• 제목/요약/키워드: Sanguinarine

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Biochemistry, Molecular Biology, and Metabolic Engineering of Benzylisoquinoline Alkaloid Biosynthesis

  • Peter J. Facchini;Park, Sang-Un;David A. Bird;Nailish Samanani
    • 식물조직배양학회지
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    • 제27권4호
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    • pp.269-282
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    • 2000
  • Benzylisoquinoline alkaloids are a diverse group of natural products that include many pharmacologically active compounds produced in a limited number of plant families. Despite their complexity, intensive biochemical research has extended our knowledge of the chemistry and enzymology of many important benzylisoquinoline alkaloid pathways, such as those leading to the analgesic drugs morphine and codeine, and the antibiotics sanguinarine and berberine. The use of cultured plant cells as an experimental system has facilitated the identification and characterization of more than 30 benzylisoquinoline alkaloid biosynthetic enzymes, and the molecular cloning of the genes that encode at least 8 of these enzymes. The recent expansion of biochemical and molecular technologies has creat-ed unique opportunities to dissect the mechanisms involved in the regulation of benzylisoquinoline alkaloid biosynthesis in plants. Research has suggested that product accumulation is controlled by the developmental and inducible regulation of several benzylisoquinoline alkaloid biosynthetic genes, and by the subcellular compartmentation of biosynthetic enzymes and the intracellular localization and trafficking of pathway intermediates. In this paper, we review our current understanding of the biochemistry, cell biology, and molecular regulation of benzylisoquinoline alkaloid biosynthesis in plants. We also summarize our own research activities, especially those related to the establishment of protocols for the genetic transformation of benzylisoquinoline alkaloid-producing species, and the development of metabolic engineering strategies in these plants.

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Differential Induction of Protein Expression and Benzophenanthridine Alkaloid Accumulation in Eschscholtzia californica Suspension Cultures by Methyl Jasmonate and Yeast Extract

  • Cho, Hwa-Young;Rhee, Hong-Soon;H. Yoon, Sung-Yong;Park, Jong-Moon
    • Journal of Microbiology and Biotechnology
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    • 제18권2호
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    • pp.255-262
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    • 2008
  • Methyl jasmonate (MJ) and yeast extract (YE) induce protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cell cultures. One hundred ${\mu}M$ MJ primarily induced dihydrosanguinarine $(509.0{\pm}7.4mg/l)$ ; 0.2g/l YE induced sanguinarine $(146.8{\pm}3.8mg/l)$ and an unknown compound. These results occur because dihydrobenzophenanthridine oxidase (DHBO) is induced by YE and not by MJ. YE and chitin (CHI) had similar effects on sanguinarine production and DHBO expression. Differential induction of secondary metabolites was shown in E. californica suspension cultures and the expression of proteins confirmed the metabolite results. Furthermore, treatment by various oligosaccharides helped us to understand the elicitation effect of YE in signal transduction pathways.

수종의 상용 세치제들의 향균 및 향염효과 비교연구 (Comparative study on the antimicrobial and antiinflammatory activity of commercially available toothpastes)

  • 류인철
    • Journal of Periodontal and Implant Science
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    • 제26권2호
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    • pp.557-566
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    • 1996
  • It is known that some natural extracts from plants have a various range of antimicrobial and antiinflammatory activity. There are lots of clinical trials to develop toothpastes containing natural extracts for prevention of dental caries and gingival inflammation. The purpose of this study was to evaluate antimicrobial and antiinflammatory activity of magnolol containing toothpastes and other commercial toothpastes. Eleven kinds oftoothpastes were used. They include magnolol, sanguinarine, Myrrha, Mori radicis cortex,Cimicifugae rhizoma, sodium fluoride, aminocaprolactic acid etc. Six strains of bacteria were used for this test, ego Porphylomonas gingivalis, Prevotellain-termedia, Actinobacillus actinomy cetemcomitans, Streptococcus mutans, Stretococcus sanguis, and Actinomyces species. Antimicrobial activity was determined by an agar dillution method and a broth microdillution method. Antiinflammatory activity was assessed by the inhibition of $PGE_2$ production from gingival fibroblast with the addition of rHIL-1 and centrifuged solution of toothpastes. Control group was only rHIL-1 additive sample. $PGE_2$ enzyme immunoassay systemfAmersham, In. Buckinghamshire, U.K). $PGE_2$ level was measured by ELISA reader with 450 nm, The results from the study revealed that toothpastes containing natural extracts generally had high antimicrobial and antiinflammatory activity. Especially magnolol containing toothpaste showed higher antimicrobial activity than other toothpastes, and sanguinarine containing toothpaste showed particularly high antimicrobial activity in A. actinomicetemcomitans and A. viscosus. In some degree all toothpastes inhibited $PGE_2$ production, but magnolol containing toothpaste was potent inhibitor of $PGE_2$. Sodium chloride containing toothpaste had also effective result. The results suggested that toothpastes containing natural extracts were promising in plaque control and prevention of dental caries and gingivitis.

