Isoflavonoids produced by Iris pseudacorus leaves treated with cupric chloride

Hanawa, Fujinori; Tahara, Satoshi; Mizutani, Junya

doi:10.1016/0031-9422(91)84117-b

Cited by 85 publications

(49 citation statements)

References 29 publications

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“…The juice of the roots of I. germanica is applied to sores and used to remove freckles from the skin. It is employed as an ingredient of composition for purifying blood and for venereal diseases [61]. Human neutrophils are known to be the first line of defense against invading microorganisms.…”

Section: Iris Germanicamentioning

confidence: 99%

Discovery of drug candidates from some Turkish plants and conservation of biodiversity

Şener

Orhan

2005

Pure and Applied Chemistry

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Section: Iris Germanicamentioning

confidence: 99%

Discovery of drug candidates from some Turkish plants and conservation of biodiversity

Şener

Orhan

2005

Pure and Applied Chemistry

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“…IFS has been suggested to have evolved from an ancestral P450 which is also the ancestor of flavone synthase II (CYP93B) (Sawada et al 2002;Sawada and Ayabe 2005). Regarding the biosynthesis of Iris isoflavonoids, I. pseudacorus leaves have been reported to contain a flavanone with a 2Ј-hydroxyl which could be a precursor of a particular isoflavone with the same substitution also contained in the same source (Hanawa et al 1991a(Hanawa et al , 1991b. In the leguminous isoflavonoid biosynthesis, 2Ј-hydroxyl is introduced through the action of a P450 of CYP81E subfamily after the isoflavone structure is constructed (Akashi et al 1998;Shimada et al 2000;Liu et al 2003).…”

Section: Discussionmentioning

confidence: 99%

“…HPLC analysis of isoflavones in the adventitious roots Aqueous 3 mM CuCl 2 solution (1 ml) (Hanawa et al 1991a(Hanawa et al , 1991b or an equal volume of water sterilized with a membrane filter (Millex-GV; Millipore, Bedford, MA, USA) was added to a 2 ml Eppendorf tube containing 3-week-old adventitious roots (500 mg) grown on the solid medium. After incubation for 48 h in the dark, the adventitious roots were collected by suction filtration and homogenized in MeOH.…”

Section: Plant Materials and Culture Conditionsmentioning

confidence: 99%

Isoflavonoid production by adventitious-root cultures of Iris germanica (Iridaceae)

Akashi

Ishizaki

Aoki

et al. 2005

Plant Biotechnology

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We established the adventitious-root cultures of Iris germanica, a monocotyledonous plant known for isoflavonoid production. Irigenin (5,7,3Ј-trihydroxy-6,4Ј,5Ј-trimethoxyisoflavone) and iristectorigenin A (5,7,3Ј-trihydroxy-6,4Ј-dimethoxyisoflavone) along with their 7-O-b-D-glucosides, iridin and iristectorin A, respectively, were found as the major components in adventitious roots in the liquid medium, and the total isoflavone content was about 3.6 mmol per g fresh weight in 3-week-old cultures, which was much higher than the 0.7 mmol per g dry weight in the rhizome previously reported (Ali et al. 1983 Phytochemistry 22: 2061. Abiotic stress was applied by addition of 3 mM cupric chloride (CuCl 2 ) to the liquid medium. The isoflavone glucoside content was increased during the initial 6 h of CuCl 2 treatment, which was followed by a decrease; the aglycone level continued to increase throughout the 48 h of treatment. The decrease in glucoside content was negatively correlated with the increase in aglycone content between 6 and 48 h. The total isoflavone content (glucosidesϩaglycones) at 6 h after the start of CuCl 2 treatment was 1.4-fold the initial value, and nearly the same content was maintained for 48 h. Thus, the main effect of CuCl 2 treatment appeared to be the induction of hydrolysis of isoflavone glucosides. A cDNA of chalcone synthase was cloned, and the mRNA was expressed in the culture producing isoflavones.

