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Spiroalanpyrroids A and B, sesquiterpene alkaloids with a unique spiro-eudesmanolide–pyrrolizidine skeleton from Inula helenium

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Abstract

Spiroalanpyrroids A (1) and B (2), two sesquiterpene alkaloids with an unprecedented eudesmanolide–pyrrolizidine spiro[5.5] framework, were isolated together with two new sesquiterpene-amino acid adducts, helenalanprolines A (3) and B (4), from the roots of Inula helenium. Their structures were elucidated by spectroscopic data analysis, ECD calculations, and single-crystal X-ray diffraction analysis. A plausible biosynthetic pathway was proposed for 1 and 2. Bioassays showed that compounds 3 and 4 significantly inhibited nitric oxide production in lipopolysaccharide-induced RAW264.7 macrophages with IC50 values of 15.8 and 13.5 μM, respectively.

Graphical abstract: Spiroalanpyrroids A and B, sesquiterpene alkaloids with a unique spiro-eudesmanolide–pyrrolizidine skeleton from Inula helenium

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Publication details

The article was received on 12 Oct 2019, accepted on 27 Nov 2019 and first published on 29 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01248F
Org. Chem. Front., 2020, Advance Article

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    Spiroalanpyrroids A and B, sesquiterpene alkaloids with a unique spiro-eudesmanolide–pyrrolizidine skeleton from Inula helenium

    Y. Cai, Z. Wu, X. Zheng, C. Wang, J. Wang, X. Zhang, G. Qiu, K. Zhu, S. Cao and J. Yu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01248F

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