Chemical Constituents from the Flower of Hosta plantaginea with Cyclooxygenases Inhibition and Antioxidant Activities and Their Chemotaxonomic Significance

Abstract

Two new phenolic glucosides, hostaflavanone A (1) and anti-1-phenylpropane-1,2-diol-2-O-β-d-glucopyranoside (2), together with six known compounds, anti-1-phenylpropane-1,2-diol (3), phenethyl-O-β-d-glucopyranoside (4), phenethanol-β-d-gentiobioside (5), phenethyl-O-rutinoside (6), (1S, 3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (7), and (1R, 3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (8), were isolated from the flower of Hosta plantaginea, and their structures were elucidated by nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HRESIMS), and circular dichroism (CD) analyses. The cyclooxygenases (COX-1 and COX-2) inhibition and antioxidant activities of compounds 1 and 4–6 were investigated, and they showed moderate cyclooxygenases inhibition activities. Moreover, only compound 1 exhibited moderate antioxidant activity, with an IC50 value of 83.2 μM, while 4–6 showed insignificant activity with IC50 values of 282, 257, and 275 μM, respectively. This is the first report of compounds 3 and 5–8 from the Liliaceae family. The chemotaxonomic significance of the isolated compounds was also summarized.

Anti-inflammatory and antioxidant activities of flavonoids from the flowers of Hosta plantaginea

“…This study investigated chemically the owers of H. plantaginea and isolated two avonol glycosides, plantanones A (1) and B (2) along with 10 known ones (3)(4)(5)(6)(7)(8)(9)(10)(11)(12).…”

“…8 Previous phytochemical studies on H. plantaginea afforded structurally diverse and biologically active compounds, such as steroids, alkaloids, avonoids and fatty acids, and some of them showed potent anti-inammatory, cytotoxic, antibacterial, antiviral, and antioxidant activities. 7,9 In order to provide more evidence regarding the efficacy and safety of H. plantaginea owers in clinical applications, we investigated the chemical constituents of H. plantaginea owers, which led to the isolation of 12 avonoids, including two new compounds, plantanones A (1) and B (2), together with 10 known ones (3-12) ( Fig. 1).…”

Hosta plantaginea (Lam.) Aschers (Yuzan): an overview on its botany, traditional use, phytochemistry, quality control and pharmacology

“…3). Among them, kaempferol (31) and its derivatives (32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43)(44)(45)(46) as well as quercetin (47) belong to avonols, which are the main active ingredients of H. plantaginea and most of them are avonoid glycosides with 3-and/or 7-linked glycans. In fact, 22 avonoids were isolated and identied from the owers of H. plantaginea by us and in Yu's previous work in 2017-2019.…”

“…In fact, 22 avonoids were isolated and identied from the owers of H. plantaginea by us and in Yu's previous work in 2017-2019. [37][38][39][40][41] This is the rst report on the isolation of avonones and avans from the Liliaceae family. 38…”

Chemical characterization and anti-inflammatory activity of phytoconstituents from Swertia alata

“…with C(1), C(2), C(4), C(23), and C(24), of H-C(9) with C(5), C(8), and C(10), of H-C(12) with C(11), C(13), C(14), and C(18), of H-C(18) with C(13), C(14), C(16), and C(28), and of H-C(22) with C(28), indicated the relative positions of these groups in the molecule SA-1(Figure. 3a).The IR data, Mass fragmentation pattern, 1 H NMR and13 C NMR chemical shifts of the isolated compound SA-1 were comparable with related compound viz, oleanolic acid.…”