• Title/Summary/Keyword: Indole alkaloid

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An Indole Alkaloid from the Fruiting Body of Boletus umbriniporus (암갈색그물버섯(Boletus umbriniporus)에서 분리한 indole alkaloid)

  • Lee, Yoon-Ju;Hwang, Byung-Soon;Song, Ja-Gyeong;Kim, Dae-Won;Woo, E-Eum;Lee, In-Kyoung;Yun, Bong-Sik
    • The Korean Journal of Mycology
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    • v.43 no.1
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    • pp.68-70
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    • 2015
  • Mushrooms are valued as a nutritional food and also as an important source of useful medicinal components. They produce various secondary metabolites which have interesting biological activities and unique chemical structures. As part of our ongoing investigation on chemical constituents and bioactive components of Korean native mushrooms, compound 1, an indole alkaloid, was isolated from the fruiting body of Boletus umbriniporus. B. umbriniporus is characterized by its yellow flesh, which changes to pallid blue when exposed to air, and its chemical constituent has not been reported. Chemical structure of compound 1 was determined to be flazin on the basis of ESI-mass, $^1H$ NMR, $^{13}C$ NMR, $^1H-^1H$ COSY, HMQC, and HMBC analysis. This compound was isolated from the fruiting body of B. umbriniporus for the first time.

Vinblastine Determination Measured by a Sensitive ELISA Inhibition Assay (ELISA Inhibition Assay에 의한 Vinblastine의 측정)

  • Jae Wha kim;Mi Young Han;Hee Gu Lee;Eun Young Song;Tai Wha Chung;Kyung Soo Nam;In Seong Choe
    • Biomedical Science Letters
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    • v.2 no.1
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    • pp.121-126
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    • 1996
  • Specific monoclonal antibodies(mAbs) against bis-indole alkaloids related to vinblastine were established to develop a simple and specific immunoassay system for the quantitation of Vinca alkaloids. Vinca alkaloids were extracted from tissue cultured cells of periwinkle plant (Vinca rosea L.). Spleen cells from Balb/c mice immunized with vinblastine-bovine serum albumin(VBL-BSA) conjugate as immunogen were fused with myeloma cells(Sp2/0-Ag.14) in the presence of polyethylene glycol. In the preliminary experiments, 32 clones which highly reacted with VBL-BSA conjugate were selected by ELISA(Enzyme-linked immunosorbent assay).These clones were further analyzed by inhibition assay of ELISA. The results obtained with two typical monoclonal antibodies, KN-1 and KN-2, were described. KN-1 exhibited considerable reactivities with soluble dimeric bis-indole alkaloids, whereas no cross reacted with monomeric bis-indole alkaloids. However KN-2 showed cross reactivity with mono- and di-meric bis-indole alkaloids. Furthermore, KN-1 was applied to the immunoassay system for determining the VBL amounts of in vitro cultured cell extracts. This assay system could detect dimeric vinca alkaloid as low as 0.05 nM.

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Selection of Protoplasts-Derived Cell Lines for High Yields Indole Alkaloids from Suspension Cultures of Vinca (Catharanthus roseus) (일일초(Catharanthus roseus) 현탁배양으로부터 원형질체유래 Indole Alkaloid 고생산성 세포주 선발)

  • 김석원;정경희
    • KSBB Journal
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    • v.6 no.1
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    • pp.1-7
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    • 1991
  • To produce economically important indole alkaloids by cell cultures, we selected protoplastsderived clones (protoclones) of vinca (Catharanthus roseus) for high yields of catharanthine and ajmalicine. Protoplasts were enzymatically isolated from suspension-cultured cells. The highest plating efficiency (1%) was obtained when protoplasts were plated at a density of 1$\times$105 protoplasts/ml in a culture medium solidified with 0.4% Seaplaque agarose. The growth rates of 40 protoclones subcultured on a solid medium varied over a wide range. Protoclone VPC-6, which had the highest growth rate, was observed to produce relatively high yields of catharanthine and ajmalicine when cultured in a liquid medium. Although the original cell line did not produce catharanthine at a detectable level by HPLC, protoclone VPC-10 produced it at a level of 5.9$\mu\textrm{g}$/g fresh weight of cells for 10 days of culture. Under the same conditions, protoclone VPC-15 produced ajmalicine at a level of 133.6$\mu\textrm{g}$/g, of which productivity was improved about ,3 times than that of the original cell line. The results indicate that differences in the growth rate and indole alkaloid yield among the protoclones reflect the somaclonal variation in suspnsion-cultured cells.

