Regulated preparation of Crocin-1 or Crocin-2′ Triggered by the Cosolvent DMSO Using Bs-GT/At-SuSy One-Pot Reaction

Liu, Feng; Ding, Fangyu; Shao, Wenming; He, Bingfang; Wang, Guangji

doi:10.1021/acs.jafc.9b05000

Cited by 10 publications

(8 citation statements)

References 24 publications

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“…When the concentration of DMSO was above 10%, the conversion of resveratrol was rapidly decreased. This may be caused by the inhibition of enzyme activity using the reaction mixture containing a relatively high concentration of DMSO …”

Section: Resultsmentioning

confidence: 99%

Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGT_BL1-AtSuSy Cascade Reaction

Chen

Wang

et al. 2021

J. Agric. Food Chem.

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Polydatin, resveratrol-3-O-β-glucoside, possesses various biological activities. However, the regioselective glucosylation of resveratrol by UDP-glycosyltransferases (UGTs) constitutes a persistent problem. In this study, semi-rational design and iterative combinatorial mutagenesis were carried out to screen the mutants of UGT BL 1 and the high specificity with the glycosylation of the 3-OH group of resveratrol was explored. The triple mutant I62G/M112D/K143G exhibited near-perfect control of polydatin synthesis (regioselectivity ∼ 99%), and the ratio of polydatin to resveratrol-4′-O-β-glucoside was finally enhanced by 786-fold. Molecular docking revealed that the mutant could form three H-bonds between 3-, 5-, and 4′-OH groups of resveratrol and the residues around the active center, resulting in the oriented-binding of resveratrol. Furthermore, UGT BL 1 mutant coupling sucrose synthase AtSuSy can synthesize polydatin at an unprecedented high titer of 10.33 g/L, together with efficient UDPG regeneration (RC max = 54). This study provides an efficient approach for the regioselective biosynthesis of polydatin.

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Section: Resultsmentioning

confidence: 99%

Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGT_BL1-AtSuSy Cascade Reaction

Chen

Wang

et al. 2021

J. Agric. Food Chem.

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“…The poor solubility of aglycones could inhibit the in vitro UGT-SuSy cascade reactions. DMSO is a versatile organic solvent to promote the dissolution of hydrophilic aglycones [28]. The Cy7G titer increased from 2.60 to 4.70 mM when the DMSO concentration increased to 10% (v/v).…”

Section: Optimization Of Ugt88e18-susy Cascade Reaction For Cy7g Syntmentioning

confidence: 99%

Biocatalytic Synthesis of Calycosin-7-O-β-D-Glucoside with Uridine Diphosphate–Glucose Regeneration System

Min

et al. 2020

Catalysts

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Calycosin-7-O-β-D-glucoside (Cy7G) is one of the principal components of Radix astragali. This isoflavonoid glucoside is regarded as an indicator to assess the quality of R. astragali and exhibits diverse pharmacological activities. In this study, uridine diphosphate-dependent glucosyltransferase (UGT) UGT88E18 was isolated from Glycine max and expressed in Escherichia coli. Recombinant UGT88E18 could selectively and effectively glucosylate the C7 hydroxyl group of calycosin to synthesize Cy7G. A one-pot reaction by coupling UGT88E18 to sucrose synthase (SuSy) from G. max was developed. The UGT88E18–SuSy cascade reaction could recycle the costly uridine diphosphate glucose (UDPG) from cheap sucrose and catalytic amounts of uridine diphosphate (UDP). The important factors for UGT88E18–SuSy cascade reaction, including UGT88E18/SuSy ratios, different temperatures, and pH values, different concentrations of dimethyl sulfoxide (DMSO), UDP, sucrose, and calycosin, were optimized. We produced 10.5 g L−1 Cy7G in the optimal reaction conditions by the stepwise addition of calycosin. The molar conversion of calycosin was 97.5%, with a space–time yield of 747 mg L−1 h−1 and a UDPG recycle of 78 times. The present study provides a new avenue for the efficient and cost-effective semisynthesis of Cy7G and other valuable isoflavonoid glucosides by UGT–SuSy cascade reaction.

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“…Due to the limitation of obtaining this type of compound, the commercial prices of the two major crocins-crocins I and II-are extremely expensive. Though synthetic biology methods [17,19] have been attempted to be used to produce crocins I and II, isolation from plant resources is still the only method for their largescale production. However, except for saffron, only a few distantly related plants, such as Gardenia jasminoides (which grows in many countries) [17], produce crocins.…”

Section: Introductionmentioning

confidence: 99%

Scale-Up Preparation of Crocins I and II from Gardeniajasminoides by a Two-Step Chromatographic Approach and Their Inhibitory Activity Against ATP Citrate Lyase

Guan

Liu

et al. 2021

Molecules

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Crocins are highly valuable natural compounds for treating human disorders, and they are also high-end spices and colorants in the food industry. Due to the limitation of obtaining this type of highly polar compound, the commercial prices of crocins I and II are expensive. In this study, macroporous resin column chromatography combined with high-speed counter-current chromatography (HSCCC) was used to purify crocins I and II from natural sources. With only two chromatographic steps, both compounds were simultaneously isolated from the dry fruit of Gardenia jasminoides, which is a cheap herbal medicine distributed in a number of countries. In an effort to shorten the isolation time and reduce solvent usage, forward and reverse rotations were successively utilized in the HSCCC isolation procedure. Crocins I and II were simultaneously obtained from a herbal resource with high recoveries of 0.5% and 0.1%, respectively, and high purities of 98.7% and 99.1%, respectively, by HPLC analysis. The optimized preparation method was proven to be highly efficient, convenient, and cost-effective. Crocins I and II exhibited inhibitory activity against ATP citrate lyase, and their IC50 values were determined to be 36.3 ± 6.24 and 29.7 ± 7.41 μM, respectively.

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Regulated preparation of Crocin-1 or Crocin-2′ Triggered by the Cosolvent DMSO Using Bs-GT/At-SuSy One-Pot Reaction

Cited by 10 publications

References 24 publications

Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGT_BL1-AtSuSy Cascade Reaction

Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGT_BL1-AtSuSy Cascade Reaction

Biocatalytic Synthesis of Calycosin-7-O-β-D-Glucoside with Uridine Diphosphate–Glucose Regeneration System

Scale-Up Preparation of Crocins I and II from Gardeniajasminoides by a Two-Step Chromatographic Approach and Their Inhibitory Activity Against ATP Citrate Lyase

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Regulated preparation of Crocin-1 or Crocin-2′ Triggered by the Cosolvent DMSO Using Bs-GT/At-SuSy One-Pot Reaction

Cited by 10 publications

References 24 publications

Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGTBL1-AtSuSy Cascade Reaction

Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGTBL1-AtSuSy Cascade Reaction

Biocatalytic Synthesis of Calycosin-7-O-β-D-Glucoside with Uridine Diphosphate–Glucose Regeneration System

Scale-Up Preparation of Crocins I and II from Gardeniajasminoides by a Two-Step Chromatographic Approach and Their Inhibitory Activity Against ATP Citrate Lyase

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Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGT_BL1-AtSuSy Cascade Reaction

Highly Regioselective and Efficient Biosynthesis of Polydatin by an Engineered UGT_BL1-AtSuSy Cascade Reaction