Journal Article10.1021/acs.joc.2c00071
Discovery and Biomimetic Synthesis of a Polycyclic Polymethylated Phloroglucinol Collection from Rhodomyrtus tomentosa.
Lu-Ming Deng,W.P. Tang,Shu-Qin Wang,Jian Song,Xiao-Jun Huang,Hao-yue Zhu,Yao-Lan Li,Wen-Cai Ye,Li‐Jun Hu,Ying Wang +9 more
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TL;DR: Inspired by a previously reported biomimetic synthesis study, four new naturally occurring phloroglucinol trimers 1-4 with unusual 6/5/ 5/6/6-fused hexacyclic ring systems exhibited significant in vitro antiviral activity against the respiratory syncytial virus.
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Abstract: Inspired by a previously reported biomimetic synthesis study, four new naturally occurring phloroglucinol trimers 1-4 with unusual 6/5/5/6/6/6-fused hexacyclic ring systems, along with two known analogues (5 and 6) and two known biogenetically related dimers (10 and 11), were isolated from Rhodomyrtus tomentosa. Their structures and absolute configurations were unambiguously elucidated by spectroscopic analysis, X-ray diffraction, and electronic circular dichroism calculation. By mimicking two potentially alternative biosynthetic pathways, the first asymmetric syntheses of 1-4 and the racemic syntheses of 5 and 6 were achieved in only five to six steps without the need for protecting groups. Furthermore, phloroglucinol dimers 10 and 11 exhibited significant in vitro antiviral activity against the respiratory syncytial virus.
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Citations
Recent Advances in Chemistry and Antioxidant/Anticancer Biology of Monoterpene and Meroterpenoid Natural Product
Benedict J. Barras,Taotao Ling,Fatima R. Rivas +2 more
TL;DR: This review is a collection of representative updates in biologically active monoterpene and meroterpenoid natural products and focuses on the recent findings of the pharmacological potential of these bioactive compounds as well as the newly developed synthetic strategies employed to access them.
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Synthesis of Rhodomyrtone Analogs Modified at C7
TL;DR: In this article , the authors developed a route to rhodomyrtone analogs that feature different acyl groups at C7, where electrophilic substitution reactions on the aryl part of the rhodomeyrtone core led to C5 derivatives, the C5 position was blocked by a chlorine.
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Asymmetric total synthesis of polycyclic xanthenes and discovery of a WalK activator active against MRSA
Min-Jing Cheng,Yue Wu,Hao Zeng,Tianhong Zhang,Yanxia Hu,Shiyi Liu,Rui-Qin Cui,Chunxia Hu,Quanming Zou,Chuang‐Chuang Li,Wen‐Cai Ye,Wei Huang,Lei Wang +12 more
TL;DR: A concise approach for the collective asymmetric total synthesis of polycyclic xanthene myrtucommulone D and five related congeners is outlined and the discovery of an antibacterial agent against both drug-sensitive and drug-resistant S. aureus is found.
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Tautomeric cinnamoylphloroglucinol-monoterpene adducts from Cleistocalyx operculatus and their antiviral activities.
Jian-Guo Song,Jia-Xin Liu,Rui-Li Huang,Wei Tang,Xiao-Jun Huang,Ying Wang,Wen-Cai Ye +6 more
TL;DR: A novel class of cinnamoylphloroglucinol-monoterpene adducts featuring an unusual C-4-C-1' linkage between 2,2,4-trimethyl-cinnamyl-β-triketone and modified linear monoterpenoid motifs exhibited significant in vitro antiviral activity against respiratory syncytial virus (RSV).
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Oligomeric phloroglucinols with hAChE inhibitory and antibacterial activities from tropic Rhodomyrtus tomentosa
E-E Luo,Simei Liu,Zhao-Jie Wang,Ling-Yun Chen,Cheng-Qin Liang,Mu-Yuan Yu,Xu-Jie Qin +6 more
- 01 Sep 2023
TL;DR: The mixture of 3a and 3b displayed the most significant anti-MRSA values with MIC and MBC values of both 0.50 μg/mL, and scanning electron microscope studies revealed that they could destroy the biofilm structures of MRSA.
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Rhodomyrtials A and B, Two Meroterpenoids with a Triketone-Sesquiterpene-Triketone Skeleton from Rhodomyrtus tomentosa: Structural Elucidation and Biomimetic Synthesis.
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TL;DR: Two unprecedented triketone-sesquiterpene-triketone adducts and five biogenetically related intermediates were isolated from the leaves of Rhodomyrtus tomentosa and exhibited potent metastatic inhibitory activity against DLD-1 cells by suppressing the activation of matrix metalloproteinase (MMP)-2 and MMP-9.
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