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Glycoglycerolipid and others

(total 115)
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No Structure COMMON NAME NAME DATA No INFORMANT SYMBOL FORMULA MOL.WT(ave) Download BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINT BOILING POINT DENSITY REFRACTIVE INDEX OPTICAL ROTATION SOLUBILITY UV SPECTRA IR SPECTRA NMR SPECTRA MASS SPECTRA OTHER SPECTRA
1
Seminolipid, sulfogalactoglycerolipid
Galactosyldiacylglycerol 3-sulfate
 GGG0001
Ineo Ishizuka
SGG, SM4g
Inhibition of arylsulfatase activities (Ref. 0048). Labeled by intracranial injection of [35S]sulfate (Ref. 0061). Labeled by intraperitoneal injection of [35S]sulfate (Ref. 0015/0066). Atigenicity against mice (monoclonal antibody) (Ref. 0043/0050). A component of myelin (Ref. 0069/0070/0208).



Silicagel TLC (Ref. 0207).
Nerve tissues of gadoid fishes (Ref. 0207/0208).




[0015] / [0043] / [0048] / [0050] / [0061] / [0066] / [0069] / [0070] / [0207] / [0208]
2
Lyso-seminolipid
3-Sulfogalactosyl-(1-3)-sn-1-alkylglycerol
 GGG0002
Ineo Ishizuka
Lyso-SM4g
 Download ChemDraw structure file

Behavior in the Folch partition (Ref. 0027).

LSIMS (Ref. 0036).
The absorption of the Azure A complex of the peracetylated derivative (Ref. 0027).
TLC (Ref. 0058).
Review (Ref. 0208). Porcine testis (Ref. 0058). Brain (Ref. 0016). Prepared from human seminolipid by mild alkaline deacylation (Ref. 0064). The product of mild alkaline deacylation of seminolipid (Ref. 0059/0063). Derived from seminolipid by the action of the lipase of the secondary lysosome (rat liver) (Ref. 0086).



Sulph I monoclonal antibody (Ref. 0050).
[0016] / [0027] / [0050] / [0058] / [0059] / [0063] / [0064] / [0086] / [0208]
3
Monogalactosyldiglyceride, galactosyldiacylglycerol
1,2-Di-O-acyl-3-[b-galactopyranosyl]-sn-glycerol
 GGG0003
Ineo Ishizuka
GalDAG
 Download ChemDraw structure file
(Ref. 0209).
(Ref. 0229)
1H-NMR in light water (Ref. 0229).
FAB-MS: molecular species (Ref. 0113).


The acidophilic alga Dunaliella acidophila, 1.4% of the dry weight (Ref. 0113); Cyanobacterium Phormidium tenue(Ref. 0227); plant (Ref. 0209); Bull frog and axolotl (Ref. 0237); porcine testis (Ref. 0058); cod brain (Ref. 0021/0074); human brain (Ref. 0009); the brain of rat treated chronically with diazepam (Ref. 0055); frog brain (Ref. 0029); rat brain (Ref. 0060), regional distribution in rat brain (Ref. 0020)the primary culture of fetal rat brain (Ref. 0037); subcellular distribution in sheep brain (Ref. 0020); chemical synthesis (Ref. 0229).
(Ref. 0210/0229)

Cloning of the gene for UDPgalactose:1,2-diacylglycerol 3-beta-D-galactosyltransferase (Ref. 0246)
Treatment with lipase (Ref. 0227).
The acidophilic alga Dunaliella acidophila, the major molecular species 18:3/16:4 (Ref. 0113); cod brain, more than 90% was diacyl species (Ref. 0021/0074), rat brain, fatty acid composition:16:0, 43.8%;18:1, 23.4%; 18:0, 20.9% (Ref. 0060).
[0009] / [0020] / [0021] / [0029] / [0037] / [0055] / [0058] / [0060] / [0074] / [0113] / [0209] / [0210] / [0227] / [0229] / [0237] / [0246]
4
Monogalactosylglyceride, galactosylalkylacylglycerol,
Galb1-3-1-alkyl-2-acylGro
 GGG0004
Ineo Ishizuka
GalAAG, GalEAGro
 Download ChemDraw structure file




TLC (Ref. 0058)
Porcine testis (Ref. 0058)rat testis (Ref. 0087/0071)frog brain (Ref. 0029)human testis (Ref. 0064)rat brain (Ref. 0060).
(Ref. 0210)


In vivo biosynthesis in rat testis (Ref. 0071)
cod brain, less than 91% was alkylacyl species (Ref. 0021/0074); rat brain, fatty acid composition, 16:0, 33.1%; 18:1, 26.6%; 18:0, 21.7% (Ref. 0060).
[0021] / [0029] / [0058] / [0060] / [0064] / [0071] / [0074] / [0087] / [0210]
5
2,3-Diphytanyl-1-[6-sulfo-a-mannopyranosyl-1-2-a-glucopyranosyl]-sn-glycerol
 GGG0005
Ineo Ishizuka
S-DGD-1
 Download ChemDraw structure file
Increased depending on the salt concentration of the medium (Ref. 0102).
830cm-1, C-O-S (Ref. 0101).
1H-NMR (Ref. 0103).
Negative FAB (NH4 SALT) [M-1]- , 1073; [M-NH4]-, 1055 (Ref. 0103).


