Isoflavones from an Insect-Resistant Variety of Soybean and the Molecular Structure of Afrormosin

Caballero, P.; Smith, C. Michael; Fronczek, Frank R.; Fischer, Nikolaus H.

doi:10.1021/np50048a030

Cited by 56 publications

(42 citation statements)

References 2 publications

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“…11) Spectral data ( 13 C-NMR, Table 1) resembled those published for 4Ј,6-dimethoxy-7-hydroxy-isoflavone (1) known as afrormosin 12) and castanin 13) respectively and 4Ј,6-dimethoxy-5Ј,7-dihydroxy-isoflavone (2) known as odoratin, which have been previously detected in D. odorata and Glycine max respectively. 4,5,11,12) Final confirmation of the structure of compounds 1 and 2 was achieved through X-ray diffraction analysis (Figs.…”

Section: T Cruzi Gapdh-inhibitory Activitysupporting

confidence: 59%

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Isolation and Structure Determination of Bioactive Isoflavones from Callus Culture of Dipteryx odorata

Januário

Lourenço

Domézio

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Great commercial value has been credited to the seeds of Dipteryx odorata WILLD. (AUBL.) (Leguminoseae) native from Amazon and also known as tonka beans or cumaru, because they are considered rich source of coumarins, used in cosmetics and perfumery.1) The presence of umbelliferone in seeds of tonka beans was described by Sullivan who also reported other natural compounds like isoflavonoids, triterpenoids, fatty acids and cassane diterpenoids on seeds of this species.2) Additionally some micromolecules specific of the heartwood of D. odorata as isoflavones retusin, retusin 8-methyl ether, 3Ј-hydroxyretusin 8-methyl ether, odoratin, dipteryxin, dipteryxine and odoratine; the triterpenes lupeol and betulin; and methyl esters of fatty acids have been isolated. 3,4) Isoflavonoids have gained considerable importance due to the diverse broad of biological activities correlated to them, including antioxidative, oestrogenic, inseticidal, piscicidal, antifungal, antimicrobial and contraceptive properties. 5,6) The pharmacological properties of isoflavonoids and the correlation between the consumption of isoflavonoids and reduction on the level of incidence of cardiovascular disease and cancer have increase the interest in the search for biologically active compounds from plant species of both, leguminous and non-leguminous sources. 7)In this work we report the establishment of D. odorata callus cultures focusing on a comparative study related to the production of tripanossomatidal GAPDH inhibitory isoflavones accumulated in roots of the intact plant and in callus cultures of this species. ExperimentalPlant Material Dipteryx odorata plants were collected in the campus of Universidade do Amazonas in Manaus, Brazil. Voucher specimen is deposited under the number HUAM 7276 in the Herbarium of the Universidade do Amazonas.Seed Disinfestations Seeds of D. odorata were soaked in sterile distilled water and maintained under agitation overnight. Seeds were then immersed in 2% Benomyl solution for 4 h under agitation, washed in 70% hydroalcoholic solution, dipped in 1% CaClO for 40 min, washed for three times with sterile distilled water and inoculated into glass flasks (8.5 cmϫ2.5 cm i.d.) containing 5 ml MS medium 8) added with 30 g/l sucrose and 2.0 g/l Phytagel, pH was adjusted to 6.0 before autoclaving. Flasks were sealed with polypropylene closures (Bellco), autoclaved at 121°C and 105 kPa for 20 min and maintained at 25Ϯ2°C, 55-60% relative humidity under 16 h photoperiod with 40 mmol m Ϫ2 s Ϫ1, 85 W coolwhite GE fluorescent lamps.Callus Induction Leaves, hypocotyl, and roots of D. odorata seedlings produced in vitro were used as explants for callus induction. Explants were inoculated onto semisolid MS medium supplemented with 2.0 mg/l 2,4-D, 0.5 mg/l 6-BAP and 340 mg/l KH 2 PO 4 and 2.0 g/l Phytagel, pH ajusted to 6.0. Callus were harvested and subcultured in 30-d intervals.General Analytical Procedures TLC was carried out on silica gel G pre-coated plates (Sigma-Aldrich) using CHCl 3 -MeOH (9 : 1) as solvent system. Spots...

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Section: T Cruzi Gapdh-inhibitory Activitysupporting

confidence: 59%

“…4,5,11,12) Final confirmation of the structure of compounds 1 and 2 was achieved through X-ray diffraction analysis (Figs. 1, 2).…”

Section: T Cruzi Gapdh-inhibitory Activitymentioning

confidence: 99%

Isolation and Structure Determination of Bioactive Isoflavones from Callus Culture of Dipteryx odorata

Januário

Lourenço

Domézio

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Many 5-deoxyisoflavones and their derivatives have phytoalexin activity (Tahara and Ibrahim 1995). Examples of soybean 5-deoxyisoflavones and their derivatives related to defenses include coumestrol (5-deoxyisoflavone derivative), phaseol (5-deoxyisoflavone derivative), and afrormosin (5-deoxyisoflavone) that may promote resistance against soybean looper Chrysodeixis includens (Lepidoptera: Noctuidae) herbivory (Caballero et al 1986). As a well-established antibiotic, glyceollin (5-deoxyisoflavone derivative) can significantly reduce feeding by southern corn rootworm Diabrotica undecimpunctata howardi (Coleoptera: Chrysomelidae) and Mexican bean beetle Epilachna varivestis (Coleoptera: Coccinellidae) larvae (Fischer et al 1990).…”

