Phytosphingosine-type Ceramide Research Articles

Funtulaticamide, a phytosphingosine-type ceramide from Funtumia elastica Preuss Stapf. (Apocynaceae) trunk bark with potential antileishmanial activity

Phytochemical investigations of the trunk bark extract of Funtumia elastica (Preuss) Stapf, afforded a new ceramide namely, funtulaticamide (1) along with six known compounds: funtulatine (2), methyl ursolate (3), epicatechin (4), myricetin (5), sucrose (6) and 5-hydroxypyridine-3-carboxamide (7). Their structures were determined on the basis of various spectroscopic and chemical methods, as well as comparison with literature. Compounds were mostly isolated for the first time from this plant, and no evidence could be found on a previous report of a phytosphingosine-type ceramide in the genus Funtumia. Similarly, compound 7 is isolated from the Apocynaceae family for the first time. Hence, the chemophenetic significance of isolates was briefly introduced. In addition, compound 2 exhibited a moderate activity against Leishmania donovani 1S (MHOM/SD/62/1S) with an IC50 value of 15.9 μM.

Self gelating isoracemosol A, new racemosaceramide A, and racemosol E from Barringtonia racemosa

Phytochemical investigation into the CHCl3 extract of the fruits of Barringtonia racemosa resulted in the isolation of two new metabolites along with isoracemosol A and betulinic acid as known metabolites. The new compounds were characterised as phytosphingosine-type ceramide [(2S,3S,4R)-2-[(2R)-2-hydroxyhexadecanoyl amino]-hexacos-8(E)-ene-1,3,4-triol, 1] and racemosol E [21β-acetoxy-22α-(2-methylbutyroxy)-olean-12-ene-3β,16α,28-triol, 2] on the basis of extensive spectroscopic data analysis and chemical modifications. In addition, the self-gelating property of isoracemosol A (3) was investigated for the first time, which leads to the unexpected agglomerated porous-like morphology.

The impact of ceramides NP and AP on the nanostructure of stratum corneum lipid bilayer. Part I: neutron diffraction and 2H NMR studies on multilamellar models based on ceramides with symmetric alkyl chain length distribution

We investigated the lamellar structure of ternary stratum corneum (SC) lipid model systems based on either the phytosphingosine type ceramide (CER) [NP] or CER[AP], supplemented by cholesterol and stearic acid as representative free fatty acid species. For the CER[NP] based membrane, neutron diffraction measurements revealed the coexistence of two lamellar phases, which markedly differ in their hydration properties. CER[NP] forms an extremely rigid and stable bilayer backbone and is at least partly sequestered in a separate phase which coexists with a second lamellar phase. At increased temperature, a structural re-organization of the lipids was observed. One of the lamellar phases disappeared, while the remaining phase increased its repeat distance by about 1 Å. Such a behaviour has not been described for SC lipid model membranes based on CER[AP] so far. Further, 2H NMR spectroscopic measurements on two SC lipid model systems based on either CER[NP] or CER[AP] in addition to cholesterol and perdeuterated stearic acid revealed a state of high lamellar order present in both samples, emphasizing the importance of the phytosphingosine-type ceramides for the proper formation of stable SC bilayer structures. However, the CER[NP] based ternary model showed a state of higher lamellar order than the CER[AP] based system. Our results demonstrate that slight changes in the ceramides' head groups (CER[NP] with 3 hydroxyl groups vs. CER[AP] with 4 hydroxyl groups) have a dramatic influence on the morphology of the lipid structures formed by these lipids.

A New Ceramide from Suillus luteus and Its Cytotoxic Activity against Human Melanoma Cells

A new phytosphingosine-type ceramide, suillumide (1), was isolated from the EtOH extract of the basidiomycete Suillus luteus (L.) S. F. Gray, along with ten known compounds: ergosta-4,6,8(14),22-tetraen-3-one, ergosterol, ergosterol peroxide, suillin, (E)-3,4,5-trimethoxycinnamic alcohol, 5 alpha,6 alpha-epoxyergosta-8,22-diene-3beta,7 beta-diol, (R)-1-palmitoylglycerol, ergosta-7,9(11),22-triene-3beta,5 alpha,6 beta-triol, cerevisterol, and 4-hydroxybenzoic acid. The structure of 1 was determined on the basis of spectroscopic and mass-spectrometric analyses, as well as by chemical methods. Compound 1 and its synthetic diacetyl derivative 2 were tested for their cytotoxic activities against the human melanoma cell line SK-MEL-1. Both drugs showed IC(50) values of ca. 10 microM after 72 h of exposure.

A Ceramide and Cerebroside from the Starfish Asterias amurensis Lütken and Their Plant-Growth Promotion Activities

The new phytosphingosine-type ceramide asteriaceramide A (1) and glucocerebroside asteriacerebroside G (2), together with two known cerebrosides, asteriacerebrosides A and B, were isolated from lipophilic fractions of the whole bodies of the Northern Pacific starfish Asterias amurensis Lütken. The water-soluble fraction afforded two known asterosaponins, glycoside B(2) and asterosaponin-1. The structures of 1 and 2 were determined on the basis of chemical and spectroscopic evidence as (2S,3S,4R,13Z)-2-[(2'R)-2-hydroxyhexadecanoylamino]-13-docosene-1,3,4-triol (1) and 1-O-(beta-d-glucopyranosyl)-(2S,3R,4E,13Z)-2-[(2'R)-2-hydroxytetradecanoylamino]-4,13-docosadiene-1,3-diol (2). Compounds 1, 2, and asteriacerebrosides A and B promoted plant growth in sprouts of Brassica campestris.

