• Title/Summary/Keyword: Isoquinoline

Search Result 111, Processing Time 0.023 seconds

PHOTOCATALYTIC ISOQUINOLINE PRODUCTION AND N-ALKYLATION BY PLATINIZED TITANIUM(IV) OXIDE PARTICLES SUSPENDED IN ALCOHOLIC SOLUTION OF PHENETHYLAMINES

  • Bunsho Ohtani;Yoshiko Moriguchi;Nishimoto, Sei-Ichi;Tomoyuki Inui
    • Journal of Photoscience
    • /
    • v.1 no.2
    • /
    • pp.107-111
    • /
    • 1994
  • Photocatalytic ($\lambda$$_{ex}$ > 300 nm) reaction at room temperature by platinized titanium (IV) oxide particles produced 1-methyl-1, 2, 3, 4-tetrahydroisoquinolines (MIQ's) from phenethylamines in aqueous ethanol suspension under deaerated atmosphere. Among the phenethylamines, dopamine (2-(3, 4-dihydroxyphenyl) ethylamine) showed the highest reactivity to give MIQ almost selectively under the neutralized conditions. The other phenethylamines gave predominantly N-alkylated and N, N-dialkylated products in the methanol or ethanol solutions. The reaction mechanism includes a Schiff base intermediate to undergo either nucleophilic attack leading to MIQ or reduction to N-alkylated products.

  • PDF

Allelopathic Potential and Substances from Cork Tree (Pbellodendron amurense Rupr.)

  • Park, Young-Goo;Choi, Myung-Suk;Yang, Jae-Kyung;Paik, Ki-Hyon
    • Journal of the Korean Wood Science and Technology
    • /
    • v.29 no.3
    • /
    • pp.92-98
    • /
    • 2001
  • Allelopathic effects of the cork tree (Phellodendron amurense Rupr.) on several crops and soil miro-organisms were assessed using germination bioassay and antimicrobial assay, and allelochemicals were identified. In a germination bioassay, extract of cork tree inhibited at high concentration on germination of several crop seeds such as cabbage, lettuce, and cucumber. However, aqueous extracts inhibited powerfully growth of test organisms such as Streptococus aureus, S. aureus, S. typhimurium, and E. coli as bacteria, and Candida albicans as yeast, and Botrytis cineria and Alternata alternaria as fungi.. The cork tree extract showed strong antimicrobial activities against isolated soil fungi. The allelochemicals were separated using Silica gel, Sephadex LH-20 gel column chromatography and HPLC. The substances were analyzed by UV spectrometry and EI-mass spectrometry. The active allelochemicals were identified as isoquinoline alkaloids, berberine and palmatine.

  • PDF

Determination of Protoberberine Alkaloids in Phellodendri Cortex and Preparation by Spectrophotometric Method (흡광도측정법에 의한 황백과 제제 중 프로토베르베린 알칼로이드의 정량)

  • 엄동옥;정윤철
    • YAKHAK HOEJI
    • /
    • v.45 no.1
    • /
    • pp.34-38
    • /
    • 2001
  • The Phellodendri Cortex of Phellodendron amurense (Rutaceae) is known to contain a number of isoquinoline alkaloid, and berberine, palmatine, jateorrhizine, phellodendrine and magnoflorine are the major constituents of protoberberine alkaloids. For the determination of protoberberine alkaloids from Phellodendri Cortex and berberine chloride from the preparation, the new spectrophotometric method was developed with a simple and selective sample clean-up using thiocyanatocobaltate[II] complex ion. Samples were extracted with 0.1 mM hydrochloric acid, potassium biphthalate reagent, thiocyanatocobaltate reagent and 1.2-dichloroethane for 60 min. The absorbance of protoberberine alkaloid complexes in 1.2-dichloroethane solution was measured at 625 nm. Calibration curve for berberine was linear over the concentration range of 0.05~0.30 mg/ml 1.2-dichloroethane. The method proved to be rapid, simple and reliable for the determination of protoberberine alkaloids from Phellodendri Cortex and berberine chloride from the preparation.

