Two New Furan-2-Carboxylic Derivatives from the Leaves of Nicotiana tabacum and Their Anti-Tobacco Mosaic Virus Activiti
- PDF / 175,606 Bytes
- 4 Pages / 594 x 792 pts Page_size
- 39 Downloads / 142 Views
TWO NEW FURAN-2-CARBOXYLIC DERIVATIVES FROM THE LEAVES OF Nicotiana tabacum AND THEIR ANTI-TOBACCO MOSAIC VIRUS ACTIVITIES
Xue Wang,1,2 Li-Jia Huang,1,2 Meng-Jie Liang,1,2 Yin-Ke Li,2 Wan-Li Zeng,2 Hai-Ying Xiang,2 Jing Li,2 Xin Liu,2 Qi-Li Mi,2 Ya-Dong Guo,2 Guang-Yu Yang,1,3 Liang Deng,1* and Qian Gao1,2*
Two new furan-2-carboxylic derivatives (1 and 2), together with three known compounds (3–5), were isolated from the leaves of Nicotiana tabacum. Their structures were determined by means of HR-ESI-MS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1 and 2 were tested for their anti-TMV activities. The results showed that compounds 1 and 2 exhibited high anti-TMV activity with inhibition rates of 33.2 and 30.8%. These rates are close to that of positive control. Keywords: Nicotiana tabacum, furan-2-carboxylic derivatives, anti-tobacco mosaic virus activity. Nicotiana tabacum is a stout annual plant of the Tomentosae family. As an important economic crop grown widely in the world, its leaves are used as a raw material for the tobacco industry [1]. In addition, it is also used as insecticide, anesthetic, diaphoretic, sedative, and emetic agents in Chinese folk medicine [2, 3]. Investigation of its chemical constituents and bioactivities is important to provide valuable clues for phytochemistry [4, 5]. In previous studies, many new bioactive compounds, diterpenoids [6, 7], sesquiterpenoids [8–10], flavonoids [11–13], alkaloids [14–16], coumarins [15, 16], furans [17, 18], and the like, had been identified from this plant. Furan derivatives are an important class of secondary metabolites containing a five-membered ring and oxygen as heteroatom. This group of compounds can be found naturally in plants, algae, and microbes [19, 20]. The structure–activity relationships for furan derivatives have generated wide interest among medicinal chemists because they possess a diverse set of properties that allow a wide range of applications in medicine [21, 22]. In our continuing efforts to utilize N. tabacum and identify bioactive natural products, the phytochemistry investigation of the leaves of Yunyan-210 tobacco (a variety of N. tabacum widely cultivated in China) led to the isolation of two new (1, 2) and three known (3–5) furan-2-carboxylic derivatives. This paper deals with the isolation, structural elucidation, and anti-TMV activities of these compounds. HO
3
7
MeO 16
5
9 11
14
OMe
13
HO O 1
15
R 1, 2
MeO
MeO O
COOMe 12
HO
HO
3
O
COOMe
COOH
4
O
COOH
5
1: R = H; 2: R = OH
1) School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, 650500, Kunming, P. R. China, e-mail: [email protected]; 2) Key Laboratory of Tobacco Chemistry of Yunnan Province, China Tobacco Yunnan Industrial Co., Ltd., 650231, Kunming, P. R. China, e-mail: [email protected]; 3) Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, 650031, Kunming, P. R. Chi
Data Loading...
