Nematicidal quinone derivatives from three Rubia plants. Issue 17 (26th April 2018)

• Record Type: Journal Article
• Authors: Zhao, Si-Meng; Kuang, Bin; Zeng, Guang-Zhi; Wang, Zhe; Wang, Jia; Chen, Xiao-Qiang; Tan, Ning-Hua
• Is Part Of: Tetrahedron. Volume 74:Issue 17(2018)
• Page Start: 2115
• Page End: 2120
• Publication Date: 2018-04-26
• Subjects: Rubia -- Rubia alata -- Rubia wallichiana -- Rubia schumanniana -- Quinones -- Nematicidal activity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.02.065
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Five new quinone derivatives, rubiasins D-F (1 –3 ), rubialatones A and B (4 and5 ), have been isolated from the roots and rhizomes of three Rubia species, Rubia alata, R. wallichiana and R. schumanniana, together with 26 known quinones (6 –31 ). Their structures have been elucidated on the basis of NMR, MS spectra and computational methods. The compounds have been evaluated for their toxicity to the saprophytic nematode Caenorhabditis elegans and the root-knot nematode Meloidogyne incognita . Compounds1, 6 and7 showed toxicity to C. elegans with the LC50 values at 8.50, 9.44 and 44.82 μg/mL, respectively; and6 showed toxicity to M. incognita with the LC50 value at 35.22 μg/mL. Meanwhile, compounds1 and6 showed inhibitory effect on egg hatch of C. elegans with the LC50 values at 5.60 and 48.95 μg/mL. Graphical abstract: Highlights: Five new quinones and 26 known ones were isolated from three Rubia plants. Their structures were elucidated by NMR, MS spectra and computational methods. All quinones were evaluated for their toxicity to C. elegans and M. incognita.