Fatty Acid Glycosides Research Articles

Strawberry fatty acyl glycosides enhance disease protection, have antibiotic activity and stimulate plant growth

An increasing interest in the development of products of natural origin for crop disease and pest control has emerged in the last decade. Here we introduce a new family of strawberry acyl glycosides (SAGs) formed by a trisaccharide (GalNAc-GalNAc-Glc) and a monounsaturated fatty acid of 6 to 12 carbon atoms linked to the glucose unit. Application of SAGs to Arabidopsis thaliana (hereafter Arabidopsis) plants triggered a transient oxidative burst, callose deposition and defense gene expression, accompanied by increased protection against two phytopathogens, Pseudomonas viridiflava and Botrytis cinerea. SAGs-induced disease protection was also demonstrated in soybean infected with the causal agent of target spot, Corynespora cassiicola. SAGs were shown to exhibit important antimicrobial activity against a wide-range of bacterial and fungal phytopathogens, most probably through membrane destabilization, and the potential use of SAGs as a biofungicide for postharvest disease protection was demonstrated on lemon fruits infected with Penicillium digitatum. Plant growth promotion by application of SAGs was shown by augmented primary root elongation, secondary roots development and increased siliques formation in Arabidopsis, whereas a significant increment in number of seed pods was demonstrated in soybean. Stimulation of radicle development and the induction of an auxin-responsive reporter system (DR5::GUS) in transgenic Arabidopsis plants, suggested that SAGs-stimulated growth at least partly acts through the auxin response pathway. These results indicate that strawberry fatty acid glycosides are promising candidates for the development of environmental-friendly products for disease management in soybean and lemon.

Isolation and characterization of novel acetylcholinesterase inhibitors from Ficus benghalensis L. leaves.

Metabolic profiling of the crude methanolic extract of Ficus benghalensis leaves has revealed the presence of different phenolic and nitrogenous compounds including cerebrosides and tetrapyrrole pigments. A phytochemical study of the ethyl acetate fraction resulted in the identification of three known compounds, namely carpachromene (1), alpha amyrine acetate (2), and mucusoside (3) together with one new fatty acid glycoside, named 2-O-α-l-rhamnopyranosyl-hexacosanoate-β-d-glucopyranosyl ester (4). The compounds were identified using 1D, 2D NMR, and HR-ESIMS techniques as well as via comparison to other literature. Studies on the acetylcholinesterase inhibition potential and antioxidant activity were carried out on the total methanolic leaf extract, ethyl acetate fraction, and the isolated compounds. The results revealed the potent acetylcholinesterase inhibition of mucusoside alongside a new compound. Docking studies were also performed to confirm the possible interaction between the isolated compounds and acetylcholinesterase accompanying Alzheimer's disease progress.

Noni (Morinda citrifolia L.) fruit juice reverses age-related decline in neural-immune interactions in the spleens of old F344 rats

Ethnopharmacological relevanceVarious parts of the tropical plant, Morinda citrifolia L. (Noni), have been widely used in traditional medicine in South and Southeast Asia for several centuries. The therapeutic effects of the noni are believed to be mediated through several phytochemicals such as anthraquinones, iridoid, fatty acid glycosides, alcohols, etc. Aim of the studyThe aim of the study is to investigate the effects of Morinda citrifolia fruit juice (noni fruit juice; NFJ) on neural-immune interactions through the involvement of intracellular signaling pathways both in vitro and in vivo in the splenic lymphocytes of young and old male F344 rats. Material and methodsIn the in vitro study, splenocytes from young and old F344 rats were isolated and treated with 0.0001–1% concentrations of NFJ for a period of 24h, while in the in vivo study, old F344 rats were orally administered (5ml/kg body weight) with NFJ (5%, 10% and 20%) twice daily for 60 days. After the treatment period, concanavalin A (Con A)-induced lymphocyte proliferation, cytokines (IL-2, IFN-γ, IL-6, and TNF-α) production, expression of tyrosine hydroxylase (p-TH), nerve growth factor (NGF), m-TOR, IκB-α, p-NF-κB (p50 and p65), p-ERK, p-Akt, p-CREB and lipid peroxidation, protein carbonyl formation, nitric oxide (NO) production were examined in the splenocytes. ResultsIn vitro NFJ incubation of splenic lymphocytes increased Con A-induced lymphocyte proliferation, IL-2 and IFN-γ production, and expression of p-ERK, p-Akt, and p-CREB in young and old rats. In vivo treatment of old rats with NFJ increased lymphoproliferation, IL-2 and IFN-γ production, the expression of p-TH, NGF, and NO production, and suppressed IL-6 production, lipid peroxidation, protein carbonyl formation, and the expression of IκB-α and p-NF-κB (p50) in the splenocytes. ConclusionTaken together, these results suggest that Morinda citrifolia fruit juice enhanced neural-immune interactions and cell survival pathways while inhibiting inflammatory processes that may be useful in the treatment of age-associated diseases.

