4.8 Article

Phomopsterones A and B, Two Functionalized Ergostane-Type Steroids from the Endophytic Fungus Phomopsis sp TJ507A

Journal

ORGANIC LETTERS
Volume 19, Issue 1, Pages 258-261

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03557

Keywords

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Funding

  1. Program for New Century Excellent Talents in University, State Education Ministry of China [NCET-2008-0224]
  2. National Natural Science Foundation of China [31200258, 31370372, 31270395, 81573316, 81641129]
  3. National Science and Technology Project of China [2011ZX09102-004]

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Two new functionalized ergostane-type steroids, phomopsterones A (1) and B (2), were isolated from the plant-derived Phomopsis sp. TJ507A. Their structures were determined on the basis of spectroscopic data, a modified Mosher's method, X-ray crystallographic analysis, and quantum chemical calculations. Compound 1 is an unprecedented ergosteroid featuring a, rearranged bicyclo[3.3.1]nonane motif resulting from B-ring scission and a subsequent 180 degrees rotation of the ring A during biosynthesis. Compound 2 exhibited anti-inflammatory activity.

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