Issue 14, 2024

Xanthrysols A–D, novel meroterpenoids with antiviral activities from Xanthostemon chrysanthus

Abstract

(+)/(−)-Xanthrysol A (1), an enantiomeric pair of novel macrocyclic meroterpenoids, along with three enantiomeric pairs of biogenetically related meroterpenoids (+)/(−)-xanthrysols B–D (2–4), were isolated and identified from the leaves of Xanthostemon chrysanthus. Structurally, compounds 1–4 are unique phenylpropanoyl–phloroglucinol-based meroterpenoids with three kinds of new carbon skeletons. Notably, xanthrysol A (1) features an unprecedented 6/6/16 fused ring system, incorporating a 2,4,16-trioxatricyclo[12.6.2.017,21]docosane core. Their structures with absolute configurations were established by comprehensive spectroscopic analyses, single-crystal X-ray diffraction, and quantum chemical calculations. A plausible biogenetic pathway for 1–4 was proposed. Moreover, xanthrysol A demonstrated potent antiviral activity against respiratory syncytial virus (RSV) and acyclovir-resistant strains of herpes simplex virus type 1 (HSV-1/106, HSV-1/blue and HSV-1/153) with IC50 values ranging from 4.68 to 8.10 μM. Time-of-addition assays showed that compound 1 specifically acts on the early stages of the virus replication process in both RSV and HSV-1.

Graphical abstract: Xanthrysols A–D, novel meroterpenoids with antiviral activities from Xanthostemon chrysanthus

Supplementary files

Article information

Article type
Research Article
Submitted
21 Mar 2024
Accepted
30 Apr 2024
First published
20 May 2024

Org. Chem. Front., 2024,11, 3814-3820

Xanthrysols A–D, novel meroterpenoids with antiviral activities from Xanthostemon chrysanthus

F. Liu, J. Gu, Z. Zhang, Q. Zhan, H. Yang, Y. Hu, J. Zhang, W. Tang, W. Ye and L. Wang, Org. Chem. Front., 2024, 11, 3814 DOI: 10.1039/D4QO00520A

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