Three New Hydroxytetradecenals from Amomum tsao-ko with Protein Tyrosine Phosphatase 1B and Glycogen Phosphorylase Inhibitory Activity
Xiaolu Qin1,3, Xinyu Li1,3, Yi Yang2, Mei Huang2, Shengli Wu1, Pianchou Gongpan1, Lianzhang Wu2, Juncai He2, Changan Geng1,3,*
1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China
2 Nujiang Green Spice Industry Research Institute, Lushui, 673100, China
3 University of Chinese Academy of Sciences, Beijing, 100049, China
* Corresponding Author: Changan Geng. Email: 
Phyton-International Journal of Experimental Botany https://doi.org/10.32604/phyton.2024.048192
Received 30 November 2023; Accepted 27 March 2024; Published online 06 May 2024
Abstract
The fruits of
Amomum tsao-ko (Cao-Guo) were documented in Chinese Pharmacopoeia for the treatment of abdominal pain, vomiting, and plague. In our previous study, a series of diarylheptanes and flavonoids with
α-glucosidase and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity have been reported from the middle-polarity part of
A. tsao-ko, whereas the antidiabetic potency of the low-polarity constituents is still unclear. In this study, three new hydroxytetradecenals, (2
E, 4
E, 8
Z, 11
Z)-6
R-hydroxytetradeca-2,4,8,11-tetraenal (
1), (2
E, 4
E, 8
Z)-6
R-hydroxytetradeca-2,4,8-trienal (
2) and (2
E, 4
E)-6
R-hydroxytetradeca-2,4-dienal (
3) were obtained from the volatile oils of
A. tsao-ko. The structures of compounds
1–3 were determined using spectroscopic data involving 1D and 2D nuclear magnetic resonance (NMR), high-resolution mass spectra (HRMS), and specific rotation ([
α]). Their hypoglycemic activity was evaluated against glycogen phosphorylase (GPa) and PTP1B. Compounds
1 and
2 displayed moderate activity against PTP1B with inhibition rates of 33.8%−50.3% at 100 and 200 µM. Moreover, compound
1 exhibited an obvious inhibitory effect on GPa (IC = 31.7 µM), whereas compound
2 was inactive. This study demonstrates hydroxytetradecenals as the characteristic components of
A. tsao-ko with therapeutic potential in diabetes.
Keywords
Cao-Guo; PTP1B and GPa inhibitors; diabetes mellitus; volatile oils
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