Comprehensive analysis of phenolic compounds from Solanum glaucophyllum Desf. including the new glaucophylloside

Although Solanum glaucophyllum Desf. (SG) has been in the focus of scientific interest since the late 1960s, mainly due to its known calcinogenic properties, the plant has been very little studied from a phytochemical point of view. Actually, only 8 phenolic glycosides, such as avicularin, quercetin-rutinoside and quercetin-apiosyl-rutinoside, have been described in the literature. [ 1 ] The aim was therefore to comprehensively isolate, identify and quantify phenolic compounds. First, a crude extract was prepared from dried leaf material. With different reversed-phase chromatography systems 3 novel compounds for SG were isolated. These were unequivocally identified by HR-MS and 2D-NMR as 3/4- O -p-coumaroylglucaric acid, 3/4- O -caffeoylglucaric acid and 3- O -caffeoylquinic acid. LC-MS/MS experiments led to the detection of a total of 16 glucaric acid and 6 quinic acid derivatives. These were subsequently quantitated using commercial reference standards or isolated pure substances in MRM mode. Furthermore, a total of 5 quercetin derivatives was isolated from the crude extract. The structures of two novel compounds were elucidated after permethylation of the target fraction and subsequent separation by normal phase chromatography. 7- O -β-glucosyl-rutin (1) was novel in SG, while 7-O-β-glucosyl-apiosyl-rutin (Glaucophylloside, 2) ([ Fig. 1 ]) was described for the first time in literature. Fig. 1 Structure of 7- O -beta-glucosyl-rutin (1) and glaucophylloside (2) The independent synthesis of authentic reference material (1- O -caffeoyl-, 3- O -caffeoyl- and 3- O -feruloyl-β-glucoside) led to the identification and quantification of 5 cinnamic acid glucosides. In summary, 33 phenolic compounds were quantitated in SG and 29 of these substances were detected in this plant for the first time. Thus, the phytochemical spectrum of SG was considerably expanded with this work. [ 2 ] Publication History Article published online: 05 March 2026 © 2026. Thieme. All rights reserved. Georg Thieme Verlag KG Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany