Saturated and unsaturated sterols of nitrogen-fixing blue-green algae (cyanobacteria)

doi:10.1016/0031-9422(88)80434-5

Phytochemistry

Volume 27, Issue 6, 1988, Pages 1735-1740

https://doi.org/10.1016/0031-9422(88)80434-5 Get rights and content

Abstract

Five species of filamentous nitrogen-fixing blue-green algae (Cyanobacteria), (Anabaena cylindrica, Anabaena solitaria, Anabaena viguieri,

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Cyanobacteria are a type of prokaryotic organism, also called blue-green algae, that can survive in various environments, even harsh ones, and are found worldwide in aquatic and terrestrial environments. They are photosynthetic microorganisms that create a wide range of secondary metabolites and other beneficial compounds. Cyanobacteria develop secondary metabolites that allow them to thrive in response to biotic or abiotic stress factors, frequently resulting in increased synthesis of secondary metabolites. These secondary metabolites have a variety of different molecular structures, ranging from low-molecular-weight compounds such as the photoprotective mycosporine-like amino acids to more complicated polysaccharides. In addition, the presence of these cyanobacteria in irrigation water and soil as a natural habitat made the role of the secondary substances that they secrete not only limited to protecting them or increasing their growth in unfavorable conditions, but scientists found that these substances improved the characteristics of agricultural soil and protected economic crops from pests and pathogenic microorganisms. Furthermore, it increases its ability to withstand unsuitable weather and environmental factors and even increases the growth of the plants compared to its absence in the rhizosphere. In this chapter, most of the cyanobacterial secondary metabolites (hormones, vitamins, polysaccharides, peptides, free fatty acids, flavonoids, phenolic acids, phytols, terpenoids, antibiotics, pigments, carotenoids, and sterols) and their potentiality in promoting plant growth and abiotic stress resistance will be discussed in detail.
C<inf>30</inf> and C<inf>31</inf> steranes in Permian fossil conifers Protophyllocladoxylon
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steranes in all the conifer trunk samples indicate that the source of extracted hydrocarbons from trunk samples is probably eukaryotic rather than prokaryotic. However, a prokaryotic origin of the C30 4-methylsteranes still cannot be excluded, such as a fresh-water cyanobacteria (Kohlhase and Pohl, 1988) or bacterium Methylococcus capsulatus grown on methane (Bird et al., 1971) or other unknown species, although some of the sterols they produced do not have alkyl groups at C-24. Kimble et al., (1974) also reported 4-methylsteranes in the Messel oil shale deposited in shallow swampy lakes during the Eocene, and suggested either a bacterial origin of 4-methylsterols or a diagenetic pathway of 4-methylsterols.
Steroids with alkyl groups at C-2 and C-3 are not known yet in any living organism, while 4-methylsteranes are previously thought specific to 4-methylsteroids bio-synthesized by limited types of organisms, such as dinoflagellates, microalgae, and certain bacteria. Here we investigate the occurrence of C₃₀ 2α-, 3β-, 4α-methyl-24-ethylcholestanes, C₃₁ 3β,24-diethylcholestanes, and 3,4-dimethyl-24-ethylcholestane, which are tentatively identified in fourteen fossil conifer Protophyllocladoxylon trunk samples from the upper Permian Wutonggou and Guodikeng formations in northwest China. In contrast to the paucity of alkyl steranes in the background sediments, abundant C₃₀ 4α-methyl-24-ethylcholestanes in fossil conifers from diverse fluvial–lacustrine environments suggest that conifers were the most likely biological origin for the 4-methyl steranes in conifer trunk samples, although origins from associated fungi might also be possible. Alternatively, these C-4 methyl steranes might have possible algal or prokaryotic origins. It is noteworthy that diagenetic methylation or bacterial alkylation at early stages of diagenesis during burial may have caused a re-arrangement of classical 24-ethylsterols that were bio-synthesized by plants to generate C-2 and C-3 alkylated steranes. This study reports the presence of 4-methylsteranes in conifer fossils for the first time, pointing toward a likely origin from higher plants. This study also provides the first report of C-2 and C-3 alkylated steranes in plant fossils, a.llowing for the possibility that plants may produce functionalised sterol precursors of orphan alkylsteranes that are abundant in geological sediments but whose functionalised precursors are not known from any living organisms.
