Nedjalka Handjieva

Iridoid glucosides from three Veronica species

Abstract A new iridoid glucoside, 6′-O-menthiafoloylmussaenosidic acid, was isolated from the methanolic extract of Veronica bellidioides along with 11 known iridoid glucosides and the aromatic glucosides, picein and 4-O-glucopyranosylzingeron. The structure of the new iridoid was elucidated on the basis of its spectral data. Geniposidic acid and 4-O-glucopyranosylzingeron were found for the first time in the genus Veronica and verminoside in V. bellidioides. Nine known iridoids of which the major ones were mussaenoside and aucubin were found in V. alpina, and nine known iridoids with amphicoside as the major one were found V. kellererii.

Iridoid glucosides from Plantago cornuti, Plantago major and Veronica cymbalaria

Abstract The new iridoid glucoside from the rare Δ8,9 type, 10-acetoxymajoroside, was isolated from Plantago cornuti and P. major along with known iridoids. The main constituents in V. cymbalaria were the known catalpol, amphicoside and verproside together with alpinoside, aucubin, 6-O-veratroylcatalpol and verminoside. The iridoid alpinoside with a 8,9-double bond was found for the first time in genus Veronica.

Iridoid glucosides of the genus Veronica s.l. and their systematic significance

Abstract. 16 iridoid glucosides and 3 aromatic compounds were isolated from Bulgarian natural populations of Veronica L. and Pseudolysimachion Opiz species. The distribution of 11 compounds in 34 species (96 samples) was shown. Seven Veronica and Pseudolysimachion species were screened for iridoids for the first time and a phenylethanoid glycoside, calceolarioside C, was found for the first time in the genus Veronica. The systematic significance of iridoid glucosides at subspecies, species, sectional, and generic levels is discussed. A correlation between the chemical characters (iridoids and flavonoids) and the chromosome base numbers of the perennial Veronica species was established. Origin of the annual species from the perennials through two evolutionary lines was supposed.

Triterpene saponins and iridoid glucosides from Galium rivale

Three new glycosides of the oleanene-type triterpenes, rivalosides C-E (1-3), along with three known triterpene saponins, momordin IIb (4) and rivalosides A-B (5-6), and five known iridoid glucosides: monotropein, scandoside, deacetylasperulosidic acid, geniposidic acid and asperulosidic acid, were isolated from aerial parts of Galium rivale. The structures of the new compounds were elucidated by spectral methods and chemical means as 2alpha-acetoxy-3alpha, 19alpha-dihydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranosyl-(1--> 6)-beta-D-glucopyranoside, 2alpha,3alpha, 19alpha-trihydroxy-olean- 12-en-28-oic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranoside and 3-O-beta-D-glucuronopyranosyl-24-hydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranoside, for rivalosides C-E, respectively. The taxonomic significance of the rivalosides in G. rivale was discussed.

Constituents of Essential Oils from Nepeta cataria L., N. grandiflora M.B. and N. nuda L.

ABSTRACT Essential oils from Bulgarian populations of Nepeta nuda L. and N. cataria L. (two origins) and of the Caucasian endemic N. grandiflora M.B. (Lamiaceae) were analyzed by GC/MS, TLC and chemical transformation. Iridoids of the nepetalactone type were the main constituents, accompanied by other terpenoids. Some of the constituents were found for the first time in the genus Nepeta from natural sources.

Iridoid patterns of genus Plantago L. and their systematic significance

The distribution of 14 iridoid glucosides in 14 Plantago L. species (44 samples corresponding to 18 taxa) was shown. P. tenuiflora and P. gentianoides were studied for iridoids for the first time. The iridoid patterns showed a good correlation with morphological and other chemical features of the representatives of genus Plantago. The studied species are grouped together according to the iridoid patterns: species containing mainly aucubin (P. major, P. cornuti, P. gentianoides); species containing aucubin and aucubin derivatives (P. subulata, P. media); species containing aucubin and catalpol (P. lanceolata, P. altissima, P. argentea, P. lagopus, P. atrata); species containing aucubin and plantarenaloside (P. afra, P. scabra).

Iridoid glycosides from Linaria species

Abstract The iridoid composition of four Liniria species has been investigated. Two new iridoids along with known compounds were isolated and identified. The new iridoid glucoside, 7,8-epi-antirrinoside, found in L. dalmatica, is the first iridoid glucoside with an α-orientation of the 7,8-epoxide ring, while 6β-hydroxyantirride, found in L. genistifolia and L. peloponnesiaca, appears as a second representative of the rare antirride iridoid type. Antirride was found for the first time in L. simplex. Structure elucidations were carried out mainly by spectral methods and molecular mechanics calculations. Chemosystematic relationships are also discussed.

Comparative Analysis of the Composition of Flower Volatiles from Lamium L. Species and Lamiastrum galeobdolon Heist. ex Fabr.

Abstract The volatiles of fresh flowers from nine natural populations of four Lamium species and Lamiastrum galeobdolon were analyzed by GC/MS. 49 compounds, 43 of them new for Lamium and Lamiastrum, were identified. The studied samples showed similarity of the volatile profiles and dependence of the oil-composition on the collection site. Significant amounts of squalene were found in all samples. The presence of homological series of straight chain alkanes from C12 to C31 was shown. Phenethyl alcohol was found only in L. maculatum f. alba.

Iridoid glucosides from Galium album and G. lovcense

Abstract The iridoid composition of Galium album ssp. album, G. album ssp. pychnotrichum and G. lovcense was studied. Eleven known iridoids were isolated and identified. Two new iridoids, 7- O -acetyl-10-acetoxyloganin and 7β-hydroxy-11-methyl forsythide, were isolated from G. lovcense , and their structure elucidated.

Iridoid glucosides from Linaria vulgaris

Abstract Two new antirrinoside derivatives, 6- O - trans - p -coumaroyl antirrinoside and 6- O - cis - p -coumaroyl-antirrinoside, have been isolated from aerial parts of Linaria vulgaris . In addition, antirrinoside and procumbide have been isolated. Procumbide has been found for the first time in Scrophulariaceae.