Dihydrostilbenes and flavonoids from whole plants of Jacobaea vulgaris

Shinae Lee; Min-Gyung Son; Young-Mi Kim; Chae-Yeong An; Hyun Ji Kim; Piseth Nhoek; Pisey Pel; Hongic Won; Yoonkyung Lee; Narae Yun; Jin-Hyub Paik; Badamtsetseg Bazarragchaa; Hyun Woo Kim; Young Hee Choi; Won Keun Oh; Chang Hoon Lee; Young-Won Chin

doi:10.1016/j.phytochem.2024.114107

Dihydrostilbenes and flavonoids from whole plants of Jacobaea vulgaris

Phytochemistry. 2024 Jun:222:114107. doi: 10.1016/j.phytochem.2024.114107. Epub 2024 Apr 23.

Authors

Shinae Lee¹, Min-Gyung Son¹, Young-Mi Kim¹, Chae-Yeong An¹, Hyun Ji Kim², Piseth Nhoek¹, Pisey Pel¹, Hongic Won¹, Yoonkyung Lee³, Narae Yun⁴, Jin-Hyub Paik⁵, Badamtsetseg Bazarragchaa⁶, Hyun Woo Kim², Young Hee Choi², Won Keun Oh¹, Chang Hoon Lee², Young-Won Chin⁷

Affiliations

¹ Natural Products Research Institute and Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 08826, Republic of Korea.
² College of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Gyeonggi-do, 10326, Republic of Korea.
³ Plant Resources Division, National Institute of Biological Resources, Incheon, 22689, Republic of Korea.
⁴ Department of Botany, Honam National Institute of Biological Resources, Mokpo, 58762, Republic of Korea.
⁵ International Biological Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Daejeon, 34141, Republic of Korea.
⁶ Natural History Museum of Mongolia, Ulannbaatar 15141, Mongolia.
⁷ Natural Products Research Institute and Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 08826, Republic of Korea. Electronic address: [email protected].

PMID: 38663823
DOI: 10.1016/j.phytochem.2024.114107

Abstract

The isolation of previously undescribed 12 compounds from the MeOH extract of Jacobaea vulgaris whole plants is disclosed, comprising 11 dihydrostilbenes (1-11) and one flavanone (12), and eight known compounds (six flavonoids, one dihydrostilbene, and one caffeoylquinic acid). Structural elucidation employed spectroscopic methods, including 1D and 2D NMR spectroscopy, HRESIMS, and ECD calculations. Evaluation of the compounds' effects on PCSK9 and LDLR mRNA expression revealed that compounds 1 and 3 downregulated PCSK9 mRNA while increasing LDLR mRNA expression, suggesting potential cholesterol-lowering properties.

Keywords: Asteraceae; Dihydrostilbenes; Flavonoids; Jacobaea vulgaris; LDLR; PCSK9.

MeSH terms

Flavonoids* / chemistry
Flavonoids* / isolation & purification
Flavonoids* / pharmacology
Humans
Molecular Structure
Proprotein Convertase 9 / genetics
Proprotein Convertase 9 / metabolism
RNA, Messenger / genetics
RNA, Messenger / metabolism
Receptors, LDL / metabolism
Stilbenes* / chemistry
Stilbenes* / isolation & purification
Stilbenes* / pharmacology

Substances

Flavonoids
Stilbenes
Proprotein Convertase 9
Receptors, LDL
PCSK9 protein, human
LDLR protein, human
RNA, Messenger