Antimicrobial abietane-type diterpenoids from Torreya grandis

Jiao-Jiao Cui; Wei-Jia Li; Cheng-Lei Wang; Yi-Qi Huang; Wei Lin; Bin Zhou; Jian-Min Yue

doi:10.1016/j.phytochem.2022.113278

Antimicrobial abietane-type diterpenoids from Torreya grandis

Phytochemistry. 2022 Sep:201:113278. doi: 10.1016/j.phytochem.2022.113278. Epub 2022 Jun 16.

Authors

Jiao-Jiao Cui¹, Wei-Jia Li², Cheng-Lei Wang³, Yi-Qi Huang³, Wei Lin², Bin Zhou⁴, Jian-Min Yue⁵

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203, People's Republic of China.
² Department of Pathogen Biology, School of Medicine & Holistic Integrative Medicine, Nanjing University of Chinese Medicine, Nanjing, 210023, People's Republic of China.
³ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203, People's Republic of China.
⁴ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203, People's Republic of China. Electronic address: zbbrush@simm.ac.cn.
⁵ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203, People's Republic of China. Electronic address: jmyue@simm.ac.cn.

PMID: 35716715
DOI: 10.1016/j.phytochem.2022.113278

Abstract

Twelve undescribed abietane-type diterpenoids, along with ten known analogues were isolated from the twigs and leaves of Torreya grandis var. merrillii Hu. Their structures were characterized by spectroscopic data analyses, single-crystal X-ray diffraction, and ECD spectra. Torgranols A-C possess three different architectures shaped via a common 6,7-seco-procedure and subsequent ring formations. In particular, torgranol A represents the first example of a 6,7-seco-abietane diterpenoid featuring a unique oxygen bridge between C-3 and C-6. The biosynthetic pathways for torgranols A-C were proposed. Some compounds displayed antimicrobial activities against Mycobacterium tuberculosis and/or Staphylococcus aureus.

Keywords: Abietane; Antimicrobial activities; Diterpenoid; Taxaceae; Torgranols A−L; Torreya grandis var. merrillii Hu.

MeSH terms

Abietanes / chemistry
Abietanes / pharmacology
Anti-Bacterial Agents / pharmacology
Anti-Infective Agents* / pharmacology
Diterpenes* / chemistry
Plant Leaves / chemistry
Taxaceae*

Substances

Abietanes
Anti-Bacterial Agents
Anti-Infective Agents
Diterpenes