Journal
INDUSTRIAL CROPS AND PRODUCTS
Volume 172, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.indcrop.2021.114010
Keywords
Dryopteris crassirhizoma; beta-tocopherol derivatives; Isolation; Structural elucidation
Categories
Funding
- National Natural Science Foundations of China [82003609, 81973190, 81803376]
- Guang-dong Basic and Applied Basic Research Foundation [2020A1515110453]
- Science and Technology Planning Project of Guangdong Province [2020B121201013]
- China Postdoctoral Sci-ence Foundation [2019M663403]
- Macao Youth Scholars Program [AM201931]
- high performance public computing service plat-form of Jinan University
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Five beta-tocopherol derivatives were isolated from the rhizomes of Dryopteris crassirhizoma, with compound 1 showing comparable anti-respiratory syncytial virus activity to the positive control ribavirin. This suggests potential new applications for the rhizomes of D. crassirhizoma and its derivatives in the pharmaceutical industry.
Dryopteris crassirhizoma Nakai (Dryopteridaceae), a thick-stemmed wood fern, is a semi-evergreen plant mainly distributed in North and Northeast China. It is of great value in horticultural and medicinal applications. In this study, five beta-tocopherol derivatives, drycrasspherols A-E (1-5), with three kinds of skeletons, were isolated from the rhizomes of Dryopteris crassirhizoma. Compounds 1-2 represent the basic architecture featuring a phenol motif fused with the phytyl-type diterpene via a pyran ring, compounds 3-4 possess an unprecedented tetracyclic system in which a 4-methylcyclohexanone is incorporated into the base unit of 1. Interestingly, compound 5 is a novel dimer constructed from two monomers via a pyran ring to form a pentacyclic system. These structures were elucidated by comprehensive spectroscopic data and quantum chemical electronic circular dichroism (ECD) calculations. Importantly, compound 1 exhibited the comparable anti-respiratory syncytial virus activity with an IC50 value of 6.50 +/- 1.25 mu M to the positive control ribavirin. This study suggested the rhizomes of D. crassirhizoma as well as the beta-tocopherol derivatives had new potential applications in pharmaceutical industry.
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