Structurally Diverse Polymethylated Phloroglucinol Meroterpenoids from <i>Baeckea frutescens</i>

doi:10.1007/s13659-018-0189-3

Natural Products and Bioprospecting

2018, Vol. 8

Issue (6) : 431-439 DOI: 10.1007/s13659-018-0189-3

ORIGINAL ARTICLES

Structurally Diverse Polymethylated Phloroglucinol Meroterpenoids from Baeckea frutescens

Yin-E Zhi¹, Xu-Jie Qin¹, Hui Liu¹, Yuan Zeng¹, Wei Ni¹, Li He², Zu-Ding Wang³, Hai-Yang Liu¹

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, and Yunnan Key Laboratory of Medicinal Chemistry, Kunming 650201, China;
2 Department of Dermatology, The First Affiliated Hospital of Kunming Medical University, Kunming 650032, China;
3 Kunming Botanee Bio-Technique Co. Ltd, Kunming 650106, China

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Abstract Phytochemical investigation of the MeOH extract of twigs and leaves of Baeckea frutescens led to the isolation of seven new polymethylated phloroglucinol meroterpenoids (PPMs), named baeckfrutones M-S (1-7). Their structures and absolute configurations were determined by spectroscopic analyses, chiral-phase HPLC analysis, and electronic circular dichroism (ECD) calculations. PPM 1 is a novel meroterpenoid possessing a 6/6/5/3 tetracyclic skeleton in PPMs, whereas 3 and 4 are the first hydroxytasmanone type phloroglucinol-monoterpene hybrids. (+)-2 and 7 displayed potent antiinflammatory activity with IC₅₀ values of 20.86±0.60 and 36.21±1.18 lL, respectively.

Keywords Baeckea frutescens Myrtaceae Polymethylated phloroglucinol meroterpenoids Anti-inflammatory activity

Fund:This work was financially supported by the National Natural Science Foundation of China (Nos. 31570363 and 31770391), Key Research and Development Plan of Yunnan Province-Special Project of Science and Technology in Yunnan Province (2017IB007), Major Biomedical Project of Yunnan Province (2018ZF005), and Innovation Team of the Ministry of Education (No. IRT-17R49), and the Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China (P2017-ZZ04 and P2017-KF06), Kunming Institute of Botany, Chinese Academy of Sciences.

Corresponding Authors: Hai-Yang Liu E-mail: haiyangliu@mail.kib.ac.cn

Issue Date: 21 November 2018

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Yin-E Zhi,Xu-Jie Qin,Hui Liu, et al. Structurally Diverse Polymethylated Phloroglucinol Meroterpenoids from Baeckea frutescens[J]. Natural Products and Bioprospecting, 2018, 8(6): 431-439.

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http://npb.kib.ac.cn/EN/10.1007/s13659-018-0189-3 OR http://npb.kib.ac.cn/EN/Y2018/V8/I6/431

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