A highly stereoselective synthesis of C-24 and C-25 oxysterols from desmosterol

Zhao, Qian; Qian, Chao; Chen, Xinzhi

doi:10.1016/j.steroids.2016.03.003

Cited by 7 publications

(2 citation statements)

References 28 publications

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“…Even though the readily standard substances are not yet for a large-scale production, several research laboratories provided synthesis methods for COPs: (1) Synthesis from natural products such as saponins; (2) Chemical synthesis from cholesterol; (3) Catalytic oxidation of cholesterol through electrochemical reaction [102][103][104][105][106].…”

Section: Cops Standard Compoundsmentioning

confidence: 99%

“…However, these synthesis methods are mainly focused on hydroxycholesterol with a limited variety so far. In addition, these synthesis methods usually have disadvantages of complicated protocols and with low yields [102][103][104]. Furthermore, it cannot avoid the interference raised by self-oxidation of cholesterol when using cholesterol as a raw material for synthesis [105].…”

Section: Cops Standard Compoundsmentioning

confidence: 99%

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New Function of Cholesterol Oxidation Products Involved in Osteoporosis Pathogenesis

Che

Yang

Tang

et al. 2022

IJMS

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Osteoporosis (OP) is a systemic bone disease characterized by decreased bone strength, microarchitectural changes in bone tissues, and increased risk of fracture. Its occurrence is closely related to various factors such as aging, genetic factors, living habits, and nutritional deficiencies as well as the disturbance of bone homeostasis. The dysregulation of bone metabolism is regarded as one of the key influencing factors causing OP. Cholesterol oxidation products (COPs) are important compounds in the maintenance of bone metabolic homeostasis by participating in several important biological processes such as the differentiation of mesenchymal stem cells, bone formation in osteoblasts, and bone resorption in osteoclasts. The effects of specific COPs on mesenchymal stem cells are mainly manifested by promoting osteoblast genesis and inhibiting adipocyte genesis. This review aims to elucidate the biological roles of COPs in OP development, starting from the molecular mechanisms of OP, pointing out opportunities and challenges in current research, and providing new ideas and perspectives for further studies of OP pathogenesis.

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Section: Cops Standard Compoundsmentioning

confidence: 99%

Section: Cops Standard Compoundsmentioning

confidence: 99%

New Function of Cholesterol Oxidation Products Involved in Osteoporosis Pathogenesis

Che

Yang

Tang

et al. 2022

IJMS

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Oxidation and Reduction

Banerji¹

2020

Organic Reaction Mechanisms · 2016

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CYP109E1 from Bacillus megaterium Acts as a 24‐ and 25‐Hydroxylase for Cholesterol

et al. 2019

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In this study, the ability of CYP109E1 from Bacillus megaterium DSM319 to metabolize cholesterol was investigated. This steroid was identified as a new substrate to be converted by CYP109E1 with adrenodoxin and adrenodoxin reductase as redox partners in vitro. The biotransformation was successfully reproduced in vivo by using Bacillus megaterium cells that overexpressed CYP109E1. To enhance the production of cholesterol derivatives, an Escherichia coli based whole‐cell system that harbored CYP109E1 was established. This novel system showed a 3.3‐fold higher activity than that of the B. megaterium system, yielding about 45 mg L−1 of these products. Finally, the reaction products were isolated and identified to be the highly important cholesterol derivatives 24(S)‐ and 25‐hydroxycholesterol.

show abstract

A highly stereoselective synthesis of C-24 and C-25 oxysterols from desmosterol

Cited by 7 publications

References 28 publications

New Function of Cholesterol Oxidation Products Involved in Osteoporosis Pathogenesis

New Function of Cholesterol Oxidation Products Involved in Osteoporosis Pathogenesis

Oxidation and Reduction

CYP109E1 from Bacillus megaterium Acts as a 24‐ and 25‐Hydroxylase for Cholesterol

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