ol6b01944_si_006.cif (924.84 kB)
Rhodomyrtials A and B, Two Meroterpenoids with a Triketone-Sesquiterpene-Triketone Skeleton from Rhodomyrtus tomentosa: Structural Elucidation and Biomimetic Synthesis
dataset
posted on 2016-08-02, 19:45 authored by Ya-Long Zhang, Chen Chen, Xiao-Bing Wang, Lin Wu, Ming-Hua Yang, Jun Luo, Can Zhang, Hong-Bin Sun, Jian-Guang Luo, Ling-Yi KongRhodomyrtials
A and B (1 and 2), two unprecedented triketone-sesquiterpene-triketone
adducts, along with five biogenetically related intermediates, rhodomentone
A (3) and tomentodiones A–D (4–7), were isolated from the leaves of Rhodomyrtus tomentosa. Their structures and absolute configurations were determined by
a combination of NMR spectroscopy, chemical conversion, and X-ray
diffraction analysis. Compounds 1 and 2 were
biomimetically synthesized via 5 and 4,
respectively, rather than 3, revealing their key ordering
of biosynthetic events and confirming their structural assignments.
Compound 7 exhibited potent metastatic inhibitory activity
against DLD-1 cells by suppressing the activation of matrix metalloproteinase
(MMP)-2 and MMP-9.
History
Usage metrics
Categories
Keywords
adductRhodomyrtus tomentosatomentodioneMMPchemicalconversionmatrixbiosyntheticCompoundmetalloproteinaseassignmentcombinationDLDactivationNMRmetastaticintermediateMeroterpenoidconfigurationElucidationSkeletondiffractionanalysisBiomimetic Synthesis RhodomyrtialsbiogeneticallyspectroscopyrhodomentoneStructuralbiomimetically
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC