Antimicrobially Active Isoquinoline Alkaloids from<i>Litsea cubeba</i>

Feng, Tao; Xu, Yan; Cai, Xiang‐Hai; Du, Zhi‐Zhi; Luo, Xiao‐Dong

doi:10.1055/s-0028-1088344

Cited by 34 publications

(16 citation statements)

References 12 publications

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“…Previous phytochemical studies revealed alkaloids, lignans, and volatile oil as its major constituents, and aporphine alkaloids were undoubtedly most representative [16]. These ingredients showed bioactivities on cardiovascular diseases, anticancer, relieving asthma, and significantly attenuating adjuvant arthritis [17][18][19][20]. Our pharmaceutical investigation demonstrated that aporphine alkaloids (compounds 1, 3, 7, and 12) showed significant anti-inflammatory and anti-nociceptive effects in vivo, demonstrated by tests of carrageenan-induced paw edema in rat and xylene-induced ear edema in mouse, and reduce acetic acid-induced writhing as well as the licking time in formalin test and increase reaction latencies in hot plate test (data not shown), suggesting that DCJ alkaloids are responsible for its traditional use of relieving pain and provide scientific evidence for its clinical use.…”

Section: Introductionmentioning

confidence: 99%

Characterization and simultaneous quantification of biological aporphine alkaloids in Litsea cubeba by HPLC with hybrid ion trap time‐of‐flight mass spectrometry and HPLC with diode array detection

Zhang

Guo

et al. 2015

J of Separation Science

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The root and rhizome of Litsea cubeba (Lour) Pers., named 'Dou-chi-jiang' in Chinese, has been traditionally used for treatment of cardiovascular and cerebrovascular diseases, rheumatic arthralgia, and other diseases in China. Aporphine alkaloids are its characteristic ingredients and responsible for its bioactivities, especially anti-inflammatory and analgesic effects. A sensitive and reliable high-performance liquid chromatography with diode array detection-tandem mass spectrometry method was developed for characterization and simultaneous determination of biological aporphine alkaloids in 'Dou-chi-jiang'. The optimized chromatographic conditions were performed on an Eclipse XDB C18 column with a gradient of acetonitrile/water containing 0.1% formic acid as the mass spectrometry mobile phase and acetonitrile/water containing 0.2% diethylamine (pH 3.10, adjusted by acetic acid) as the liquid chromatography mobile phase. The fragmentation pathways by loss of CO, ·CH3 , ·NH3 , and ·NH2 CH3 were detected as characteristic for aporphine alkaloids. Based on these characteristics, total 12 analogues were identified. The quantification method was validated in terms of linearity, precision, and accuracy for six major aporphine alkaloids, which was successfully applied for simultaneous determination in ten batches of samples. The established method is simple, rapid, and specific for characterization and quantitation of aporphine alkaloids in 'Dou-chi-jiang' and other traditional Chinese medicines rich in this kind of ingredient.

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Section: Introductionmentioning

confidence: 99%

Characterization and simultaneous quantification of biological aporphine alkaloids in Litsea cubeba by HPLC with hybrid ion trap time‐of‐flight mass spectrometry and HPLC with diode array detection

Zhang

Guo

et al. 2015

J of Separation Science

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“…Pers. (Lauraceae) has long been used as a folk remedy in Traditional Chinese Medicine (TCM) for the treatment of rheumatic diseases (Feng et al 2009). Many pharmacological activities of L. cubeba extract and its compounds have been reported such as anticancer, antibacterial, antioxidant and antiinflammatory immunological activities.…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory constituents from the root of Litsea cubeba in LPS-induced RAW 264.7 macrophages

