Pentenyl Coumarins from the Roots and Stems of Nicotiana rustica and their Bioactivity
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PENTENYL COUMARINS FROM THE ROOTS AND STEMS OF Nicotiana rustica AND THEIR BIOACTIVITY
Bing-Biao Cai,1 Qi-Li Mi,1,2 Qian Gao,1 Jing Li,1 Chun-Man Song,1 Xin Liu,1 Yong Xu,1 Jin Wang,1 Guang-Yu Yang,1 Xue-Mei Li,1 Qiu-Fen Hu,1,2 Zhang-Yu Chen,1* and Yin-Ke Li1*
Two new pentenyl coumarins (1 and 2), together with three known pentenyl coumarins (3–5), were isolated from the roots and stems of Nicotiana rustica. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1–5 were tested for their anti-rotavirus activity. The results revealed that compounds 1–5 exhibited potent anti-rotavirus activity with therapeutic index (TI) value in the range of 11.1–15.7. Keywords: Nicotiana rustica, coumarins, anti-rotavirus activity. Nicotiana rustica L. (Solanaceae) is an important economic crop originating from South America and Mexico, and is now widely planted all over the world [1]. In addition to its leaves that are used as auxiliary raw material in the tobacco industry [2, 3], people also use its aerial parts as insecticide, sedative, diaphoretic, anesthetic, and emetic agents in Chinese folk medicines [3, 4]. In previous phytochemical investigations, some bioactive metabolites, such as sesquiterpene [5–7], alkaloids [8–10], phenolic compounds [11, 12], and the like, had been isolated from this plant. The roots and stems of N. rustica are the main by-product in tobacco planting, and the multipurpose utilization of the roots and stems of Nicotiana plants is an interesting topic that has aroused more and more attention [13–15]. Coumarins, also known as benzopyran-2-ones, is an important kind of secondary metabolites found in many high plants and is probably produced by plants as a defense chemical to discourage predation. There is growing interest in coumarins due to their diversity in structural complexity and as promising therapeutic agents with low toxicity [16, 17]. In order to increase the pharmacodynamic value of N. rustica, our group has investigated the chemical constituents of the roots and stems of this plants. As a result, two new pentenyl coumarins (1 and 2), together with three known pentenyl coumarins (3–5), were isolated from this plant. Here, the isolation, structure elucidation, and anti-rotavirus activity of compounds 1–5 are described. OH 2''
4'
1'' 5
1'
4
9
3'
3
RO
7
10
O
2
5'
O
1, 2
O 3
OMe
O
HO
O OH
O
4
O
O
O
5
1: R = Me; 2: R = H
1) Key Laboratory of Tobacco Chemistry of Yunnan Province, China Tobacco Yunnan Industrial Co., Ltd., 650231, Kunming, P. R. China, e-mail: [email protected]; [email protected]; 2) School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, 650500, Kunming, P. R. China. Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2020, pp. 870–873. Original article submitted December 17, 2019. 1008
0009-3130/20/5606-1008 ©2020 Springer Science+Business Media, LLC
TABLE 1. 1H (500 MHz) and 13C (125 MHz) NMR Data of Co
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