Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 14, Pages 3086-3094Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403678
Keywords
Natural products; Drug discovery; Antiviral agents; Polycycles; Structure elucidation
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Funding
- State Education Ministry of China, Program for New Century Excellent Talents in University [NCET-2008-0224]
- National Natural Science Foundation of China (NSFC) [31370372, 31200258, 31270395, 81202423]
- National Science and Technology Project of China [2011ZX09102-004]
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Eight rare pyrrole-based cytochalasans, termed armochaetoglobins K-R (1-8), along with three known analogues (9-11), were isolated from the solid culture broth of Chaetomium globosum TW1-1, a symbiotic fungus derived from the medicinal terrestrial arthropod Armadillidium vulgare. Their structures were elucidated using a combination of spectroscopic analysis, a single-crystal X-ray diffraction experiment, and an electronic circular dichroism (ECD) calculation. Compounds 4-8 represent the first examples of chaetoglobosin-type cytochalasans with an sp(3) methine carbon at C-18. All of the isolates were evaluated for their anti-HIV activities in vitro, and compounds 2-4, 7, 8, and 10 showed significant anti-HIV activities, with EC50 values ranging from 0.11 to 0.55 mu M, and selectivity index (SI) values ranging from 12.33 to 75.42. A plausible biosynthetic pathway was proposed to explain the origin of the pyrrole ring.
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