Norcrassin A, a novel C16 tetranorditerpenoid, and bicrotonol A, an unusual dimeric labdane-type diterpenoid, from the roots of Croton crassifolius

A novel C16 tetranorditerpenoid, norcrassin A (1), and an unusual dimeric labdane-type diterpenoid, bicrotonol A (2), were isolated from the roots of Croton crassifolius. Norcrassin A (1) featured a new carbon skeleton with an unprecedented 5/5/5/6 tetracyclic system. Bicrotonol A (2) possessed an u...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (10), p.1745-1750
Main Authors: Zhang, Zhan-Xin, Wu, Pei-Qian, Li, Hui-Hong, Qi, Feng-Ming, Fei, Dong-Qing, Hu, Qiao-Ling, Liu, Ying-Hong, Huang, Xiao-Ling
Format: Article
Language:English
Subjects:
Absolute configuration
Alzheimer's disease
Crystals
Diffraction
Mass spectrometry
Mass spectroscopy
Monomers
Neurodegenerative diseases
NMR
Nuclear magnetic resonance
Roots
Single crystals
X-ray diffraction
X-rays
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Summary:A novel C16 tetranorditerpenoid, norcrassin A (1), and an unusual dimeric labdane-type diterpenoid, bicrotonol A (2), were isolated from the roots of Croton crassifolius. Norcrassin A (1) featured a new carbon skeleton with an unprecedented 5/5/5/6 tetracyclic system. Bicrotonol A (2) possessed an unusual tetrahydroxypyran ring linkage connecting two labdane diterpenoid monomers. The structures of all compounds, including the absolute configuration, were elucidated by the interpretation of their NMR spectroscopic data, high resolution mass spectrometry, and single-crystal X-ray diffraction. A plausible biosynthetic pathway of 1 is proposed. The anti-Alzheimer's Disease (AD) activities of 1 and 2 are also evaluated using the AD pathological model.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02991h