10.1021/acs.orglett.6b01944.s006
Ya-Long Zhang
Ya-Long
Zhang
Chen Chen
Chen
Chen
Xiao-Bing Wang
Xiao-Bing
Wang
Lin Wu
Lin
Wu
Ming-Hua Yang
Ming-Hua
Yang
Jun Luo
Jun
Luo
Can Zhang
Can
Zhang
Hong-Bin Sun
Hong-Bin
Sun
Jian-Guang Luo
Jian-Guang
Luo
Ling-Yi Kong
Ling-Yi
Kong
Rhodomyrtials A and B, Two Meroterpenoids with a Triketone-Sesquiterpene-Triketone
Skeleton from <i>Rhodomyrtus tomentosa</i>: Structural Elucidation
and Biomimetic Synthesis
American Chemical Society
2016
adduct
Rhodomyrtus tomentosa
tomentodione
MMP
chemical
conversion
matrix
biosynthetic
Compound
metalloproteinase
assignment
combination
DLD
activation
NMR
metastatic
intermediate
Meroterpenoid
configuration
Elucidation
Skeleton
diffraction
analysis
Biomimetic Synthesis Rhodomyrtials
biogenetically
spectroscopy
rhodomentone
Structural
biomimetically
2016-08-02 19:45:41
Dataset
https://acs.figshare.com/articles/dataset/Rhodomyrtials_A_and_B_Two_Meroterpenoids_with_a_Triketone-Sesquiterpene-Triketone_Skeleton_from_i_Rhodomyrtus_tomentosa_i_Structural_Elucidation_and_Biomimetic_Synthesis/3509741
Rhodomyrtials
A and B (<b>1</b> and <b>2</b>), two unprecedented triketone-sesquiterpene-triketone
adducts, along with five biogenetically related intermediates, rhodomentone
A (<b>3</b>) and tomentodiones A–D (<b>4</b>–<b>7</b>), were isolated from the leaves of <i>Rhodomyrtus tomentosa</i>. Their structures and absolute configurations were determined by
a combination of NMR spectroscopy, chemical conversion, and X-ray
diffraction analysis. Compounds <b>1</b> and <b>2</b> were
biomimetically synthesized via <b>5</b> and <b>4</b>,
respectively, rather than <b>3</b>, revealing their key ordering
of biosynthetic events and confirming their structural assignments.
Compound <b>7</b> exhibited potent metastatic inhibitory activity
against DLD-1 cells by suppressing the activation of matrix metalloproteinase
(MMP)-2 and MMP-9.