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Studies on the Alkaloid from Polygala tenuifolia Willdenow (원지의 염기성성분에 관한 연구)

  • 김제훈
    • YAKHAK HOEJI
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    • v.8 no.2
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    • pp.59-61
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    • 1964
  • A new alkaloid, named tenuidine was isolated from Polygala tenuifolia Willdenow. Its molecular formula corresponded to $C_{21}$ $H_{31}$ $O_{5}$ $N_{3}$ and its constants were m.p.256, [.alpha.]$_{D}$$^{18.5}$=1200.deg.(ethanol). Its infrared absorption spectra exhibited bands at 3.300, 1600, 1580, 1500 $cm^{-1}$ / confirming indole ring and at 2800-2700 $cm^{-1}$ / indicating quinoline ring. Bands at 1610, 1530 $cm^{-1}$ / indicated the presences of benzene ring and 1642$cm^{-1}$ / carbochelate.e.e.

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Cytotoxic Effect and Constituent Profile of Alkaloid Fractions from Ethanolic Extract of Ficus septica Burm. f. Leaves on T47D Breast Cancer Cells

  • Nugroho, Agung Endro;Akbar, Fiki Fatihah;Wiyani, Anggie;Sudarsono, Sudarsono
    • Asian Pacific Journal of Cancer Prevention
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    • v.16 no.16
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    • pp.7337-7342
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    • 2015
  • The study aimed to investigate the profile of alkaloids in two ethyl acetate soluble fractions, namely fractions A and B from an ethanolic extract of Ficus septica leaves and cytotoxic effect on T47D breast cancer cells. Preparation of both fractions involved maceration of leaves with 70% (v/v) ethanol, filtration with $Al_2O_3$, precipitation with 0.1 N HCl, Mayer reagent, and 0.1 N NaOH, and also partition with ethyl acetate. Qualitative thin layer chromatography (TLC) was conducted to determine the profile of alkaloids in the two fractions, using alkaloid specific reagents such as Dragendorff, sodium nitrite, and Van Urk-Salkowski. Cytotoxic effects of both fractions on T47D cells were evaluated using MTT assay with a concentration series of 1.56; 3.12; 6.25; 12.5; 25 and $50{\mu}g/mL$. The TLC test showed that fractions A and B contained alkaloids with Rx values of 0.74 and 0.80 for fraction A and 0.74, 0.84, 0.92 for fraction B with regard to yohimbine using the mobile phase of n-buthanol:glacial acetic acid:distilled water (3:1:1 v/v/v). Moreover, an indole alkaloid was detected with Rx values of 0.80 and 0.84, respectively. Fractions A and B exhibited high cytotoxic effects on T47D cells with IC50 values of 2.57 and $2.73{\mu}g/mL$, respectively. In conclusion, overall the results of this study showed that fractions of Ficus septica contain alkaloids including indole alkaloid or its derivatives and possess a cytotoxic effect on T47D cells. This research supports the idea that alkaloids in F. septica have anticancer activity.

A Novel Bromoindole Alkaloid from a Korean Colonial Tunicate Didemnum sp.

  • Hahn, Dongyup;Kim, Geum Jin;Choi, Hyukjae;Kang, Heonjoong
    • Natural Product Sciences
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    • v.21 no.4
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    • pp.278-281
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    • 2015
  • Chemical investigation on a colonial marine tunicate, Didemnum sp. led to the isolation of a series of indole alkaloids including a new (1) and two known metabolites (2-3). Based on the spectroscopic analysis including 1D and 2D NMR along with MS spectra, the structure of 1 (16-epi-18-acetyl herdmanine D) was elucidated as a new amino acid derivative. The absolute configuration of 1 was determined by comparison of specific rotation with the known compound. The structures of compounds 2 and 3 were also identified as bromoindole containing compounds N-(6-bromo-1H-indole-3-carbonyl)-L-arginine and (6-bromo-^1H-indol-3-yl) oxoacetamide, respectively, based on $^1H$ and $^{13}C$ NMR data, MS data and specific rotation value. Their pharmacological potentials as antibacterial agents and FXR antagonists were investigated, but no significant activity was found. However, the structural similarity of compound 1 to compound 4 suggested the anti-inflammatory potential of compound 1.