Characterization of Nutrients in the Leaves and Fruits of Embaúba (Cecropia Pachystachya) Trécul

The fruits and leaves of the embaúba tree (Cecropia Pachystachya Trécul) harvested in the region of the state of Rio de Janeiro were analyzed for moisture, protein, fat, ash, soluble fiber, insoluble fiber, carbohydrates, pH, acidity and minerals. The fresh fruit and leaves had 71.8 and 62.4% moisture, 0.54 and 1.13% protein, 0.68 and 0.46% total fat, 0.50 and 0.96% ash, 0.11 and 0.19% soluble fiber, 2.60 and 2.19% insoluble fiber, 23.8 and 32.7% total carbohydrates, 0.04 and 0.06% acidity and pH values of 5.98 and 5.1, respectively. The fruit and leaves are also good sources of magnesium (Mg), potassium (K), manganese (Mn) and iron (Fe). They provide >100% of the dietary reference intake (DRI) for adults. Lyophilized fruits and leaves were also extracted by hot, pressurized, dry methanol (100°C, 10 MPa). This solubilized 27% of the fruit and 15% of the leaves. The extract was partitioned between water and methylene chloride (CH2Cl2). The amphiphilic compounds went into the CH2Cl2 phase. They accounted for 2.13% and 5.15% of the lyophilized fruit and leaves, respectively. The amino acid concentrations were also measured. NMR analysis showed that the methanolic extract contained primarily fatty acid glycosides, with smaller amounts of aromatic compounds. The NMR spectra of the amphiphilic compounds showed the presence of triglycerides in the fruit, but not the leaves. This will give regulators several ways of determining whether or not food products labeled as containing embauba are genuine. In addition, it will help regulators decide if embaúba should be classified as generally regarded as safe (GRAS). It will also help regulators decide what should be on the label for food products made from embauba.https://doi.org/10.21423/jrs-v04n04p029 (DOI assigned 5/14/2019)

A Fatty Acid Glycoside from a Marine-Derived Fungus Isolated from Mangrove Plant Scyphiphora hydrophyllacea

To study the antimicrobial components from the endophytic fungus A1 of mangrove plant Scyphiphora hydrophyllacea Gaertn. F., a new fatty acid glucoside was isolated by column chromatography from the broth of A1, and its structure was identified as R-3-hydroxyundecanoic acid methylester-3-O-α-l-rhamnopyranoside (1) by spectroscopic methods including 1D and 2D NMR (HMQC, 1H-1H COSY and HMBC) and chemical methods. Antimicrobial assay showed compound 1 possessed modest inhibitory effect on Saphylococcus aureus and methicillin-resistant S. aureus (MRSA) using the filter paper disc agar diffusion method.