Review (Ref. 0208). Halococcus saccharolyticus (Ref. 0103), an extremely halophilic bacterium strain R-4)29% by weight of the polar lipid)(Ref. 0101). Extremely halophilic bacteria strains Gla-2.2, M-2.5, M-2.38 (Ref. 0102).



Strain R-4 lacks in phosphatidylglycerol sulfate (ether species) suggesting for the replacement by this sulfoglycolipid (Ref. 0101)
Phytanyl ether (Ref. 0101).
[0101] / [0102] / [0103] / [0208]
6
2,3-Diphytanyl-1-[a-mannopyranosyl-1-2-a-glucopyranosyl]-sn-glycerol
 GGG0006
Ineo Ishizuka
DGD
 Download ChemDraw structure file



[a]D +59.43deg, [M]D 581 (Ref. 0112)

An extremely halophilic bacterium strain R-4 (Ref. 0101). Extremely halophilic strains Gla-2.2, Y-27, Gaa-3, Gaa-6, Gca-19, M-2.5, and Ma-2.38; H. vallismortis, H. marismortui, H. salinarium, H. cutirubrum (Ref. 0102).



Diphytanyl ether (Ref. 0101).
[0101] / [0102] / [0112]
7
Phospholipid I
Glcpa1-2Galfb-X
 GGG0007
Ineo Ishizuka
PGL-I
 Download ChemDraw structure file

1220, P=O; 1110, P-O- + C-O-C; 1050, P-O-C (Ref. 0104).
1H-NMR: at 30degC in deuterated chloroform and methanol. 3.37 ppm, CH2-O-; 3.77 ppm, CH-O-. 13C-NMR: 99.1 ppm, a-Glcp; 106.7 ppm b-Galf (Ref. 0104).

ORD: MD +137deg (calc'd +202deg) (Ref. 0104)

Methanospirillum hungatei GP1, 50% (wt%) of the total lipid (Ref. 0104).



Phosphatidylglycerol (2,3-di-O-phytanyl-sn-glycerol-1-phosphoryl-1'-sn-glycerol) in M. hungatei has an opposite optical configuration to that of halophilic bacteria
[0104]
8
Phospholipid II
Galfb1-6Galfb1-X
 GGG0008
Ineo Ishizuka
PGL-II
 Download ChemDraw structure file

Fig. (Ref. 0104).
13C-NMR: 109.0 ppm, b-Galf; 108.4 ppm, b-Galf (Ref. 0104).

ORD: MD -352deg (Ref. 0104)

Methanospirillum hungatei GP1, the major glycolipid 14% (wt%) of the total lipid (Ref. 0104).



X = dibiphytanyldiglycerol tetraether esterified with glycerophosphoric acid (Ref. 0104).
[0104]
9
2,3-Di-O-phytanyl-1-O-[a-D-glucopyranosyl-(1'-2')-O-b-D-galactofuranosyl]-sn-glycerol
 GGG0009
Ineo Ishizuka
DGD-I
 Download ChemDraw structure file

1110, C-O-C; 1050, C-OH; 1385, 1375, isopropyl (Ref. 0104).
1H-NMR: 3.2-4.4 ppm, -CH2-O-, -CH-O-. 13C-NMR:L 98.5 ppm, a-Glcp; 106.1 ppm, b-Galf (Ref. 0104).

ORD OF DIPHYTANYLGLYCEROL: [a]D +8.6deg. ORD OF INTACT GLYCOLIPID: [a]D = +150deg (Ref. 0104)

Methanospirillum hungatei GP1, the major glycolipid 17% (wt%) of the total lipid.




[0104]
10
2,3-Di-O-phytanyl-1-O-[b-D-galactofuranosyl-(1'-6')-b-D-galactofuranosyl]-sn-glycerol
 GGG0010
Ineo Ishizuka
DGD-II
 Download ChemDraw structure file

1110, C-O-C; 1050, C-OH (Ref. 0104).


ORD OF INTACT GLYCOLIPID: [a]D= -369deg (Ref. 0104)

Methanospirillum hungatei GP1, a minor glycolipid 2% (wt%) of the total lipid (Ref. 0104).




[0104]
11
Glcpa1-2Galfb1-1-dibiphytanyl-sn-Gro tetraether
2,3-Di-O-phytanyl-1-O-[a-D-glucopyranosyl-(1'-2')-O-b-D-galactofuranosyl]-sn-diglycerol tetraether
 GGG0011
Ineo Ishizuka
DGT-I
 Download ChemDraw structure file

1110 cm, C-O-C; 1050cm, C-OH (Ref. 0104)


ORD: MD +221deg (Calc'd +205deg) (Ref. 0104)

Methanospirillum hungatei GP1, a minor glycolipid 0.5% (wt%) of the total lipid (Ref. 0104). Caldariella acidophila partial structure (Ref. 0105).




