Sesquiterpenoids with diverse carbon skeletons from the roots of Cichorium glandulosum and their anti-inflammatory activities

  • Fitoterapia. 2019 Jul;136:104170. doi: 10.1016/j.fitote.2019.104170.
Ting Dang  1 ,  Guijuan Zheng  2 ,  Qihua Zhang  2 ,  Pengfei Jin  2 ,  Hanqi Zhang  2 ,  Linjie Su  3 ,  Dongmei Qin  4 ,  Guangmin Yao  5
Affiliations
  • 1. Key Laboratory of Xinjiang Phytomedicine Resource and Utilization, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832000, People's Republic of China; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
  • 2. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
  • 3. Key Laboratory of Xinjiang Phytomedicine Resource and Utilization, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832000, People's Republic of China.
  • 4. Key Laboratory of Xinjiang Phytomedicine Resource and Utilization, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832000, People's Republic of China. Electronic address: [email protected].
  • 5. Key Laboratory of Xinjiang Phytomedicine Resource and Utilization, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832000, People's Republic of China; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. Electronic address: [email protected].
PMID: 31085308 DOI: 10.1016/j.fitote.2019.104170
Abstract

A total of thirteen sesquiterpenoids with diverse skeletons including four new sesquiterpenoids, glandulosines A - D (1-4), a new natural product, glandulosine E (5), and eight known sesquiterpene lactones (6-13) were isolated from the roots of Cichorium glandulosum Boiss. et Huet (Asteraceae). Their structures were determined by extensive spectroscopic experiments including NMR, electronic circular dichroism (ECD), calculated ECD, Rh2(OCOCF3)4-induced ECD, and single-crystal X-ray diffraction analysis, as well as chemical methods. This is the first report of the crystal structure of 11β,13-dihydrolactucin (11). Thirteen isolated sesquiterpenoids (1-13) were evaluated for their anti-inflammatory activities in vitro, and three guaiane sesquiterpene lactones, glandulosine E (5), scorzoside (9), and lactucin (10) showed moderate inhibitory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages.

Keywords
Anti-inflammatory activity; Cichorium glandulosum Boiss. et Huet (Asteraceae); ECD calculation; Rh(2)(OCOCF(3))(4)-induced ECD; Sesquiterpenoids.
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