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.