[0104] / [0105]
12
Galfb1-6Galfb1-1-dibiphytanyl-sn-Gro tetraether
2,3-Di-O-phytanyl-1-O-[b-D-galactofuranosyl-(1'-6')-b-D-galactofuranosyl]-sn-diglycerol tetraether
 GGG0012
Ineo Ishizuka
DGT-II
 Download ChemDraw structure file

1110 cm, C-O-C; 1050, C-OH (Ref. 0104).


ORD: MD -227deg (Calc'd -322deg) (Ref. 0104)

Methanospirillum hungatei GP1, a minor glycolipid 0.2% (wt%) of the total lipid (Ref. 0104).




[0104]
13
O-b-D-glucopyranosyl-(1-4)-O-2-acylamido-2-deoxy-b-D-glucopyranosyldiacylglycerol
 GGG0013
Ineo Ishizuka
Glycolipid C
 Download ChemDraw structure file

1730, acylester; 1645, amide; 1545, amide (Ref. 0107)




Bacillus acidocaldarius (15.9% of total cell lipid or 24.9% of gycolipid) (Ref. 0107).




[0107]
14
O-b-D-glucopyranosyl-(1-4)-O-2-acylamido-2-deoxy-b-D-glucopyranosylmonoacylglycerol
 GGG0014
Ineo Ishizuka
Glycolipid D
 Download ChemDraw structure file





Bacillus acidocaldarius, 26.5% of total lipid or 41.3% of glycolipid (Ref. 0107)




[0107]
15
6-Sulfoquinovosyldiacylglycerol, SQDG
6-Sulfo-a-D-quinovopyranosyl-(1-3')-1',2'-di-O-acyl-sn-glycerol
 GGG0015
Ineo Ishizuka
Acidic lipid K
 Download ChemDraw structure file
Relation with photosynthesis (Ref. 0208).
1160, 1030-1050, sulfonate; 1730, acyl ester (Ref. 0107)
1-NMR: 4.87ppm, H-1; 13C-NMR (Ref. 0123) 1H-NMR (2D) (Ref. 0242)
FDMS: m/z 601, [M+Na]+ (Ref. 0123) FAB-MS (Ref. 0242)
Absorption of the anthrone sulfuric acid assay, 592 nm (Ref. 0107)

Review (Ref. 0208). Bacillus acidocaldarius, 43.2% of the acidic lipid fraction (Ref. 0107); plant chloroplast membrane (Ref. 0208); sea urchin Anthocidaris crassispina, the shell, 30 nmol/g (Ref. 0123); sea urchin Pseudocentrotus depressus, eggs and sperms (Ref. 0124). Sea urchin, Strongylocentrotus intermedius (Ref. 0242).



Determination of molecular species by hydrazinolysis (Ref. 0122)
Fattu acids(Ref. 0210)
[0107] / [0122] / [0123] / [0124] / [0208] / [0210] / [0242]
16
TDG-2
2,3-Di-Phytanyl-1-O-[b-D-Glucopyranosyl-(1'-6')-O-a-D-Mannopyranosyl-(1'-2')-O-a-D-Glucopyranosy]-sn-Glycerol
 GGG0016
Ineo Ishizuka
Download ChemDraw structure file

1H-NMR, 4.95 ppm =b-Glc H-1; 4.47 ppm = a-Glc H-1, a-Man H-1 (Ref. 0108)

[a]D +8deg FOR DIETHER MOIETY. [a]D +34.6deg FOR THE TRIGLYCOSYL DIETHER (Ref. 0108)

Halobacterium marismortui, 11mol% of total lipid (Ref. 0108)




[0108]
17
S-TeGD (GL-1)
S-TeGD
 GGG0017
Ineo Ishizuka
Download ChemDraw structure file

3400: OH, 2920: CH2, 1450: CH3, 1380: ISOPROPYL DOUBLET 1100: C-O-C DIETHYL ETHER, 1245: SULFATE S=O, 815: SULFATE S-O-C (Ref. 0109)


[a]D +52.0, [M]+ 733 (Ref. 0109).

Halobacterium cutirubrum: 1.5-2.5% of the total polar lipids (Ref. 0109)




[0109]
18
TeGD-1 (GL-2)
TeGD-1
 GGG0018
Ineo Ishizuka
Download ChemDraw structure file





Halobacterium cutirubrum: 0.5% of the total polar lipids (Ref. 0109)




[0109]
19
TGD-1 (GL-3)
TGD-1
 GGG0019
Ineo Ishizuka
Download ChemDraw structure file



[a]D +46.8 (Ref. 0109). [a]D +47.02 (Ref. 0112). [M]+ 533 (Ref. 0109) [M]+ 536 (Ref. 0112).

Halobacterium cutirubrum: 5% of the total polar lipids (Ref. 0109)




[0109] / [0112]
20
Tetraglycosyl-N-acyldiacylglycerol
Galfb1-2Galpa1-6GlcpN(acyl)b1-2Glcpa1-3acyl2Gro
 GGG0020
Ineo Ishizuka
Download ChemDraw structure file

1545, amide I; 1640, AMIDE II (Ref. 0110).
1H-NMR : 0.85 ppm, iso-methyl; 2.1,N-acetylmethyl (Ref. 0110).

[a]D +38.5 pm 0.5deg (Ref. 0110).

