Characterization of Sesquiterpene Dimers from the Flowers of Inula japonica and the Structural Revisions of Related Compounds

J Nat Prod. 2024 Jul 26;87(7):1754-1762. doi: 10.1021/acs.jnatprod.4c00269.

Zheng Niu ¹, Chun-Yan Chen ², Yan Zhou ¹, Guan-Ke Liu ¹, Bing-Yang Zhang ¹, Mahmood Brobbey Oppong ³, De-Qin Zhang ², Tie Yao ², Feng Qiu ¹ ²

Affiliations

1 Tianjin Key Laboratory of Therapeutic Substance of Traditional Chinese Medicine, School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, P.R. China.
2 National Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 301617, P.R. China.
3 Department of Pharmaceutical Chemistry, School of Pharmacy, College of Health Sciences, University of Ghana, MR36+H7 Accra, Ghana.

PMID: 38982404 DOI: 10.1021/acs.jnatprod.4c00269

Abstract

Sesquiterpene dimers are mainly found in the Asteraceae family. However, conflicting reports on the structures of these compounds can be found in the literature. Herein, we describe ten sesquiterpene dimers isolated from the flowers of Inula japonica, including configurational revisions of japonicone H (1-1), japonicone D (2-1), inulanolide A (4-1), japonicone X (5-1), and inulanolide F (5-2) to compounds 1, 2, 4, and 5, respectively. Five new related metabolites (3 and 6-9) are also described. Application of GIAO NMR/DP4+ analyses and ECD/OR calculations enabled us to revise the absolute configurations of an additional 13 sesquiterpene dimers isolated from Plants of the genus Inula. Compounds 1, 2, 4, and 6 exhibited inhibition of nitric oxide production in lipopolysaccharide activated RAW264.7 macrophages with IC₅₀ values of 4.07-10.00 μM.

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