Fen Liu, Ji-Hong Gu, Zi-Yue Zhang, Qiong Zhan, Hai-Xia Yang, Yun Hu, Jin-Yan Zhang, Wei Tang, Wen-Cai Ye and Lei Wang
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引用次数: 0
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.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.