Flavobacterium thermophilum, 8.6% of dry cell (Ref. 0110)



Glycolipids constitute approx. 71% of the total lipid (Ref. 0110).
[0110]
21
S-TGD-1
2,3-Di-Phytanyl-1-O-[b-D-Galactopyranosyl-3'-Sulfate-(1'-6')-O-a-D-Mannopyranosyl-(1'-2')-O-a-D-Glucopyranosy]-sn-Glycerol
 GGG0021
Ineo Ishizuka
Download ChemDraw structure file

1265cm-1: S=O, 830cm-1: S-O-C (Ref. 0112)
1H-NMR

NH4 salt, [a]D +46.79deg; NH4salt [M]+ 578.7

Review (Ref. 0208). Halobacterium cutirubrum, 24% of polar lipids (Ref. 0012)




[0012] / [0112] / [0208]
22
Digalactosyldiacylglycerol
1,2-Di-O-acyl-3-(a-galactopyranosyl-1-6-b-galactopyranosyl)-sn-glycerol
 GGG0023
Ineo Ishizuka
Download ChemDraw structure file


FAB-MS: molecular species (Ref. 0113)


The acidophilic alga Dunaliella acidophila, 0.6% of the dry weight (Ref. 0113); Cyanobacterium Phormidium tenue(Ref. 0227); plant thylakoid membrane (Ref. 0209).



The acidophilic alga Dunaliella acidophila, the major molecular species 18:3/16:2, 18:3/16:1, and 18:3/16:0 (Ref. 0113)
[0113] / [0209] / [0227]
23
PID
2,3-Di-O-Phytanyl-sn-Glycero-1-Phosphoryl-1'-myo-L-Inosytol
 GGG0024
Ineo Ishizuka
Download ChemDraw structure file



[a]D +2.3deg (Ref. 0114)

Pyrococcus woesei(Thermococcales, Archaea): 90%(W/W) of total polar lipids




[0114]
24
PGD
2,3-Di-O-Phytanyl-sn-Glycero-1(a-D-Glucopyranosyl-3-Phosphate)
 GGG0025
Ineo Ishizuka
Download ChemDraw structure file

1365-1375,ISOPROPYL DOUBLET; 1255,1060, PHOSPHATE; 1085, C-O-C (Ref. 0114)
13C-NMR, 69.3,70.3, 70.4, 70.9, 78.1; -CH2-O- AND CH-O-, 98.3 ppm. 1H-NMR 4.98 ppm, J1,2 1.0 Hz (H-1,Glca) (Ref. 0114)
POS-FAB: m/z 916: [M+Na]+ NEG-FAB: m/z 893: [M-H]+ (Ref. 0114)
[a]D +34deg (Ref. 0114).

Thermococcales AN1 (Archaea): 40% of total polar lipids (Ref. 0114)




[0114]
25
1-O-(a-D-glucopyranosyl)-2,3-di-O-phytanyl-sn-glycerol
 GGG0026
Ineo Ishizuka
Download ChemDraw structure file
Inhibited DNA polymerase a, b and reverse transcriptase (Ref. 0245)
+37.0 (Ref. 0244)
IR data (CHCl3) (Ref. 0244)
13C-NMR (benzene/methanol, 7:1, RT) 103.87ppm C-1, b-Glcp (1J 159Hz) (Ref. 0116) 1H-NMR (Ref. 0244)
NEGATIVE FAB-MS (Ref. 0116) (Ref. 0244) Positive FABMS (Ref. 0244)
DI-O-PHYTANYLETHER: MD= +56.1.

Methanococcus voltae: 2.8%(W/W) of total polar lipids (Ref. 0116)
from 1-bromo-2-phytene and 1,2-O-Isopropylidene-L-threitol (Ref. 0244)



[0116] / [0244] / [0245]
26
2,3-Di-O-Phytanyl-1-O-[b-D-Glucopyranosyl-(1-6)-b-D-Glucopyranosyl]-sn-Glycerol
 GGG0027
Ineo Ishizuka
Download ChemDraw structure file

13C-NMR (Ref. 0116) 103.84: C-1, Glcp 104.12: C-1', Glcp 1H-NMR (Ref. 0116) J1,2: 7.8 AND 7.6; 13C-NMR (Ref. 0117) 70.45: C-6 innner Glcp 62.82: C-6 innner Glcp
FAB-MS DI-O-ALKYLGLYCERYLETHER m/z 653.9:(M+1) INTACT LIPID M/z 999.77: [M+Na], m/z 1015.7:[M+K] (Ref. 0117)


Methanococcus voltae: 62.5%(W/W) of total polar lipids (Ref. 0116) Methanobacterium thermoautotrophicum (Ref. 0117)



One mole of either sodium or potassium ion is bound to the lipid of M. thermoautotrophicum (Ref. 0117)
[0116] / [0117]
27
2,3-Di-O-Phytanyl-1-[Phosphoryl-2-Acetamido-2-Deoxy-b-D-Glucopyranosyl]-sn-Glycerol
 GGG0028
Ineo Ishizuka
Download ChemDraw structure file

FT-IR 1240cm-1: P=O, 1040cm-1: P-O-C, 1740cm-1: C=O, 1360,1380cm-1: ISOPROPYL 1550cm-1: AMIDE STRETEH (Ref. 0116)
13C-NMR 94.54: C-1, 2J(C,P)=7.4Hz 54.61: C-2, 3J(C,P) = 7.5 Hz 1H-NMR 1.85 ppm: CH3 (ACETOAMIDE), 3J1,2 = 10.5 Hz (Ref. 0116)
NEGATIVE FAB-MS m/z 934:[M-H]-, m/z 935:[M]- (Ref. 0116)
[M]D = -533.04 (Ref. 0116).

