Distribution of diacylglycerylhomoserines, phospholipids and fatty acids in thirteen moss species from Southwestern Siberia

doi:10.1016/0305-1978(95)93660-U

Biochemical Systematics and Ecology

Volume 23, Issue 1, January 1995, Pages 71-78

https://doi.org/10.1016/0305-1978(95)93660-U Get rights and content

Abstract

The total lipids extracted from 13 moss species belonging to nine families collected of southwestern Siberia were examined for their fatty acids by capillary GC-MS. The total lipids from Sphagnum nemoreum, S. squarrosum and Helodium blandowii yielded 2.25, 3.02 and 3.70% (of total fatty acids) as acetylenic acids, respectively. Some unusual acetylenic acids were found, i.e. 8a,11,14–20:3 and 6a,9,12,15–18:4. High levels of 16:1 fatty acid were found. Very long-chain fatty acids (C24–C26) were determined. The quantities of total, neutral, polar and glycolipids were estimated. Quantitative determination of polar lipid not containing phosphorus as diacylglyceryltrimethylhomoserine (DGTS) as performed; this varied from 13.3 to 38.3% of total polar lipids.

References (39)

V.M. Dembitsky
Lipids of bryophytes
Prog. Lipid Res.
(1993)
V.M. Dembitsky et al.
Acetylenic acids of the Dicranaceae
Phytochemistry
(1994)
V.M. Dembitsky et al.
Diacylglyceryltrimethylhomoserines and phospholipids of some green marine macrophytes
Phytochemistry
(1989)
V.M. Dembitsky et al.
Diacylglyceryltrimethylhomoserines and phospholipids of some lichen species
Phytochemistry
(1993)
V.M. Dembitsky et al.
Acetylenic acids and lipid compositions of some mosses from Russia
Phytochemistry
(1993)
V.M. Dembitsky et al.
Polar lipid and fatty acid compositions of some bryophytes
Phytochemistry
(1993)
W. Eichenberger
Distribution of diacylglycyl-O-4′-(N,N,N-trimethyl)homoserine in different algae
Pl. Sci. Lett.
(1982)
C.E. Hansen et al.
Effects of culture conditions on accumulation of arachidonic and eicosapentaenoic acids in cultured cells of Rhytidiadelphus squarrosus and Eurhynchium striatum
Phytochemistry
(1991)
G.R. Jamieson et al.
Gas-liquid chromatography characteristics of some long-chain acetylenic methyl esters
J. Chromatogr
(1976)
G.R. Jamieson et al.
Lipids of Fontinalis antipyretica
Phytochemistry
(1976)

S.V. Khotimchenko et al.

Polar lipids of marine macrophytic algae as chemotaxonomic markers

Biochem. Syst. Ecol.

(1990)

G. Kohn et al.

Distribution and chemotaxonomic significance of acetylenic fatty acids in mosses of the Dicranales

Phytochemistry

(1987)

N. Sato et al.

Distribution of diacylglyceryltrimethylhomoserine in selected species of vascular plants

Phytochemistry

(1984)

N. Sato et al.

Distribution of diacylglyceryltrimethylhomoserine and phosphatydilcholine in nonvascular plants

Pl. Science

(1985)

N. Sato et al.

Analysis and biosynthesis of di-acylglyceryl-N,N,N-trimethylhomoserine in cells of Marchancia in suspension culture

Pl. Sci.

(1988)

P. Sewon

Fatty acyl composition of monogalactosyldiacyl glycerols in bryophyta

Phytochemistry

(1992)

T. Yamada et al.

An unusual lipid in the human pathogenic fungus Epidermophyton floccosum

Biochim. Biophys. Acta

(1979)

R.H. Al-Hasan et al.

Arachidonic and eicosapentaenoic acids in lipids of Bryum bicolor Dicks. Effects of controlled temperature and illumination

Bryologist

(1989)

B. Anderson et al.

9,12,15-Octadecatrien-6-ynoic acid: New acetylenic acid from mosses

Lipids

(1974)

Cited by (30)

