Biosynthesis of glyceollins I, II and III in soybean

Banks, Stephen W.; Dewick, Paul M.

doi:10.1016/s0031-9422(00)97682-9

Cited by 43 publications

(35 citation statements)

References 19 publications

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“…The biosynthesis of all three glyceollin isomers occurs within soybean tissues starting with daidzein through several intermediate structures, including glycinol shown in Fig. 3 (Banks and Dewick, 1983). Glycinol, which we have shown previously to be estrogenic (Boué et al, 2009), is derived from daidzein via a pterocarpan by cyclization and 6␣-hydroxylation with retention of configuration (Banks and Dewick, 1983;Hagmann et al, 1984).…”

Section: Discussionmentioning

confidence: 92%

“…3 (Banks and Dewick, 1983). Glycinol, which we have shown previously to be estrogenic (Boué et al, 2009), is derived from daidzein via a pterocarpan by cyclization and 6␣-hydroxylation with retention of configuration (Banks and Dewick, 1983;Hagmann et al, 1984). For the synthesis of the glyceollins, glycinol is prenylated to produce glyceollidin I and II, followed by cyclization into the corresponding glyceollins (Zä hringer et al, 1981).…”

Section: Discussionmentioning

confidence: 99%

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Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy

Zimmermann

Tilghman

Boué³

et al. 2009

J Pharmacol Exp Ther

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Glyceollins, a group of novel phytoalexins isolated from activated soy, have recently been demonstrated to be novel antiestrogens that bind to the estrogen receptor (ER) and inhibit estrogen-induced tumor progression. Our previous publications have focused specifically on inhibition of tumor formation and growth by the glyceollin mixture, which contains three glyceollin isomers (I, II, and III). Here, we show the glyceollin mixture is also effective as a potential antiestrogenic, therapeutic agent that prevents estrogenstimulated tumorigenesis and displays a differential pattern of gene expression from tamoxifen. By isolating the individual glyceollin isomers (I, II, and III), we have identified the active antiestrogenic component by using competition binding assays with human ER␣ and in an estrogen-responsive element-based luciferase reporter assay. We identified glyceollin I as the active component of the combined glyceollin mixture. Ligand-receptor modeling (docking) of glyceollin I, II, and III within the ER␣ ligand binding cavity demonstrates a unique type II antiestrogenic confirmation adopted by glyceollin I but not isomers II and III. We further compared the effects of glyceollin I to the antiestrogens, 4-hydroxytamoxifen and ICI 182,780 (fulvestrant), in MCF-7 breast cancer cells and BG-1 ovarian cancer cells on 17␤-estradiol-stimulated expression of progesterone receptor and stromal derived factor-1␣. Our results establish a novel inhibition of ER-mediated gene expression and cell proliferation/ survival. Glyceollin I may represent an important component of a phytoalexin-enriched food (activated) diet in terms of chemoprevention as well as a novel therapeutic agent for hormonedependent tumors.Breast cancer accounts for 25% of all female cancers, making it the most common cancer in women in the western world (Greenlee et al., 2000Lester, 2007 Ali and Coombs, 2002). For patients with hormone receptor-positive breast cancer, several promising endocrine agents are currently available with promising results. Therapies have been developed to reduce estrogen levels or to block signaling through estrogen receptors (ER) (Pink and Jordan, 1996;Howell, 2006). These agents include tamoxifen, a selective estrogen

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Section: Discussionmentioning

confidence: 92%

Section: Discussionmentioning

confidence: 99%

Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy

Zimmermann

Tilghman

Boué³

et al. 2009

J Pharmacol Exp Ther

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“…These isoflavones, as well as coumestrol and other flavonoids, predominantly act as estrogenic chemicals but may also exhibit antiestrogenic activity in a dose-dependent manner (17,18,31). We have shown that under stress conditions or elicitor treatment, the concentrations of the constitutive isoflavones increase and several isoflavone phytoalexins are produced.…”

Section: Isolation Of Glycinolmentioning

confidence: 99%

Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max)

et al. 2008

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The primary induced isoflavones in soybean, the glyceollins, have been shown to be potent estrogen antagonists in vitro and in vivo. The discovery of the glyceollins' ability to inhibit cancer cell proliferation has led to the analysis of estrogenic activities of other induced isoflavones. In this study, we investigated a novel isoflavone, glycinol, a precursor to glyceollin that is produced in elicited soy. Sensitive and specific in vitro bioassays were used to determine that glycinol exhibits potent estrogenic activity. Estrogen-based reporter assays were performed, and glycinol displayed a marked estrogenic effect on estrogen receptor (ER) signaling between 1 and 10 microM, which correlated with comparable colony formation of MCF-7 cells at 10 microM. Glycinol also induced the expression of estrogen-responsive genes (progesterone receptor and stromal-cell-derived factor-1). Competitive binding assays revealed a high affinity of glycinol for both ER alpha (IC(50) = 13.8 nM) and ER beta (IC(50) = 9.1 nM). In addition, ligand receptor modeling (docking) studies were performed and glycinol was shown to bind similarly to both ER alpha and ER beta. Taken together, these results suggest for the first time that glycinol is estrogenic and may represent an important component of the health effects of soy-based foods.

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“…The biosynthetic pathways for medicarpin in red clover and alfalfa (5,6), glyceollin in soybean (2), and phaseollin in French bean (19) have been elucidated on the basis of incorporated radiolabeled precursors and biogenetic relationships. The pathways function in localized plant cells only in response to the presence of elicitors (4).…”

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confidence: 99%

Induction of Medicarpin Biosynthesis in Ladino Clover Callus by p-Chloromercuribenzoic Acid Is Reversed by Dithiothreitol

Gustine

1987

Plant Physiol.

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Treatment of Ladino clover (Trifolium repens L.) callus with 1 millimolar p-chloromercuribenzoic acid (PCMBA) stimulated the biosynthesis of the phytoalexin medicarpin. Increased medicarpin concentration was detected at 6 hours, and maximum level was achieved by 36 hours. Dithiothreitol (DTT), added to callus at 2, 6, 10, and 18 hours following addition of PCMBA, partially counteracted the effect of PCMBA in the cells. The greatest effect on reversal of medicarpin accumulation was found at the earlier times for DTT addition. Compared to a 24-hour PCMBA control, final medicarpin concentrations were 9 to 19%, 37 to 45%, and 92 to 105% of the control value when DTT was added at 0.5, 1 or 2 hours, 3 or 4 hours, and 6, 8, 10, or 12 hours, respectively, after PCMBA addition. The results indicate that stimulation of medicarpin biosynthesis is reversible, but once activated, the pathway is not shut down by removal of elicitor.

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Biosynthesis of glyceollins I, II and III in soybean

Cited by 43 publications

References 19 publications

Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy

Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy

Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max)

Induction of Medicarpin Biosynthesis in Ladino Clover Callus by p-Chloromercuribenzoic Acid Is Reversed by Dithiothreitol

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