Chemical Relationships between Liverworts of the Family Lejeuneaceae (Porellales, Jungermanniopsida)

Abstract

The major purpose of this study was to determine the chemical relationships between liverwort species belonging to the Lejeuneaceae family on the basis of sesqui-and diterpenoid composition. GC/MS analysis of the 31 liverwort specimens belonging to the Lejeuneaceae family indicated variability of the chemical composition of terpenoids depending on liverwort species. Each of the analyzed liverworts is characterized by the presence of particular compounds. However, there are some characteristic components, which can be chemical markers of this liverwort family. These are the pinguisane and monocyclofarnesane type sesquiterpenoids, the fusicoccane type diterpenoids, and also the sesquiterpene hydrocarbon, isolepidozene. Chemical data also showed the differences among liverworts classified in the two subfamilies, the Ptychanthoideae and Lejeuneoideae. All of the mentioned characteristic components are present in species of the subfamily Ptychanthoideae. On the other hand, among the characteristic components, only -pinguisene was detected in Cololejeunea stotleriana, Colura irrorata, and Myriocoleopsis gymnocolea classified in the subfamily Lejeuneoideae (subtribe Cololejeuneinae). The latter component was found to be a marker for members of the subtribe Cololejeuneinae. Neither isolepidozene nor the pinguisanes, fusicoccanes and monocyclofarnesanes were found in Lejeunea topoensis (subfamily Lejeuneoideae). The existence of the chemical polymorphism between both subfamilies is also evident from PCA analysis.

Chemical Originalities of New Caledonian Liverworts from Lejeuneaceae Family

“…Monocyclofarnesane sesquiterpenes from the striatene group were previously detected only in the Ptychantoideae [3]. We detected here the presence of three striatene derivatives, and particularly striatol (13), as a major compound of two Cheilolejeunea species (C. germanii and C. intertexta) that belong to the Lejeunoideae group.…”

“…Classification of genus and species inside these subfamilies is considered complicated, especially because of the morphological plasticity of the Lejeuneaceae. In this context, chemical analysis of terpenoids contained in oil bodies of the liverworts is considered as an efficient method to elaborate the phylogeny of this group [2,3]. However, only few Lejeuneaceae species have been studied yet for their chemical content.…”

Fingerprinting of Secondary Metabolites of Liverworts: Chemosystematic Approach

“…Each of the analyzed liverworts was characterized by the presence of particular compounds; however, there were some characteristic components that can be used as chemical markers of this liverwort family. These were the pingiusane (14, 121-127) and monocyclofarnesane (128, 129) type sesquiterpenoids, and the fusicoccane (131-133) type diterpenoids, together with the sesquiterpene hydrocarbon, isolepidozene (130), Table 2 (40). All of the mentioned characteristic components were present in the subfamily Ptychanthoideae.…”

“…, herbertane dimers(27,28), tridensanes(29), ricciocarpanes(30,31), modified pacifigorgianes(32,33), pinguisanes(13,14), pinguisane dimers(34)(35)(36), neotrifaranes (37), chenopodanes(38,39), and riccardiphanes(40)(41)(42), among others (15;Figures 2 and 3).The second group of the components widely represented in liverworts are diterpenoids. Compounds of spiroclerodane(43,44), 5,10-seco-clerodane (45, 46), 9,10-seco-clerodane(47, 48), epi-homoverrucosane(49, 50), fusicoccanelabdane dimers (51), fusicoccane-aromadendrane dimers (52), fusicoccane-bibenzyl dimers (53), seco-infuscane (54), infuscane (55), abeo-labdane (56-59), sacculatane(11,12), hatcherane (60), and sphenolobane (61, 62) types are representative of diterpenoids found only in the liverworts.…”

GC/MS Fingerprinting of Solvent Extracts and Essential Oils Obtained from Liverwort Species

“…The contents of the oil bodies of the Marchantiophyta are easily extracted with solvents using ultrasonic apparatus, to obtain extracts, and by steam or hydrodistillation to receive essential oils. Gas chromatographic profiling of the volatile extracts and as well as from essential oils received from the liverworts has been applied in differentiating liverworts species and chemotypes within species [3,[18][19][20][21][22]. There are also a few comprehensive reviews, which are dealing with the use of liverwort components in chemosystematic studies [2,5,6,16,23].…”