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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 38, 2023 - Issue 1
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Research Article

New dammarane-type triterpenoids from hydrolyzate of total Gynostemma pentaphyllum saponins with protein tyrosine phosphatase 1B inhibitory activity

Daopeng Tana Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, China;b Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou, ChinaORCID Iconhttps://orcid.org/0000-0003-4385-2759View further author information
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Jianmei Wanga Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Xianting Wanga Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Lin Qina Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, China;b Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Yimei Dua Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, China;b Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Changkuo Zhaoa Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Peijun Liua Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Qianru Zhanga Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, China;b Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Feifei Maa Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, China;b Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Jian Xiea Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, China;b Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou, ChinaView further author information
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Di Wua Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, China;b Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou, ChinaCorrespondence[email protected]
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Yuqi Hea Guizhou Engineering Research Center of Industrial Key-technology for Dendrobium Nobile, Zunyi Medical University, Zunyi, Guizhou, China;b Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou, ChinaCorrespondence[email protected]
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Article: 2281263 | Received 21 Sep 2023, Accepted 05 Nov 2023, Published online: 15 Nov 2023

Figures & data

Table 1. 1H and 13C NMR data of compounds 1–5 (in CD3Cl, J in Hz at 400 MHz and 100 MHz).

Figure 1. Chemical structures of compounds 1–9.

Figure 1. Chemical structures of compounds 1–9.

Figure 2. HMBC, COSY and NOESY correlations of compounds 1–5.

Figure 2. HMBC, COSY and NOESY correlations of compounds 1–5.

Figure 3. Crystal structure of compounds 1.

Figure 3. Crystal structure of compounds 1.

Scheme 1. Hypothetical mechanism for the formation of ring F in compound 1.

Scheme 1. Hypothetical mechanism for the formation of ring F in compound 1.

Figure 4. Lineweaver-Burk plots for PTP1B inhibition of compounds 3 (A), 4 (B) and 9 (C). Dixon plots for PTP1B inhibition of compounds 3 (D), 4 (E) and 9 (F). Each value was expressed as means ± SD of three replications.

Figure 4. Lineweaver-Burk plots for PTP1B inhibition of compounds 3 (A), 4 (B) and 9 (C). Dixon plots for PTP1B inhibition of compounds 3 (D), 4 (E) and 9 (F). Each value was expressed as means ± SD of three replications.

Figure 5. Docking pose of compounds from G. pentaphyllum with PTP1B target.

Figure 5. Docking pose of compounds from G. pentaphyllum with PTP1B target.

Table 2. Inhibitory activity of dammarane-type triterpenoids from G. pentaphyllum against PTP1B.

Table 3. The molecular docking results of dammarane-type triterpenoids from G. pentaphyllum against PTP1B.

Table 4. ADME profile of dammarane-type triterpenoids from G. pentaphyllum as predicted by SwissADME.

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