Journal
JOURNAL OF NATURAL PRODUCTS
Volume 80, Issue 5, Pages 1493-1504Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.6b01178
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Funding
- National Natural Science Foundation of China [81641129, 31370372, 81573316]
- Fundamental Research Fund for the Central Universities [2016YXMS149]
- Program for New Century Excellent Talents in University, State Education Ministry of China [NCET-2008-0224]
- National Science and Technology Project of China [2011ZX09102-004]
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The new polyprenylated acylphloroglucinol derivatives 1-15 and the known furohyperforin (16) were isolated from the stems and leaves of Hypericum perforatum. Their structures were determined by analyses of NMR and HRESIMS data. Their absolute configurations were elucidated by a combination of electronic circular dichroism (ECD) and Rh-2(OCOCF3)(4)-induced ECD, as well as X-ray diffraction crystallography. The new hyperforatin F (9) contains a unique acetyl functionality at C-1 of the bicydo[3.3.1]nonane core. Hyperforatins G (10) and H (11) are similarly the first examples of naturally occurring [3.3.1]-type polycyclic prenylated acylphloroglucinols possessing a carbonyl functionality at C-32. The compounds were tested for their acetylcholinesterase (AChE) inhibitory activities and cytotoxic activities against a panel of human tumor cell lines. Compounds 3, 5, 6, 8, and 9 exerted moderate inhibitory activities (IC50 3.98-9.13 mu M) against AChE.
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