Phytosterol-rich compressed fluids extracts from Phormidium autumnale cyanobacteria with neuroprotective potential
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For this, higher pressures were also chosen to enable triterpenoid structure solubilization. Imbimbo et al. [50] reported a working pressure of 350 bar for bioactive intracellular metabolite extraction from Galdieria phlegre cyanobacteria, while for Arthrospira platensis and Arthrospira maxima, pressures of 300 and 350 bar were required [51,52]. Individual responses corresponding to target major sterols in the P. autumnale biomass (STIGMA, SITO, and CHO) were evaluated.
Phormidium autumnale (P. autumnale) is a cyanobacteria with an unknown metabolic system, since only few studies have been reported. Among the produced metabolites, sterols profile is important considering the ability to this cyanobacterium in producing such compounds and their important benefits for human health. In this study, compressed fluid technologies were evaluated to obtain phytosterol-rich extracts from P. autumnale cyanobacteria for investigating their potential neuroprotective properties. A preliminary study was performed by comparing gas-expanded liquid extraction and supercritical fluid extraction using ethanol as a co-solvent. The following steps were optimized using a two-level factorial design and considering solvent composition and pressure as experimental factors. The bioactive potential of the optimized compressed fluid extract was tested using in vitro bioactivity assays, including acetylcholinesterase, lipoxygenase inhibition, and antioxidant capacity. The supercritical fluid multi-optimization response presented optimum phytosterol enrichment conditions at 266.3 bar of pressure and 7% of ethanol. Moreover, the optimized extract had higher in-vitro neuroprotective activity than the non-enriched extract, presenting the biochemical half maximal inhibitory concentration (IC₅₀) values of 65.80 μg mL⁻¹ for acetylcholinesterase, 58.20 μg mL⁻¹ for lipoxygenase inhibition, and 7.40 μg mL⁻¹ for antioxidant activity. In-silico molecular docking analyses showed the specificity of sterol interaction with acetylcholinesterase active sites. These results provide evidence for further exploring P. autumnale as a source of bioactive phytosterols, demonstrating that compressed fluid technologies are powerful tools to obtain phytosterol-rich extracts.
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Microalgae are important natural sources of interesting high value compounds that could be used in pharmaceutical and nutraceutical applications. Of particular interest is the production and exploitation of microalgal phytosterols; compounds with known biological benefits such as cholesterol reduction, anti-inflammatory activity and even anti-cancer properties. The global market for phytosterols is expected to reach $USD 935 million by 2022. Phytosterols of commercial importance are β-sitosterol, campesterol, brassicasterol, stigmasterol and ergosterol. The current sources of phytosterols are the vegetable and tall oils harvested from land plants. However, it is anticipated that the terrestrial sources will not be able to meet increased demand through 2030 and beyond. Calculations of estimated lipid and phytosterol productivity suggest that microalgae could yield 678–6035 kg. ha⁻¹. y⁻¹ of phytosterol which is more than the current productivity of phytosterols from rapeseed plants, highlighting the economic potential for sourcing phytosterols from environmentally sustainable saline microalgae production. However, there are many challenges that need to be met. The sterol content of microalgae varies according to species and, at present, there is little information on how to manipulate culturing conditions to enhance sterol production in microalgae. Approaches could include nutrient limitation, and/or changing salinity, light and temperature. Molecular approaches such as genetic modification, knocking down or over expression of specific genes and blocking competitive biosynthetic pathways would be desirable. However, an improved understanding of the pathway of sterol biosynthesis in microalgae is necessary for effective use of these molecular approaches. This paper discusses the potential for sterol production from microalgae as an adjunct to current plant-based sources and highlights those areas where we need more information to produce these high value products in an environmentally and economically sustainable fashion.
