Crassicaulisine, a new sulphonoglycolipid from the red alga Chondria crassicaulis Harv

Shao, Ziying; Cai, Jin; Ye, Qizhuang; Guo, Yue

doi:10.1080/10286020290024004

Cited by 16 publications

(6 citation statements)

References 9 publications

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“…[24], reported the isolation of the sulfoglycolipid crassicaulisine, with myristoyl and palmitoyl as acyl groups at positions 1 and 2 of glycerol respectively, from the red alga Chondria crassicaulis . Compound 1 , the major SQDG of L. variegata , corresponds to the positional isomer of crassicaulisine, where palmitoyl and miristoyl acyl groups are interchanged, i.e.…”

Section: Resultsmentioning

confidence: 99%

The Tropical Brown Alga Lobophora variegata: A Source of Antiprotozoal Compounds

et al. 2010

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Lobophora variegata, a brown alga collected from the coast of the Yucatan peninsula, Mexico, was studied for antiprotozoal activity against Giardia intestinalis, Entamoeba histolytica and Trichomonas vaginalis. The whole extract showed the highest activity against T. vaginalis, with an IC50 value of 3.2 μg/mL. For the fractions, the best antiprotozoal activity was found in non-polar fractions. The chloroform fraction of the extract contained a major sulfoquinovosyldiacylglycerol (SQDG), identified as 1-O-palmitoyl-2-O-myristoyl-3-O-(6‴-sulfo-α-d-quinovopyranosyl)-glycerol (1), together with small amounts of 1,2-di-O-palmitoyl-3-O-(6‴-sulfo-α-d-quinovopyranosyl)-glycerol (2) and a new compound identified as 1-O-palmitoyl-2-O-oleoyl-3-O-(6‴-sulfo-α-d-quinovopyranosyl)-glycerol (3). Their structures were elucidated on the basis of chemical and enzymatic hydrolysis and careful analysis of FAB-MS and NMR spectroscopic data. This is the first report on the isolation of SQDGs from L. variegata. The mixture of 1–3 showed good activity against E. histolytica and moderate activity against T. vaginalis with IC50s of 3.9 and 8.0 μg/mL, respectively, however, the activity of 1–3 is not as effective as metronidazole. These results afford ground information for the potential use of the whole extract and fractions of this species in protozoal infections.

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Section: Resultsmentioning

confidence: 99%

The Tropical Brown Alga Lobophora variegata: A Source of Antiprotozoal Compounds

et al. 2010

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“…The structure of 3 is reminiscent of galactolipids which have been found in both terrestrial plants (Cateni et al, 2003; Jung et al, 1996) and marine algae (Shao at al., 2002; Deal et al, 2003). The most closely related structure to 3 was 1- O -(palmitoyl)-2- O -(5,8,11,14,17-eicosapentaenoyl)-3- O -β-D-galactopyranosyl-glycerol, identified by spectral analysis of a glycolipid mixture from the red alga Chondria armata , with one trans and four cis double bonds in the acyl fatty chain (Al-Fadhli et al, 2006).…”

Section: Resultsmentioning

confidence: 99%

Antineoplastic unsaturated fatty acids from Fijian macroalgae

et al. 2008

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Phytochemical analysis of Fijian populations of the green alga Tydemania expeditionis led to the isolation of two new unsaturated fatty acids, 3(″)-hydroxy-octadeca-4(E),6(Z),15(Z)-trienoic acid (1) and 3(″)-hydroxy-hexadeca-4(E),6(Z)-dienoic acid (2), along with the known 3(″)-hydroxyoctadeca-4(E),6(Z)-dienoic acid (4). Investigations of the red alga Hydrolithon reinboldii led to identification of a new glycolipid, lithonoside (3), and five known compounds, 15-tricosenoic acid, hexacosa-5,9-dienoic methyl ester, β-sitosterol, 10(S)-hydroxypheophytin A, and 10(R)-hydroxypheophytin A. The structures of 1-3 were elucidated by spectroscopic methods (1D and 2D-NMR spectroscopy and ESI-MS). Compounds 1, 2, and 4, containing conjugated double bonds, demonstrated moderate inhibitory activity against a panel of tumor cell lines (including breast, colon, lung, prostate and ovarian cells) with IC 50 values ranging from 1.3 to 14.4 μM. The similar cell selectivity patterns of these three compounds suggest that they might act by a common, but unknown, mechanism of action.

