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. 2023 Feb 21;28(5):2027.
doi: 10.3390/molecules28052027.

New Type of Tannins Identified from the Seeds of Cornus officinalis Sieb. et Zucc. by HPLC-ESI-MS/MS

Jun Li  1 , Lin Chen  1 , Hua Jiang  1 , Min Li  1 , Lu Wang  1 , Jia-Xing Li  1 , Yue-Yue Wang  1 , Qing-Xia Guo  1
Affiliations

New Type of Tannins Identified from the Seeds of Cornus officinalis Sieb. et Zucc. by HPLC-ESI-MS/MS

Jun Li et al. Molecules. .

Abstract

There is a lack of information on the compound profile of Cornus officinalis Sieb. et Zucc. seeds. This greatly affects their optimal utilization. In our preliminary study, we found that the extract of the seeds displayed a strong positive reaction to the FeCl3 solution, indicating the presence of polyphenols. However, to date, only nine polyphenols have been isolated. In this study, HPLC-ESI-MS/MS was employed to fully reveal the polyphenol profile of the seed extracts. A total of 90 polyphenols were identified. They were classified into nine brevifolincarboxyl tannins and their derivatives, 34 ellagitannins, 21 gallotannins, and 26 phenolic acids and their derivatives. Most of these were first identified from the seeds of C. officinalis. More importantly, five new types of tannins were reported for the first time: brevifolincarboxyl-trigalloyl-hexoside, digalloyl-dehydrohexahydroxydiphenoyl (DHHDP)-hexdside, galloyl-DHHDP-hexoside, DHHDP-hexahydroxydiphenoyl(HHDP)-galloyl-gluconic acid, and peroxide product of DHHDP-trigalloylhexoside. Moreover, the total phenolic content was as high as 79,157 ± 563 mg gallic acid equivalent per 100 g in the seeds extract. The results of this study not only enrich the structure database of tannins, but also provide invaluable aid to its further utilization in industries.

Keywords: Cornus officinalis Sieb. et Zucc.; mass spectrometry; polyphenol; seed extract; tannin.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The total ion chromatogram of seeds water extract of Cornus officinalis Sieb. et Zucc. in the negative ESI model (the new type tannins are red dotted).
Figure 2
Figure 2
Postulated fragmentation pathways of brevifolincarboxyl-trigalloyl-hexoside (illustrated by 1,4,6-O-trigalloyl- 3-O-brevifolincarboxyl-β-D-glucose).
Figure 3
Figure 3
Rearrangement and decarboxylation of DHHDP moiety in digalloyl-DHHDP-hexoside (illustrated by 1,6-O-digalloyl-2,4-O-DHHDP-β-D-glucoside).
Figure 4
Figure 4
Proposed decarboxylation route of the DHHDP moiety.
Figure 5
Figure 5
Structure of tannin type of A1–A7.
Figure 6
Figure 6
Suggested biosynthesis route of brevifolincarboxyl moiety from the DHHDP moiety.
Figure 7
Figure 7
Examples of the structures of the tannin type of B1–B14.
Figure 7
Figure 7
Examples of the structures of the tannin type of B1–B14.
Figure 8
Figure 8
Examples of the structures of the tannin type of C1–C8.
Figure 9
Figure 9
Structures of phenolic acids.
Figure 10
Figure 10
Structures of the non-phenolic compounds.
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