Annotinolide F and lycoannotines A-I, further Lycopodium alkaloids from Lycopodium annotinum

  • Phytochemistry. 2017 Nov:143:1-11. doi: 10.1016/j.phytochem.2017.07.003.
Yu Tang  1 ,  Juan Xiong  1 ,  Yike Zou  2 ,  Wei Wang  3 ,  Chao Huang  1 ,  Hai-Yan Zhang  3 ,  Jin-Feng Hu  4
Affiliations
  • 1. Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai, 201203, PR China.
  • 2. Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA, 19104-6323, United States.
  • 3. CAS Key Laboratory of Receptor Research, Shanghai Institute of Material Medica, Chinese Academy of Sciences, No. 555 Zuchongzhi Road, Shanghai, 201203, PR China.
  • 4. Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai, 201203, PR China. Electronic address: [email protected].
PMID: 28738241 DOI: 10.1016/j.phytochem.2017.07.003
Abstract

Seven lycopodine-type (annotinolide F and lycoannotines A-F), two lycodine-type (lycoannotines G and H), and one fawcettimine-type (lycoannotine I) previously undescribed naturally occurring Lycopodium Alkaloids together with thirteen known ones were isolated from the whole plant of Lycopodium annotinum. Their structures and absolute configurations were determined by extensive spectroscopic methods, single-crystal X-ray diffraction, chemical transformation, and electronic circular dichroism (ECD) calculations. Among the isolates, annotinolide F, lycoannotines A and B are unusual 7,8-seco-lycopodane derivatives, and annotinolide F even further possesses a rare 8,5-lactone framework through a lactonization after the C-7/C-8 bond cleavage. Lycoannotine C is an uncommon 8,15-seco lycopodine-type alkaloid, whereas lycoannotine I represents the first example of a naturally occurring C-9/N bond cleavage product of fawcettimine-type alkaloid. Among them, only lycoannotine I was found to show considerable anti-butyrylcholinesterase (anti-BuChE) activity.

Keywords
Anhydrolycodoline (PubChem CID: 102442792); Annotinolide F; Fawcettidine (PubChem CID: 442473); Lycoannotines; Lycodine (PubChem CID: 5462443); Lyconnotine (PubChem CID: 442487); Lycophlegmine (PubChem CID: 158260); Lycopodatine C (PubChem CID: 11708569); Lycopodiaceae; Lycopodine (PubChem CID: 5462445); Lycopodium alkaloids; Lycopodium annotinum; Obscurumine B (PubChem CID: 12188648).
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