  • PDF

Isolation and Determination of Alkaloids in Coptis Rhizome by Forming Complex (착체 생성에 의한 황련 알칼로이드의 분리 및 정량)

  • 임소연;김대근;신태용;임종필;엄동옥
    • YAKHAK HOEJI
    • /
    • v.46 no.4
    • /
    • pp.226-230
    • /
    • 2002
  • The Coptis Rhizome is known for containing a number of isoquinoline type alkaloids. Berberine, coptisine and palmatine are the major constituents of alkaloids. The alkaloids were isolated and determined by forming complex from Coptis japonica (Ranunculaceae). For the determination of these alkaloids, a new spectrophotometric method was developed with a simple and selective sample clean-up using thiocyanatocobaltate[II] complex ion. The absorbance of alkaloidal complex in l,2-dichloroethane solution was measured at 625 nm. A calibration curve for the alkaloids isolated from Coptis Rhizome was linear over the concentration range of 0.2-0.3 mg/mι. The method proved to be rapid, simple and reliable for the isolation and the determination of the alkaloids in Coptis Rhizome.

Effects of Bulbocapnine on Dopamine Content in PC12 Cells (Bulbocapnine이 PC12 세포중의 도파민 함량에 미치는 영향)

  • Shin, Jeong-Soo;Lee, Myung-Koo
    • YAKHAK HOEJI
    • /
    • v.42 no.2
    • /
    • pp.170-174
    • /
    • 1998
  • The effects of bulbocapnine, an aporphine isoquinoline alkaloid, on dopamine content in PC12 cells were investigated. Bulbocapnine decreased the dopamine content dose-dependentl y (39.2% inhibition at 2O${\mu}$M for 24 hr). The $IC_{50}$ value of bulbocapnine was 22.7${\mu}$M. Dopamine content was lowered at 6 hr after exposure to bulbocapnine. And then, the decreased dopamine level was almost maintained at 36 hr and recovered to the control level at about 60 hr. Tyrosine hydroxylase, the rate limiting enzyme in the catecholamine blosynthetic pathway, was also inhibited at 20${\mu}$M of bulbocapnine by 23.1% relative to control. We, therefore, hypothesized that the inhibition of tyrosine hydroxylase by bulbocapnine with a single treatment might be partially contributed to the decrease in dopamine content in PC12 cells.

  • PDF

Cytotoxic Constituents from the Whole Plant of Corydalis pallida

  • Kim Hyang Rim;Min Hye-Young;Jeong Yeon Hee;Lee Sang Kook;Lee Nam Sook;Seo Eun-Kyoung
    • Archives of Pharmacal Research
    • /
    • v.28 no.11
    • /
    • pp.1224-1227
    • /
    • 2005
  • Here we report the cytotoxic activity of three known compounds isolated for the first time from Corydalis pallida (Papaveraceae). An isoquinoline alkaloid, berberine, exhibited cytototoxic activity against two human cancer cell lines, HT-1080 (human fibrosarcoma) and SNU-638 (human stomach adenocarcinoma), with $IC_{50}$ values of 3.2 and 3.4 $\mu$g/mL, respectively. N­trans-feruloyltyramine and N-trans-feruloylmethoxytyramine were also isolated from this plant but were inactive.

Synthesis and Antitumor Activity of 3-Arylisoquinoline Derivatives

  • Cho, Won-Jea;Yoo, Su-Jeong;Park, Myun-Ji;Chung, Byung-Ho;Lee, Chong-Ock
    • Archives of Pharmacal Research
    • /
    • v.20 no.3
    • /
    • pp.264-268
    • /
    • 1997
  • In order to study the structure-activity relationship of 7, 8-dimethoxy-2-methyl-3-(4, 5-methylenedioxy-2-vinylphenyl)isoquinoline-1(2H) -one (2), which has exhibited significant antitumor activity, chemical modifications of 2 were performed to yield the corresponding products (3-7). Further systematic uses of an efficient procedure for the synthesis of 3-arylisoquinoline derivatives produced the substituted compounds (9a-9g), which were tested for in vitro antitumor activity against five different human cancer cell lines.

