2. Academic Validation
  3. Neolignans with a Rare 2-Oxaspiro[4.5]deca-6,9-dien-8-one Motif from the Stem Bark of Cinnamomum subavenium

Neolignans with a Rare 2-Oxaspiro[4.5]deca-6,9-dien-8-one Motif from the Stem Bark of Cinnamomum subavenium

  • J Nat Prod. 2015 Jul 24;78(7):1740-4. doi: 10.1021/np5010533.
Yongji Lai 1 2,  Tingting Liu 1,  Rongjian Sa 3,  Xialan Wei 1,  Yongbo Xue 1,  Zhaodi Wu 1,  Zengwei Luo 1,  Ming Xiang 1,  Yonghui Zhang 1,  Guangmin Yao 1
Affiliations

Affiliations

  • 1 †Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
  • 2 §Department of Pharmacy, The Central Hospital of Wuhan, Wuhan 430014, People's Republic of China.
  • 3 ‡Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, People's Republic of China.
PMID: 26087384 DOI: 10.1021/np5010533
Abstract

Two pairs of racemic spirodienone neolignans with a rare 2-oxaspiro[4.5]deca-6,9-dien-8-one motif, named (±)-subaveniumins A (1) and B (2), were isolated from the bark of Cinnamomum subavenium. The chiral separation of the (+)-1, (-)-1, (+)-2, and (-)-2 enantiomers was accomplished via high-performance liquid chromatography on a chiral column. Their structures were elucidated using single-crystal X-ray diffraction and spectroscopic analyses (UV, IR, HRESIMS, and 1D and 2D NMR). The absolute configurations of the enantiomers were determined by comparing the experimental and calculated electronic circular dichroic spectra. The (+)-1, (-)-1, (+)-2, and (-)-2 enantiomers exhibited moderate inhibitory effects against NO production in RAW264.7 mouse macrophages induced by lipopolysaccharide, with IC50 values of 17.9, 5.6, 15.1, and 4.3 μM, respectively.

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