Abstract
Two new aryltetralin lactone lignans, petasitesins A and B were isolated from the hot water extract of the leaves of butterbur (Petasites japonicus) along with six known compounds. The chemical structures of lignans 1 and 2 were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Petasitesin A and cimicifugic acid D showed significant inhibitory effects on the production of both prostaglandin E2 (PGE2) and NO in RAW264.7 macrophages. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were inhibited by compound 1 in RAW264.7 cells. Furthermore, compounds 1 and 3 exhibited strong affinities with both iNOS and COX-2 enzymes in molecular docking studies.
Highlights
Petasites japonicus Maxim (Asteraceae), known as butterbur, Japanese butterbur, and giant butterbur, is used as a botanical dietary supplement in the USA
We describe isolation of the secondary nuclear magnetic resonance (NMR) spectroscopic data, and by electronic circular dichroism (ECD) and metabolites from the leaves of(VCD)
Compound 1 was obtained as a dark brownish powder, and its molecular formula was identified as C18 H14 O6 by High resolution electrospray ionization mass spectrometry (HRESIMS) (m/z 325.0714 [M−H]− ; calculated for C18 H13 O6, 325.0712)
Summary
Petasites japonicus Maxim (Asteraceae), known as butterbur, Japanese butterbur, and giant butterbur, is used as a botanical dietary supplement in the USA. The aerial parts of P. japonicus have been used in traditional Japanese folk medicine as an antipyretic, antitussive, or wound healing agent [1]. The constituents of P. japonicus have been reported and include flavonoids [2], sesquiterpenes [3,4,5], triterpenes [6], and various types of phenolic compounds [7]. Biomolecules 2019, 9, 806 aryltetralin lactone lignans (1 and 2) along with six previously known compounds (Figure 1). The chemical structures of the new lignans 1 and 2 were determined by interpretation of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, and by electronic circular dichroism (ECD)
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