Planta Med 2023; 89(12): 1170-1177
DOI: 10.1055/a-2090-0733
Natural Product Chemistry and Analytical Studies
Original Papers

Lyonensinols A – C, 24-Norursane-Type Triterpenoids from the Twigs and Leaves of Lyonia doyonensis and Their Potential Anti-inflammatory and PTP1B Inhibitory Activities

Ming-Zhu Zhang
1   School of Pharmacy, Nanchang University, Nanchang, Peopleʼs Republic of China
Meng-Yuan Jiang
1   School of Pharmacy, Nanchang University, Nanchang, Peopleʼs Republic of China
Ling-Ping Kong
1   School of Pharmacy, Nanchang University, Nanchang, Peopleʼs Republic of China
Cai-Ying Liu
1   School of Pharmacy, Nanchang University, Nanchang, Peopleʼs Republic of China
Huai-Xin Kang
2   The Hospital of Nanchang University, Nanchang, Peopleʼs Republic of China
Ai-Hong Liu
3   Center of Analysis and Testing, Nanchang University, Nanchang, Peopleʼs Republic of China
Bin Wang
1   School of Pharmacy, Nanchang University, Nanchang, Peopleʼs Republic of China
Shui-Chun Mao
1   School of Pharmacy, Nanchang University, Nanchang, Peopleʼs Republic of China
› Author Affiliations
This work was financially supported by the National Natural Science Foundation of China (Nos. 82060633, 81860616, and 21362024) and the Natural Science Foundation of Jiangxi Province, China (Nos. 20212ACB206034, 20202BAB206084, and 20181BAB205086). We acknowledge Dr. G.-D. Li (Yunnan University of Chinese Medicine). We are also grateful to Prof. J. Li (Shanghai Institute of Materia Medica, CAS) for the bioassay help.


Lyonia doyonensis is a deciduous shrub native to high-altitude regions of Asia. So far, there is no report on any chemical and biological properties of L. doyonensis. An EtOH extract of L. doyonensis twigs and leaves showed inhibitory activities on protein tyrosine phosphatase 1B and lipopolysaccharide-induced inflammation in BV-2 microglial cells. A phytochemical investigation of this extract led to the isolation of a, so far only ambiguously described, 24-norursane-type triterpenoid, now named lyonensinol A (1), along with its two new derivatives, lyonensinols B and C (2 and 3), and six known triterpenoids (4 – 9). Their structures were elucidated by detailed analysis of spectroscopic data. A combination of chemical conversions, electronic circular dichroism, and Mo2(OAc)4-induced electronic circular dichroism was used to confirm their absolute configurations. Lyonensinols B (2) and C (3) represent the first examples of norursane-type triterpenoids acylated with a p-coumaroyl moiety. The potential anti-inflammatory and protein tyrosine phosphatase 1B inhibitory activities of all the isolates were evaluated. Compounds 3, 7, and 8 at 10 µM showed potent inhibitory activities on lipopolysaccharide-induced nitric oxide production in BV-2 microglial cells, with nitric oxide levels decreasing to 31.5, 41.9, and 27.1%, respectively, while compounds 3, 4, 7, and 8 exhibited notable inhibitory activities against protein tyrosine phosphatase 1B, with IC50 values ranging from 1.7 to 18.2 µM. Interestingly, compounds 3 and 8, bearing a C-3 trans-p-coumaroyl group, showed not only more potent anti-inflammatory effects, but also exhibited stronger protein tyrosine phosphatase 1B inhibition than their respective stereoisomers (2 and 7) with a cis-p-coumaroyl group.

Supporting Information

Publication History

Received: 05 January 2023

Accepted after revision: 08 May 2023

Accepted Manuscript online:
09 May 2023

Article published online:
21 June 2023

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