Polyketides from the endophytic fungus Phomopsis sp. sh917 by using the one strain/many compounds strategy

• DOI: 10.1016/j.tet.2017.02.019
• Publication Date: 2017-02-08T10:01:39Z
• Authors: Jian-Wei Tang; Wei-Guang Wang; Ao Li; Bing-Chao Yan; Rong Chen; Xiao-Nian Li; Xue Du; Han-Dong Sun; Jian-Xin Pu
• Keywords: Phomopsis; Absolute Configuration; Strain (injury)

Abstract On the basis of One Strain/Many Compounds (OSMAC) strategy, five new polyketides, named phomopsiketones A-C (1–3), (10S)-10-O-β-D-4′-methoxymannopyranosyldiaporthin (7), and clearanol H (10), and two new natural products, 4 and 5, along with three known ones, 6, 8 and 9, were isolated from an endophytic fungus, Phomopsis sp. sh917, harbored in stems of Isodon eriocalyx var. laxiflora. Their structures were elucidated by spectroscopic methods. The absolute configurations of 1, 3, and 7 were further confirmed by single crystal X-ray diffraction experiment. Compounds 2, 4, 6, 9 and 10 were assigned absolute configurations on the basis of circular dichroism (CD) or optical rotation (OR) data comparison. In addition, antiangiogenic activity of compounds 2, 3, 5, and 6 were evaluated by using human umbilical vascular endothelial cells (HUVECs) in a cell-culture model of angiogenesis. Especially, compound 6 sufficiently inhibited vascular endothelial growth factor (VEGF)-induced angiogenic processes in vitro, including migration, invasion, and tube formation of HUVECs.