The limited deglucosylation process of β-glucosidase in Bacillus cereus H62L for biotransforming secoisolariciresinol diglucoside into mammalian lignans

Chin Fa Hwang, Hui Er Wang, Yaw Bee Ker, Chiung Chi Peng, Kuan Chou Chen, Robert Y. Peng

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The amount of major lignans present in the alkaline extract of the defatted flaxseed (in mg/g) is as follows: secoisolariciresinol diglucoside (SDG, 109.80), p-coumaric acid glucoside (CAG, 70.21), ferulic acid glucoside (FAG, 68.81), secoisolariciresinol (SECO, 0.49), coumaric acid (CA, 0.37), and ferulic acid (FA, 0.85). When biotransformed, SDG yields two valuable mammalian lignans (MLG): enterodiol (END) and enterolactone (ENL). Bacillus cereus strain H62-L1 was isolated and tested for the process of bioconversion. Kinetic analysis revealed the sequential reaction SDG (A) → CAG (B) → END (C) → ENL (D) to be reversible at the first step with the generalized reaction type Ak2k1Bk3Ck4D. The obtained rate coefficients were as follows: k1 = 0.001-0.028 h-1, k 2 = 0.006-0.077 h-1, k3 = 0.013 h-1, and k4 = 0.002 h-1, and the overall kinetic parameter k1/(k2 + k3) varied from 0.05 to 1.32, mostly not favoring the forward deglucosylation reaction. SDG with higher purity favored the forward reaction. In conclusion, to facilitate the production rate, we propose (i) using substrate SDG with high purity at a higher concentration; (ii) using an allosteric inhibitor to block the reverse reaction from SECO to SDG; or (iii) genetically modifying Bacillus cereus H62-L1.

Original languageEnglish
Pages (from-to)1632-1640
Number of pages9
JournalProcess Biochemistry
Volume46
Issue number8
DOIs
Publication statusPublished - Aug 2011

Fingerprint

ferulic acid
Bacillus cereus
Glucosidases
Lignans
Coumaric Acids
Flax
Bioconversion
Acids
Glucosides
Kinetic parameters
Kinetics
Substrates
secoisolariciresinol diglucoside
2,3-bis(3'-hydroxybenzyl)butyrolactone
2,3-bis(3'-hydroxybenzyl)butane-1,4-diol

Keywords

  • Enterodiol
  • Flaxseeds
  • Glucosidase
  • Mammalian lignans
  • Secoisolariciresinol diglucoside

ASJC Scopus subject areas

  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Bioengineering

Cite this

The limited deglucosylation process of β-glucosidase in Bacillus cereus H62L for biotransforming secoisolariciresinol diglucoside into mammalian lignans. / Hwang, Chin Fa; Wang, Hui Er; Ker, Yaw Bee; Peng, Chiung Chi; Chen, Kuan Chou; Peng, Robert Y.

In: Process Biochemistry, Vol. 46, No. 8, 08.2011, p. 1632-1640.

Research output: Contribution to journalArticle

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abstract = "The amount of major lignans present in the alkaline extract of the defatted flaxseed (in mg/g) is as follows: secoisolariciresinol diglucoside (SDG, 109.80), p-coumaric acid glucoside (CAG, 70.21), ferulic acid glucoside (FAG, 68.81), secoisolariciresinol (SECO, 0.49), coumaric acid (CA, 0.37), and ferulic acid (FA, 0.85). When biotransformed, SDG yields two valuable mammalian lignans (MLG): enterodiol (END) and enterolactone (ENL). Bacillus cereus strain H62-L1 was isolated and tested for the process of bioconversion. Kinetic analysis revealed the sequential reaction SDG (A) → CAG (B) → END (C) → ENL (D) to be reversible at the first step with the generalized reaction type Ak2k1Bk3Ck4D. The obtained rate coefficients were as follows: k1 = 0.001-0.028 h-1, k 2 = 0.006-0.077 h-1, k3 = 0.013 h-1, and k4 = 0.002 h-1, and the overall kinetic parameter k1/(k2 + k3) varied from 0.05 to 1.32, mostly not favoring the forward deglucosylation reaction. SDG with higher purity favored the forward reaction. In conclusion, to facilitate the production rate, we propose (i) using substrate SDG with high purity at a higher concentration; (ii) using an allosteric inhibitor to block the reverse reaction from SECO to SDG; or (iii) genetically modifying Bacillus cereus H62-L1.",
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T1 - The limited deglucosylation process of β-glucosidase in Bacillus cereus H62L for biotransforming secoisolariciresinol diglucoside into mammalian lignans

AU - Hwang, Chin Fa

AU - Wang, Hui Er

AU - Ker, Yaw Bee

AU - Peng, Chiung Chi

AU - Chen, Kuan Chou

AU - Peng, Robert Y.

PY - 2011/8

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AB - The amount of major lignans present in the alkaline extract of the defatted flaxseed (in mg/g) is as follows: secoisolariciresinol diglucoside (SDG, 109.80), p-coumaric acid glucoside (CAG, 70.21), ferulic acid glucoside (FAG, 68.81), secoisolariciresinol (SECO, 0.49), coumaric acid (CA, 0.37), and ferulic acid (FA, 0.85). When biotransformed, SDG yields two valuable mammalian lignans (MLG): enterodiol (END) and enterolactone (ENL). Bacillus cereus strain H62-L1 was isolated and tested for the process of bioconversion. Kinetic analysis revealed the sequential reaction SDG (A) → CAG (B) → END (C) → ENL (D) to be reversible at the first step with the generalized reaction type Ak2k1Bk3Ck4D. The obtained rate coefficients were as follows: k1 = 0.001-0.028 h-1, k 2 = 0.006-0.077 h-1, k3 = 0.013 h-1, and k4 = 0.002 h-1, and the overall kinetic parameter k1/(k2 + k3) varied from 0.05 to 1.32, mostly not favoring the forward deglucosylation reaction. SDG with higher purity favored the forward reaction. In conclusion, to facilitate the production rate, we propose (i) using substrate SDG with high purity at a higher concentration; (ii) using an allosteric inhibitor to block the reverse reaction from SECO to SDG; or (iii) genetically modifying Bacillus cereus H62-L1.

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