A new anti-inflammatory β-carboline alkaloid from the hairy-root cultures of <i>Eurycoma longifolia</i>

Ngoc, Pham Bich; Pham, Thanh Binh; Nguyen, Hai Dang; Tran, Thi Thu Huong; Chu, Ha Hoang; Chau, Van Minh; Lee, Jeong‐Hyung; Dat, Nguyen Tien

doi:10.1080/14786419.2015.1056187

Cited by 29 publications

(16 citation statements)

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“…The results indicated the potential of a number of β-carboline-type alkaloids and canthinone-type alkaloids in the compound library as anti-inflammatory agents. Compounds ( 21 , 46 , and 57 ) have been reported with inhibitory NO production activities [21–23], but compounds ( 11 – 13 , 15 , 22 , 23 , 27 , 29 – 31 , 37 , 41 , 42 , 47 , 55 , 64 , 71 , 72, and 76 ) were not reported as inhibitors of NO production.…”

Section: Resultsmentioning

confidence: 99%

Identification of β-carboline and canthinone alkaloids as anti-inflammatory agents but with different inhibitory profile on the expression of iNOS and COX-2 in lipopolysaccharide-activated RAW 264.7 macrophages

Liu

Luan

et al. 2018

J Nat Med

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A compound library, which consists of 75 natural β-carboline-type or canthinone-type alkaloids from Simaroubaceae plants and their chemical synthetic analogues, was screened for the anti-inflammatory activity by inhibition of the overproduction of inflammatory mediator nitric oxide (NO) in lipopolysaccharide (LPS)-activated RAW 264.7 macrophage cells. Six compounds, namely, benzalharman ( 23 ), kumujian ( 27 ), 1-ethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid ( 37 ), 1-acetophenone-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid ( 42 ), cathin-6-one ( 46 ), and 9-methoxy-cathin-6-one ( 57 ), exhibited significant inhibitory activity on the overproduction of NO with good dose dependency. Further investigation demonstrated that all of the six compounds down-regulated the high expression of inducible nitric oxide synthase (iNOS) protein. Among them, two canthinone-type alkaloids ( 46 and 57 ) potently down-regulated cyclooxygenase-2 (COX-2) protein expression in a dose-dependent manner and also inhibited the overproduction of inflammatory mediator prostaglandin E 2 (PGE 2 ). However, the β-carboline-type alkaloids ( 23 , 27 , 37 , and 42 ) exhibited no obvious inhibition on the overproduction of PGE 2 and the expression of COX-2 protein. The results suggested that β-carboline-type alkaloids and canthinone-type alkaloids may exert an anti-inflammatory effect through different mechanism. Electronic supplementary material The online version of this article (10.1007/s11418-018-1251-5) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Identification of β-carboline and canthinone alkaloids as anti-inflammatory agents but with different inhibitory profile on the expression of iNOS and COX-2 in lipopolysaccharide-activated RAW 264.7 macrophages

Liu

Luan

et al. 2018

J Nat Med

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“…7‐methoxy‐(9H‐β‐carbolin‐1‐il)‐( E )‐1‐propenoic acid (7‐MCPA) was isolated from the hairy root cultures of E. longifolia as previously described [Ngoc et al, ]. The chemical structure is shown in Figure .…”

Section: Methodsmentioning

confidence: 99%

“…The chemical structure is shown in Figure . 7‐MCPA was obtained as amorphous yellow powder, showed a [M + H] + peak at m/z 269, by electron spray ionization‐mass spectrometry [Ngoc et al, ] and the purity of 7‐MCPA was checked by 1 H and 13 C NMR spectra [Ngoc et al, ]. 7‐MCPA was solubilized with dimethyl sulfoxide and used at a final concentration of less than 0.05% dimethyl sulfoxide.…”

