Discovery and Semisynthesis of Aurantiacin A: A Unique Ascorbylated 9-<i>epi</i>-<i>ent</i>-Kaurane Diterpenoid from the Untapped Plant <i>Isodon aurantiacus</i>
Aurantiacin A (<b>1</b>), a unique ascorbylated meroditerpenoid composed of an unusual 9-<i>epi</i>-spiro-lactone-type <i>ent</i>-kaurane diterpenoid core, ascorbic acid (vitamin C), and syringic acid, and three new 9-<i>epi</i>-spiro-lactone-type <i>ent</i>-kauranoids, aurantiacins B-D (<b>2</b>-<b>4</b>), were isolated from an untapped species, <i>Isodon aurantiacus</i>. Their structures were determined by spectroscopic data analysis, semisynthesis, floating chirality distance geometry calculations, and quantum chemical calculations. Aurantiacin A (<b>1</b>) was found to induce lysosomal biogenesis, and the potential mechanisms underlying this effect were preliminarily explored.
Authors
- Xiao Ding (ORCID: https://orcid.org/0000-0002-3287-7611)
- Suping Chen (ORCID: https://orcid.org/0009-0004-3522-9291)
- Xiao‐Zheng Su
- Chun‐Lei Xiang (ORCID: https://orcid.org/0000-0001-8775-6967)
- Pema‐Tenzin Puno (ORCID: https://orcid.org/0000-0001-5212-3000)
- Liang Zhang (ORCID: https://orcid.org/0000-0002-7672-1168)
- Kun Hu (ORCID: https://orcid.org/0000-0003-4420-2467)
- Han‐Dong Sun (ORCID: https://orcid.org/0000-0001-7551-3028)
- Xian-Xiang Dong
Institutions
- Kunming Institute of Botany (CN)
- Chinese Academy of Sciences (CN)
- Institute of Organic Chemistry with Centre of Phytochemistry (BG)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-03
- DOI
- https://doi.org/10.1021/acs.orglett.5c00586
- Citations
- 2
- Primary Topic
- Bioactive Natural Diterpenoids Research
- Type
- article
- Field-Weighted Citation Impact
- 1.61
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Youth Innovation Promotion Association of the Chinese Academy of Sciences
- Yunnan Provincial Science and Technology Department
- West Light Foundation of the Chinese Academy of Sciences
- National Science Fund for Distinguished Young Scholars