4.4 Article

Baeckfrutones A-L, polymethylated phloroglucinol meroterpenoids from the twigs and leaves of Baeckea frutescens

Journal

TETRAHEDRON
Volume 74, Issue 46, Pages 6658-6666

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.09.050

Keywords

Baeckea frutescens; Polymethylated phloroglucinol meroterpenoids; Baeckfrutones A-L; Cytotoxicity; Anti-inflammatory activity

Funding

  1. National Natural Science Foundation of China [31570363, 31770391]
  2. Key Research and Development Plan of Yunnan Province-Special Project of Science and Technology in Yunnan Province [2017IB007]
  3. Major Bio-Medical Project of Yunnan Province [2017AB001, 2018ZF005]
  4. Scientific and Technological Projects of Yunnan Province [2017FB128]
  5. Innovation Team of the Ministry of Education [IRT-17R49]
  6. Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China [P2017-ZZ04, P2017-KF06]
  7. Kunming Institute of Botany, Chinese Academy of Sciences

Ask authors/readers for more resources

Twelve new polymethylated phloroglucinol meroterpenoids (PPMs), baeckfrutones A-L (1-12), were isolated from the twigs and leaves of Baeckea frutescens. Their structures and absolute configurations were unambiguously established by extensive spectroscopic methods (HRESIMS, NMR, and ECD) and single crystal X-ray diffraction. PPM 1 is a rare PPM comprising enone-type phloroglucinol and alpha-phellandrene units, whereas 2-4, 6, and 7, are the first hybrids of enone-type phloroglucinol and sabinene moieties with different stereochemistry. (-)-2 and 11 showed remarkable cytotoxicities against DU145 and HCT116 cells with IC50 values of 1.33 and 12.89 mu M, respectively. 6, 7, (+)-9, and 10 displayed significant anti-inflammatory activity with inhibitory rates of 74.64, 75.37, 55.13, and 75.01% at the concentration of 50 mu M, respectively. (C) 2018 Elsevier Ltd. All rights reserved.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
Article Chemistry, Organic

Facile synthesis of quinoxaline catalyzed by iron-based carbon material in water

Fuying Zhu, Yamei Lin

Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.

TETRAHEDRON (2024)

Article Chemistry, Organic

Simple approach towards phosphorus-substituted spiro 1,3,4-thiadiazolines

Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova

Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.

TETRAHEDRON (2024)

Article Chemistry, Organic

Recent advances in the synthesis of 2-cyclopentenones

Jisna Jose, Thomas Mathew

Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.

TETRAHEDRON (2024)