Iridoid glucosides in the genus Veronica (Plantaginaceae) from New Zealand

被引:10
作者
Kroll-Moller, Phillip [1 ]
Pedersen, Katja D. [1 ]
Gousiadou, Chrysoula [1 ]
Kokubun, Tetsuo [2 ]
Albach, Dirk [3 ]
Taskova, Rilka [4 ]
Garnock-Jones, Phil J. [4 ]
Gotfredsen, Charlotte H. [1 ]
Jensen, Soren Rosendal [1 ]
机构
[1] Tech Univ Denmark, Dept Chem, Bldg 207, DK-2800 Lyngby, Denmark
[2] Kew, Royal Bot Gardens, Richmond TW9 3AB, Surrey, England
[3] Carl von Ossietzky Univ Oldenburg, Inst Biol & Umweltwissensch, D-26111 Oldenburg, Germany
[4] Victoria Univ Wellington, Sch Biol Sci, POB 600, Wellington 6140, New Zealand
关键词
Veronica hookeri; Veronica pinguifolia; Plantaginaceae; Iridoid glucosides; Phenylethanoid glycosides; Chemotaxonomy; Molecular phylogeny; CHEMICAL MARKERS; HEBES VERONICA; GLYCOSIDES; PHYLOGENY;
D O I
10.1016/j.phytochem.2017.04.025
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Four simple iridoid glucosides, three known esters of catalpol, seven esters of aucubin, and two phenylethanoids were isolated from Veronica hookeri (syn. Hebe ciliolata; Plantaginaceae). Of these, none of four aromatic (p-methoxybenzoyl, isovanilloyl, veratroyl, caffeoyl) 6-O-esters of aucubin and 6"-O-benzoyl mussaenosidic acid, had been reported from nature before. Similarly, three simple iridoid glucosides, two esters of 6-O-rhamnopyranosylcatapol, and two phenylethanoid glucosides, as well as 1-O-benzoy1-3-alpha-glucuronosylglycerol, and 1-O-beta-benzoyl rutinoside were isolated from Veronica pinguifolia (syn. Hebe pinguifolia). The compound 3"-O-benzoyl-2"-O-caffeoyl 6-O-rhamnopyranosylcatalpol had not been reported previously. The pattern of the structural features of the iridoid glucosides is overlaid onto the latest molecular phylogenetic framework of Veronica sects. Hebe and Labiatoides, and discussed in the context of evolutionary trends. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:174 / 180
页数:7
相关论文
共 24 条
[1]   Phylogeny of Veronica in the Southern and Northern Hemispheres based on plastid, nuclear ribosomal and nuclear low-copy DNA [J].
Albach, Dirk C. ;
Meudt, Heidi M. .
MOLECULAR PHYLOGENETICS AND EVOLUTION, 2010, 54 (02) :457-471
[2]   In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis [J].
Angeles Ramirez-Cisneros, M. ;
Yolanda Rios, Maria ;
Berenice Aguilar-Guadarrama, A. ;
Rao, Praveen P. N. ;
Aburto-Amar, Rola ;
Rodriguez-Lopez, Veronica .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (20) :4505-4508
[3]  
Bayly M., 2006, ILLUSTRATED GUIDE NZ
[4]  
Bentham G., 1848, PRODROMUS SYSTEMATIS, P27
[5]   A glycerol α-d-glucuronide and a megastigmane glycoside from the leaves of Guettarda speciosa L. [J].
Cai, Wen-Hu ;
Matsunami, Katsuyoshi ;
Otsuka, Hideaki ;
Shinzato, Takakazu ;
Takeda, Yoshio .
JOURNAL OF NATURAL MEDICINES, 2011, 65 (02) :364-369
[6]  
Galindez JD, 2001, Z NATURFORSCH C, V56, P513
[7]  
Grayer-Barkmeijer R. J., 1973, BIOCH SYST, V1, P101, DOI [DOI 10.1016/0305-1978(73)90023-9, 10.1016/0305-1978(73)90023-9]
[8]  
Grayer-Barkmeijer R. J, 1979, THESIS
[9]   Unusual iridoid glycosides in Veronica sects. Hebe and Labiatoiides [J].
Jensen, Soren Rosendal ;
Gotfredsen, Charlotte Held ;
Grayer, Renee J. .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2008, 36 (03) :207-215
[10]   Veronica:: Iridoids and cornoside as chemosystematic markers [J].
Jensen, SR ;
Albach, DC ;
Ohno, T ;
Grayer, RJ .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2005, 33 (10) :1031-1047