Heavy metal stress induces adaptative responses in the liverwort Conocephalum conicum L. (Dum.): An integrated biologic and metabolomic study
2023, Environmental and Experimental Botany
Bioaccumulation, ultrastructural and DNA damage, oxidative stress, and metabolomic analyses were carried out in vitro on the liverwort Conocephalum conicum L. in response to the heavy metal concentrations measured in two sites along the Sarno river (C1 and C2) representative of two different environmental conditions. Bioaccumulation and bioconcentration data confirm C. conicum is a good bioindicator. Our TEM observations showed typically preserved ultrastructure of the chloroplasts in C1 samples, nearly identical to the chloroplasts of the control sample (CTRL; freshly collected and not exposed), whereas in C2 samples they appeared misshaped, swollen and with poorly developed thylakoids in a rather clear stroma. DNA damage, antioxidant enzymatic activity, ROS production and localization showed no difference between CTRL and C1 samples, instead significant differences between C1 and C2 samples. In addition, in this study, we used for the first time the untargeted MS-based molecular networking to examine the role of heavy metal stress in the differential production of the secondary metabolites (SM) in C. conicum. Metabolome analysis evidenced no changes between CTRL and C1 samples, instead a dramatic change in SM production under metal stress conditions, in particular a remodeling of the lipid metabolism through the production of members of betaine and oxidated lipid classes, as well as production of flavonoids was observed. All the occurred variations respond consistently with the heavy metal concentration trend so we can propose them as pollution biomarkers.
Lipidomes of Icelandic bryophytes and screening of high contents of polyunsaturated fatty acids by using lipidomics approach
2023, Phytochemistry
Citation Excerpt :
The major fatty acids present in all species and samples are 16:0, 18:1, 18:2, 18:3, 20:4, and 20:5, and also minor 16:1, 16:2, and 16:3. This is in agreement with most of the previous studies (Beike et al., 2014; Dembitsky and Rezanka, 1995; Hansen Patricia Rossi, 1990). 16:0 is the most common fatty acid in all examined bryophyte species except for samples of R. ericoides 46, Hylocomium splendens 47, and Rhytidiadelphus triquetrus 60, in which the counts of 18:3 surpass 16:0 (Fig. 5).
Bryophytes (mosses, liverworts, and hornworts) have interested researchers because of their high chemical diversity and their potential uses in pharmaceutical, food, and cosmetic industries. Specifically, long-chain polyunsaturated fatty acids (l-PUFA) such as arachidonic acid (AA) and eicosapentaenoic acid (EPA) are commonly found in bryophytes, but not in vascular plants. Bryophytes accumulate PUFAs in cold or even freezing temperature to keep the cell fluidity. Iceland has a long history of bryophyte vegetation. These bryophytes are highly adapted to the harsh environment in Iceland and therefore are expected to produce high amounts of PUFAs. However, despite the fact that hundreds of mosses and liverworts have been found in Iceland, their lipid profiles largely remain unknown. In this study, we performed untargeted lipidomics by using UPLC-ESI-QTOF-MS as a rapid screening strategy to examine the lipid compositions of 39 local bryophyte species in Iceland and aimed to find high AA and EPA producers. A total of 280 lipid molecular species from 15 lipid classes were quantified with isotope-labeled internal standards. AA and EPA were abundantly distributed in the phospholipids (mainly PC and PE) and glycerolipids (MGDG and DGDG) in six moss species, namely Racomotrium lanuginosum, R. ericoides, Bryum psedotriquetrium, Plagiomnium ellipticum, Hylocomium splendens, and Rhytidiadelphus triquetrus. Two of the six species (B. psedotriquetrium and H. splendens) also accumulated high concentrations of PUFA-containing-triacylglycerols.
Epoxy acetylenic lipids: Their analogues and derivatives
2014, Progress in Lipid Research
Citation Excerpt :
Using the lipases from Candida cylindracea and from Candida rugosa, Jie et al. [54] were able to catalyse the release of 10-undecynoic acid and of 9-octadecynoic acid from their corresponding TAG; however, 13-docosynoic acid was less readily released in the case of glycerol tri-(13-docosynoate). Many mosses and liverworts contain acetylenic fatty acids exclusively occurring in TAG or in small amounts in the more polar lipid fraction, i.e., phospho- and/or glycolipids [38,56–67]. Notably, the P. ginseng root has long been used as a medicinal herb in East Asian countries.
Currently, approximately 250 natural acetylenic epoxy structures are known. The present review describes research concerning biologically active epoxy acetylenic lipids and related compounds isolated from different sources. Intensive searches for new classes of pharmacologically potent agents produced by living organisms have resulted in the discovery of dozens of such compounds that possess high anticancer, cytotoxic, antibacterial, antiviral, and other activities. Acetylenic epoxides primarily belong to a class of molecules containing triple bond(s) and epoxy group(s) belonging to different lipid classes and/or other groups. This review emphasises natural and synthetic acetylenic epoxides and other related compounds as important sources of leads for drug discovery. The present review is the first article devoted to natural acetylenic epoxides.
Distribution of polar membrane lipids in permafrost soils and sediments of a small high Arctic catchment
2010, Organic Geochemistry
