Nine Unique Iridoids and Iridoid Glycosides From Patrinia scabiosaefolia

Zhenhua Liu; Yun Niu; Li Zhou; Lijun Meng; Sitan Chen; Mengke Wang; Jiangmiao Hu; Wenyi Kang

doi:10.3389/fchem.2021.657028

Nine Unique Iridoids and Iridoid Glycosides From Patrinia scabiosaefolia

Front Chem. 2021 Mar 29:9:657028. doi: 10.3389/fchem.2021.657028. eCollection 2021.

Authors

Zhenhua Liu^{1

2

3}, Yun Niu^{1

4}, Li Zhou^{1

4}, Lijun Meng^{1

4}, Sitan Chen^{1

4}, Mengke Wang^{1

4}, Jiangmiao Hu^{2

3}, Wenyi Kang^{1

4}

Affiliations

¹ National Center for Research and Development of Edible Fungus Processing Technology, Henan University, Kaifeng, China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China.
³ College of Life Sciences, University of Chinese Academy of Sciences, Beijing, China.
⁴ Joint International Research Laboratory of Food & Medicine Resource Function, Henan University, Kaifeng, China.

Abstract

Patrinia scabiosaefolia is a medical and edible Chinese herb with high nutritional and medicinal value. The continuing study of its chemical constituents led to the discovery of nine unique iridoids and iridoid glycosides, including three new iridoids (1-3) and six previously unknown irioid glycosides (5-10), and one known compound (4). Among them, compound 1 was a deformed iridoid, while compounds 3, 5-7, and 10 formed a new ring in their skeletons which was uncommon in this genus. For compound 3, the new ring existed between C-3 and C-10, while a 1,3-dioxane appeared between C-7 and C-10 in compounds 5-7 and 10. Moreover, compound 10 was a bis-iridoid glycoside, which was the first reported in P. scabiosaefolia. And the sugar of irioid glycosides (5-10) was glucose at C-11, except in 9 which had a 5-deoxyglucose moiety. All their structures were confirmed based on the extensive spectroscopic analysis, including IR, UV, HR-ESI-MS, ECD, and 1D- and 2D-NMR experiments. Their cytotoxic activities against HL-60, A-549, SMMC-7721, MCF-7, SW480 were also tested.

Keywords: Patrinia scabiosaefolia; bis-iridoid glycoside; cytotoxic activity; iridoid; iridoid glycoside.