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“…Methanolysis of the glycolipids gave rise to the same galactosylglycerol which on ESI-MS provided a pseudomolecular ion at m/z 309 representing deacylated glycolipid with the sodiated sugar moiety. Recently, Shao et al (2002) reported the presence of a new sulfonoglycolipid, crassicaulisine with palmitoyl and myrsitoyl as acyl groups, from the red alga belonging to the same genus, Chondria crassicaulis. Acyl groups in PF 1-3 were characterized as the corresponding acids or caboxylate ions (ESI-MS), and the principal components were arachidonic acid in PF 1-2, palmitic acid and eicosapentaenoic acid in PF 3 .…”

Section: Discussionmentioning

confidence: 99%

Glycolipids from the red alga Chondria armata (Kütz.) Okamura

Al-Fadhli¹,

Wahidulla²,

D’Souza³

2006

Glycobiology

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Three distinct fractions containing polar glycolipids (PF(1-3)) were isolated from the chloroform soluble fraction of crude methanolic extract of red alga Chondria armata (Kütz.) Okamura on gel chromatography over Sephadex LH20. Their structure was elucidated by multidimensional nuclear magnetic resonance (NMR) techniques like 1H, 1H correlation spectroscopy (COSY), 1H, 1H total COSY (TOCSY), 1H, 13C heteronuclear multiple quantum coherence (HMQC), and 1H, 13C heteronuclear multiple bond correlation (HMBC) complemented by electrospray ionization mass spectrometry (ESI-MS) in the positive ion mode. The coupling constant of the anomeric proton in 1H NMR spectrum and sign of rotation indicated an exclusive configuration of the sugar molecules in the glycerolipids. Major glycolipids were identified as (2R)-2-O-(5,8,11,14-eicosatetranoyl)-3-O-alpha-d-galactopyranosyl-sn-glycerol (GL2), its pentacetate (GL1), and (2R)-1-O-(palmitoyl)-2-O-(5,8,11, 14,17-eicosapentanoyl)-3-O-beta-d-galactopyranosyl-sn-glycerol (GL3). Each was methanolysed to give the same galactosylglycerol which on ESI-MS provided a pseudomolecular ion at m/z 309 representing deacylated glycolipid with the sodiated sugar moiety. Additionally, six minor glycolipids were also identified on the basis of ESI-MS. These include a 1,2-di-O-acyl-3-O-(acyl-6'-galactosyl)-glycerol (GL1a), sulfonoglycolipids 2-O-palmitoyl-3-O-(6'-sulfoquinovopyranosyl)-glycerol (GL2a) and its ethyl ether derivative (GL2b), 1-oleoyl-2-palmitoyl-3-O-galactosyl glycerol (GL3a), and 1,2-diacyl phosphatidyl glycerol (GL3b). GL1, GL1a, and GL2b are new to the literature. The novelty of the remaining identified compounds lies in the diversity of their fatty acid composition. Antimicrobial properties of these glycolipids against pathogens were evaluated. The yeast Candida albicans and the bacteria Klebsiella sp. were as sensitive as the standard Nystatin and antibiotic Streptomycin against PF3. Considerable activity was expressed by the same metabolite against the fungus Cryptococcus neoformans as compared to the control. Weak activity against the bacteria Shigella flexineri and Vibrio cholerae and the fungus Aspergillus fumigatus was also observed. Fraction PF2 was weakly active against some strains whereas all of them were resistant to its acetyl derivative PF1. Antimicrobial activity of glycolipids is being reported here for the first time.

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Crassicaulisine, a new sulphonoglycolipid from the red alga Chondria crassicaulis Harv

Abstract: A new sulphonoglycolipid, crassicaulisine, has been isolated from the red alga Chondria crassicaulis Harv.. Four known compounds were also found from the title plant. The structure of the new compound was elucidated on the basis of chemical reactions and spectroscopic analysis.

Cited by 16 publications

References 9 publications

The Tropical Brown Alga Lobophora variegata: A Source of Antiprotozoal Compounds

The Tropical Brown Alga Lobophora variegata: A Source of Antiprotozoal Compounds

Antineoplastic unsaturated fatty acids from Fijian macroalgae

Glycolipids from the red alga Chondria armata (Kütz.) Okamura

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