Multigram Synthesis of Glyceollin I

Luniwal, Amarjit; Khupse, Rahul; Reese, Michael D.; Liu, Jidong; El-Dakdouki, Mohammad H.; Malik, Neha; Fang, Lei; Erhardt, Paul

doi:10.1021/op200112g

Cited by 21 publications

(35 citation statements)

References 60 publications

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“…This transition was accelerated with acid: after 5 min 32% was converted and within 20 min all 6a-hydroxy-pterocarpans were converted. This is in agreement 11 The other three subclasses of isoflavonoids showed little conversion (∼15%) and acid did not accelerate this conversion. This suggests that the 6a-hydroxyl group of 6a-hydroxy-pterocarpans in particular is susceptible to acid.…”

Section: Identification Of Isoflavonoids In Untreated Andsupporting

confidence: 89%

“…These findings are in accordance with previous data. 11 They suggest that the 6a-hydroxy-pterocarpan glyceollin I forms the thermodynamically more stable 6a,11a-pterocarpene dehydroglyceollin I upon water loss. 11 Structures of the main prenylated 6a-hydroxypterocarpans and 6a,11a-pterocarpenes are shown in Figure 1.…”

Section: Identification Of Isoflavonoids In Untreated Andmentioning

confidence: 99%

“…11 They suggest that the 6a-hydroxy-pterocarpan glyceollin I forms the thermodynamically more stable 6a,11a-pterocarpene dehydroglyceollin I upon water loss. 11 Structures of the main prenylated 6a-hydroxypterocarpans and 6a,11a-pterocarpenes are shown in Figure 1. Note that the nomenclature of glyceollins and dehydroglyceollins is ambiguous in literature, as elaborated in the footnote of Table 1.…”

Section: Identification Of Isoflavonoids In Untreated Andmentioning

confidence: 99%

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Structural Changes of 6a-Hydroxy-Pterocarpans Upon Heating Modulate Their Estrogenicity

Schans

Vincken

Bovee³

et al. 2014

J. Agric. Food Chem.

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The isoflavonoid composition of an ethanolic extract of fungus-treated soybean sprouts was strongly altered by a combined acid/heat treatment. UHPLC-MS analysis showed that 6a-hydroxy-pterocarpans were completely converted to their respective, more stable, 6a,11a-pterocarpenes, whereas other isoflavonoids, from the isoflavone and coumestan subclasses, were affected to a much lesser extent (loss of ∼15%). Subsequently, mixtures enriched in prenylated 6a-hydroxy-pterocarpans (pools of glyceollin I/II/III and glyceollin IV/VI) or prenylated 6a,11a-pterocarpenes (pools of dehydroglyceollin I/II/III and dehydroglyceollin IV/VI) were purified, and tested for activity on both human estrogen receptors (ERα and ERβ). In particular, the response toward ERα changed, from agonistic for glyceollins to antagonistic for dehydroglyceollins. Toward ERβ a decrease in agonistic activity was observed. These results indicate that the introduction of a double bond with the concomitant loss of a hydroxyl group in 6a-hydroxy-pterocarpans extensively modulates their estrogenic activity.

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Section: Identification Of Isoflavonoids In Untreated Andsupporting

confidence: 89%

Section: Identification Of Isoflavonoids In Untreated Andmentioning

confidence: 99%

Section: Identification Of Isoflavonoids In Untreated Andmentioning

confidence: 99%

See 1 more Smart Citation

Structural Changes of 6a-Hydroxy-Pterocarpans Upon Heating Modulate Their Estrogenicity

Schans

Vincken

Bovee³

et al. 2014

J. Agric. Food Chem.

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“…As anticipated from analogous literature methods [9] and previous experiments within our labs, coupling of the isoprene synthon 17 with phenol 18 was accompanied by intramolecular cyclization to afford chromene 19 in excellent yield [7]. Catalytic hydrogenation readily afforded 11 .…”

Section: Resultsmentioning

confidence: 58%

“…Although reported at 25%, in our case we were able to achieve only a 10% yield of crude intermediate 14 (NMR), making this process the lowest yielding step in the overall sequence. In addition to addressing the Grignard reaction, we imagined that the initial sequence of reactions leading to intermediate 11 might be accomplished in fewer steps by taking advantage of a high-yielding approach to various chromenes that we had utilized previously within our labs [7]. Finally, we also felt that it would be worthwhile to substitute the reagents used in step ( j ) with a composite that reflects greener chemistry [8].…”

Section: Resultsmentioning

confidence: 99%

Practical synthesis of a chromene analog for use as a retinoic acid receptor alpha antagonist lead compound

Jetson

Malik

Luniwal

et al. 2013

European Journal of Medicinal Chemistry

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Retinoic acid receptor alpha (RARα) selective compounds may guide the design of drugs that can be used in conjunction with hormonal adjuvant therapy in the treatment of breast cancer. Herein we report a modified synthesis of a known RARα antagonist, 2-fluoro-4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)chroman-6-yl]carbonyl]amino]benzoic acid and a synthesis of its unknown, desfluoro analog, 4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)chroman-6-yl]carbonyl]amino]benzoic acid. The modified route allows for facile reaction workups, increased yields, lower cost and incorporates a green alternative step. Structure–activity relationship studies determined through functional cell-based assays, demonstrated antagonism to RARα for both compounds. Molecular modeling within the RARα binding pocket was used to compare binding interactions of the desfluoro analog to a known RAR antagonist.

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Regulation of phytoalexin biosynthesis for agriculture and human health

Ahmed

Kovinich

2020

Phytochem Rev

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Phytoalexins are diverse secondary metabolites of plants that are biosynthesized transiently and in relatively low amounts in response to pathogens and certain abiotic stresses. They commonly have potent antimicrobial and medicinal activities. As such, scientists have attempted to increase their accessibility by inventing diverse in vitro and in vivo approaches. Among these approaches, bioengineering plant transcription factors that directly regulate phytoalexin biosynthesis genes may be the most promising. Recent research has identified conserved transcription factors that directly regulate distinct phytoalexin biosynthesis pathways in different plant species. The intriguing results provide new insight into how conserved defense signaling pathways in plants result in lineage-specific biochemical defenses.These recent findings also suggest that a common transcription factor network could be engineered to enhance the biosynthesis of different phytoalexins in plants. However, the picture is far from complete since one or more transcription factors required to fully activate phytoalexin biosynthesis remain unidentified, and the exact mechanism of how the conserved factors regulate diverse phytoalexin pathways remains to be clarified. Here we review the agricultural and medicinal importance of phytoalexins, recent approaches to increase their accessibility, and the mechanisms that plants employ to activate and limit their biosynthesis. This review contributes to providing a systems level understanding of the regulation of phytoalexin biosynthesis so that effective bioengineering strategies can be developed to enhance phytoalexin biosynthesis for medicine and agriculture.

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Multigram Synthesis of Glyceollin I

Cited by 21 publications

References 60 publications

Structural Changes of 6a-Hydroxy-Pterocarpans Upon Heating Modulate Their Estrogenicity

Structural Changes of 6a-Hydroxy-Pterocarpans Upon Heating Modulate Their Estrogenicity

Practical synthesis of a chromene analog for use as a retinoic acid receptor alpha antagonist lead compound

Regulation of phytoalexin biosynthesis for agriculture and human health

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