Identification of a naturally-occurring 8-[α-D-glucopyranosyl-( 1→6)-β-D-glucopyranosyl] daidzein from cultivated kudzu root

Van Dao Nguyen, Byoung Cheol Min, Myung Ok Kyung, Jong Tae Park, Byong Hoon Lee, Chung Hyo Choi, Nam Seok Seo, Yong Ro Kim, Dong Uk Ahn, Sung-Joon Lee, Cheon Seok Park, Jung Wan Kim, Kwan Hwa Park

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Introduction - Kudzu root (Radix puerariae) is a rich source of isoflavones that are effective in preventing osteoporosis, heart disease and symptoms associated with menopause. The major isoflavonoids in kudzu root extracts were reported as puerarin, daidzin and daidzein. Recently, an unknown isoflavonoid (compound 1) was detected from one-year-old kudzu root cultivated in Vietnam. Objective - To identify a novel compound 1 in kudzu root extract and determine the structure of the compound by ESI+ TOF MS-MS, 1H-, 13C-NMR and enzymatic hydrolysis. Methodology - Samples were prepared by extraction of one-year-old kudzu root with 50% ethanol and the isoflavonoids were purified using recycling preparative HPLC. Unknown compound 1 was detected using UV-light at 254 nm in TLC and HPLC analyses. The molecular weight of 1 was determined using a TOF mass spectrometer equipped with an electrospray ion source. The structure of 1 was determined from the 13C and 1H NMR spectra recorded at 100.40 and 400.0 MHz, respectively. Results - ESI+ TOF MS-MS analysis shows that 1 is a puerarin diglycoside. The interglycosidic linkage of diglycoside determined by 1H-, 13C-NMR, and enzymatic hydrolysis suggests that 1 has a glucosyl residue linked to puerarin by an α-1,6-glycosidic bond. This compound is the first naturally-occurring 8-[α-D-glucopyranosyl-(1→6) -β-D-glucopyranosyl]daidzein in kudzu root. The concentration of glucosyl-α-1,6-puerarin in kudzu root was 2.3 mg/g as determined by HPLC. Conclusion - The results indicate that puerarin diglycoside is one of the major isoflavonoids in kudzu root and has a significant impact on the preparation of highly water-soluble glycosylated puerarin.

Original languageEnglish
Pages (from-to)450-455
Number of pages6
JournalPhytochemical Analysis
Volume20
Issue number6
DOIs
Publication statusPublished - 2009 Dec 1

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Pueraria
Pueraria montana var. lobata
daidzein
isoflavonoids
Enzymatic hydrolysis
Nuclear magnetic resonance
enzymatic hydrolysis
High Pressure Liquid Chromatography
Isoflavones
Mass spectrometers
Hydrolysis
Ion sources
daidzin
Ultraviolet radiation
menopause
puerarin
Recycling
osteoporosis
extracts
heart diseases

Keywords

  • Glucosyl-puerarin
  • Isoflavone
  • Puerarin
  • Radix puerariae
  • Transglycosylation

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Drug Discovery
  • Food Science
  • Biochemistry
  • Analytical Chemistry
  • Plant Science

Cite this

Nguyen, V. D., Min, B. C., Kyung, M. O., Park, J. T., Lee, B. H., Choi, C. H., ... Park, K. H. (2009). Identification of a naturally-occurring 8-[α-D-glucopyranosyl-( 1→6)-β-D-glucopyranosyl] daidzein from cultivated kudzu root. Phytochemical Analysis, 20(6), 450-455. https://doi.org/10.1002/pca.1146

Identification of a naturally-occurring 8-[α-D-glucopyranosyl-( 1→6)-β-D-glucopyranosyl] daidzein from cultivated kudzu root. / Nguyen, Van Dao; Min, Byoung Cheol; Kyung, Myung Ok; Park, Jong Tae; Lee, Byong Hoon; Choi, Chung Hyo; Seo, Nam Seok; Kim, Yong Ro; Ahn, Dong Uk; Lee, Sung-Joon; Park, Cheon Seok; Kim, Jung Wan; Park, Kwan Hwa.

In: Phytochemical Analysis, Vol. 20, No. 6, 01.12.2009, p. 450-455.

Research output: Contribution to journalArticle

Nguyen, VD, Min, BC, Kyung, MO, Park, JT, Lee, BH, Choi, CH, Seo, NS, Kim, YR, Ahn, DU, Lee, S-J, Park, CS, Kim, JW & Park, KH 2009, 'Identification of a naturally-occurring 8-[α-D-glucopyranosyl-( 1→6)-β-D-glucopyranosyl] daidzein from cultivated kudzu root', Phytochemical Analysis, vol. 20, no. 6, pp. 450-455. https://doi.org/10.1002/pca.1146
Nguyen, Van Dao ; Min, Byoung Cheol ; Kyung, Myung Ok ; Park, Jong Tae ; Lee, Byong Hoon ; Choi, Chung Hyo ; Seo, Nam Seok ; Kim, Yong Ro ; Ahn, Dong Uk ; Lee, Sung-Joon ; Park, Cheon Seok ; Kim, Jung Wan ; Park, Kwan Hwa. / Identification of a naturally-occurring 8-[α-D-glucopyranosyl-( 1→6)-β-D-glucopyranosyl] daidzein from cultivated kudzu root. In: Phytochemical Analysis. 2009 ; Vol. 20, No. 6. pp. 450-455.
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AU - Choi, Chung Hyo

AU - Seo, Nam Seok

AU - Kim, Yong Ro

AU - Ahn, Dong Uk

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N2 - Introduction - Kudzu root (Radix puerariae) is a rich source of isoflavones that are effective in preventing osteoporosis, heart disease and symptoms associated with menopause. The major isoflavonoids in kudzu root extracts were reported as puerarin, daidzin and daidzein. Recently, an unknown isoflavonoid (compound 1) was detected from one-year-old kudzu root cultivated in Vietnam. Objective - To identify a novel compound 1 in kudzu root extract and determine the structure of the compound by ESI+ TOF MS-MS, 1H-, 13C-NMR and enzymatic hydrolysis. Methodology - Samples were prepared by extraction of one-year-old kudzu root with 50% ethanol and the isoflavonoids were purified using recycling preparative HPLC. Unknown compound 1 was detected using UV-light at 254 nm in TLC and HPLC analyses. The molecular weight of 1 was determined using a TOF mass spectrometer equipped with an electrospray ion source. The structure of 1 was determined from the 13C and 1H NMR spectra recorded at 100.40 and 400.0 MHz, respectively. Results - ESI+ TOF MS-MS analysis shows that 1 is a puerarin diglycoside. The interglycosidic linkage of diglycoside determined by 1H-, 13C-NMR, and enzymatic hydrolysis suggests that 1 has a glucosyl residue linked to puerarin by an α-1,6-glycosidic bond. This compound is the first naturally-occurring 8-[α-D-glucopyranosyl-(1→6) -β-D-glucopyranosyl]daidzein in kudzu root. The concentration of glucosyl-α-1,6-puerarin in kudzu root was 2.3 mg/g as determined by HPLC. Conclusion - The results indicate that puerarin diglycoside is one of the major isoflavonoids in kudzu root and has a significant impact on the preparation of highly water-soluble glycosylated puerarin.

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