A new miroestrol glycoside from the roots of Pueraria mirifica

Bang, Myun‐Ho; Lee, Do-Gyeong; Baek, Yoon-Su; Cho, Jin‐Gyeong; Han, Min‐Woo; Choi, Kyoung-Sook; Chung, Dae‐Kyun; Ko, Sung-Kwon; Oh, Chang-Hwan; Cho, Soo-Yeul; Chai, Kap-Yong; Kim, Jin-Ho; Baek, Nam‐In

doi:10.1007/s10600-013-0634-9

Cited by 5 publications

(3 citation statements)

References 9 publications

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“…Previously, miroestrol-3- O -β- d -glucopyranoside was isolated at a yield of 23 mg/40 kg PM root. 41 Thus, the compound may be cleaved to yield MI. The DZ content in the PM extract was more abundant than that in GT, which corresponded to the higher DZe yield than GTe.…”

Section: Resultsmentioning

confidence: 99%

Transformation of Pueraria candollei var. mirifica phytoestrogens using immobilized and free β-glucosidase, a technique for enhancing estrogenic activity

et al. 2021

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Section: Resultsmentioning

confidence: 99%

Transformation of Pueraria candollei var. mirifica phytoestrogens using immobilized and free β-glucosidase, a technique for enhancing estrogenic activity

et al. 2021

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“…Perhaps those intermediates or deoxymiroestrol are initially synthesized in mature leaves and are converted to a soluble form of glycoside that is readily transported across organs and is then stored predominantly in tuberous cortices. In fact, a glycosylated form of miroestrol has been identified in the P. mirifica tuber [42]. Examples of such transports are also known in tobacco, where nicotine is transported from the roots where it is biosynthesized site to the leaves where it is accumulated.…”

Section: Discussionmentioning

confidence: 99%

Transcriptome analysis of Pueraria candollei var. mirifica for gene discovery in the biosyntheses of isoflavones and miroestrol

et al. 2019

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BackgroundPueraria candollei var. mirifica, a Thai medicinal plant used traditionally as a rejuvenating herb, is known as a rich source of phytoestrogens, including isoflavonoids and the highly estrogenic miroestrol and deoxymiroestrol. Although these active constituents in P. candollei var. mirifica have been known for some time, actual knowledge regarding their biosynthetic genes remains unknown.ResultsMiroestrol biosynthesis was reconsidered and the most plausible mechanism starting from the isoflavonoid daidzein was proposed. A de novo transcriptome analysis was conducted using combined P. candollei var. mirifica tissues of young leaves, mature leaves, tuberous cortices, and cortex-excised tubers. A total of 166,923 contigs was assembled for functional annotation using protein databases and as a library for identification of genes that are potentially involved in the biosynthesis of isoflavonoids and miroestrol. Twenty-one differentially expressed genes from four separate libraries were identified as candidates involved in these biosynthetic pathways, and their respective expressions were validated by quantitative real-time reverse transcription polymerase chain reaction. Notably, isoflavonoid and miroestrol profiling generated by LC-MS/MS was positively correlated with expression levels of isoflavonoid biosynthetic genes across the four types of tissues. Moreover, we identified R2R3 MYB transcription factors that may be involved in the regulation of isoflavonoid biosynthesis in P. candollei var. mirifica. To confirm the function of a key-isoflavone biosynthetic gene, P. candollei var. mirifica isoflavone synthase identified in our library was transiently co-expressed with an Arabidopsis MYB12 transcription factor (AtMYB12) in Nicotiana benthamiana leaves. Remarkably, the combined expression of these proteins led to the production of the isoflavone genistein.ConclusionsOur results provide compelling evidence regarding the integration of transcriptome and metabolome as a powerful tool for identifying biosynthetic genes and transcription factors possibly involved in the isoflavonoid and miroestrol biosyntheses in P. candollei var. mirifica.

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“…Perhaps, those intermediates or deoxymiroestrol would be initially synthesized in mature leaves and converted to a soluble form of glycoside, readily transported across organs, and stored mainly in tuberous cortices. In fact, a glycosylated form of miroestrol has been identified in P. mirifica tuber [38]. Examples of such transports are known: in tobacco, nicotine is transported from the roots, which is the true biosynthetic site, to the leaves where it accumulates.…”

Section: Discussionmentioning

confidence: 99%

De novo transcriptome assembly reveals putative biosynthetic genes involved in the biosyntheses of isoflavones and miroestrol in Pueraria candollei var. mirifica

Suntichaikamolkul

Tantisuwanichkul

Prombutara

et al. 2019

Preprint

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Background Pueraria candollei var. mirifica, a Thai medicinal plant used traditionally as a rejuvenating herb, is known as a rich source of phytoestrogens, including isoflavonoids and the highly estrogenic miroestrol and deoxymiroestrol. Although these active constituents in P. mirifica have been known for some time, actual knowledge regarding their biosynthetic genes remains unknown. Results A de novo transcriptome analysis was conducted using combined P. candollei var. mirifica tissues of young leaves, mature leaves, tuberous cortices, and cortex-excised tubers. The assembly of 166,923 contigs was used for a functional annotation against protein databases, and as a library for the identification of genes possibly involved in the biosynthesis of isoflavonoid and miroestrol. Twenty-one differential expressed genes (DEGs) from four separate libraries were identified as candidates involved in the biosynthesis pathways and had their expressions validated by qRT-PCR. Notably, isoflavonoid profiling generated by LC-MS/MS was positively correlated to the expression levels of isoflavonoid biosynthetic genes across the four types of tissues. In addition, R2R3 MYB transcription factors were also identified that may be involved in the regulation of isoflavonoid biosynthesis in P. candollei var. mirifica. To confirm the function of the key-isoflavone biosynthetic gene, P. candollei var. mirifica isoflavone synthase (PmIFS) identified in our library was transiently co-expressed with the Arabidopsis MYB12 transcription factor (AtMYB12) in Nicotiana benthamiana leaves. Remarkably, the combined expression of those proteins led to the production of isoflavone genistein. Conclusions Our results provide compelling evidence regarding the integration of transcriptome and metabolome as a powerful tool for unraveling biosynthetic pathways in plants.

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A new miroestrol glycoside from the roots of Pueraria mirifica

Cited by 5 publications

References 9 publications

Transformation of Pueraria candollei var. mirifica phytoestrogens using immobilized and free β-glucosidase, a technique for enhancing estrogenic activity

Transformation of Pueraria candollei var. mirifica phytoestrogens using immobilized and free β-glucosidase, a technique for enhancing estrogenic activity

Transcriptome analysis of Pueraria candollei var. mirifica for gene discovery in the biosyntheses of isoflavones and miroestrol

De novo transcriptome assembly reveals putative biosynthetic genes involved in the biosyntheses of isoflavones and miroestrol in Pueraria candollei var. mirifica

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