Antineuroinflammatory constituents from the root extract of Paris verticillata

Two new cyclopropanoic fatty acid glycosides, named parisveroside A (1) and parisveroside B (2), were isolated from a MeOH extract of the roots of Paris verticillata (Liliaceae) together with three other known compounds, salicin (3), 3-(β-d-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (4), and allantoin (5). Their structures were elucidated on the basis of spectroscopic data, including 1D and 2D NMR, HR-FAB-MS, and chemical evidence. To investigate the antineuroinflammatory effects of the isolated compounds (1–5), nitric oxide (NO) production was evaluated in the lipopolysaccharide-activated microglia cell line, BV-2. Compounds 2 and 4 significantly inhibited NO production with IC50 values of 74.8 and 60.5 µmol/L, respectively.

A novel cyclopropyl-containing fatty acid glucoside from the seeds of Litchi chinensis

3,12-Dihydroxy- cis-3,4-methylenedodecanoic acid 3- O-β- d-glucopyranoside, trivially named litchioside C ( 1), the first cyclopropyl-containing fatty acid glycoside, was isolated along with three previously uncharacterized galactosylacylglycerols from the seeds of Litchi chinensis. Its structure was established on the basis of spectroscopic analysis including HRESIMS and 2D NMR spectra. Its antioxidant and antibacterial activities were evaluated and its biogenetic pathway was discussed.

Astonishing diversity of natural surfactants: 1. Glycosides of fatty acids and alcohols

Alkyl and fatty acid glycosides have become of great commercial interest in general and specifically for the pharmaceutical, cosmetic, and food industries. Natural surfactants are good sources for future chemical preparation of these glycosides. This review article shows an astonishing diversity of natural surfactants that could be used in laboratories and industry. More than 250 natural surfactants, including their chemical structures and biological activities, are described in this review article.

Glycolipids of the filamentous fungus Absidia corymbifera F-295

The lipids extracted with CHCl 3/MeOH mixtures from mycelium of the lower filamentous fungus Absidia corymbifera F-295 were found to contain three glycolipids. Based on the IR, 1H and 13C NMR spectra, plasma-desorption ionisation (PDI) mass spectra as well as chemical degradation results, the glycolipids were established to be 1- O-β- d-glucopyranosyl-2- N-(2′- d-hydroxyhexadecanoyl)-9-methylsphinga-4( E),8( E)-dienine (glucosyl ceramide) and 2- O-(6′- O-β- d-galactopyranosyl)-β- d-galactopyranosides of 2- d-hydroxy and erythro-2,3-dihydroxy fatty acids C 9, C 11, and C 13. They accounted for about 3.4, 0.8, and 0.4%, respectively, of the total lipids extracted. No lipids identical to the above monohydroxy and dihydroxy fatty acid glycosides have been reported.

Bioactive Saponins and Glycosides. IX. Notoginseng (2): Structures of Five New Dammarane-Type Triterpene Oligoglycosides, Notoginsenosides-E, -G, -H, -I, and -J, and a Novel Acetylenic Fatty Acid Glycoside, Notoginsenic Acid .BETA.-Sophoroside, from the Dried Root of Panax notoginseng (BURK.) F. H. CHEN.

Following the characterization of notoginsenosides-A, -B, -C, and -D, new dammarane-type triterpene oligoglycosides, notoginsenosides-E, -G, -H, -I, and -J, and a novel acetylenic fatty acid glycoside, notoginsenic acid β-sophoroside, were isolated from the glycoside fraction with hepatoprotecting activity obtained from the dried roots of Panax notoginseng (BURK.) F. H. CHEN. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence as follows : notoginsenoside E; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 12β, 20(S)-trihydroxy-25-hydroperoxydammar-23-ene, G; 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 7β, 20(S)-trihydroxydammar-5, 24-diene, H; 6-O-[β-D-xylopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 6α, 12β, 20(S), 25-pentahydroxydammar-23-ene, I; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl]-3β, 20(S)-dihydroxydammar-24-ene, J; 6-O-(β-D-glucopyranosyl)-20-O-(β-D-glucopyranosyl)-3β, 6α, 12β, 20(S), 24ζ, 25-hexahydroxydammarane, and notoginsenic acid β-sophoroside; 10-hydroxydaca-4, 6-diynoic acid 10-O-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside, respectively.

