Camganoids A and B, two new sesquiterpenes with different carbon skeletons isolated from fruits of Cinnamomum migao

Yongzhen Xiao; Ishaq Muhammad; Xianpeng Ma; Huajun Yu; Shikai Yan; Xue Xiao; Huizi Jin

doi:10.1016/j.chmed.2021.09.016

Camganoids A and B, two new sesquiterpenes with different carbon skeletons isolated from fruits of Cinnamomum migao

Chin Herb Med. 2022 Sep 17;14(4):638-642. doi: 10.1016/j.chmed.2021.09.016. eCollection 2022 Oct.

Authors

Yongzhen Xiao¹, Ishaq Muhammad¹, Xianpeng Ma², Huajun Yu², Shikai Yan^{1

3}, Xue Xiao⁴, Huizi Jin^{1

3}

Affiliations

¹ Department of Natural Product Chemistry, School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, China.
² Guizhou Jingcheng Pharmaceutical Co., Ltd., Guiyang 550200, China.
³ Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, China.
⁴ Institute of Chinese Medicinal Sciences, Guangdong Pharmaceutical University, Guangzhou 510006, China.

Abstract

Objective: To isolate and identify the undescribed compounds from the fruits of Cinnamomum migao and evaluate its nitric oxide inhibition potential.

Methods: The chromatographic techniques of silica gel, Sephadex, and HPLC were used for isolation and purification of the compounds, while HR-ESI-MS, 1D NMR, 2D NMR, ECD, and X-ray diffraction techniques were used to characterize and confirm the isolated compounds. Moreover, the anti-inflammatory activity of the isolated compounds was carried out to check inhibitory potential against the production of nitric oxide with RAW264.7 cells stimulated by LPS.

Results: Camganoid A (1), a novel sesquiterpene possessing an unprecedented skeleton, and camganoid B (2), containing a unique eight-membered sesquiterpene moiety with a new carbon skeleton, were isolated and identified from the fruits of C. migao. The absolute configurations of 1 and 2 were confirmed by single crystal X-ray diffraction and electronic circular dichroism (ECD) calculations. Among these compounds, compound 1 exhibited potent inhibitory activity against the production of nitric oxide with IC₅₀ value of 4.59 μmol/L in RAW264.7 cells stimulated by LPS.

Conclusion: The isolation of two new skeletons from the fruits part of C. migao possessed unique skeletons which have not been reported before.

Keywords: Cinnamomum migao H. W. Li; nitric oxide inhibition; sesquiterpene.