Methanococcus voltae: 7.2%(W/W) of total polar lipids (Ref. 0116)




[0116]
28
a-Galactosyldiacylglycerol
1,2(2,3)-Di-O-acyl-3(1)-a-galactopyranosyl-sn-glycerol
 GGG0029
Ineo Ishizuka
Download ChemDraw structure file

1H-NMR (Ref. 0132)



Treponema pallidum Kazan 5 and other treponemas : The major component (9.5% of dry cell) (Ref. 0126/0127); Treponema hyodysenteriae b78 (29.9% of the total lipid, the total lipid was16.4% of the cell dry weight) (Ref. 0128).



The major phospholipid of treponema was phosphatidylglycerol and diphosphatidylglycerol. Glycolipids could not be detected in leptospirae (Ref. 0127) The preparation from T. hyodysenteriae contained 1-alk-1-enyl species (88.3%) and an additional fatty acyl ester (Ref. 0128)
Saturated C14-C16 chains comprized more than 95% of acyl and alkenyl chains (Ref. 0211)
[0126] / [0127] / [0128] / [0132] / [0211]
29
Acylmonogalactosyldiacylglycerol
1,2-Di-O-acyl-3-[6-O-acyl-b-galactopyranosyl]-sn-glycerol
 GGG0030
Ineo Ishizuka
Download ChemDraw structure file

1H-NMR: exclusively demonstrated that the preparation was not a mixture of isomers as reported previously (Ref. 0132).



Wheat flour (Ref. 0131). Spinach envelope isolated at pH 8.5, 0.8 mol% of the total lipid; spinach homogenates, formed in vitro at 4



Enzymatic formation (Ref. 0136).
[0131] / [0132] / [0134] / [0135] / [0136]
30
Acylmonogalactosylmonoacylglycerol
1-O-Acyl-3-[6-O-acyl-b-galactopyranosyl]-sn-glycerol
 GGG0031
Ineo Ishizuka
Download ChemDraw structure file

Slightly more hydrophobic than monogalactosyldiacylglycerol (Ref. 0137).
1H-NMR of the TMS or acetyl derivative in CDCl3. An acyl ester causes a conspicuous downfield shift of the signal of the geminal proton (Ref. 0137).
EI-MS (Ref. 0137)

2D-TLC separation of the total lipid (Ref. 0133).
Leaf homogenates (Ref. 0137).



Enzymatic experiments with radioactive substrates showed that acylgalactosylmonoglyceride can originate in vitro from monogalactosyl monoglyceride (Ref. 0137).
[0133] / [0137]
31
b-Glucopyranosyl-sn-dialkylglycerol
1,2-Di-O-alkyl-3-b-glucopyranosyl]-sn-glycerol
 GGG0032
Ineo Ishizuka
Download ChemDraw structure file





Chemical synthesis (Ref. 0138).




[0138]
32
b-Galactofuranosyldiacylglycerol
1,2-Di-O-acyl-3(1)-b-galactofuranosyl-sn-glycerol
 GGG0033
Ineo Ishizuka
Download ChemDraw structure file

b-Furanose form (Ref. 0140), [a]/5890 -80deg (Ref. 0141). Hydrolysis with phospholipase A2, treatment with HF, 32P-labeling followed by 2D-TLC (Ref. 0142), the optical rotation values gave obvious evidence for a b-furanose form.
13C-spectrum.
[Spectrum 0001](I.Ishizuka)



Bacteroides Symbiosus (Ref. 0140). Mycoplasma mycoides, 1.3% of the total lipid (Ref. 0141). Bifidobacterium bifidum var. Pennsylvanicus (Ref. 0142).



The GalfGro preparation from the phosphogalactolipids of B. bifidum is likely Gal1-3-sn-Gro (Ref. 0180). Labeled with 14C-Gro,14C-oleate, and 14C-glucose (the distribution of 14C radioactivity among the lipid components described) (Ref. 0141). 14C-glucose most heavily labeled this glycolipid.
[0140] / [0141] / [0142] / [0180]
33
2',3'-diacyl-b-galactofuranosyldiacylglycerol
1,2-Di-O-acyl-3(1)-[2',3'-di-O-acyl-b-galactofuranosyl]-sn-glycerol
 GGG0034
Ineo Ishizuka
Download ChemDraw structure file





Bifidobacterium bifidum var. Pennsylvanicus (Ref. 0143).




[0143]
34
3'-acyl-b-galactofuranosyldiacylglycerol
1,2-Di-O-acyl-3(1)-[3'-O-acyl-b-galactofuranosyl]-sn-glycerol
 GGG0035
Ineo Ishizuka
Download ChemDraw structure file





Bifidobacterium bifidum var. Pennsylvanicus (Ref. 0143).



