Synthesis of 8β-hydroxy-9(11),13-abietadien-12-one from (+)-dehydroabietylamine and its AhR ligand activity

[1] R. Paduch, M. Trytek, S.K. Kr´

ol, J. Kud, M. Frant, M. Kandefer-Szersze´

n,

J. Fiedurek, Biological activity of terpene compounds produced by

biotechnological methods, Pharm Biol. 54 (6) (2016) 1096–1107.

[2] Z.E. Suntres, J. Coccimiglio, M. Alipour, The bioactivity and toxicological actions

of carvacrol, Crit Rev Food Sci Nutr. 55 (3) (2015) 304–318.

[3] X.H. Cheng, Y.Q. Xiong, Advances in studies on pharmacological activities of

pentacyclic triterpenoid saponins, Chinese Traditional and Herbal Drugs. 38 (2007)

792–795.

[4] K. Nishino, K. Someya, R. Ksouri, et al., Abietane diterpenes from Salvia officinalis

leaves as aryl hydrocarbon receptor ligands, Phytochem Lett. 41 (2021) 78–82.

[5] M. Till, D. Riebniger, H.-J. Schmitz, D. Schrenk, Potency of various polycyclic

aromatic hydrocarbons as inducers of CYP1A1 in rat hepatocyte cultures, Chem

Biol Interact. 117 (2) (1999) 135–150.

[6] S. Zhang, C. Qin, S.H. Safe, Flavonoids as aryl hydrocarbon receptor agonists/

antagonists: effects of structure and cell context, Environ. Health Perspect. 111

(16) (2003) 1877–1882.

[7] J. Adachi, Y. Mori, S. Matsui, H. Takigami, J. Fujino, H. Kitagawa, C.A. Miller,

T. Kato, K. Saeki, T. Matsuda, Indirubin and indigo are potent aryl hydrocarbon

receptor ligands present in human urine, J Biol Chem. 276 (34) (2001)

31475–31478.

[8] S. Medjakovic, A. Jungbauer, Red clover isoflavones biochanin A and formononetin

are potent ligands of the human aryl hydrocarbon receptor, J Steroid Biochem. 108

(1-2) (2008) 171–177.

[9] R. Zhang, J. Sun, L. Ma, X. Wu, G. Pan, H. Hao, F. Zhou, J. A, C. Liu, H. Ai, L. Shang,

H. Gao, Y. Peng, P. Wan, H. Wu, G. Wang, Induction of cytochromes P450 1A1 and

1A2 by tanshinones in human HepG2 hepatoma cell line, Toxicol Appl Pharmacol.

252 (1) (2011) 18–27.

[10] J. Dusek, A. Carazo, F. Trejtnar, L. Hyrsova, O. Holas, T. Smutny, S. Micuda,

P. Pavek, Steviol, an aglycone of steviol glycoside sweeteners, interacts with the

pregnane X (PXR) and aryl hydrocarbon (AHR) receptors in detoxification

regulation, Food Chem Toxicol. 109 (2017) 130–142.

[11] A. Poland, E. Glover, Genetic expression of aryl hydrocarbon hydroxylase by

2,3,7,8-tetrachlorodibenzo-p-dioxin: evidence for a receptor mutation in

genetically non-responsive mice, Mol Pharmacol. 11 (1975) 389–398.

[12] M. Veldhoen, K. Hirota, A.M. Westendorf, J. Buer, L. Dumoutier, J.-C. Renauld,

B. Stockinger, The aryl hydrocarbon receptor links TH17-cell-mediated

autoimmunity to environmental toxins, Nature. 453 (7191) (2008) 106–109.

[13] F.J. Quintana, A.S. Basso, A.H. Iglesias, T. Korn, M.F. Farez, E. Bettelli,

M. Caccamo, M. Oukka, H.L. Weiner, Control of Treg and TH17 cell differentiation

by the aryl hydrocarbon receptor, Nature. 453 (7191) (2008) 65–71.

[14] H.-K. Wang, C.-H. Yeh, T. Iwamoto, H. Satsu, M. Shimizu, M. Totsuka, Dietary

flavonoid naringenin induces regulatory T cells via an aryl hydrocarbon receptor

mediated pathway, J Agric Food Chem. 60 (9) (2012) 2171–2178.

...