The distribution of bacteriohopanepolyols (BHPs) and intact polar membrane lipids (IPLs) was studied in different soil profiles and in fluvial and marine sediments along the pathway of transport in a small catchment in the high Arctic at Ny-Ålesund, Svalbard (79°N, 12°E). Both groups of cellular membrane lipids have been used as biomarkers for determining major microbial groups and biogeochemical processes in natural environments. Little is known about their distribution and usefulness as environmental markers in the Arctic. In this study, we show that both membrane lipid groups are variably distributed in the drainage area of the Brøggerbreen Glacier, with highest abundance and diversity in the organic mat overlying the mineral soils, as well as in mossy surface soil. The BHP and IPL composition and abundance both indicate a larger community of phototrophic bacteria in the organic mats and fluvial sediments. The greater diversity and abundance of BHPs relative to IPLs in sub-soils, including probable markers for cyanobacteria, suggest a greater resistance to degradation. In contrast, IPL concentration decreased strongly with soil depth, pointing to their rapid degradation. Bacterial IPLs are thus thought to reflect more reliably the biomass of viable phototrophic bacteria. The high concentrations of proposed soil marker BHPs, adenosylhopane and related structures vs. published results and their relative increase with soil depth suggest better preservation and more effective accumulation of the compounds at low temperature.
Changes in microbial community structure and function following Sphagnum peatland restoration
2010, Soil Biology and Biochemistry
Citation Excerpt :
In fact, we detected the same proportion of fungal PLFA in all our samples, but they could be extracted from different functional groups or different morphological states. One also needs to be cautious when interpreting the relation between mosses and fungi, since the fatty acid 18:2ω6,9 can also be found in some mosses (Dembitsky and Rezanka, 1995) and in some cyanobacteria (Lechevalier and Lechevalier, 1988). Methanogens are another important microbial group found in natural peatlands that are susceptible to vary in relation with vegetation and environmental conditions, but this group is impossible to identify using simple PLFAs extractions (Kaur et al., 2005).
This study examines the recovery of the microbial compartment following active restoration of a North American ombrotrophic peatland extracted for horticultural peat-based substrates and restored by the Sphagnum moss transfer method. We used phospholipid fatty acids (PLFAs) to portrait the microbial community structure and Community Level Physiological Profiles (CLPP) to describe the functional diversity of the microbial communities. Our results indicate that the PLFA profiles were different between the beginning and the end of the growing season, but that it was impossible to distinguish five different vegetation classes found along the disturbance-recovery gradient on the basis of the microbial community structure. The pH, the cover of mosses, Ledum groenlandicum and Eriophorum vaginatum var. spissum were the best environmental predictors for the PLFA composition. The newly formed peat found in aerobic conditions beneath restored Sphagnum carpets had the highest decomposition capacity, whereas the lowest rates were found in the surface samples of non-restored conditions or in the deepest horizons of the natural samples. A large proportion of the variation in the physiological profiles was explained with variables related to the vegetation cover, the physicochemical environment and the microbial structure of the community, which is very promising for future monitoring studies. Overall, this study demonstrates that the recovery of particular plant groups, namely mosses and shrubs in restored peatlands might be the driver of changes occurring in the structure of the microbial communities in restored peatlands.
Arsenolipids
2004, Progress in Lipid Research
Natural arsenolipids are analogues of neutral lipids, like monoglycerides, glycolipids, phospho- and also phosphonolipids. They have been found in microorganisms, fungi, plants, lichens, in marine mollusks, sponges, other invertebrates, and in fish tissues. This review presented structures of natural arsenolipids (and derivatives), their distribution, biogenesis in algae and invertebrates, synthesis, and also biological activity. Arsenolipids are thought to be end products of arsenate detoxification processes, involving reduction and oxidative methylation and adenosylation. The proposed biogenesis of arsenolipids is based on the natural occurrence of arsenic metabolites, and all the intermediates in the proposed pathway have been identified as natural products of algal origin. Different arseno species are shown to be inhibitors of glycerol kinase, bovine carbonic anhydrase, and also is an effective therapy for acute promyelocytic leukemia, and there has been promising activity noted in other hematologic and solid tumors. Arsonoliposomes demonstrated high anti-trypanosomal activity against Trypanosoma brucei and inhibit growth of some types of cancer cells (HL-60,C6 and GH3).

View all citing articles on Scopus

View full text

Distribution of diacylglycerylhomoserines, phospholipids and fatty acids in thirteen moss species from Southwestern Siberia

Abstract

Prog. Lipid Res.

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Pl. Sci. Lett.

Phytochemistry

J. Chromatogr

Phytochemistry

Biochem. Syst. Ecol.

Phytochemistry

Phytochemistry

Pl. Science

Pl. Sci.

Phytochemistry

Biochim. Biophys. Acta

Arachidonic and eicosapentaenoic acids in lipids of Bryum bicolor Dicks. Effects of controlled temperature and illumination

Bryologist

9,12,15-Octadecatrien-6-ynoic acid: New acetylenic acid from mosses

Lipids