14C-labeling using 14C-UDP-galactose (Ref. 0143).
[0143]
35
a-Galactofuranosyldiacylglycerol
1,2-Di-O-acyl-3(1)-a-galactofuranosyl-sn-glycerol
 GGG0036
Ineo Ishizuka
Download ChemDraw structure file

Intact galactosyldiacylglycerol, galactosylglycerol, and intact acylated diglucosylcholesterol (Ref. 0144).


A 2,3'-di-O-acyl derivative was described (Ref. 0144).

Acholeplasma axanthum. The major component of this organism was acylated diglucosylcholesterol, followed by galactosyldiacylglycerol and glucosylcholesterol (Ref. 0144).




[0144]
36
1-Alkenyl,2--O-acyl-3(1)-b-galactofuranosylglycerol
 GGG0037
Ineo Ishizuka
Download ChemDraw structure file





Butyrivibrio sp. (Ref. 0145).



Its n-valeryl or n-butyryl esters were described (Ref. 0145).
[0145]
37
a-Glucopyranosyldiacylglycerol
1,2-Di-O-acyl-3-a-glucopyranosylglycerol
 GGG0038
Ineo Ishizuka
Download ChemDraw structure file

(Ref. 0146)

EI-MS: acetate of GlcGro and Glc2Gro (Ref. 0152).
Positional distribution of fatty acids (including unsaturated and cyclopropane acids) (Ref. 0152).

Streptococcus pneumoniae (Pneumococcus) (Ref. 0146/0147). Streptococcus (diplococcus) pneumoniae, 11% of total lipid (11 mg/g) (Ref. 0148/0209). Pseudomonas diminuta, 7.2-10.7% (ca. 31 mg/g) (Ref. 0149). Pseudomonas vesicularis (Ref. 0150). Streptococcus lactis and streptococcus hemolyticus (pyogenes, type 4) (Ref. 0151/0209).




[0146] / [0147] / [0148] / [0149] / [0150] / [0151] / [0152] / [0209]
38
Rubiwettin RG1
b-D-glucopyranosyl 3-(3'-hydroxytetradecanoyl)oxydecanoate
 GGG0039
Ineo Ishizuka
RG1
 Download ChemDraw structure file
A surface-active exolipid (Ref. 0235).
(Ref. 0235)
1H-NMR (Ref. 0235)
Negative and positive FAB-MS of the native and permethylated RG1 (Ref. 0235)

On TLC, acidic lipids make rounded, conical spot in neutral solvent systems. Coeluted with monoglucuronyldiacylglycerol from a silicic acid column by chloroform/methanol, 95:5 (Ref. 0158). The lower plant usually contains Glc-acyl2Gro (Ref. 0160).
Serratia rubidaea (Ref. 0235).
(Ref. 0229/0234)


Rubiwettin R1 (3-(3'-hydroxytetradecanoyl)oxydecanoate) (Ref. 0235).
[0158] / [0160] / [0229] / [0234] / [0235]
39
a-Mannosyldiacylglycerol
1,2-Di-O-acyl-3-b-mannopyranosyl-sn-glycerol
 GGG0040
Ineo Ishizuka
Download ChemDraw structure file





Mycrococcus lysodeikticus (Ref. 0163/0164/0165) . Chemical synthesis, 16:0/16:0 species (Ref. 0162).



Biosynthesis (Ref. 0165/0166). Lennarz, in search of an intermediate of glycoprotein biosynthesis (Ref. 0167/0168), discovered this compound by radioactive labeling of the cell (Ref. 0166).
[0162] / [0163] / [0164] / [0165] / [0166] / [0167] / [0168]
40
a-N-Acetylglucosaminyldiacylglycerol
1,2(2,3)-Di-O-acyl-3(1)-a-2-deoxy-2-acetamidoglucopyranosyl-sn-glycerol
 GGG0041
Ineo Ishizuka
Download ChemDraw structure file


EI-MS (Ref. 0160).


Streptococcus hemolyticus, a minor component (Ref. 0169).




[0160] / [0169]
41
b-N-Acetylglucosaminyldiacylglycerol
1,2(2,3)-Di-O-acyl-3(1)-b-2-deoxy-2-acetamidoglucopyranosyl-sn-glycerol
 GGG0042
Ineo Ishizuka
Download ChemDraw structure file





Bacillus megaterium: 5% of the total lipid glucosamine (Ref. 0170).



This glycolipid could be distinguished chromatographically from 2'-(O-b-glucosaminyl)phosphatidylglycerol and 3'-(O-b-glucosaminyl)phosphatidylglycerol in the lipid extract (Ref. 0170).
[0170]
42
a-heptaosyldiacylglycerol
1,2(2,3)-Di-O-acyl-3(1)-a-D-glycero-D-glucoheptopyranosyl-sn-glycerol
 GGG0043
Ineo Ishizuka
Download ChemDraw structure file





Pseudomonas vesicularis (Ref. 0150).



