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Open AccessArticle

Design and Synthesis of a Compound Library Exploiting 5-Methoxyleoligin as Potential Cholesterol Efflux Promoter

1
Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060 Vienna, Austria
2
Department of Pharmacology, School of Pharmacy, Qingdao University, 308 Ningxia Road, Qingdao 266071, China
3
Department of Pharmacognosy, University of Vienna, Althanstraße 14, 1090 Vienna, Austria
4
Ludwig Boltzmann Institute for Digital Health and Patient Safety, Medical University of Vienna, Spitalgasse 23, 1090 Vienna, Austria
5
Institute of Genetics and Animal Breeding of the Polish Academy of Sciences, Jastrzebiec, 05-552 Magdalenka, Poland
6
Institute of Neurobiology, Bulgarian Academy of Sciences, 23 Acad. G. Bonchev str., 1113 Sofia, Bulgaria
7
Institute of Pharmacy/Pharmacognosy, Center for Molecular Biosciences Innsbruck, University of Innsbruck, Innrain 80/82, 6020 Innsbruck, Austria
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(3), 662; https://doi.org/10.3390/molecules25030662
Received: 17 December 2019 / Revised: 29 January 2020 / Accepted: 30 January 2020 / Published: 4 February 2020
(This article belongs to the Special Issue Lignans II)
5-Methoxyleoligin and leoligin are natural occurring lignans derived from Edelweiss (Leontopodium nivale ssp. alpinum), displaying potent pro-angiogenic and pro-arteriogenic activity. Cholesterol efflux from macrophages is associated with reverse cholesterol transport which inhibits the development of cardiovascular disease. Within this study, we developed a modular and stereoselective total synthesis of 5-methoxyleoligin which can be readily used to prepare a novel compound library of related analogs. The target 5-methoxyleoligin was synthesized exploiting a recently disclosed modular route, which allows also rapid synthesis of analogous compounds. All obtained products were tested towards macrophage cholesterol efflux enhancement and the performance was compared to the parent compound leoligin. It was found that variation on the aryl moiety in 2-position of the furan ring allows optimization of the activity profile, whereas the ester-functionality does not tolerate significant alterations. View Full-Text
Keywords: natural product synthesis; cardiovascular diseases; lignans; macrophage cholesterol efflux natural product synthesis; cardiovascular diseases; lignans; macrophage cholesterol efflux
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MDPI and ACS Style

Linder, T.; Geyrhofer, S.; Papaplioura, E.; Wang, L.; Atanasov, A.G.; Stuppner, H.; Dirsch, V.M.; Schnürch, M.; Mihovilovic, M.D. Design and Synthesis of a Compound Library Exploiting 5-Methoxyleoligin as Potential Cholesterol Efflux Promoter. Molecules 2020, 25, 662.

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