Section: Methodsmentioning

confidence: 99%

7-Methoxy-(9H-β-Carbolin-1-il)-(E)-1-Propenoic Acid, a β-Carboline Alkaloid FromEurycoma longifolia, Exhibits Anti-Inflammatory Effects by Activating the Nrf2/Heme Oxygenase-1 Pathway

et al. 2015

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Eurycoma longifolia is an herbal medicinal plant popularly used in Southeast Asian countries. In the present study, we show that 7-methoxy-(9H-β-carbolin-1-il)-(E)-1-propenoic acid (7-MCPA), a β-carboline alkaloid isolated from E. longifolia, exerted anti-inflammatory effects by activating the nuclear factor-E2-related factor 2 (Nrf2)/heme oxygenase-1 (HO-1) pathway. 7-MCPA inhibited lipopolysaccharide (LPS)-induced production of nitric oxide (NO), prostaglandin E2 (PGE2 ), and interleukin-6 (IL-6) in RAW264.7 cells and rescued C57BL/6 mice from LPS-induced lethality in vivo. LPS-induced expression of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and IL-6 was also significantly suppressed by treatment of 7-MCPA in RAW264.7 cells. 7-MCPA induced nuclear translocation of Nrf2 and increased transcription of its target genes, such as HO-1. Treating RAW264.7 cells with 7-MCPA increased the intracellular level of reactive oxygen species (ROS) and the phosphorylation level of p38 mitogen-activated protein kinase (MAPK); however, co-treatment with the antioxidant N-acetyl-cysteine (NAC) blocked 7-MCPA-induced p38 MAPK phosphorylation. Moreover, NAC or SB203580 (p38 MAPK inhibitor) blocked 7-MCPA-induced nuclear translocation of Nrf2, suggesting that 7-MCPA activated Nrf2 via a ROS-dependent p38 pathway. 7-MCPA induced HO-1 protein and mRNA expression and knockdown of Nrf2 with siRNA or SB203580 blocked 7-MCPA-mediated induction of HO-1 expression. Inhibiting Nrf2 or HO-1 abrogated the anti-inflammatory effects of 7-MCPA in LPS-stimulated RAW264.7 cells. We also demonstrated that 7-MCPA suppressed LPS-induced nuclear factor κB (NF-κB) activation. These results provide the first evidence that 7-MCPA exerts its anti-inflammatory effect by modulating the Nrf2 and NF-κB pathways and may be a potential Nrf2 activator to prevent or treat inflammatory diseases.

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“…[26] (2) Alkaloids including β-carboline alkaloid,[4041] cathine-6-one alkaloids. [42] (3) Triterpenes including tirucallane and eurylene.…”

Section: Introductionmentioning

confidence: 99%

“…The traditional uses or phytochemical properties of E longifolia from several literature reviews are antianxiety,[4546] antibacterial,[2529474849] anticancer,[35385051] antifungal,[28] anti-inflammation,[40415253] antimalarial,[54555657] antioxidant,[52] antiparasitic,[58] antiulcer,[59] ergogenic activities,[6061] and reproductive improvement. [626364656667]…”

Section: Introductionmentioning

confidence: 99%

Review ergogenic effect of long jack, Eurycoma Longifolia

Khanijo

Jiraungkoorskul

2016

Phcog Rev

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Eurycoma longifolia (family: Simaroubaceae) is commonly distributed in the Southeast Asia and Indo-China. In particular, the aqueous extract and decoction of its root are a well-known folk medicine which enhances sexuality, fertility, and antiaging. Furthermore, it has been shown to possess anti-inflammatory, antimalarial, antimicrobial, and antioxidant properties. Its common phytochemical components include alkaloids, flavonoids, phenolics, saponins, tannins, and triterpenes. This plant is rich in various quassinoids including eurycolactone, eurycomalactone, eurycomanol, eurycomanone, and eurycomaoside all of which has been reported to contribute to its remedial properties including increased muscle strength, endurance in cycling time, and reduced anxiety and stress. Based on established literature on the health benefits of E. longifolia, this review article has attempted to compile E. longifolia to be one of the choices of ergogenic plants.

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A new anti-inflammatory β-carboline alkaloid from the hairy-root cultures of Eurycoma longifolia

Cited by 29 publications

References 11 publications

Identification of β-carboline and canthinone alkaloids as anti-inflammatory agents but with different inhibitory profile on the expression of iNOS and COX-2 in lipopolysaccharide-activated RAW 264.7 macrophages

Identification of β-carboline and canthinone alkaloids as anti-inflammatory agents but with different inhibitory profile on the expression of iNOS and COX-2 in lipopolysaccharide-activated RAW 264.7 macrophages

7-Methoxy-(9H-β-Carbolin-1-il)-(E)-1-Propenoic Acid, a β-Carboline Alkaloid FromEurycoma longifolia, Exhibits Anti-Inflammatory Effects by Activating the Nrf2/Heme Oxygenase-1 Pathway

Review ergogenic effect of long jack, Eurycoma Longifolia

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