The major fatty acids were a cis-octadecenoic acid and hexadecanoic acid. C15 and C17 acids were minor components (Ref. 0150).
[0150]
43
Digalactosyldiacylglycerol
1,2-Di-O-acyl-3-(b-galactopyranosyl-1-2-b-galactopyranosyl)-sn-glycerol
 GGG0044
Ineo Ishizuka
Download ChemDraw structure file





Bifidobacterium bifidum (Ref. 0143).




[0143]
44
Acyldigalactofuranosyldiacylglycerol
1,2-Di-O-acyl-3-(b-galactofuranosyl-1-2-(3-O-acyl)b-galactofuranosyl)-sn-glycerol
 GGG0045
Ineo Ishizuka
Download ChemDraw structure file





Bifidobacterium bifidum (Ref. 0143).




[0143]
45
Galactosylglucosyldiacylglycerol
1,2-Di-O-acyl-3-(a-galactopyranosyl-1-2-b-glucopyranosyl)-sn-glycerol
 GGG0046
Ineo Ishizuka
Download ChemDraw structure file




Separation of glycoglycerolipids from phospholipids by using Kanto-Kagaku silicic acid and chloroform/acetone gradient (Ref. 0172/0173/0174).
Streptococcus pneumoniae (Pneumococcus) I-192, 18.8 mg/g dry weight, 34% of total lipid (Ref. 0171). Pneumococcus sp. (Ref. 0146). Streptococcus (diplococcus) pneumoniae IR/4, 33%, 33 mg/g dry cell (Ref. 0172). Lactobacillus casei (Ref. 0173), 19.9 mol% (Ref. 0155/0174).



The phoshoglycolipid of Lactobacilus casei was erraneously a ssigned as glucosylphosphoatidylglycerol (Ref. 0173).
[0146] / [0155] / [0171] / [0172] / [0173] / [0174]
46
Galactosylacylglucosyldiacylglycerol
1,2-Di-O-acyl-3-[a-galactopyranosyl-1-2-(6-O-acyl)-b-glucopyranosyl]-sn-glycerol
 GGG0047
Ineo Ishizuka
Download ChemDraw structure file





Lactobacillus casei, 0.7 mol% of the total lipid (Ref. 0155).




[0155]
47
Diglucosyldiacylglycerol, a-kojibiosyldiacylglycerol
1,2-Di-O-acyl-3-(a-glucopyranosyl-1-2-a-glucopyranosyl)-sn-glycerol
 GGG0048
Ineo Ishizuka
Download ChemDraw structure file

Deacylated glucosyldiacylglycerol (=Glc2Gro) follows the law of Howorth (Ref. 0174).
1H-NMR of deacylated Glc2acyl2Gro (Ref. 0174).



Streptococcus lactis (serogroup N) (Ref. 0175/0176), 7.9 mol% of total lipid (Ref. 0151); streptococcus faecium (faecalis) (Ref. 0154/0177). Streptococcus pyogenes (hemolyticus) 44.3% (57.6 mol%), 66 mg/g dry cell (Ref. 0151/0178). Acholeplasma laidlawii (Ref. 0153).




[0151] / [0153] / [0154] / [0174] / [0175] / [0176] / [0177] / [0178]
48
Glucosylacylglucosyldiacylglycerol, acyl-a-kojibiosyldiacylglycerol
1,2-Di-O-acyl-3-(6-O-acyl-a-glucopyranosyl-1-2-a-glucopyranosyl)-sn-glycerol
 GGG0049
Ineo Ishizuka
Download ChemDraw structure file



2D-TLC, HF treatment, hydrolysis with a-galactosidase (Ref. 0179).

Streptococcus lactis Kiel 42172 (Ref. 0179). Streptococcus lactis (serogroup N), a minor but a common constituent of all 7 strains of group N streptococci (Ref. 0180).



Determination of the position of the acyl group by two-step methylation method (Ref. 0180).
[0179] / [0180]
49
Diglucosyldiacylglycerol, b-gentiobiosyldiacylglycerol
1,2-Di-O-acyl-3-(b-glucopyranosyl-1-6-b-glucopyranosyl)-sn-glycerol
 GGG0050
Ineo Ishizuka
Download ChemDraw structure file

Precise determination of deacylated glycolipids and extensive discussions on the molar rotation (Ref. 0183).
1H-NMR of permethylated glycolipids (Ref. 0183).

DiPtdGro and PtdA could be neatly separated from other lipids (Ref. 0183). Stereochemical configuration of Gro moiety and the location of GroP (Ref. 0174).

Staphylococcus aureus (Ref. 0156/0174/0181). Staphylococcus lactis I3, 0.7 mg/g dry cell = 3% of the total lipid (Ref. 0138/0157/0175). Staphylococcus lactis 7944, 1-2% of the total lipid (Ref. 0182). Staphylococcus epidermidis (Ref. 0183). Bacillus subtilis (Ref. 0175/0138). Bacillus cereus (Ref. 0184).




