Fissistonones A and B: Two Phenylpropanoyl Prenylated Naphthoquinones with Rearranged Carbon Skeletons from <i>Fissistigma oldhamii</i>
Fissistonones A and B (<b>1</b> and <b>2</b>), two naphthoquinone derivatives with rearranged carbon skeletons, were obtained from the leaves of <i>Fissistigma oldhamii</i>. Structurally, compounds <b>1</b> and <b>2</b> featured an unprecedented phenylpropanoyl benzobicyclo[3.3.1]nonene core, which could be biosynthetically traced back to a planar naphthoquinone precursor via a cascade of intramolecular bond formation and ring cleavage. In addition, compounds <b>1</b> and <b>2</b> exhibited significant inhibitory activities on IL-8 production in the human keratinocyte HaCaT cell line.
Authors
- Jun‐Cheng Su (ORCID: https://orcid.org/0000-0002-1458-5383)
- Yang Chen (ORCID: https://orcid.org/0000-0003-0206-1889)
- Yun-Qi Fan
- Ni-Ping Li
- Hai-Wang Yang
- Lei Wang (ORCID: https://orcid.org/0000-0001-9242-1109)
- Ji‐Hong Gu (ORCID: https://orcid.org/0000-0001-7680-8143)
- Wentao Wei (ORCID: https://orcid.org/0000-0003-2196-6608)
- Jian‐Guo Song (ORCID: https://orcid.org/0000-0003-3843-355X)
- C.W. Lai
Institutions
- Guangzhou University of Chinese Medicine (CN)
- Ministry of Education of the People's Republic of China (CN)
- Guangxi Normal University (CN)
- Laboratoire de Chémo-biologie synthétique et thérapeutique (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-03
- DOI
- https://doi.org/10.1021/acs.joc.5c00815
- Citations
- 1
- Primary Topic
- Phytochemical compounds biological activities
- Type
- article
- Field-Weighted Citation Impact
- 0.81
Funders
- Natural Science Foundation of Guangxi Zhuang Autonomous Region
- National Natural Science Foundation of China
- Guangzhou Municipal Science and Technology Project