Caffeic acid ester derivatives and flavonoids of genus Arnaldoa (Asteraceae, Barnadesioideae)

被引:8
作者
Ccana-Ccapatinta, Gari, V [1 ]
Ferreira, Paola L. [2 ]
Groppo, Milton [2 ]
Da Costa, Fernando B. [1 ]
机构
[1] Univ Sao Paulo, Sch Pharmaceut Sci Ribeirao Preto, Lab Pharmacognosy, AsterBioChem Res Team, Av Do Cafe S-N, BR-14040903 Ribeirao Preto, SP, Brazil
[2] Univ Sao Paulo, Dept Biol, Lab Plant Systemat, Fac Philosophy Sci & Letters Ribeirao Preto FFCLR, Av Dos Bandeirantes 3900, BR-14040901 Ribeirao Preto, SP, Brazil
基金
瑞典研究理事会; 巴西圣保罗研究基金会;
关键词
Compositae; Phenylpropanoids; Flavonoids; ACYL-QUINIC ACIDS; TITHONIA-DIVERSIFOLIA; GLYCOSIDES; ASSIGNMENT; SUBFAMILY; CHEMISTRY;
D O I
10.1016/j.bse.2019.103911
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
The phytochemical composition of Arnaldoa species is barely known. In this work, the occurrence of caffeic acid ester derivatives and flavonoids in A. argentea, A. macbrideana and A. weberbaueri was established by liquid chromatography associated to high-resolution mass spectrometry analyses and comparison with data from isolated compounds. The distribution of chlorogenic acids in the genus Arnaldoa is herein described for the first time. The metabolite profile of Arnaldoa species was compared to that of Tithonia diversifolia, a known and rich source of chlorogenic acids and sesquiterpene lactones. In addition to the mono- and dicaffeoyl quinic acids present in T. diversifolia, Arnaldoa species exhibited the mono- and dicaffeoyl tartaric acids. Furthermore, mass features correspondent to that of sesquiterpene lactones present in T. diversifolia were not observed in Arnaldoa species. The chemotaxonomic implications of caffeic acid ester derivatives and flavonoid glycosides, as well as the potential absence of sesquiterpene lactones in the genus Arnaldoa and subfamily Barnadesioideae are discussed.
引用
收藏
页数:4
相关论文
共 29 条
[1]   An Unambiguous Nomenclature for the Acyl-quinic Acids Commonly Known as Chlorogenic Acids [J].
Abranko, Laszlo ;
Clifford, Michael N. .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2017, 65 (18) :3602-3608
[2]  
[Anonymous], 1993, ARNALDOA
[3]   Flavonol glycosides from Eschscholtzia californica [J].
Beck, MA ;
Häberlein, H .
PHYTOCHEMISTRY, 1999, 50 (02) :329-332
[4]   FLAVONOID CHEMISTRY OF BARNADESIOIDEAE (ASTERACEAE) [J].
BOHM, BA ;
STUESSY, TF .
SYSTEMATIC BOTANY, 1995, 20 (01) :22-27
[5]   Regio- and stereoselective synthesis of the major metabolite of quercetin, quercetin-3-O-β-D-glucuronide [J].
Bouktaib, M ;
Atmani, A ;
Rolando, C .
TETRAHEDRON LETTERS, 2002, 43 (35) :6263-6266
[6]   A NEW SUBFAMILY OF THE ASTERACEAE [J].
BREMER, K ;
JANSEN, RK .
ANNALS OF THE MISSOURI BOTANICAL GARDEN, 1992, 79 (02) :414-415
[7]  
Calabria LM, 2007, NAT PROD COMMUN, V2, P277
[8]   Chemistry and medicinal uses of the subfamily Barnadesioideae (Asteraceae) [J].
Ccana-Ccapatinta, Gari V. ;
Monge, Marcelo ;
Ferreira, Paola L. ;
Da Costa, Fernando B. .
PHYTOCHEMISTRY REVIEWS, 2018, 17 (03) :471-489
[9]   Absolute configuration assignment of caffeic acid ester derivatives from Tithonia diversifolia by vibrational circular dichroism: the pitfalls of deuteration [J].
Ccana-Ccapatinta, Gari V. ;
Sampaio, Bruno L. ;
dos Santos, Fernando M., Jr. ;
Batista, Joao M., Jr. ;
Da Costa, Fernando B. .
TETRAHEDRON-ASYMMETRY, 2017, 28 (12) :1823-1828
[10]   Chlorogenic acids and the acyl-quinic acids: discovery, biosynthesis, bioavailability and bioactivity [J].
Clifford, Michael N. ;
Jaganath, Indu B. ;
Ludwig, Iziar A. ;
Crozier, Alan .
NATURAL PRODUCT REPORTS, 2017, 34 (12) :1391-1421