Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Phytochemistry. 2017 Aug;140:174-180. doi: 10.1016/j.phytochem.2017.04.025.
Epub  2017 May 24.

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

Kroll-Møller P(1), Pedersen KD(1), Gousiadou C(1), Kokubun T(2), Albach D(3), 
Taskova R(4), Garnock-Jones PJ(4), Gotfredsen CH(1), Jensen SR(5).

Author information:
(1)Department of Chemistry, The Technical University of Denmark, Build. 207, 
DK-2800, Lyngby, Denmark.
(2)Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3AB, UK.
(3)Institut für Biologie und Umweltwissenschaften, Carl von 
Ossietzky-Universität Oldenburg, 26111, Oldenburg, Germany.
(4)School of Biological Sciences, Victoria University of Wellington, P.O. Box 
600, Wellington, 6140, New Zealand.
(5)Department of Chemistry, The Technical University of Denmark, Build. 207, 
DK-2800, Lyngby, Denmark. Electronic address: srj@kemi.dtu.dk.

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-benzoyl-3-α-glucuronosylglycerol, and 
1-O-β-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.

Copyright © 2017 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2017.04.025
PMID: 28550715 [Indexed for MEDLINE]


2. Front Pharmacol. 2017 May 1;8:232. doi: 10.3389/fphar.2017.00232. eCollection 
2017.

In Vitro and In Silico Antidiabetic and Antimicrobial Evaluation of Constituents 
from Kickxia ramosissima (Nanorrhinum ramosissimum).

Amin A(1), Tuenter E(1), Foubert K(1), Iqbal J(2), Cos P(3), Maes L(3), Exarchou 
V(1), Apers S(1), Pieters L(1).

Author information:
(1)Laboratory of Natural Products and Food Research and Analysis, Department of 
Pharmaceutical Sciences, University of AntwerpAntwerp, Belgium.
(2)Centre for Advanced Drug Research, COMSATS Institute of Information 
TechnologyAbbottabad, Pakistan.
(3)Laboratory of Microbiology, Parasitology and Hygiene, Faculty of 
Pharmaceutical, Biomedical and Veterinary Sciences, University of 
AntwerpAntwerp, Belgium.

Background and Aims:Kickxia ramosissima (Wall.) Janch (or Nanorrhinum 
ramosissimum (Wall.) Betsche is a well-known medicinal plant in Pakistan that is 
traditionally used in diabetic and inflammatory conditions. Because little 
information is available on its phytochemical composition, a range of 
constituents were isolated and evaluated in vitro in assays related to the 
traditional use. Methods: Dried whole plant material was extracted and 
chromatographically fractionated. Isolated constituents were evaluated in silico 
and in vitro in assays related to the traditional use against diabetes 
(inhibition of α-glucosidase activity; inhibition of advanced glycation 
endproducts) and in inflammatory conditions (inhibition of AAPH induced linoleic 
acid peroxidation, inhibition of 15-LOX, antimicrobial activity). Results: 
Phytochemical analysis of the extracts and fractions led to isolation of 7 
compounds, including the iridoids kickxiasine (being a new compound), 
mussaenosidic acid, mussaenoside and linarioside; the flavonoids 
pectolinarigenin and pectolinarin; and 4-hydroxy-benzoic acid methyl ester. The 
iridoids showed weak antiglycation activity. The flavonoids, however, showed 
interesting results as pectolinarigenin was highly active compared to 
pectolinarin. In the α-glucosidase inhibition assay, only weak activity was 
observed for the iridoids. However, the flavonoid pectolinarigenin showed good 
activity, followed by pectolinarin. In the 15-LOX experiment, moderate 
inhibition was recorded for most compounds, the iridoids mussaenosidic acid and 
mussaenoside being the most active. In the AAPH assay, weak or no inhibition was 
recorded for all compounds. The in silico assays for the α-glucosidase and 
15-LOX assays confirmed the results of respective in vitro assays. 
Pectolinarigenin showed moderate antimicrobial activity against Staphylococcus 
aureus, Plasmodium falciparum K1, and Trypanosoma cruzi, but it was not 
cytotoxic on a human MRC-5 cell line. Conclusion: Our findings may in part 
contribute to explain the traditional use of K. ramosissima.

DOI: 10.3389/fphar.2017.00232
PMCID: PMC5410595
PMID: 28507520


3. Phytochemistry. 2017 May;137:72-80. doi: 10.1016/j.phytochem.2017.02.013. Epub
 2017 Feb 21.

Research survey on iridoid and phenylethanoid glycosides among seven populations 
of Euphrasia rostkoviana Hayne from the Alps.

Mari A(1), Ciocarlan A(2), Aiello N(3), Scartezzini F(3), Pizza C(1), D'Ambrosio 
M(4).