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캘리포니아 양귀비(Eschscholtzia californica) 현탁세포배양에서 전구체가 알칼로이드 생성에 미치는 영향 (Precursor Feeding Effects of Alkaloid Production in Suspension Cultures of Eschscholtzia californica)

  • 주영운;김철변상요
    • KSBB Journal
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    • 제8권5호
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    • pp.488-494
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    • 1993
  • 본 연구에서는 캘리포니아 양귀비(Eschscholtzia californica) 현탁배양세포의 주요 이차대사산물인 benzophenanthridine alkaloid의 생성을 증가시키기 위해 생합성 전구체인 tyrosine, tyramine, dopamine 그리고 L-dopa를 exponential phase 말기에 투여하였다. 그리고 이때 yeast elicitor와 전구체를 동시에 투여한 것과 비교하여 보았다. 그 결과 적당량의 전구체 투여시 benzophenanthridine alkaloid의 생성은 대조구(무처리)에 비해 증가하였다. 그리고 elicitor와 전구체를 동시에 투여해 주었을 때 대조구(elicitor만 처리)에 비해 상당히 증가하였는데, 이것은 elicitor에 의해 유도된 이차대사 관련 효소에 의해 전구체의 biotransformation이 촉진된 것이라 생각된다. 이와 같이 전구체 투여에 의해 이차대사산물의 생성을 증가시키려 할 때 전구체만 투여하는 것보다는 촉진제를 동시에 투여함으로써 최종산물의 생성을 극대화시킬 수 있으리라 생각되며, 식물세포배양의 산업화에 유용하게 이용되리라 생각된다.

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임상가를 위한 특집 1 - 충치예방과 관련된 천연물(natural products) 연구의 현황 (Natural Product Research in Dental Caries Prevention)

  • 전재규
    • 대한치과의사협회지
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    • 제50권9호
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    • pp.544-551
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    • 2012
  • Dental caries is a biofilm-related oral disease, and continues to afflict the majority of the world's population. Although fluoride, delivered in various modalities, remains the mainstay for the prevention of caries, additional approaches are required to enhance its effectiveness. Natural products have been used as a major source of innovative and effective therapeutic agents throughout human history, and have shown promise as a source of components for the development of new drugs. In addition. studies using natural products to prevent or treat oral diseases such as dental caries have received a great deal of attention. A number of compounds, such as epicatechin, allicin and sanguinarine, isolated from natural products, have also been investigated for their efficacy against oral microbial pathogens. However, the use of natural products as an anti-caries agent in clinical practice was controversial because of inadequate knowledge concerning their mechanisms of action and chemical characterization. This study focuses on the current knowledge of natural products in dental caries prevention and suggests natural products are importance sources for the prevention of dental caries.

Achiral and Chiral Determination of Benzophenanthridine Alkaloids from Methanol Extracts of Hylomecon Species by High Performance Liquid Chromatography

  • Kang, Jong-Seong;Long, Pham-Hoai;Lim, Hwan-Mi;Kim, Young-Ho;Gottfried-Blaschke
    • Archives of Pharmacal Research
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    • 제26권2호
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    • pp.114-119
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    • 2003
  • A high performance liquid chromatographic (HPLC) method was developed for the qualitative and quantitative determination of benzophenanthridine alkaloids from the methanol extracts of Hylomecon hylomeconoides and H. vernale (Papaveraceae). Achiral and chiral methods were adapted for the separation of 6-methoxydihydrosanguinarine (1), 6-acetonyldihydrosanguinarine (2) and dihydrosanguinarine (3). The achiral reversed phase HPLC method made it possible the simultaneous separation and determination of 1, 2 and 3 within 20 min on ODS column using acetonitrile-phosphate buffer (50 mM, pH 7.0) (50 : 50, v/v). The separation and determination of 1 and 2 enantiomers was available using chiral columns. The same amount of (+) and (-)-enantiomers of 1 was found from the methanol extract of specimen, indicated that 1 could be the artifact produced by the reaction of sanguinarine with methanol. H. hylomeconoides showed higher level of 1 and 3 in compared with H. vernale, especially in root samples permitting the possibility of chemical discrimination between two species.

Determination of isoquinoline alkaloids by UPLC-ESI-Q-TOF MS: Application to Chelidonium majus L.

  • Jeong, Won Tae;Lim, Heung Bin
    • 분석과학
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    • 제30권6호
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    • pp.379-389
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    • 2017
  • In this study, we set up an analytical method that can be used for rapid and accurate determination of representative isoquinoline alkaloids in medicinal plants using UPLC-ESI-Q-TOF MS (ultra pressure liquid chromatography-electrospray ionization-quadrupole-time-of-flight mass spectrometry). The compounds were eluted on a C18 column with 0.1 % formic acid and acetonitrile, and separated with good resolution within 13 min. Each of the separated components was characterized by precursor ions (generated by ESI-Q-TOF) and fragment ions (produced by collision-induced dissociation, CID), which were used as a reliable database. We also performed method validation: analytes showed excellent linearity ($R^2$, 0.9971-0.9996), LOD (5-25 ng/mL), LOQ (17-82 ng/mL), accuracy (91.6-97.4 %) as well as intra- and inter-day precisions (RSD, 1.8-3.2 %). In the analysis of Chelidonium majus L., magnoflorine, coptisine, sanguinarine, berberine and palmatine were detected by matching retention times and characteristic fragment ion patterns of reference standards. We also confirmed that, among the quantified components, coptisine was present in the highest quantity. Furthermore, alkaloid profiling was carried out by analyzing the fragment ion patterns corresponding to peaks of unknown components. In this manner, protopine, chelidonine, stylopine, dihydroberberine, canadine, and nitidine were tentatively identified. We also proposed the molecular structure of the fragment ions that appear in the mass spectrum. Therefore, we concluded that our suggested method for the determination of major isoquinoline alkaloids by UPLC-Q-TOF can be useful not only for quality control, but also for rapid and accurate investigation of phytochemical constituents of medicinal plants.