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Issue 2, 2020
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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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Supplementary files

Article information


Submitted
12 Oct 2019
Accepted
27 Nov 2019
First published
29 Nov 2019

Org. Chem. Front., 2020,7, 303-309
Article type
Research Article

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, 7, 303
DOI: 10.1039/C9QO01248F

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