Antibacterial Aromatic Sesquiterpenes from the Leaves of Nicotiana tabacum

Two new aromatic sesquiterpenes, 1-isopropyl-5-methoxy-3,7-dimethylnaphthalene ( 1 ) and 3-hydroxymethyl-1-isopropyl-5-methoxy-7-methylnaphthalene ( 2 ), as well as five known sesquiterpenes ( 3–7 ), were isolated from the leaves of Nicotiana tabacum (a mutant tobacco for solanesol synthesis gene kn...

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Bibliographic Details
Published in:Chemistry of natural compounds 2023-07, Vol.59 (4), p.692-696
Main Authors: Dai, Jia-Meng, Xiong, Wen, Wang, Wen-Yuan, Wang, Hui-Ping, Zhao, Wei, Li, Yong, Li, Yin-Ke, Hu, Qiu-Fen, Wang, Wei-Guang, Shang, Shan-Zhai, Cai, Jie-Yun
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Eau de Cologne
Genetic modification
Methicillin
NMR
Nuclear magnetic resonance
Organic Chemistry
Plant Sciences
Sesquiterpenes
Staphylococcus aureus
Tobacco
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Summary:Two new aromatic sesquiterpenes, 1-isopropyl-5-methoxy-3,7-dimethylnaphthalene ( 1 ) and 3-hydroxymethyl-1-isopropyl-5-methoxy-7-methylnaphthalene ( 2 ), as well as five known sesquiterpenes ( 3–7 ), were isolated from the leaves of Nicotiana tabacum (a mutant tobacco for solanesol synthesis gene knockout by CRISPR-Cas9 gene editing). Their structures were determined by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 were tested for their anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) activity. The results revealed that compounds 1 and 2 showed good inhibition with IZD of 12.8 ± 2.0 and 15.2 ± 2.2 mm, respectively. In addition, compounds 1 and 2 have a weak floral fragrance, and they have the potential for use as an essence for cigarettes.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-023-04089-2