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“…A subfração 150-170 (Hex/AcOEt 30%) forneceu um sólido incolor (0,0454 g), identificado como sendo a cumaronocromona lupinalbina A (7). 11,12 A subfração 183-213 (Hex/AcOEt 30%, 0,1138 g) foi purificada por cromatografia flash, obtendo-se na fração Hex/AcOEt 25% um sólido incolor (0,0177 g), identificado como sendo a isoflavona genisteína (8).…”

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Constituintes químicos e avaliação da atividade antibacteriana de Macroptilium lathyroides (L.) Urb. (Fabaceae)

Sousa¹,

Gois²,

Lemos³

et al. 2013

Quím. Nova

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Recebido em 11/4/13; aceito em 11/6/13; publicado na web em 2/8/13 CHEMICAL CONSTITUENTS AND EVALUATION OF ANTIBACTERIAL ACTIVITY OF Macroptilium lathyroides (L.) Urb. (Fabaceae). The chemical investigation of the stems and branches of Macroptilium lathyroides led to the isolation of a mixture of β-sitosterol and stigmasterol. The extracts from the roots allowed the isolation of lasiodiplodin, a mixture of stigmast-4-en-6β-ol-3-one and stigmast-4,22-dien-6β-ol-3-one, de-O-methyllasiodiplodin, genistein and lupinalbin A. The structures of the isolated compounds were assigned on the basis of their NMR data, including comparison of their spectral data with values described in the literature. The antibacterial activity of crude extracts from stems, branches and roots was evaluated. This is the first report involving the chemical investigation of this species.Keywords: Macroptilium lathyroides; lasiodiplodin derivatives; coumaronochromone. INTRODUÇÃOO gênero Macroptilium, pertencente à família Fabaceae, compreende cerca de 20 espécies distribuídas nas Américas. Algumas espécies deste gênero são usadas como forrageiras, como adubo verde e na medicina popular. 1Macroptilium lathyroides (L.) Urb., conhecida popularmente como "Feijão-de-Pombinha" ou "Feijão-do-Campo", 2 é originária da parte tropical da América do Sul e foi introduzida na Índia tropical e subtropical, Austrália, África e Sudeste da América do Norte. 3 A ausência de relatos sobre a composição química desta espécie serviu como estímulo adicional para a investigação fitoquímica da mesma.O presente trabalho descreve os resultados obtidos do estudo fitoquímico dos galhos, talos e raízes de M. lathyroides e, ainda, os resultados da avaliação da atividade antibacteriana dos seus extratos brutos. PARTE EXPERIMENTAL Procedimentos experimentais geraisOs pontos de fusão foram determinados em aparelho Mettler Toledo, com placa aquecedora modelo FP82HT e central de processamento FP90, acoplado a um microscópio óptico monocular. As determinações foram realizadas a uma velocidade de aquecimento de 5 o C/min e os valores obtidos não foram corrigidos. Os espectros de absorção na região do infravermelho (IV) foram obtidos em espectrômetro ABB, modelo FTLA 2000-102, utilizando--se pastilhas de KBr.Os espectros 1D e 2D de ressonância magnética nuclear (RMN) foram registrados em espectrômetro Bruker DRX-500, operando a 500,13 MHz para Os espectros de massas de baixa resolução foram obtidos por impacto eletrônico a 70 eV em espectrômetro Shimadzu, modelo QP 5000, DI-50.A determinação de rotação óptica foi realizada em um Polarímetro 341 da Perkin-Elmer, à temperatura de 20 o C. Para as cromatografias de adsorção em coluna (CC) utilizou-se gel de sílica 60 (0,063-0,200 mm, Vetec) ou gel de sílica 60 (0,04-0,063 mm, Merck) como fase estacionária. Utilizou-se na eluição cromatográfica os solventes hexano, diclorometano, acetato de etila e metanol, puros ou em misturas binárias em gradiente de polaridade crescente. As análises cromatográficas em camada delgada (CCD) foram efetuad...

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Isoflavonoids produced by Iris pseudacorus leaves treated with cupric chloride

Cited by 85 publications

References 29 publications

Discovery of drug candidates from some Turkish plants and conservation of biodiversity

Discovery of drug candidates from some Turkish plants and conservation of biodiversity

Isoflavonoid production by adventitious-root cultures of Iris germanica (Iridaceae)

Constituintes químicos e avaliação da atividade antibacteriana de Macroptilium lathyroides (L.) Urb. (Fabaceae)

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