Flavonoids produced by Iris pseudacorus leaves treated with cupric chloride

Hanawa, Fujinori; Tahara, Satoshi; Mizutani, Junya

doi:10.1016/0031-9422(91)83613-p

Cited by 27 publications

(17 citation statements)

References 13 publications

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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%

“…Preliminary 1 H NMR analysis suggested that both peaks represented the mixtures of two components. The materials were further subjected to cellulose column chromatography, which could separate 1a and 1b from the control tissues and 2a and 2b from the CuCl 2 -treated tissues (Figure 3) C NMR spectra were identical with those reported for irigenin (5,7,3Ј-trihydroxy-6,4Ј,5Ј-trimethoxyisoflavone) (Ali et al 1983) and iristectorigenin A (5,7,3Ј-trihydroxy-6,4Ј-dimethoxyisoflavone) (Hanawa et al 1991a), respectively. The validity of the structures was further granted by 2D NMR spectra; in particular, the heteronuclear multiple bond coherence (HMBC) spectra.…”

Section: Identification Of Isoflavonesmentioning

confidence: 98%

“…Isoflavone production in the adventitious-root cultures and the effect of CuCl 2 treatment As a pilot experiment, constituents in the root tissues with and without treatment with 3 mM CuCl 2 solution (Hanawa et al 1991a(Hanawa et al , 1999b for 48 h were analyzed by HPLC. MeOH extracts of both intact and water-treated (the control for CuCl 2 treatment) tissues gave a major HPLC peak (peak 1) at Rt 6.6 min (Figure 2A).…”

Section: Culture Of Adventitious Roots Of I Germanicamentioning

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%

“…They accumulate mainly in the rhizomes, but the leaves of Iris pseudacorus treated with an abiotic stress agent, cupric chloride (CuCl 2 ), also produce isoflavonoids (Hanawa et al 1991a(Hanawa et al , 1999b. Thus, the plants of this genus can be nice materials to explore the mechanism of biosynthesis and the physiological functions of non-leguminous isoflavonoids.…”

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confidence: 99%

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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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Section: Discussionmentioning

confidence: 99%

Section: Identification Of Isoflavonesmentioning

confidence: 98%

Section: Culture Of Adventitious Roots Of I Germanicamentioning

confidence: 99%

Section: Plant Materials and Culture Conditionsmentioning

confidence: 99%

mentioning

confidence: 99%

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

Akashi

Ishizaki

Aoki

et al. 2005

Plant Biotechnology

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Innovative GACP Approaches for Obtaining the QualityIris hybridaLeaves for the Pharmaceutical Industry

Мykhailenko

Buydin

Ivanauskas

et al. 2022

Chemistry & Biodiversity

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The ever‐growing demand for active compounds of plant origin contributes to the implementation of cultivation methods for medicinal plants, according to the WHO guideline “Good Agricultural and Collection Practice (GACP) for Starting Materials of Herbal Origin” to obtain high‐quality raw material with the stable phytocomponent composition. Therefore, the development of the cultivation and processing stages of Iris varieties leaves is necessary and promising. The present article showed the potential of proper cultivation with GACP recommendations on affecting the phenolic compounds content in Iris×hybrida hort. ‘Indian Pow Waw’, Iris×hybrida hort. ‘Galleon Gold’, and Iris×hybrida hort. ‘Mini Dinamo’ leaves. The cultivation process was carried out on the experimental sites of the flowering and ornamental plants department of M.M. Hryshko National Botanical Garden of the National Academy of Sciences of Ukraine (Kyiv, Ukraine) during 2018–2021. A positive effect of Iris samples proper cultivation and content of isoflavonoids (tectoridin, nigricin D‐glucoside, genistin, iristectorigenin B, nigricin, irigenin, irisolidone), xanthone mangiferin, and also chlorogenic acid in Irises leaves by HPLC has been established. According to the analysis mangiferin (7.57∼28.75 μg/g), genistin (3324.82∼14642.10 μg/g), irisolidone (673.53∼2015.81 μg/g), and irigenin (3904.37∼1595.94 μg/g) were the dominant components and these compounds can be proposed as chemical markers for Iris raw material. The obtained results indicate a significant positive effect of the introduction and observance of the proper cultivation of medicinal plants to obtain a stable bioactive compounds content, in this case, on the example of Iris genus plants. Further work on the implementation of the good practice recommendation is planned to be carried out for various medicinal plants, since only controlled cultivation makes it possible to obtain high‐quality raw materials with a standardized composition.

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Accuracy mass screening and identification of phenolic compounds from the five parts of Abutilon theophrasti Medic. by reverse‐phase high‐performance liquid chromatography‐electrospray ionization‐quadrupoles‐time of flight‐mass spectrometry

Tian

Wang²,

Shen³

et al. 2012

J of Separation Science

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A rapid and resolutive reverse-phase high-performance liquid chromatography-electrospray ionization-quadrupoles-time of flight-mass spectrometry method was established for the screening and identification of the phenolic compounds in the 70% ethanolic extracts from the five parts (roots, stems, leaves, seeds, and exocarps) of Abutilon theophrasti Medic.. Separation and detection conditions were optimized by using a 22 mixing standard, which included phenolic acids, flavonoids and a naphthalene compound. Optimum LC separation was achieved on a C(18) analytical column (250 mm x 4.6 mm id, 5 μm) by gradient elution with water containing 0.1% v/v formic acid (pH 2.4) and acetonitrile as mobile phases, at a flow rate of 1.0 mL/min. The developed method was applied to the study on the constituents of A. theophrasti Medic., and 16 compounds were unequivocally identified with standards. Meanwhile, 37 constituents were tentatively identified by comparing with references. In addition, accurate molecular formulae were conjectured for unknown compounds. To our knowledge, little is known about how these compounds are distributed in A. theophrasti Medic.. Hence, it is clear that the comprehensive analysis of the phenolic compounds of A. theophrasti Medic. is helpful for the quality control and understanding the usage and function of the herb and its products.

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Flavonoids produced by Iris pseudacorus leaves treated with cupric chloride

Cited by 27 publications

References 13 publications

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

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

Innovative GACP Approaches for Obtaining the QualityIris hybridaLeaves for the Pharmaceutical Industry

Accuracy mass screening and identification of phenolic compounds from the five parts of Abutilon theophrasti Medic. by reverse‐phase high‐performance liquid chromatography‐electrospray ionization‐quadrupoles‐time of flight‐mass spectrometry

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