Human Endogenous Natural Products
Yingjie Bai, Liyun Zhang, and Xiaoguang Lei
Contents
1
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 314
2
Endogenous Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 314
2.1
Endogenous Amines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 314
2.2
Steroid Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 317
2.3
Fatty Acid-Derived Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 320
3
Host–Microbe Co-metabolism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 322
3.1
Presence and Function of the Human Microbiota . . . . . . . . . . . . . . . . . . . . . . . . . . 322
3.2
Co-Metabolism of Tryptophan and Other Aromatic Amino Acids . . . . . . . . . . . . 324
3.3
Co-Metabolism of Bile Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 324
3.4
Co-Metabolism of Choline . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 327
3.5
Co-Metabolism of Cysteine and Other Sulfur-Containing Compounds . . . . . . . . 328
4
Human Natural Products and Disease . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 328
4.1
Steroidogenic Inherited Diseases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 328
4.2
Trimethylamine Oxide and Atherosclerosis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 329
5
Techniques for the Identification of Metabolites . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 329
5.1
Mass Spectrometry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 331
Y. Bai · L. Zhang
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry
and Molecular Engineering of Ministry of Education, Synthetic and Functional Biomolecules
Center, College of Chemistry and Molecular Engineering, Peking University, 282 Chengfu Road,
Haidian District, Beijing, China
e-mail: yjbai2013@pku.edu.cn
L. Zhang
e-mail: liyun.zhang@pku.edu.cn
X. Lei (B)
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry
and Molecular Engineering of Ministry of Education, Synthetic and Functional Biomolecules
Center, College of Chemistry and Molecular Engineering, College of Chemistry and Molecular
Engineering and Peking-Tsinghua Center for Life Science, Peking University, 282 Chengfu Road,
Haidian District, Beijing, China
e-mail: xglei@pku.edu.cn
© The Author(s), under exclusive license to Springer Nature Switzerland AG 2021
A. D. Kinghorn, H. Falk, S. Gibbons, J. Kobayashi, Y. Asakawa, J.-K. Liu (eds.),
Progress in the Chemistry of Organic Natural Products, Vol. 114,
https://doi.org/10.1007/978-3-030-59444-2_4
313
Yingjie Bai, Liyun Zhang, and Xiaoguang Lei
Contents
1
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 314
2
Endogenous Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 314
2.1
Endogenous Amines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 314
2.2
Steroid Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 317
2.3
Fatty Acid-Derived Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 320
3
Host–Microbe Co-metabolism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 322
3.1
Presence and Function of the Human Microbiota . . . . . . . . . . . . . . . . . . . . . . . . . . 322
3.2
Co-Metabolism of Tryptophan and Other Aromatic Amino Acids . . . . . . . . . . . . 324
3.3
Co-Metabolism of Bile Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 324
3.4
Co-Metabolism of Choline . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 327
3.5
Co-Metabolism of Cysteine and Other Sulfur-Containing Compounds . . . . . . . . 328
4
Human Natural Products and Disease . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 328
4.1
Steroidogenic Inherited Diseases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 328
4.2
Trimethylamine Oxide and Atherosclerosis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 329
5
Techniques for the Identification of Metabolites . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 329
5.1
Mass Spectrometry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 331
Y. Bai · L. Zhang
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry
and Molecular Engineering of Ministry of Education, Synthetic and Functional Biomolecules
Center, College of Chemistry and Molecular Engineering, Peking University, 282 Chengfu Road,
Haidian District, Beijing, China
e-mail: yjbai2013@pku.edu.cn
L. Zhang
e-mail: liyun.zhang@pku.edu.cn
X. Lei (B)
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry
and Molecular Engineering of Ministry of Education, Synthetic and Functional Biomolecules
Center, College of Chemistry and Molecular Engineering, College of Chemistry and Molecular
Engineering and Peking-Tsinghua Center for Life Science, Peking University, 282 Chengfu Road,
Haidian District, Beijing, China
e-mail: xglei@pku.edu.cn
© The Author(s), under exclusive license to Springer Nature Switzerland AG 2021
A. D. Kinghorn, H. Falk, S. Gibbons, J. Kobayashi, Y. Asakawa, J.-K. Liu (eds.),
Progress in the Chemistry of Organic Natural Products, Vol. 114,
https://doi.org/10.1007/978-3-030-59444-2_4
313