Author information:
(1)Dipartimento di Farmacia, Università degli Studi di Salerno, 84084 Fisciano 
(SA), Italy.
(2)Laboratory of Bioorganic Chemistry, Department of Physics, Università degli 
Studi di Trento, 38123 Trento, Italy.
(3)Council for Agricultural Research and Economics, Forest Monitoring and 
Management Research Unit, 38123 Trento, Italy.
(4)Laboratory of Bioorganic Chemistry, Department of Physics, Università degli 
Studi di Trento, 38123 Trento, Italy. Electronic address: 
michele.dambrosio@unitn.it.

The traditional use of extracts of Euphrasia rostkoviana to relieve ocular 
inflammation or infections is well documented and supported by clinical studies. 
Various classes of chemical compounds such as iridoids, phenylethanoids, 
flavonoids and hydroxycinnamic acids have been reported. The present work aims 
to assess the chemical diversity among seven populations of Euphrasia 
rostkoviana found in northern Italy. A meticulous separation of components led 
to the isolation and structural characterization of two previously unrecorded 
phenylethanoids methoxycrassifolioside and deoxycrassifolioside and one 
previously undescribed terpene glucoside 
(1E,6E)-8-hydroxy-3,7-dimethyl-octa-1,6-dienyl 1-O-β-D-glucopyranoside. We have 
also identified known phenylethanoids and iridoids that are reported in this 
genus for the first time. Finally, a targeted quantitative analysis for the 
standardization of herbal preparations revealed that iridoids occur in all 
populations whereas the presence and the levels of rutin and phenylethanoids are 
highly variable.

Copyright © 2017 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2017.02.013
PMID: 28233528 [Indexed for MEDLINE]


4. Nat Prod Res. 2016 Aug;30(15):1698-705. doi: 10.1080/14786419.2015.1136307.
Epub  2016 Feb 1.

Secoiridoids and other chemotaxonomically relevant compounds in Pedicularis: 
phytochemical analysis and comparison of Pedicularis rostratocapitata Crantz and 
Pedicularis verticillata L. from Dolomites.

Venditti A(1)(2), Frezza C(2), Sciubba F(1), Foddai S(2), Serafini M(2), 
Nicoletti M(2), Bianco A(1).

Author information:
(1)a Dipartimento di Chimica , Sapienza Università di Roma , Roma , Italy.
(2)b Dipartimento di Biologia Ambientale , Sapienza Università di Roma , Roma , 
Italy.

We compared the respective metabolite patterns of two Pedicularis species from 
Dolomites. Seven phenylethanoid glycosides, i.e., verbascoside (1), echinacoside 
(2), angoroside A (3), cistantubuloside B1 (4), wiedemannioside C (5), 
campneoside II (11) and cistantubuloside C1 (12), together with several iridoid 
glucosides as aucubin (6), euphroside (7), monomelittoside (8), mussaenosidic 
acid (9) and 8-epiloganic acid (13) were identified. Pedicularis verticillata 
showed also the presence of greatly unexpected secoiridoids, ligustroside (14) 
and excelside B (15), very rare compounds in Lamiales. Both PhGs and iridoids 
are considered of taxonomical relevance in the Asteridae and their occurrence in 
Pedicularis was discussed. In particular, the exclusive presence of several 
compounds such as 8-epiloganic acid (13), campneoside II (11), cistantubuloside 
C1 (12), ligustroside (14) and excelside B (15) in Pedicularis rostratocapitata, 
and angoroside A (3), cistantubuloside B1 (4) and wiedemannioside C (5) in P. 
verticillata could be considered specific markers for the two botanical 
entities.

DOI: 10.1080/14786419.2015.1136307
PMID: 26828611 [Indexed for MEDLINE]


5. Nat Prod Res. 2016;30(3):327-31. doi: 10.1080/14786419.2015.1060230. Epub 2015
 Jul 24.

Iridoids and phenylethanoid from Pedicularis kerneri Dalla Torre growing in 
Dolomites, Italy.

Venditti A(1)(2), Frezza C(2), Serafini M(2), Bianco A(1).

Author information:
(1)a Dipartimento di Chimica , Sapienza Università di Roma , P.le A. Moro 5, 
00185 Roma , Italy.
(2)b Dipartimento di Biologia Ambientale , Sapienza Università di Roma , P.le A. 
Moro 5, 00185 Roma , Italy.

In this study, we report the first phytochemical analysis of polar fraction of 
Pedicularis kerneri Dalla Torre growing in Dolomites, Italy. Several iridoid 
glucosides were isolated, namely aucubin (1), monomelittoside (2), 
plantarenaloside (3), euphroside (4), mussaenosidic acid (5) and 8-epiloganic 
acid (6), showing a composition in accordance with previous study on this genus. 
The studied samples, collected from Dolomites, presented a chemotype already 
recognised in species from North America, characterised by euphroside (4) and 
aucubin (1) as main components, but the main character was the presence of 
monomelittoside (2) never reported in this genus. The identification of 
verbascoside (7), leucosceptoside A (9) and echinacoside (10) complete the 
systematic framing of this species since is ascertained the co-occurrence of 
phenylethanoid glycosides with iridoids in Lamiales species.

DOI: 10.1080/14786419.2015.1060230
PMID: 26207992 [Indexed for MEDLINE]