Polyketides from the endophytic fungus Phomopsis sp. sh917 by using the one strain/many compounds strategy. Issue 26 (29th June 2017)

• Record Type: Journal Article
• Authors: Tang, Jian-Wei; Wang, Wei-Guang; Li, Ao; Yan, Bing-Chao; Chen, Rong; Li, Xiao-Nian; Du, Xue; Sun, Han-Dong; Pu, Jian-Xin
• Is Part Of: Tetrahedron. Volume 73:Issue 26(2017)
• Page Start: 3577
• Page End: 3584
• Publication Date: 2017-06-29
• Subjects: Endophytic fungus -- Phomopsis sp. -- OSMAC strategy -- Polyketides -- Antiangiogenic activity; UXVFEZIAVANTNF-XBGJUJFJSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.02.019
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: On the basis of One Strain/Many Compounds (OSMAC) strategy, five new polyketides, named phomopsiketones A-C (1 –3 ), (10 S )-10-O- β -D-4′-methoxymannopyranosyldiaporthin (7 ), and clearanol H (10 ), and two new natural products, 4 and5, along with three known ones, 6, 8 and9, 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 of1, 3, and7 were further confirmed by single crystal X-ray diffraction experiment. Compounds2, 4, 6, 9 and10 were assigned absolute configurations on the basis of circular dichroism (CD) or optical rotation (OR) data comparison. In addition, antiangiogenic activity of compounds2, 3, 5, and6 were evaluated by using human umbilical vascular endothelial cells (HUVECs) in a cell-culture model of angiogenesis. Especially, compound6 sufficiently inhibited vascular endothelial growth factor (VEGF)-induced angiogenic processes in vitro, including migration, invasion, and tube formation of HUVECs. Graphical abstract: Highlights: Five new polyketides were obtained from an endophytic fungus, Phomopsis sp.917, by using OSMAC strategy. All structures including absolute configurations were determined. The structures of non-aromatic polyketides1 and2, and polyketide glycoside7 were rare. Compound6 significantly inhibited vascular endothelial growth factor (VEGF)-induced angiogenic processes in vitro.