2-Phenoxychromones and Prenylflavonoids from <i>Epimedium koreanum</i> and Their Inhibitory Effects on LPS-Induced Nitric Oxide and Interleukin-1β Production

Jin, Qinghao; Lee, Chul; Lee, Jin Woo; Yeon, Eung Tae; Lee, Dong‐Ho; Han, Sang Bae; Hong, Jin Tae; Kim, Youngsoo; Lee, Mi Kyeong; Hwang, Bang Yeon

doi:10.1021/np400831p

Cited by 32 publications

(27 citation statements)

References 23 publications

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“…Inflammation plays an important role in the development of many diseases, and different cell types are recruited, including monocytes/macrophages, neutrophils and lymphocytes, to the tissue during the process of inflammation [ 12 , 13 , 14 ]. The LPS-stimulated murine macrophage model is a well-known system to assess the anti-inflammatory activities of marine- and terrestrial-derived secondary metabolites in vitro [ 15 , 16 , 17 , 18 ]. LPS could upregulate the production of various pro-inflammatory mediators, including cytokines, chemokines and enzymes, such as COX-2 and iNOS, which play critical roles in inflammatory processes via activation of the nuclear factor (NF)-κB signaling pathway [ 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and Analgesic Effects of the Marine-Derived Compound Excavatolide B Isolated from the Culture-Type Formosan Gorgonian Briareum excavatum

Lin

Feng

et al. 2015

Marine Drugs

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In recent years, several marine-derived compounds have been clinically evaluated. Diterpenes are secondary metabolites from soft coral that exhibit anti-inflammatory, anti-tumor and cytotoxic activities. In the present study, we isolated a natural diterpene product, excavatolide B, from cultured Formosan gorgonian Briareum excavatum and investigated its anti-inflammatory activities. We found that excavatolide B significantly inhibited the mRNA expression of the proinflammatory mediators, inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), in lipopolysaccharide (LPS)-challenged murine macrophages (RAW 264.7). We also examined the anti-inflammatory and anti-nociceptive effects of excavatolide B on intraplantar carrageenan-induced inflammatory responses. Excavatolide B was found to significantly attenuate carrageenan-induced nociceptive behaviors, mechanical allodynia, thermal hyperalgesia, weight bearing deficits and paw edema. In addition, excavatolide B inhibited iNOS, as well as the infiltration of immune cells in carrageenan-induced inflammatory paw tissue.

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Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and Analgesic Effects of the Marine-Derived Compound Excavatolide B Isolated from the Culture-Type Formosan Gorgonian Briareum excavatum

Lin

Feng

et al. 2015

Marine Drugs

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“…The structures of isolated flavonoids (1-4) were identified using established spectroscopic analysis methods and comparisons with previously reported data. Isolated flavonoids (1-4) were identified as epimedokoreanin B (1), 5, 7, 4′-trihydroxy-8, 3′-prenylflavone (2), neophellamuretin (3), and icariside II (4) [19]. The structure of the most effective compound, i.e., compound 1, was briefly elucidated as follows.…”

Section: Resultsmentioning

confidence: 99%

Prenylated Flavonoids from Epimedium koreanum Nakai and their Human Neutrophil Elastase Inhibitory Effects

Lee¹,

Song²,

Uddin³

et al. 2017

Rec.Nat.Prod.

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Human neutrophil elastase (HNE) has been linked to immune system functions, including inflammation, as well as the development of skin wrinkles, suggesting that HNE inhibitors have many practical applications. In this study, the methanol extract of Epimedium koreanum Nakai contained potent HNE inhibitory flavonoids (1-4) with IC 50 values of 6.06-125.80 μM. Prenyl groups within these flavonoids were critical for the inhibitory effects. For example, epimedokoreanin B (1) (IC 50 = 6.06 μM) showed 6-fold higher efficacy than that of its parent luteolin (IC 50 = 36.01 μM). A similar trend was observed for compound 2 (IC 50 = 6.28 μM) and its parent, apigenin (IC 50 = 37.94 μM). Lineweaver-Burk plots showed that the compounds exhibit mixed-type inhibition. In a detailed kinetic study, compound 1 was assigned to mixed type I and exhibited the greatest binding to the free enzyme (K I = 11.7 μM, K IS = 40.9 μM).

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“…The IR spectrum of 2 indicated the characteristic bands of hydroxyl (3423 cm −1 ) and conjugated carbonyl (1648 cm −1 ) groups. Comparing the NMR spectral data (Table 1) of 2 with those of 1 revealed that it shared the same molecular-skeleton with 1 and the major differences between them could be rationalized to the signals corresponding to the 2-hydroxy-3-methyl-3-butenyl group in 1 was replaced by a 2,2-dimethylpyran ring [ δ C 122.6 (d), 132.3 (d), 77.9 (s), 28.3 × 2 (q); δ H 6.45 (1H, d, J = 9.9 Hz), 5.78 (1H, d, J = 9.9 Hz), 1.41 (6H, s)] [13] in 2 , which was consistent with its molecular formula. This deduction was further supported by the COSY correlation of H-6″/H-7″ and the HMBC correlations of H-6″/C-8″; Me-9″/C-7″, C-10″; and Me-10″/C-7″ (Fig.…”

Section: Resultsmentioning

confidence: 99%

Minor Prenylated Flavonoids from the Twigs of Macaranga adenantha and Their Cytotoxic Activity

Yang

Wang

Peng

et al. 2015

Nat. Prod. Bioprospect.

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Three new minor prenylated flavonoids, named macadenanthins A–C (1–3), together with three known ones (4–6), were isolated from the twigs of Macaranga adenantha. Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR, UV and MS. The prenyl moieties in compounds 1–3 were further modified by cyclization and hydroxylation. The new compounds were tested for their cytotoxicity against four cancer cell lines (MCF-7, Hep G2, Hela and P388) and showed IC50 values in the range of 13.76–22.27 μM.Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-015-0059-1) contains supplementary material, which is available to authorized users.

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2-Phenoxychromones and Prenylflavonoids from Epimedium koreanum and Their Inhibitory Effects on LPS-Induced Nitric Oxide and Interleukin-1β Production

Cited by 32 publications

References 23 publications

Anti-Inflammatory and Analgesic Effects of the Marine-Derived Compound Excavatolide B Isolated from the Culture-Type Formosan Gorgonian Briareum excavatum

Anti-Inflammatory and Analgesic Effects of the Marine-Derived Compound Excavatolide B Isolated from the Culture-Type Formosan Gorgonian Briareum excavatum

Prenylated Flavonoids from Epimedium koreanum Nakai and their Human Neutrophil Elastase Inhibitory Effects

Minor Prenylated Flavonoids from the Twigs of Macaranga adenantha and Their Cytotoxic Activity

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