Isolation and Structure of Four New Ceramides from the Starfish Luidia maculata

A new sphingosine-type ceramide LMCer-1-1 (1) and three new phytosphingosine-type ceramides, LMCer-2-1 (2), LMCer-2-6 (3), and LMCer-2-7 (4), were isolated from the anti-hyperglycemic active ceramide molecular species LMCer-1 and LMCer-2, obtained from the less polar fraction of the chloroform-methanol extract of the whole bodies of Luidia maculata. The structures of these ceramides were determined on the basis of chemical and spectroscopic evidence as: (2S,3R,4E,2'R)-2-(2-hydroxyhexadecanoylamino)-16-methyl-4-octadecene-1,3-diol (1), (2S,3S,4R,2'R)-2-(2-hydroxyhexadecanoylamino)-16-methyl-octadecane-1,3,4-triol (2), (2S,3S,4R,2'R)-2-(2-hydroxydocosanoylamino)-hexadecane-1,3,4-triol (3), and (2S,3S,4R,2'R)-2-(2-hydroxydocosanoylamino)-14-methyl-hexadecane-1,3,4-triol (4).

Paxillamide: A Novel Phytosphingosine Derivative from the Fruiting Bodies of Paxillus panuoides.

The new phytosphingosine-type ceramide 1, named paxillamide (=2,3-dihydroxy-N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]tetracosanamide), was isolated from the CHCl3/MeOH extract of the fruiting bodies of the Basidiomycete Paxillus panuoides, and its structure was elucidated by spectroscopic and chemical methods.

Paxillamide: a Novel Phytosphingosine Derivative from the Fruiting Bodies of Paxillus panuoides

AbstractThe new phytosphingosine‐type ceramide 1, named paxillamide (=2,3‐dihydroxy‐N‐[(1S,2S,3R)‐2,3‐dihydroxy‐1‐(hydroxymethyl)heptadecyl]tetracosanamide), was isolated from the CHCl3/MeOH extract of the fruiting bodies of the Basidiomycete Paxillus panuoides, and its structure was elucidated by spectroscopic and chemical methods.

A new ceramide from the basidiomycete Russula cyanoxantha.

A new phytosphingosine-type ceramide (1) was isolated along with nine other compounds-5alpha,8alpha-epidioxy(22E,24R)-ergosta-6,22-dien-3beta-ol, 5alpha,8alpha-epidioxy-(24S)-ergosta-6-en-3beta-ol, (24S)-ergosta-7-ene-3beta,5alpha,6beta-triol, (22E,24R)-ergosta-7,22-dien-3beta,5alpha,6beta-triol, inosine, adenine, L-pyroglutamic acid, fumaric acid, and D-allitol from the ethanol and chloroform/methanol extract of the fruiting bodies of the basidiomycete Russula cyanoxanotha (Schaeff.) Fr. The structure of (1) was established as (2S,3S,4R,2'R)-2-(2'-hydroxytetracosanoylamino) octadecane-1,3,4-triol by means of spectroscopic and chemical methods.

Structures of new ceramides from the fruit bodies of Grifola frondosa.

Four new phytosphingosine-type ceramides, (2S,3S,4R)-2-[(2'R)-2'-hydroxydocosanoylamino]-1,3,4-octadecane triol (1), (2S,3S,4R)-2-[(2'R)-2'-hydroxytricosanoylamino]-1,3,4-octadecan etriol (2), (2S,3S,4R)-2-[(2'R)-2'-hydroxypentacosanoylamino]-1,3,4-octadec anetriol (3) and (2S,3S,4R)-2-[(2'R)-2'-hydroxyhexacosanoylamino]-1,3,4-octadeca netriol (4), have been isolated from the fruit bodies of Grifola frondosa. The structures of the new compounds were elucidated on the basis of their spectral data.

Isolation and Structure of Three New Ceramides from the StarfishAcanthaster planci

Three new phytosphingosine-type ceramides, AC-1-6, AC-1-10 and AC-1-11, were isolated from the ceramide molecular species AC-1, obtained from the less polar fraction of the CHCl3-MeOH extract of the starfish Acanthaster planci. The structures of these ceramides were determined on the basis of chemical and spectroscopic evidence as (2S,2′R,3S,4R,9Z)-2-(2-hydroxyhexadecanoylamino)-9-docosene-1,3,4-triol (AC-1-6), (2S,2′R,3S,4R,)-2-(2-hydroxytricosanoylamino)hexadecane-1,3,4-triol (AC-1-10) and (2S,2′R,3S,4R,)-2(2-hydroxytetracosanoylamino)hexadecane-1,3,4-triol (AC-1-11). Positive ion FABMS/MS of each ceramide gave important information for their structure elucidation. Mass spectrometry of the dimethyl disulfide derivatives of ceramide was also useful for the determination of the double bond position in the long-chain base.