Bioactive saponins and glycosides. VIII. Notoginseng (1): new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, and -D, from the dried root of Panax notoginseng (Burk.) F.H. Chen.

The glycosidic fraction from the dried roots of Panax notoginseng (Burk.) F.H. Chen was found to show protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. From the glycosidic fraction with hepatoprotective effect, nine new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, -D, -E, -G, -H, -I, and -J and an acetylenic fatty acid glycoside, notoginsenic acid beta-sophoroside, were isolated together with fourteen known dammarane-type triterpene oligoglycosides. The structures of notoginsenosides-A, -B, -C and -D were determined on the basis of chemical and physicochemical evidence, which included the chemical correlation with ginsenoside-Rb1 using photosensitized oxygenation, as follows: notoginsenoside A; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] 3 beta, 12 beta,20(S),25-tetrahydroxydammar -23-ene; B; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-glucopyranosyl (1-->6)-beta-D- glucopyranosyl] 3 beta, 12 beta,20(S)-trihydroxydammar-25-en-24-one, C; 3-O-[beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D -glucopyranosyl (1-->6)-beta-D-glucopyranosyl] 3 beta,12 beta,20(S)- trihydroxy-24 zeta-hydroperoxydammar-25-ene, and D; 3-O-[beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-xylopyranosyl (1-->6)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl]20(S)-protopanaxadiol, respectively.

Structure of pescaproside E, a fatty acid glycoside from Ipomoea pescaprae

Three fatty acid glycosides, designated pescaprosides A, B, and E, have been isolated from Ipomoea pescaprae (family Convolvulaceae). Chemical studies on pescaproside E, the major product, led to its characterisation as a pentaglycoside of 11-hydroxyhexadecanoic acid. Its sugar chain was esterified with 2-methylbutanoic and lauric acids. The structure of the pentaglycoside has been established as O-α- l-rhamnopyranosyl-(1 → 3)- O-[α- l-rhamnopyranosyl-(1 → 4)]- O-α- l-rhamnopyranosyl-(1 → 4)- O-β- d- fucopyranosyl-(1 → 2)- O-α- l-rhamnopyranosyl-(1 → 11)-oxyhexadecanoic acid.

Structure of dichroside D, a fatty acid glycoside from Ipomoea dichroa

Four fatty acid glycosides, designated dichrosides A, B, C, and D, have been isolated from Ipomoea dichroa (family, Convolvulaceae). On chemical investigation, dichroside D was found to be a pentaglycoside of 11-hydroxyhexadecanoic acid, and the sugar chain is highly esterified with other fatty acids. The structure of the pentaglycoside has been established as 11-{ O-β- d-glucopyranosyl-(1→4)- O-[β- d-fucopyranosyl-(1→3)]- O-α- l-rhamnopyranosyl-(1→4)- O-α- l- rhamnopyranosyl-(1→2)-α- l-rhamnopyranosyl)oxy}hexadecanoic acid.

Fermentation of long‐chain compounds by Torulopsis magnoliae. II. Factors influencing production of hydroxy fatty acid glycosides

AbstractA strain of Torulopsis magnoliae, an osmophilic yeast isolated from flowers, produced an extracellular hydroxy fatty acid glycoside of sophorose which was easily recoverable as a heavier‐than‐water “oil”. The yield of this product was greatly increased and the nature of the hydroxy fatty acid portion of the molecule was modified, within limits, by the addition of fatty acid esters, hydrocarbons, or glycerides. Yields of hydroxy fatty acids of up to 90% of the substrate added were achieved. Commercially available substrates such as tall oil fatty acids, molasses, and corn steep liquor could be used. Good aeration was necessary, and control of the concentration of nitrogenous substrates and of temperature improved the yields.