Three isoflavonoids from Iris germanica

Ali, Adel A.; El-Emary, Nasr A.; El-Moghazi, M.A.; Darwish, Faten M.; Frahm, A. W.

doi:10.1016/0031-9422(83)80045-4

Cited by 49 publications

(41 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Column chromatography of the ether soluble portion over silica and octadecylsilyl (ODS) gels gave ten compounds including 1-4. Six among them were identified as irigenin (5), 9) iridin (6), 9) tectorigenin (7), 10) tectorigin (8), 11) irisflorentin (9) 12) and rhamnocitrin (10), 13) by comparison of their physicochemical data with those reported in the literature.…”

mentioning

confidence: 99%

Isoflavonoids from Belamcanda chinensis.

Ito

Onoue

Yoshida

2001

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Isoflavonoids from Belamcanda chinensis.

Ito

Onoue

Yoshida

2001

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…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.…”

mentioning

confidence: 74%

“…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%

“…Thus, the plants of this genus can be nice materials to explore the mechanism of biosynthesis and the physiological functions of non-leguminous isoflavonoids. German iris, Iris germanica L., is known for the accumulation of a number of isoflavones (Dhar and Kalla 1972;Pailer and Franke 1973;Ali et al 1983;Atta-urRahman et al 2002), and in vitro plant regeneration from embryogenic calli has also been reported (Jéhan et al 1994;Shimizu et al 1996). In the present study, we cultured adventitious roots of I. germanica, and analyzed the accumulation of free and conjugated isoflavones.…”

mentioning

confidence: 99%

See 1 more Smart Citation

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

Akashi

Ishizaki

Aoki

et al. 2005

Plant Biotechnology

View full text Add to dashboard Cite

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.

show abstract

“…However, compound 3 is a new natural product. Compounds 4-8 were identified as 3Ј,4Ј,5Ј,5-tetramethoxy-6,7-methylenedioxyisoflavone, 10,13,14) 3Ј-methoxy-4Ј,5-dihydroxy-6,7-methylenedioxyisoflavone, 10,11,15) 3Ј,4Ј-dimethoxy-5Ј,5-dihydroxy-6,7-methylenedioxyisoflavone, 16,17) 4Ј,5-dimethoxy-3-hydroxy-6,7-methylenedioxyisoflavone, 18,19) and 5-methoxy-4Ј-hydroxy-6,7-methylenedioxyisoflavone 10) on the basis of their NMR spectral data and by comparison of their physical 1368 Vol. 50, No.…”

Section: -10) 13mentioning

confidence: 99%

New Isoflavones and Flavanol from <i>Iris potaninii</i>

Purev

Purevsuren

Narantuya³

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Iris potaninii MAZIM. (family Iridaceae) has been used in traditional Mongolian medicine for the treatment of various diseases, such as bacterial infections, cancer, and inflammation. Some benzoquinones isolated from Iris species have been used as anticancer agents in modern Chinese medicine. 1,2) In our previous papers we reported that 10 new flavones, a new isoflavone, two new quinones, and five new peltogynoids were isolated and their structures elucidated from other species of the genus.3-5) This paper describes the structure elucidation of two isoflavones (1, 2) and one flavanone (3) isolated from the roots of this plant. Results and DiscussionThe methanolic extract of the underground parts of I. potaninii was subjected to repeated chromatography on columns of silica gel, Labor RP-18, and Sephadex LH-20 and preparative thin-layer and HPLC to obtain compounds 1-9. Compound 1 was isolated as a colorless crystal. The high-resolution electron impact mass spectrum (HR-EI-MS) of 1 showed the [M] ϩ at m/z: 360.0845, in agreement with the molecular formula C 18 H 16 O 8 (Calcd 360.0831). The 1 H-NMR spectrum of 1 showed signals for three aromatic protons, and one olefinic proton along with signals for three methoxy groups. The broad-band decoupled 13 C-NMR spectrum showed resonances for all 18 carbons in molecule 1, which included three methyl, four methine, and 11 quater- The UV spectrum by the application of diagnostic shift reagents showed absorbance at l max (MeOH) (nm): 214, 260, 292, 375 sh, (ϩAlCl 3 ) 216, 264, 296 sh, 388 (unchanged), (ϩNaOAc) 272, 392. The bathochromic shift with NaOAc (260®272) indicates the presence of a free hydroxyl group at position C-7, 6) while an absence of large bathochromic shifts in band-I with AlCl 3 and NaOMe indicates that the C-5 and C-4Ј positions are free or substituted. , 6,3,4-trimethoxy-7,8,5-trihydroxyisoflavone (1), 7,4-dimethoxy-8,3,5-trihydroxy-6-O-b b-D-glucopyranosylisoflavone (2), and 5,3,3-trihydroxy-7,4-dimethoxyflavanone (3) have been isolated from the underground parts of Iris potaninii along with known isoflavones (4-8) and iriflophenone (9). The structures of the new compounds were determined using NMR and mass spectroscopic methods.

show abstract

Three isoflavonoids from Iris germanica

Cited by 49 publications

References 9 publications

Isoflavonoids from Belamcanda chinensis.

Isoflavonoids from Belamcanda chinensis.

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

New Isoflavones and Flavanol from <i>Iris potaninii</i>

Contact Info

Product

Resources

About