2. Academic Validation
  3. C19 Benzylisoquinoline Alkaloid with Unprecedented Architecture from Hypecoum erectum

C19 Benzylisoquinoline Alkaloid with Unprecedented Architecture from Hypecoum erectum

  • J Org Chem. 2021 Dec 3;86(23):16764-16769. doi: 10.1021/acs.joc.1c01990.
Hai-Lian Yuan 1,  Yun-Li Zhao 2,  Kun Hu 1,  Ying-Jie He 2,  Xing-Wei Yang 3,  Xiao-Dong Luo 1 2
Affiliations

Affiliations

  • 1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
  • 2 Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research and Development of Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China.
  • 3 School of Pharmaceutical Sciences (Shenzhen), Sun Yat-sen University, Shenzhen 518107, People's Republic of China.
PMID: 34723525 DOI: 10.1021/acs.joc.1c01990
Abstract

Hyperectumine (1), the first C19 benzylisoquinoline alkaloid with a complicated ring system, was isolated from Hypecoum erectum and structurally characterized. Its biosynthetic origin should involve a hybrid pattern of C8 + C8 + C1 + C2, from which a C17 benzylisoquinoline alkaloid might be further attacked by a malonamic acid and undergo decarboxylation and cyclization to produce 1. Compound (-)-1 exhibited moderate anti-inflammatory activity via suppression of LPS-activated inflammatory mediators in RAW 264.7 macrophage cells.

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