Chemotypification of Astrantia major L. (Apiaceae): Essential‐Oil and Lignan Profiles of Fruits

Abstract

The fruit essential oils of two populations of Astrantia major L. (Apiaceae, subfamily Saniculoideae) were analyzed in detail by GC and GC/MS analyses. Seventy-six constituents identified accounted for 92.7-94.0% of the oils. The two oils differed significantly: the wild-growing population from Serbia contained zingiberene (47.9%), β-bisabolene (9.7%), and β-sesquiphellandrene (7.9%), while the one from Poland (botanical gardens) was sesquiterpene-poor with the major contributors oleic acid (38.6%), nonacosane (15.4%), and linoleic acid (5.1%). Motivated by the unresolved taxonomical relations between the Saniculoideae and Apioideae subfamilies, we performed multivariate statistical analyses on the compositional data of these A. major samples, and additional 14 Saniculoideae and 31 Apioideae taxa. This allowed us to assess the chemotaxonomical usefulness of such chemical data in differentiating taxa from these two Apiaceae subfamilies and to corroborate the existence of at least two A. major chemotypes. Diethyl ether extracts of the two samples of A. major fruits yielded seven diaryltetrahydrofurofurano lignans. Except for eudesmin that has been found for the first time in a Saniculoideae taxon, all other lignans (magnolin, epimagnolins A and B, epieudesmin, yangambin, and epiyangambin) are new for the entire plant family Apiaceae. The lignan profiles also supported the existence of two separate A. major chemotypes.

Synthesis of small libraries of natural products: New esters of long‐chain alcohols from the essential oil of Scandix pecten‐veneris L. (Apiaceae)

“…Oil constituents were identified by comparison of their GC retention indices (relative to C 7 -C 33 alkanes [14] on the DB-5MS column) with literature values [15] and their mass spectra with those of authentic standards, as well as those from Wiley 6, NIST11, MassFinder 2.3 and a homemade MS library with the spectra corresponding to pure substances and components of known oils, and wherever possible, by co-injection with an authentic sample.…”

A ‘Low‐Level’ Chemotaxonomic Analysis of the Plant Family Apiaceae: The Case of Scandix balansaeReut. ex Boiss. (Tribe Scandiceae)

“…To fulfill the goal of our study, we have performed MVA of essential-oil composition data for 29 different Scandiceae taxa (59 samples in total) [8 -30], including the currently investigated S. balansae, and 37 taxa from other Apiaceae genera [7], amounting in total to 115 of statistically treated samples. As the MVA input data set quality is crucial for an accurate and reliable study, we decided to perform an analysis of the S. balansae essential-oil sample at hand in as much detail as possible.…”

“…Taking this into account, we performed two separate attempts to reveal the underlying evolutionary trends in the Scandiceae by comparing the available data on Scandiceae among themselves ( Table 2) and afterwards with randomly chosen members of other tribes from the Apiaceae [7]. The results of the first MVA (principal component analysis (PCA) and agglomerative hierarchical clustering (AHC)) are given in Figs.…”

“…As it was suggested in [7], PCA could be used to explore (even hypothetical) biogenic pathways: a quantitative, mathematical relationship following the general linear form between individual compounds in an oil profile would suggest that the biosynthesis of such chemicals is not only closely related, but may involve either the same enzyme system or at least a common intermediate. High coefficients (r !…”

“…þ 0.9) were noted between a number of alkanes, sesquiterpenoids, monoterpenoids, and fatty acids and fatty acid-related compounds. et Kotschy [22] alkanes could be interconnected through the regulation of one or more enzymes that convert fatty acids to alkanes by elongation or decarboxylation/decarbonylation [7]), and hexan-1-ol/(E)-hex-2-enal ( þ 0.974; green leaf volatiles). þ 0.983).…”