Acylated Cyanidin 3,7-Diglucosides in the Red-purple Flowers of <i>Sophronitis wittigiana</i> (Orchidaceae)

• Tatsuzawa Fumi

  Faculty of Agriculture, Iwate University

• Saito Norio

  Meiji-Gakuin University

• Yukawa Tomohisa

  Tsukuba Botanical Garden, National Science Museum

• Honda Toshio

  Faculty of Pharmaceutical Sciences, Hoshi University

• Shinoda Koichi

  NARO Hokkaido Agricultural Research Center

• Kato Kazuhisa

  Faculty of Agriculture, Iwate University

• Miyoshi Kazumitsu

  Faculty of Horticulture, Chiba University

Bibliographic Information

Other Title

• 赤紫色花のソフロニチス ウィッチジアナ（ラン科）から単離されたアシル化シアニジン3,7- ジグルコシド
• Acylated Cyanidin 3,7-Diglucosides in the Red-purple Flowers of Sophronitis wittigiana (Orchidaceae)

Abstract

Three new acylated cyanidin 3,7-diglucosides (1–3) were isolated from the red-purple flowers of Sophronitis wittigiana as its main floral anthocyanins. These three pigments were based on cyanidin 3,7-diglucoside as the deacylanthocyanin, and their structures were determined to be cyanidin 3-O-[6-O-(malonyl)-β-glucopyranoside)]-7-O-[6-O-(trans-caffeoyl)-β-glucopyranoside] as pigment 1, its demalonyl anthocyanin as pigment 2, and cyanidin 3-O-[6-O-(malonyl)-glucoside]-7-O-glucoside as pigment 3 by chemical and spectroscopic methods. On the other hand, five known acylated cyanidin 3,7,3′-triglucosides (4–8) were isolated from orange-red or red flowers of S. acuensis, S. brevipedunculata, S. cernua, S. coccinea var. xanthoglossa, and S. grandiflora as well as those of S. coccinea, and identified to be pigment 4 as Sophronitis coccinea anthocyanin 1 (SCA 1), pigment 5 as SCA 2, pigment 6 as SCA 3, pigment 7 as SCA 4, and pigment 8 as SCA 5 in comparison of the TLC, HPLC, and UVVis properties with standard samples of SCAs 1–5. These results showed that the three 3,7,3′-O-hydroxy groups of anthocyanins were all substituted with acylglucose and/or glucose residues in the orange-red or red flowers of six taxa of Sophronitis, whereas the 3′-O-hydroxy group was free from glucose in the red-purple flowers of S. wittigiana. Thus, the inactivation of 3′-O-glycosylation in cyanidin units might be involved in causing the blue color direction shift from orange-red or red to red-purple flower color of S. wittigiana.

Journal

• Journal of the Japanese Society for Horticultural Science

  Journal of the Japanese Society for Horticultural Science 83 (1), 64-71, 2014

  THE JAPANESE SOCIETY FOR HORTICULTURAL SCIENCE

Keywords

• acylated cyanidin 3,7-diglucoside
• Orchidaceae
• red-purple flower color
• <i>Sophronitis wittigiana</i>

Details

• CRID: 1390282680266664192
• NII Article ID: 40019948948
• NII Article ID: 130004510810
• NII Book ID: AA12177046
• DOI: 10.2503/jjshs1.ch-084
• COI: 1:CAS:528:DC%2BC2cXltFKiu70%3D
• ISSN: 1882336X
• ISSN: 18823351
• NDL BIB ID: 025159411
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I025159411
• Web Site: https://www.jstage.jst.go.jp/article/jjshs1/83/1/83_CH-084/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed