Flavonoids in the flowers of Primula ×polyantha Mill. and Primula primulina (Spreng.) H. Hara (Primulaceae). (September 2021)

• Record Type: Journal Article
• Authors: Tatsuzawa, Fumi; Mizuno, Takayuki; Kikuchi, Ryo; Kato, Kazuhisa; Ota, Toru; Murai, Yoshinori; Yangzom, Rinchen; Iwashina, Tsukasa
• Is Part Of: Phytochemistry. Volume 189(2021)
• Publication Date: 2021-09
• Subjects: Cyanidin -- Flavonols -- Flower color -- Hirsutidin -- Intermolecular copigmentation -- 7-O-Methyl-anthocyanin -- Peonidin; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2021.112827
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Two undescribed anthocyanins and two undescribed flavonols were isolated from the flowers of Primula × polyantha Mill., along with five known anthocyanins and four known flavonols. The two undescribed anthocyanins and the two undescribed flavonols were determined to be hirsutidin 3- O -β-galactopyranoside-5- O -β-glucopyranoside, 7- O -methyl-petunidin 3- O -β-galactopyranoside-5- O -β-glucopyranoside, quercetin 3- O -β-[(6""-acetylglucopyranosyl)-(1 → 2)-β-glucopyranosyl-(1 → 6)-β-glucopyranoside], and kaempferol 3- O -β-[(6""-acetylglucopyranosyl)-(1 → 2)-β-glucopyranosyl-(1 → 6)-β-glucopyranoside] using chemical and spectroscopic methods. They were also found in the flowers of the Himalayan wild species, Primula primulina (Spreng.) H. Hara except for quercetin 3- O -β-[(6""-acetylglucopyranosyl)-(1 → 2)-β-glucopyranosyl-(1 → 6)-β-glucopyranoside]. The flower color variations of P. × polyantha cultivars, reflected by the hue values (b*/a*) of the colors, were due to the glycosidic patterns in the anthocyanins and their concentrations in the petals. Moreover, in the P. × polyantha cultivars with violet-blue flowers, both the intermolecular copigmentation occurs between hirsutidin 3- O -β-galactopyranoside-5- O -β-glucopyranoside and another flavonol, quercetin 3- O -β-glucopyranosyl-(1 → 2)-β-glucopyranosyl-(1 → 6)-β-glucopyranoside. Moreover, the flower color variation was affected by the pH value. Graphical abstract: Image 1 Highlights: Seven anthocyanins and six flavonols isolated from Primula flowers. Undescribed two anthocyanins and two flavonols identified by spectroscopic methods. Observed color variations caused by glycosidic pattern and anthocyanin concentration. Copigmentation between anthocyanin and flavonol, as well as the pH value caused the violet-blue color.