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. 2022 Jul 24;27(15):4732.
doi: 10.3390/molecules27154732.

Neocornuside A-D, Four Novel Iridoid Glycosides from Fruits of Cornus officinalis and Their Antidiabetic Activity

Meng Yang  1   2 , Zhiyou Hao  1   2 , Xiaolan Wang  2   3 , Shiqi Zhou  1   2 , Denghui Zhu  1   2 , Ying Yang  1   2 , Junjun Wei  1   2 , Meng Li  1   2 , Xiaoke Zheng  1   2 , Weisheng Feng  1   2
Affiliations

Neocornuside A-D, Four Novel Iridoid Glycosides from Fruits of Cornus officinalis and Their Antidiabetic Activity

Meng Yang et al. Molecules. .

Abstract

Four previously undescribed iridoid glycosides neocornuside A-D (1-4), along with six known ones (5-10), were isolated from Cornus officinalis fruit. Their structures were elucidated by extensive spectroscopic (NMR, UV, IR, and MS) analysis and comparison with data reported in the literature. All isolates were assessed for their antidiabetic activity on the relative glucose consumption in insulin-induced insulin-resistant HepG2 cells. The results showed that compounds 1, 3, and 7 exhibited significant antidiabetic activities with EC50 values of 0.582, 1.275, and 0.742 μM, respectively. Moreover, compounds 1, 3, and 7 could improve the ability of 2-NBDG uptake of insulin-induced HepG2 cells.

Keywords: Cornus officinalis; antidiabetic activity; iridoid glycosides; structure elucidation.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of compounds 1–10 isolated from the fruits of Cornus officinalis.
Figure 2
Figure 2
The key HMBC and 1H-1H COSY correlations of compounds 1–4.
Figure 3
Figure 3
The key NOESY correlations of compounds 1–4.
Figure 4
Figure 4
Effect of compounds 1–10 on cell viability in insulin-induced HepG2 cells (x¯ ± s, n = 4).The impact of compounds 1–10 on cell viability measured by CCK-8 assay.* p < 0.05 or ** p < 0.01, versus insulin group.
Figure 5
Figure 5
Effect of compounds 1–10 on the relative glucose consumption in insulin-induced HepG2 cells (x¯ ± s, n = 4). The impact of compounds 1–10 on the relative glucose consumption measured by a glucose assay kit. # p < 0.05, versus control group; * p < 0.05 or ** p < 0.01, versus insulin group.
Figure 6
Figure 6
Effect of compounds 1, 3 and 7 on glucose uptake in insulin-induced HepG2 cells (x¯ ± s, n = 4). The 2-NBDG fluorescence measured by flow cytometry.
Figure 7
Figure 7
Effect of compounds 1, 3 and 7 on glucose uptake in insulin-induced HepG2 cells (x¯ ± s, n = 4). (A) Compound 1 corresponding histograms of the mean fluorescence intensity of 2-NBDG; (B) Compound 3 corresponding histograms of the mean fluorescence intensity of 2-NBDG; (C) Compound 7 corresponding histograms of the mean fluorescence intensity of 2-NBDG. ## p < 0.01, versus control group; * p < 0.05 or ** p < 0.01, versus insulin group.
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