Assessment of the antimicrobial activity of the lipoidal and pigment extracts of Punica granatum L. leaves
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Mass spectrum gave M+ at m/z 396 for molecular formula C28H44O and 377, 379 for [M–H3O] + and [M−HO] + fragment ions, 363 for [C27H39]+ ion which is also very distinctive for ergosterol, 299.24 was consistent with the mass of a [C21H31O]+ ion, 269 and 271 as a result of breaking of the C-17/C-20 bond. The isolated compound was compared with an authentic reference and the spectral data was confirmed with the previously published data [24]. Compound 3: α-tocopherol was obtained as oily residue, yielding 20 mg.
Punica granatum L. is one of the famous and old species belonging to Family Punicaceae. The lipoidal and natural pigment extracts of the pomegranate were screened for their antimicrobial activity against nine different microbial pathogens. Three different doses of each extract (50, 100 and 150 μl) at three different contact times (15, 30 and 60 min) were examined. Results can be cleared that, all tested microbial pathogens were inhibited by 150 μl of both extracts at 60 min. Furthermore, the removal efficiency of n-hexane extract was powerful than the pigment extract. Also, the quantitative evaluation of the pigments in the leaves was performed using spectroscopical and HPLC analyses, carotenoids and chlorophylls content of P. granatum L. leaves were spectroscopically determined (mg/g) as 6.7 ± 0.214 and 4.9 ± 0.251, respectively. Chlorophyll a and b were 2.33 ± 0.014 and 1.51 ± 0.023, respectively. HPLC analysis of lutein and β-carotene were investigated as 3.652 and 1.915 mg/g. GC/MS analysis of the saponifiable and unsaponifiable fraction of n-hexane extract was carried out and α-amyrin acetate, ergosterol, and α-tocopherol were isolated, purified and identified using different spectroscopical methods. Toxicity assessment demonstrated their high biocompatibility since no toxic effect was recorded.
Physiological effects of mercury in the lichens Cladonia arbuscula subsp. mitis (Sandst.) Ruoss and Peltigera rufescens (Weiss) Humb
2011, Chemosphere
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Therefore different ergosterol content in the two lichen species may not reflect a differential sensitivity of the mycobionts, but more likely their different composition. In fact, ergosterol is present also in some unicellular algae and cyanobacteria and higher ergosterol levels have been found in lichens which have nitrogen-fixing photobionts (Kohlhase and Pohl, 1988). In both C. arbuscula subsp. mitis and P. rufescens we found increasing Hg accumulation under increasing Hg supply in the treatment solutions.
This study aimed at investigating the cellular distribution of Hg in the lichens Cladonia arbuscula subsp. mitis and Peltigera rufescens treated with Hg²⁺ and at testing if Hg treatment affects selected physiological parameters. In both species, increasing Hg accumulation under increasing Hg supply in the treatment solutions was found. P. rufescens showed a higher intracellular accumulation. Photosynthetic parameters were negatively affected in both species, as indicated by the decrease in photosynthetic pigments content, photosynthetic efficiency and chlorophyll integrity. Cell membranes of both species endured damage as indicated by the increase in the concentration of products of lipid peroxidation and decrease in ergosterol content. Nevertheless, differences between the two species were found, suggesting a differential sensitivity to Hg.

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Saturated and unsaturated sterols of nitrogen-fixing blue-green algae (cyanobacteria)

Abstract

Comp. Biochem. Physiol.

Phytochemistry

Phytochemistry

Phytochemistry

Biochem. Biophys. Acta

J. Chromatogr.

Phytochemistry

Geochim. Cosmochim. Acta

Phytochemistry

Steroids

Tetrahedron Letters

Steroids

Steroids

Phytochemistry

Phytochemistry

Geochim. Cosmochim. Acta

Steroids

Phytochemistry

Tetrahedron Letters

Biochem. Syst.

Comp. Bichem. Physiol.

Adv. Lipid Res.

Deep-Sea Res.

Nature

Science

Phytochemistry