Alkaloids from The Roots of Tabernaemontana Macrocarpa Jack

  • Husain, Khairana;Said, Ikram M.;Din, Laily B.;Takayama, Hiromitsu;Kitajima, Mariko;Aimi, Norio
    • Natural Product Sciences
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    • v.3 no.1
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    • pp.42-48
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    • 1997
  • The roots of Tabernaemontana macrocarpa Jack (Apocynaceae) yielded nine indole alkaloids which were identified as coronaridine (2), voacangine hydroxy-indolenine (3), 3-oxo-coronaridine (4), 19-R-heyneanine (7), coronaridine pseudoindoxyl (8) and voacangine pseudoindoxyl (9) while 3-(2-oxopropyl)-coronaridine (1), 3-(2-oxopropyl)-coronaridine-pseudoindoxyl (5) and 3-(2-oxopropyl)-voacangine-pseudoindoxyl (6) were isolated as artefacts formed during the isolation process. All of the alkaloids were identified by spectroscopic methods $(UV,\;MS,\;^1H-NMR\;&\;^{13}C-NMR)$ and in comparison with the literature data.

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Development of high tryptophan GM rice and its transcriptome analysis (고 함량 트립토판 생산 GM 벼 개발 및 전사체 분석)

  • Jung, Yu Jin;Nogoy, Franz Marielle;Cho, Yong-Gu;Kang, Kwon Kyoo
    • Journal of Plant Biotechnology
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    • v.42 no.3
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    • pp.186-195
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    • 2015
  • Anthranilate synthase (AS) is a key enzyme in the biosynthesis of tryptophan (Trp), which is the precursor of bioactive metabolites like indole-3-acetic acid and other indole alkaloids. Alpha anthranilate synthase 2 (OsASA2) plays a critical role in the feedback inhibition of tryptophan biosynthesis. In this study, two vectors with single (F124V) and double (S126F/L530D) point mutations of the OsASA2 gene for feedback-insensitive ${\alpha}$ subunit of rice anthranilate synthase were constructed and transformed into wildtype Dongjinbyeo by Agrobacterium-mediated transformation. Transgenic single and double mutant lines were selected as a single copy using TaqMan PCR utilized nos gene probe. To select intergenic lines, the flanking sequence of RB or LB was digested with a BfaI enzyme. Four intergenic lines were selected using a flanking sequence tagged (FST) analysis. Expression in rice (Oryza sativa L.) of the transgenes resulted in the accumulation of tryptophan (Trp), indole-3-acetonitrile (IAN), and indole-3-acetic acid (IAA) in leaves and tryptophan content as a free amino acid in seeds also increased up to 30 times relative to the wildtype. Two homozygous event lines, S-TG1 and D-TG1, were selected for characterization of agronomic traits and metabolite profiling of seeds. Differentially expressed genes (DEGs), related to ion transfer and nutrient supply, were upregulated and DEGs related to co-enzymes that work as functional genes were down regulated. These results suggest that two homozygous event lines may prove effective for the breeding of crops with an increased level of free tryptophan content.

Isolation and Identification of Bioactive Compounds from the Tuber of Brassica oleracea var. gongylodes

  • Prajapati, Ritu;Seong, Su Hui;Kim, Hyeung Rak;Jung, Hyun Ah;Choi, Jae Sue
    • Natural Product Sciences
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    • v.26 no.3
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    • pp.214-220
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    • 2020
  • Brassica oleracea var. gongylodes (red kohlrabi) is a biennial herbaceous vegetable whose edible bulbotuber-like stem and leaves are consumed globally. Sliced red kohlrabi tubers were extracted using methanol and the concentrated extract was partitioned successively with dichloromethane (CH2Cl2), ethyl acetate (EtOAc), n-butanol (n-BuOH) and water (H2O). Repeated column chromatography of EtOAc fraction through silica, sephadex LH-20 and RP-18 gel led to isolation of eleven compounds of which compound 1 was a new glycosylated indole alkaloid derivative, 1-methoxyindole 3-carboxylic acid 6-O-β-D-glucopyranoside. Others were known compounds namely, β-sitosterol glucoside (4), 5-hydroxymethyl-2-furaldehyde (5), methyl-1-thio-β-D-glucopyranosyl disulfide (6), 5-hydroxy-2-pyridinemethanol (7), (3S,4R)-2-deoxyribonolactone (8), n-butyl-β-D-fructopyranoside (9), uridine (10) and three fructose derivatives, D-tagatose (11), β-D-fructofuranose (12) and β-D-fructopyranose (13). Similarly, isolation from CH2Cl2 fraction gave two known indole alkaloids, indole 3-acetonitrile (2) and N-methoxyindole 3-acetonitrile (3). The structure elucidation and identification of these compounds were conducted with the help of 13C and 1H NMR, HMBC, HMQC, EIMS, HR-ESIMS and IR spectroscopic data, and TLC plate spots visualization. Compounds 2, 3, 4, 5, 6, 7, 8 and 9 are noted to occur in kohlrabi for the first time. Different bioactivities of these isolated compounds have been reported in literature.