1162. Structure and stereochemistry of the vicianoside amorphin, the first rotenoid glycoside

Claisse, J. A.; Crombie, L.; Peace, Richard J.

doi:10.1039/jr9640006023

Cited by 31 publications

(23 citation statements)

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“…The 13C-NMR spectrum is shown in Table 2. All of the physicochemical data obtained for this metabolite were identical to those reported for amorphigenin (5,8) and to an authentic sample (5).…”

Section: Resultssupporting

confidence: 76%

Microbial Transformations of Natural Antitumor Agents: Products of Rotenone and Dihydrorotenone Transformation by Cunninghamella blakesleeana

Sariaslani

Rosazza

1983

Appl Environ Microbiol

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Various species of Absidia, Aspergillus, Cunninghamella, Trichothecium, Penicillium, and Phanerochaete were found to transform rotenone to one or more metabolites. Two biotransformation products were isolated from a preparativescale incubation of rotenone with Cunninghamella blakesleeana and identified as 1',2'-dihydro-1',2'-dihydroxyrotenone and 3'-hydroxyrotenone (amorphigenin). The catalytic reduction of the isopropylene side chain of rotenone resulted in the formation of 1',2'-dihydrorotenone. The latter was transformed by C. blakesleeana to 2'-hydroxy-1',2'-dihydrorotenone. Rotenoids are components of the roots, stems, and leaves of many leguminous species of the genera Derris, Lonchocarpus, Tephrosia, and Amorpha. Rotenone, a prominent component of this group, was first isolated in 1895 (12), but its structure was established only recently (2, 6, 7, 10). It is a well-characterized inhibitor of the mitochondrial respiratory chain at the level of NADH dehydrogenase (3). Rotenoids have been widely used as nonpersistent pesticides because of their effectiveness, selectivity, and apparently low environmental hazard. Although the metabolism of rotenone has been studied in mammals and insects (11, 13), no studies on the microbial metabolism or transformation of this compound have been reported. Aspects of the chemistry, biochemistry, metabolism, pharmacology, and toxicology of rotenone have been reviewed (13), and the need for further studies on the metabolism of this compound, including definitive identification of metabolites formed by various species, has been emphasized (13). This report identifies the products of rotenone and of 1',2'-dihydrorotenone when metabolized by Cunninghamella blakesleeana. MATERIALS AND METHODS Organisms and fermentation procedures. The cultures used in this study are maintained in the University of Iowa College of Pharmacy culture collection and are stored in sealed screw-capped tubes at 4°C. Organisms were grown in a medium of the following composition: soybean meal (5 g), glucose (20 g), yeast extract (5 g), NaCl (5 g), K2HPO4 (5 g), and distilled water (1.0 liter), adjusted to pH 7.0 with 5 N HCI. The media were sterilized in an autoclave at 121°C for 15 min.

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Section: Resultssupporting

confidence: 76%

Microbial Transformations of Natural Antitumor Agents: Products of Rotenone and Dihydrorotenone Transformation by Cunninghamella blakesleeana

Sariaslani

Rosazza

1983

Appl Environ Microbiol

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“…It is strong, environmentally tolerant and grows rapidly, so it can be planted anywhere, being cold hardy and resistant to dryness (Huh et al 1997). A rotenoid having the dihydrofuran ring with the isoprenoid side chain attached was isolated from Amorpha fruticosa L. for the first time (Crombie and Peace 1963;Crombie et al 1964). Methanol crude extract of Amorpha fruticosa L. seed was fractionated using dichloromethane to produce a rotenoid, 6a,12a-dihydro-a-toxicarol (Reisch et al 1976).…”

Section: Introductionmentioning

confidence: 99%

Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells

et al. 2006

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A new compound, rotenoid isoflavone glycoside named, 6'-O-beta-D: -glucopyranosyl-12a-hydroxydalpanol was isolated from the methanolic (MeOH) fruit extract of Amorpha fruticosa LINNE by means of multi-stage column chromatography. Immuno-modulatory activities of this new glycoside were compared with the partitioned fractions of Amorpha fruticosa LINNE. Both of the fractions and purified single compound showed a 19% relatively low cytotoxicity at a maximum concentration of 1.0 g/L in a cultivated normal human lung cell line (HEL299). The purified single compound showed less cytotoxicity than the crude extracts, possibly because residual toxicants were eliminated during purification processes. Cell growth of human T cells was increased by about 15% by adding 0.5 g/L of the fractions compared to the control. Specific production rates of interleukin-6 (IL-6) and tumor necrosis factor (TNF-alpha) from T cell were higher as 1.16 x 10(-4) and 1.86 x 10(-4 )pg/cell, respectively, in the purified compound, compared to 1.38 x 10(-4) and 2.22 x 10(-4 )pg/cell, respectively, by adding 0.5 g/L of the dichloromethane fraction. Natural killer cell-92MI (NK-92MI) growth supplemented with the supernatant of human T cell was up to 19% higher with the dichloromethane fraction compared with a new single compound at a concentration of 0.5 g/L. Overall, the dichloromethane fraction showed relatively higher immuno-modulatory activities compared with a new single compound, probably due to the synergic effect given by other substances existing in the fractions.

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“…The rotenoids 21-24 (Table I) and isoflavonoids 25-26 (Table II) were isolated from the petroleum ether extract of ripe Amorpha fruticosa L. fruits by means of column chromatography on silica, followed by preparative TLC and crystallization [9]. The glycoside amorphin 7was isolated from the defatted fruits by further extraction with chloroform-methanol [101, whereas its aglycone amorphigenin 14 was prepared by acidic hydrolysis of 7 [11]. Rotenone 1 was a commercial sample obtained from Aldrich Chemicals and further purified by crystallization.…”

Section: Methodsmentioning

confidence: 99%

Inhibition of Rat Heart Phosphodiesterase by some Rotenoids and Isoflavonoids

Petkov¹,

Uzunov²,

Kostova³

et al. 1983

Planta Med

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Series of natural and semisynthetic rotenoids and isoflavonoids were studied for their inhibitory activity on cyclic AMP phosphodiesterase (PDE) in rat heart. Some of the compounds showed higher inhibitory activity than that of the most potent flavonoids. The chemical transformation of the starting natural compounds failed to increase their inhibitory potency. PDE inhibition was of a noncompetitive type.

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1162. Structure and stereochemistry of the vicianoside amorphin, the first rotenoid glycoside

Cited by 31 publications

References 0 publications

Microbial Transformations of Natural Antitumor Agents: Products of Rotenone and Dihydrorotenone Transformation by Cunninghamella blakesleeana

Microbial Transformations of Natural Antitumor Agents: Products of Rotenone and Dihydrorotenone Transformation by Cunninghamella blakesleeana

Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells

Inhibition of Rat Heart Phosphodiesterase by some Rotenoids and Isoflavonoids

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