  • PDF

Oxidative Modification of Cytochrome c by Tetrahydropapaveroline, an Isoquinoline-Derived Neurotoxin

  • Kang, Jung Hoon
    • Bulletin of the Korean Chemical Society
    • /
    • v.34 no.2
    • /
    • pp.406-410
    • /
    • 2013
  • Tetrahyropapaveroline (THP) is compound derived from dopamine metabolism and is capable of causing dopaminergic neurodegenerative disorder, such as Parkinson's disease (PD). The aim of this study was to evaluate the potential of THP to cause oxidative damage on the structure of cytochrome c (cyt c). Our data showed that THP led to protein aggregation and the formation of carbonyl compound in protein aggregates. THP also induced the release of iron from cyt c. Reactive oxygen species (ROS) scavengers and iron specific chelator inhibited the THP-mediated cyt c modification and carbonyl compound formation. The results of this study show that ROS may play a critical role in THP-induced cyt c modification and iron releasing of cyt c. When cyt c that has been exposed to THP was subsequently analyzed by amino acid analysis, lysine, histidine and methionine residues were particularly sensitive. It is suggested that oxidative damage of cyt c by THP might induce the increase of iron content in cells and subsequently led to the deleterious condition. This mechanism is associated with the deterioration of organs under neurodegenerative disorder such as PD.

Rhodium(I) Complexes of 1,1$^\prime$-Bis(diphenylphosphino)-ferrocene as Efficient Catalysts in Regioselective Hydrogenation of Polynuclear Heteroaromatic Compounds

  • Kim, Tae-Jeong;Lee, Kyu-Chul
    • Bulletin of the Korean Chemical Society
    • /
    • v.10 no.3
    • /
    • pp.279-282
    • /
    • 1989
  • Two rhodium(I) complexes of the types [Rh(BPPF)(NBD)]$ClO_4$ (10) and [Rh(BPPF)$Cl]_2$ (11) (BPPF = 1,1'-bis(diphenylphosphino)-ferrocene) have been prepared and investigated as catalysts for the regioselective hydrogenation of polynuclear heteroaromatic nitrogen and sulfur compounds such as quinoline (1), acridine (2), phenanthridine (3), 7,8-benzoquinoline (4), benzothiophene (5), isoquinoline (6), indole (7), pyridine (8), and thiophene (9). Both complexes 10 and 11, except for the cases of indole (7) and mononuclear heteroaromatics 8-9, are very efficient in the selective reduction under quite mild hydrogenation conditions to give the corresponding saturated nitrogen and sulfur heterocyclic analogues of 1-6 in fast conversion rates and in excellent yields. Relative rate studies revealed that the reduction depends significantly on the steric and electronic effects of the substrates. Of the two complexes 10-11, the dimeric species 11 gives faster reaction rates in all cases studied.

Inhibitory Effects on Dopamine Biosynthsis and Protective Effect on L-DOPA-induced Neurotoxicity of liriodenine in PC12 cells

  • Jin, Chun-Mei;Lee, Jae-Joon;Yin, Shou-Yu;Kim, Yu-Mi;Yang, You-Jong;Ryu, Si-Yong;Lee, Myung-Koo
    • Proceedings of the PSK Conference
    • /
    • 2003.04a
    • /
    • pp.139.1-139.1
    • /
    • 2003
  • The effects of liriodenine, an aporphine isoquinoline alkaloid, on dopamine biosynthesis and L-DOPA-induced neurotoxicity in PC12 cells were investigated. Treatment of PC12 cells with liriodenine at 10 $\mu\textrm{M}$ showed 33.6% inhibition of dopamine content decreased at 3 h and reached a minimal level at 12 h after the exposure to liriodenine at 10 $\mu\textrm{M}$. (omitted)

  • PDF