Procyanidins and Phlobatannins from the Twigs of Rosa multiflora and Their Neuroprotective Activity

  • J Nat Prod. 2022 Apr 22;85(4):917-926. doi: 10.1021/acs.jnatprod.1c01033.
Tae Hyun Lee  1 ,  Seong-Min Hong  2  3 ,  Da Hye Yoon  2  3 ,  Sun Yeou Kim  2  3 ,  Chung Sub Kim  1  4 ,  Kang Ro Lee  1
Affiliations
  • 1. Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
  • 2. Gachon Institute of Pharmaceutical Science, Gachon University, Incheon 21936, Republic of Korea.
  • 3. College of Pharmacy, Gachon University, #191, Hambakmoero, Yeonsu-gu, Incheon 21936, Republic of Korea.
  • 4. Department of Biopharmaceutical Convergence, Sungkyunkwan University, Suwon 16419, Republic of Korea.
PMID: 35263118 DOI: 10.1021/acs.jnatprod.1c01033
Abstract

Three new procyanidins (1-3), two new phlobatannins (6 and 7), a new flavan-3,4-diol glycoside (9), and a new neolignan glycoside (10), along with three previously reported compounds (4, 5, and 8) were isolated from the twigs of Rosa multiflora. The chemical structures of the new compounds (1-3, 6, 7, 9, and 10) were characterized by spectroscopic data interpretation, including NMR (1H and 13C NMR, 1H-1H COSY, HSQC, HMBC, and NOESY) and HRESIMS analysis. Experimental ECD data analysis was conducted to assign the absolute configurations of the new compounds (1-3, 6, 7, 9, and 10). The absolute configuration of the sugar moieties was verified through a chiral derivatization method and LC-MS analysis. All the isolated compounds (1-10) were evaluated for their anti-neuroinflammatory activity based on inhibitory effects on nitric oxide production using a lipopolysaccharide-stimulated murine microglia BV-2 cell line and for their neurotrophic effects on nerve growth factor induction in C6 glioma.