activation of epidermal growth factor receptor (EGFR) and its downstream effectors, including ERK and Akt, in NCI-H292 cells. Our results show that the lignans isolated from Xinyi may prevent airway inflammatory diseases through the suppression of EGFR and its downstream effectors.

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Two New Stereoisomers of Tetrahydrofuranoid Lignans from the Flower Buds of <i>Magnolia fargesii</i>

Cited by 32 publications

References 19 publications

Chemical Constituents from the Roots and Rhizomes of Asarum heterotropoides var. mandshuricum and the In Vitro Anti-Inflammatory Activity

Chemical Constituents from the Roots and Rhizomes of Asarum heterotropoides var. mandshuricum and the In Vitro Anti-Inflammatory Activity

Four New Cytotoxic Tetrahydrofuranoid Lignans fromSinopodophyllum emodi

Lignans Isolated From Flower Buds of Magnolia fargesii Attenuate Airway Inflammation Induced by Cigarette Smoke in vitro and in vivo

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