Characterization of MK₈(H₂) from Rhodococcus sp. B7740 and Its Potential Antiglycation Capacity Measurements

Yashu Chen, Qin Mu, Kai Hu, Mo Chen, Jifang Yang, Jigang Chen, Bijun Xie, Zhida Sun, Yashu Chen, Qin Mu, Kai Hu, Mo Chen, Jifang Yang, Jigang Chen, Bijun Xie, Zhida Sun

Abstract

Menaquinone (MK) has an important role in human metabolism as an essential vitamin (VK₂), which is mainly produced through the fermentation of microorganisms. MK₈(H₂) was identified to be the main menaquinone from Rhodococcus sp. B7740, a bacterium isolated from the arctic ocean. In this work, MK₈(H₂) (purity: 99.75%) was collected through a convenient and economic extraction process followed by high-speed countercurrent chromatography (HSCCC) purification. Additionally, high-resolution mass spectrometry (HRMS) was performed for further identification and the hydrogenation position of MK₈(H₂) (terminal unit) was determined using nuclear magnetic resonance (NMR) for the first time. MK₈(H₂) showed a superior antioxidant effect and antiglycation capacity compared with ubiquinone Q10 and MK₄. High-performance liquid chromatography⁻mass spectrometer (HPLC-MS/MS) and molecular docking showed the fine interaction between MK₈(H₂) with methylglyoxal (MGO) and bull serum albumin (BSA), respectively. These properties make MK₈(H₂) a promising natural active ingredient with future food and medicine applications.

Keywords: MK8(H2); NMR; Rhodococcus sp. B7740 from Arctic ocean; UPLC-HRMS; antioxidant and antiglycation; isoprenoid quinone.

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Molecular structure of menaquinone (MK) and ubiquinone (UQ): (A) HPLC spectrum of isoprenoid quinones from Rhodococcus sp. B7740; (B) MS/MS; (C) diode array detector (DAD); (D) spectrum of MK8(H2).
Figure 2
Figure 2
High-resolution mass spectrometry (HRMS) image of: (A) MK8(H2) ((MK8(H2) + Na+) ion); (B) molecule structure of MK8(H2).
Figure 2
Figure 2
High-resolution mass spectrometry (HRMS) image of: (A) MK8(H2) ((MK8(H2) + Na+) ion); (B) molecule structure of MK8(H2).
Figure 3
Figure 3
The HPLC spectrum of MGO (A) before and (C) after incubation. The HPLC spectrum of MK8(H2) (B) before and (D) after incubation. (E) MS and (F) MS/MS spectrum of MK8(H2)–MGO adduct.
Figure 4
Figure 4
(A)Main interaction of MK8(H2) binding to the BSA at site I; (B) Molecular contacts between MK8(H2) and amino acids of BSA at site I; (C) Main interaction of MK8(H2) binding to the BSA at site II; (D) Molecular contacts between MK8(H2) and amino acids of BSA at site II.
Figure 4
Figure 4
(A)Main interaction of MK8(H2) binding to the BSA at site I; (B) Molecular contacts between MK8(H2) and amino acids of BSA at site I; (C) Main interaction of MK8(H2) binding to the BSA at site II; (D) Molecular contacts between MK8(H2) and amino acids of BSA at site II.

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