Lin

Sun

Xin

et al. 2016

Pharmaceutical Biology

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Context Litsea cubeba (Lour.) Pers. (Lauraceae) has long been used as a folk remedy in Traditional Chinese Medicine (TCM) for the treatment of rheumatic diseases. Previous studies from our laboratory indicated that L. cubeba extract showed anti-arthritic activity in rats. Objective To study L. cubeba chemically and biologically and to find the potential constituents responsible for its anti-arthritic effect. Materials and methods The compounds were isolated from the root of L. cubeba by column chromatography which eluted with PE:EtOAc gradient system, and the structures were elucidated by detailed spectroscopic data analysis; the anti-inflammatory activity of the isolated compounds was evaluated by lipopolysaccharide (LPS)-induced RAW 264.7 cells and the TNF-a and NO level were measured by ELISA (commercial kit); The iNOS and COX-2 mRNA expression were measured by RT-PCR and the phosphorylation of IkBa, IKKb, P38 and Akt were determined by western blots. Results A novel 9-fluorenone, 1-ethoxy-3,7-dihydroxy-4,6-dimethoxy-9-fluorenone (1), together with 4 known compounds, namely pinoresinol (2), syringaresinol (3), 9,90 -dimethoxysecoisolariciresinol (4) and lyoniresinol (5) were isolated from the root of L. cubeba for the first time. The IC 50 for NO inhibition on compounds 1 and 4 were 56.1 ± 1.2 and 32.8 ± 2.3 mM, respectively. The IC 50 for TNF-a inhibition were 28.2 ± 0.9 and 15.0 ± 1.0 mM, respectively. Both 1 and 4 suppress mRNA expression of iNOS, COX-2 and protein phosphorylation of IkBa, IKKb in LPS-induced RAW 264.7 cells. Discussion and conclusion Compounds 1 and 4 isolated from L. cubeba exhibited potent antiinflammatory activity through the NF-kB signal pathway. ARTICLE HISTORY

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“…8812, belongs to isoquinoline alkaloids, some of which exhibit antibacterial activity (for example, plant origin products such as berberine, canadaline, canadine, (+)-N-(methoxycarbonyl)-N-norboline). 16,17 Some of them show an activity toward S. aureus, which is analogous to JS-1. Iwasa et al 18 described antimicrobial, antimalarial, cytotoxic and anti-HIV activities of simple, natural and synthetic isoquinoline and benzylisoquinoline alkaloids.…”

Section: Genotoxicitymentioning

confidence: 98%

A novel isoquinoline alkaloid, DD-carboxypeptidase inhibitor, with antibacterial activity isolated from Streptomyces sp. 8812. Part I: Taxonomy, fermentation, isolation and biological activities

2009

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A novel isoquinoline alkaloid of molecular formula C 10 H 9 NO 4 , labeled JS-1, was isolated from the culture broth of Streptomyces sp. 8812. It was purified by acetone protein precipitation from the culture supernatant, followed by anion exchange and C18 RP HPLC columns. JS-1 is an inhibitor of exocellular DD-carboxypeptidases/transpeptidases (DD-peptidases) 64-575 II from Saccharopolyspora erythraea 64-575 II, and R39 from Actinomadura R39. JS-1 exhibits activity against Gram-negative bacteria, such as Bordetella bronchiseptica, Stenotrophomonas maltophilia, Proteus vulgaris, P. mirabilis, Burkholderia cepacia and Acinetobacter baumanii, with MIC values 10-160 lg ml À1 , and against Gram-positive bacteria, such as Staphylococcus aureus, with MIC values 40-206 lg ml À1 .

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Antimicrobially Active Isoquinoline Alkaloids fromLitsea cubeba

Cited by 34 publications

References 12 publications

Characterization and simultaneous quantification of biological aporphine alkaloids in Litsea cubeba by HPLC with hybrid ion trap time‐of‐flight mass spectrometry and HPLC with diode array detection

Characterization and simultaneous quantification of biological aporphine alkaloids in Litsea cubeba by HPLC with hybrid ion trap time‐of‐flight mass spectrometry and HPLC with diode array detection

Anti-inflammatory constituents from the root of Litsea cubeba in LPS-induced RAW 264.7 macrophages

A novel isoquinoline alkaloid, DD-carboxypeptidase inhibitor, with antibacterial activity isolated from Streptomyces sp. 8812. Part I: Taxonomy, fermentation, isolation and biological activities

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