Section: Controlmentioning

confidence: 99%

Inducible De Novo Biosynthesis of Isoflavonoids in Soybean Leaves by Spodoptera litura Derived Elicitors: Tracer Techniques Aided by High Resolution LCMS

et al. 2016

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Isoflavonoids are a characteristic family of natural products in legumes known to mediate a range of plant-biotic interactions. For example, in soybean (Glycine max: Fabaceae) multiple isoflavones are induced and accumulate in leaves following attack by Spodoptera litura (Lepidoptera: Noctuidae) larvae. To quantitatively examine patterns of activated de novo biosynthesis, soybean (Var. Enrei) leaves were treated with a combination of plant defense elicitors present in S. litura gut content extracts and L-α-[ 13 C 9 , 15 N]phenylalanine as a traceable isoflavonoid precursor. Combined treatments promoted significant increases in 13 Clabeled isoflavone aglycones (daidzein, formononetin, and genistein), 13 C-labeled isoflavone 7-O-glucosides (daidzin, ononin, and genistin), and 13 C-labeled isoflavone 7-O-(6″-O-malonyl-β-glucosides) (malonyldaidzin, malonylononin, and malonylgenistin). In contrast levels of 13 C-labeled flavones and flavonol (4′,7-dihydroxyflavone, kaempferol, and apigenin) were not significantly altered. Curiously, application of fatty acid-amino acid conjugate (FAC) elicitors present in S. litura gut contents, namely N-linolenoyl-L-glutamine and N-linoleoyl-L-glutamine, both promoted the induced accumulation of isoflavone 7-O-glucosides and isoflavone 7-O-(6″-O-malonyl-β-glucosides), but not isoflavone aglycones in the leaves. These results demonstrate that at least two separate reactions are involved in elicitor-induced soybean leaf responses to the S. litura gut contents: one is the de novo biosynthesis of isoflavone conjugates induced by FACs, and the other is the hydrolysis of the isoflavone conjugates to yield isoflavone aglycones. Gut content extracts alone displayed no hydrolytic activity. The quantitative analysis of isoflavone de novo biosynthesis, with respect to both aglycones and conjugates, affords a useful bioassay system for the discovery of additional plant defense elicitor(s) in S. litura gut contents that specifically promote hydrolysis of isoflavone conjugates.

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“…Antifungal activity and insect-feeding deterrence were found to be closely associated for several isoflavonoids from L. angustifolius (Lane et al, 1987). Afrormosin has been shown to be toxic to soybean loopers (Pseudoplusia includens; Caballero et al, 1986), and a large pool of afrormosin glucosides likely acts as a preformed insect deterrent (Wittstock and Gershenzon, 2002). Characterization of the enzymatic machinery involved in the synthesis and turnover of these and related isoflavone glucosides could provide a basis for manipulating defense responses in legumes by genetic engineering.…”

Section: Functions For Induced Isoflavonoids In Medicagomentioning

confidence: 99%

Metabolomics Reveals Novel Pathways and Differential Mechanistic and Elicitor-Specific Responses in Phenylpropanoid and Isoflavonoid Biosynthesis in Medicago truncatula Cell Cultures

et al. 2007

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High-performance liquid chromatography coupled to ultraviolet photodiode array detection and ion-trap mass spectrometry was used to analyze the intra-and extracellular secondary product metabolome of Medicago truncatula cell suspension cultures responding to yeast elicitor (YE) or methyl jasmonate (MeJA). Data analysis revealed three phases of intracellular response to YE: a transient response in mainly (iso)flavonoid metabolites such as formononetin and biochanin-A that peaked at 12 to 18 h following elicitation and then declined; a sustained response through 48 h for compounds such as medicarpin and daidzin; and a lesser delayed and protracted response starting at 24 h postelicitation, e.g. genistein diglucoside. In contrast, most compounds excreted to the culture medium reached maximum levels at 6 to 12 h postelicitation and returned to basal levels by 24 h. The response to MeJA differed significantly from that to YE. Although both resulted in accumulation of the phytoalexin medicarpin, coordinated increases in isoflavonoid precursors were only observed for YE and not MeJA-treated cells. However, MeJA treatment resulted in a correlated decline in isoflavone glucosides, and did not induce the secretion of metabolites into the culture medium. Three novel methylated isoflavones, 7-hydroxy-6,4#-dimethoxyisoflavone (afrormosin), 6-hydroxy-7,4#-dimethoxyisoflavone (alfalone), and 5,7-dihydroxy-4#,6-dimethoxy isoflavone (irisolidone), were induced by YE, and labeling studies indicated that the first two were derived from formononetin. Our results highlight the metabolic flexibility within the isoflavonoid pathway, suggest new pathways for complex isoflavonoid metabolism, and indicate differential mechanisms for medicarpin biosynthesis depending on the nature of elicitation.

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Isoflavones from an Insect-Resistant Variety of Soybean and the Molecular Structure of Afrormosin

Cited by 56 publications

References 2 publications

Isolation and Structure Determination of Bioactive Isoflavones from Callus Culture of Dipteryx odorata

Isolation and Structure Determination of Bioactive Isoflavones from Callus Culture of Dipteryx odorata

Inducible De Novo Biosynthesis of Isoflavonoids in Soybean Leaves by Spodoptera litura Derived Elicitors: Tracer Techniques Aided by High Resolution LCMS

Metabolomics Reveals Novel Pathways and Differential Mechanistic and Elicitor-Specific Responses in Phenylpropanoid and Isoflavonoid Biosynthesis in Medicago truncatula Cell Cultures

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