Anti-Inflammatory<i>ent</i>-Kaurane Diterpenoids from<i>Isodon serra</i>

Xing, Honghong; An, Li; Song, Ziteng; Li, Shanshan; Wang, Huimei; Wang, Chunyan; Zhang, Jie; Tuerhong, Muhetaer; Abudukeremu, Munira; Li, Dihua; Lee, Dong‐Ho; Xu, Jing; Lall, Namrita; Guo, Yuanqiang

doi:10.1021/acs.jnatprod.9b01281

Cited by 24 publications

(13 citation statements)

References 46 publications

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“…The remaining four ones exhibited the existence of a tetracyclic system in 1 . 7 Consequently, the four-ring was inferred to be a 6/6/6/5 fused rings A, B, C and D, a characteristic ent -kaurane diterpenoid skeleton, 8–10 based on the 2D NMR experiments (Fig. 2): the 1 H– 1 H COSY correlations of H 2 -1/H 2 -2/H 2 -3, H-5/H 2 -6/H 2 -7 and H-9/H-11/H-12/H-13/H 2 -14; the HMBC correlations from H 3 -19 to C-3, C-4, C-5 and C-18; from H 3 -20 to C-1, C-5, C-9 and C-10; from H 2 -7 to C-6 and C-8; from H-9 to C-5, C-8, C-10, C-11 and C-12; from H 2 -14 to C-8, C-9, C-13, C-15 and C-16; and from H 3 -17 to C-13, C-15 and C-16.…”

Section: Resultsmentioning

confidence: 99%

New ent-kaurane diterpenoid acids from Nouelia insignis Franch and their anti-inflammatory activity

Huang

et al. 2022

RSC Adv.

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Section: Resultsmentioning

confidence: 99%

New ent-kaurane diterpenoid acids from Nouelia insignis Franch and their anti-inflammatory activity

Huang

et al. 2022

RSC Adv.

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“…NO, as an important cellular second messenger, is synthesized by the crucial iNOS of the inflammatory response . Inhibiting the overproduction of NO is usually the consequence of suppressed expression and/or the enzyme activity of iNOS . To explore the underlying anti-inflammatory mechanism, compound 4 was selected to further examine the effect on iNOS protein expression levels and enzyme activity.…”

Section: Resultsmentioning

confidence: 99%

“…39 Inhibiting the overproduction of NO is usually the consequence of suppressed expression and/or the enzyme activity of iNOS. 40 To explore the underlying anti-inflammatory mechanism, compound 4 was selected to further examine the effect on iNOS protein expression levels and enzyme activity. Western blotting analysis indicated that the level of iNOS expression was suppressed markedly in a concentrationdependent manner by compound 4 (Figure 5a,b).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Anti-inflammatory Cassane-Type Diterpenoids from the Seed Kernels of Caesalpinia sinensis

Wang

et al. 2021

J. Nat. Prod.

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Eighteen cassane diterpenoids, including five new lactam-type (4–8), 12 new lactone-type (1–3 and 9–17), and one known compound (18), were isolated from Caesalpinia sinensis. To our knowledge, this is the first study on the seed kernels of C. sinensis, and cassane derivatives were discovered in this plant for the first time. Their structures including absolute configurations were established by extensive spectroscopic methods complemented with single-crystal X-ray diffraction analyses and ECD calculations. Compounds 4–8 were identified as a group of rare cassane diterpenoids possessing a lactam D-ring instead of a typical lactone moiety. Biological evaluation revealed that compounds 4–6 exhibited effective inhibitory effects on NO production in the LPS-induced RAW 264.7 macrophages, with IC50 values in the range 8.2–11.2 μM. Compound 4 suppressed the excessive production of NO by down-regulating the expression of inducible nitric oxide synthase enzymes (iNOS) and reducing the enzymatic activity of iNOS. Moreover, the intermolecular interaction and binding mode between compound 4 and iNOS were elaborated by conducting a molecular docking study.

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“…Several studies have reported that natural products derived from medicinal plants exert significant anti-inflammatory activities and suppress the NF-kB signalling pathway, which are potential resources of anti-inflammatory candidates (30)(31)(32)(33)(34)(35)(36)(37)(38). In this study, we discovered and characterized a novel isoquinoline alkaloid LA that possesses an unusual C-1 methyl and a N!O group, from a medicinal plant L. cubeba that is widely used for the treatment of inflammatory diseases (9)(10)(11).…”

Section: Discussionmentioning

confidence: 99%

Novel Isoquinoline Alkaloid Litcubanine A - A Potential Anti-Inflammatory Candidate

et al. 2021

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Macrophages play a critical role in innate and adaptive immunity, and the regulation of macrophage function in inflammatory disease treatment has been widely studied. Litsea cubeba is an important Chinese medicinal plant used for the treatment of inflammatory diseases. However, the inflammatory bioactive ingredients in L. cubeba and underlying molecular mechanisms are poorly understood. Herein, we first obtained and elucidated a novel isoquinoline alkaloid, Litcubanine A (LA), from L. cubeba. An in vitro study indicated that LA could significantly inhibit LPS-induced activation of inflammatory macrophages via the NF-κB pathway, leading to the decrease of inflammatory factors including iNOS, TNF-α, and IL-1β. Moreover, LA showed an inhibiting effect on the expression of NO in macrophages by directly binding to iNOS protein. Molecular simulation docking also demonstrated that active LA created an interaction with GLU 371 residue of iNOS via attractive charge derived from the N→O group, revealing its highly selective inhibition toward iNOS. By using the IκK inhibitor and iNOS inhibitor, these two regulatory targets of LA on inflammatory macrophages were verified in vitro. Finally, by using a caudal fin resection model in zebrafish larvae, and the skin wound healing model in mice, we proved in vivo that LA down-regulated the secretion of local inflammatory factors by inhibiting macrophage recruitment and activation at the early stage of the injury. Collectively, our study demonstrated that the novel isoquinoline alkaloid LA suppresses LPS-induced activation of inflammatory macrophages by modulating the NF-κB pathway, suggesting that inflammatory macrophage activation pathway is an effective target for inflammation treatment, and LA is a new pharmacophore for the development of novel and effective anti-inflammatory agents to regulate local macrophages.

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Anti-Inflammatoryent-Kaurane Diterpenoids fromIsodon serra

Cited by 24 publications

References 46 publications

New ent-kaurane diterpenoid acids from Nouelia insignis Franch and their anti-inflammatory activity

New ent-kaurane diterpenoid acids from Nouelia insignis Franch and their anti-inflammatory activity

Anti-inflammatory Cassane-Type Diterpenoids from the Seed Kernels of Caesalpinia sinensis

Novel Isoquinoline Alkaloid Litcubanine A - A Potential Anti-Inflammatory Candidate

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