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Aromatase inhibitors isolated from a flowering tea, snow Chrysanthemum (the capitula of Coreopsis tinctoria Nutt.)

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Abstract

Methanol extract from the capitula of Coreopsis tinctoria Nutt. (Asteraceae), which is also known as a flowering tea or blooming tea “Snow Chrysanthemum,” was found to inhibit the enzymatic activity of aromatase. A total of 24 known isolates (1–24) were identified from the extract, including three chalcones (1–3), an aurone (4), five flavanones (5–9), four flavanols (10–13), a flavonol (14), and two biflavanones (15, 16). Among them, okanin (1, Ki = 1.6 μM), (2S)-naringenin (5, 0.90 μM), isookanin (6, 0.81 μM), (2S)-7,3',5'-trihydroxyflavaone (7, 0.13 μM), and (2S)-5,7,3',5'-tetrahydroxyflavanone (8, 0.32 μM) exhibited relatively potent competitive inhibition. Specifically, the isolates 7 and 8, having a common 3',5'-resorcinol moiety at the B ring in their flavanone skeleton, exhibited potent inhibitory activities compared to those of a clinically applied aminoglutethimide (0.84 μM) and naturally occurring flavone, chrysin (0.23 μM), which is a common non-steroidal aromatase inhibitor. Importantly, the active flavonoid constituents (1 and 5–8) did not inhibit the activity of 5α-reductase enzyme, which normally reacts with the same substrate “testosterone,” thus, these compounds were suggested to be specific to aromatase.

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Fig. 1
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Data availability

The data that support the findings of this study are available the corresponding author upon reasonable request.

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Acknowledgements

The authors gratefully wish to thank the Division of Joint Research Center, Kindai University for the NMR and MS measurements, as well as Editage (www.editage.com) for English language editing.

Funding

This work is supported by the JSPS KAKENHI, Japan [Grant Number 22K06688 (T.M.)].

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Authors and Affiliations

  1. Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka, 577-8502, Japan

    Fenglin Luo, Yoshiaki Manse, Satoshi Ishikawa, Sakura Nishi & Toshio Morikawa

  2. Antiaging Center, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka, 577-8502, Japan

    Toshio Morikawa

  3. Xinjiang Shengming Heli High Tech Co. Ltd., Urumqi High-Tech Industrial Development Zone (New Urban District), No. 55 Dongrong Street, Xinjiang, 830000, China

    Anshin Chen

  4. Tianjin Key Laboratory of TCM Chemistry and Analysis, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin, 301617, China

    Tao Wang

  5. Institute of TCM, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin, 301617, China

    Tao Wang

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  1. Fenglin Luo
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Correspondence to Toshio Morikawa.

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Author A. C. is an employee of Xinjiang Shengming Heli High Tech Co., Ltd., while the others, F. L., Y. M., S. I., S. N., T. W., and T. M., have declared no conflict of interest.

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Luo, F., Manse, Y., Ishikawa, S. et al. Aromatase inhibitors isolated from a flowering tea, snow Chrysanthemum (the capitula of Coreopsis tinctoria Nutt.). J Nat Med 77, 387–396 (2023). https://doi.org/10.1007/s11418-022-01678-3

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