[0138] / [0156] / [0157] / [0174] / [0175] / [0181] / [0182] / [0183] / [0184]
50
Dimannosyldiacylglycerol
1,2-Di-O-acyl-3-(a-mannopyranosyl-1-2-a-mannopyranosyl)-sn-glycerol
 GGG0051
Ineo Ishizuka
Download ChemDraw structure file





Mycrococcus luteus (lysodeikticus), isolation (Ref. 0163); structure and metabolism, 7-15% of total lipid or 0.75-1.5 mg/g (Ref. 0164). Arthrobacter (Ref. 0161). Microbacterium lacticum, 46% of the total lipid, or 4.9% of dry cells (Ref. 0186).




[0161] / [0163] / [0164] / [0186]
51
Trigalactosyldiacylglycerol
1,2-Di-O-acyl-3-(a-galactopyranosyl-1-6-a-galactopyranosyl-1-6-b-galactopyranosyl-sn-glycerol
 GGG0052
Ineo Ishizuka
Download ChemDraw structure file


EI-MS of the acetate (Ref. 0191).


Potato tuber, isolation and structure, 1% of the total lipid, or 10mg/g tuber (Ref. 0187). Apple pulp (Ref. 0188/0190). Rice bran (Ref. 0160). Spinach envelope, 1.5% of the total lipid (Ref. 0189), 5.2 mol% of the total lipid (Ref. 0191). Chemical synthesis (Ref. 0192/0193).



Molecular species (Ref. 0191).
[0160] / [0187] / [0188] / [0189] / [0190] / [0191] / [0192] / [0193]
52
Trigalactosyldiacylglycerol
1,2-Di-O-acyl-3-b-galactopyranosyl-1-2-b-galactopyranosyl-1-2-b- galactopyranosyl-sn-glycerol
 GGG0053
Ineo Ishizuka
Download ChemDraw structure file





Bifidobacterium bifidum (Ref. 0143).




[0143]
53
Triglucosyldiacylglycerol, a-kojitriosyldiacylglycerol
1,2-Di-O-acyl-3-(a-glucopyranosyl-1-2-a-glucopyranosyl-1-2-a-glucopyranosyl)-sn-glycerol
 GGG0054
Ineo Ishizuka
Download ChemDraw structure file

Deacylated glucosyldiacylglycerol (=Glc2Gro) follows the law of Howorth (Ref. 0174).
1H-NMR of deacylated triglucosylglycerol (Ref. 0174).



Streptococcus pyogenes (hemolyticus), 0.9% or 6.6 mol% of the total lipid (Ref. 0151/0178). Streptococcus faecium (Ref. 0194).




[0151] / [0174] / [0178] / [0194]
54
Acyltriglucosyldiacylglycerol, acyl-a-kojitriosyldiacylglycerol
1,2-Di-O-acyl-3-(a-glucopyranosyl-1-2-a-glucopyranosyl-1-2(6-O-acyl)-a-glucopyranosyl)-sn-glycerol
 GGG0055
Ineo Ishizuka
Download ChemDraw structure file





Lactobacillus casei, 3% of the total lipid (Ref. 0155).




[0155]
55
1,2-Di-O-acyl-3-(b-glucopyranosyl-1-6-a-galactopyranosyl-1-2-a-glucopyranosyl)-sn-glycerol
 GGG0056
Ineo Ishizuka
Download ChemDraw structure file





Lactobacillus casei, less than 17% of the total lipid (Ref. 0173). Lactobacillus casei, the final structure, 26.2 mol% of the total lipid (Ref. 0155).




[0155] / [0173]
56
1,2-Di-O-acyl-3-(b-glucopyranosyl-1-6-a-galactopyranosyl-1-2-a-(6-O-acyl)glucopyranosyl)-sn-glycerol
 GGG0057
Ineo Ishizuka
Download ChemDraw structure file





Lactobacillus casei, less than 17% of the total lipid (Ref. 0155).



Also occurs as the component of lipoteichoic acids (Ref. 0155).
[0155]
57
Triglucosyldiacylglycerol, b-gentiotriosyldiacylglycerol
1,2-Di-O-acyl-3-(b-glucopyranosyl-1-6-b-glucopyranosyl-1-6-b-glucopyranosyl)-sn-glycerol
 GGG0058
Ineo Ishizuka
Download ChemDraw structure file





Lactobacillus casei, 3.2 mol% of the total lipid (Ref. 0195).




[0195]
58
A tetraglycosyldiacylglycerol
1,2-Di-O-acyl-3-(b-glucopyranosyl-1-6-b-glucopyranosyl-1-6-a-galactopyranosyl-1-2b-glucopyranosyl)-sn-glycerol
 GGG0059
Ineo Ishizuka
Download ChemDraw structure file


EI-MS of the acetate (Ref. 0191).


Lactobacillus casei, 5.5 mol% of the total lipid (Ref. 0155/0196).



Molecular species (Ref. 0191).
[0155] / [0191] / [0196]
59
A tetragalactosyldiacylglycerol
1,2-Di-O-acyl-3-(a-galactopyranosyl-1-6-a-galactopyranosyl-1-6-a-galactopyranosyl-1-6-b-galactopyranosyl-sn-glycerol
 GGG0060
Ineo Ishizuka
Download ChemDraw structure file


GC-EI-MS of the TMS derivative (Ref. 0160).


Spinach chloroplasts, about 1% of galactosylglycoglycerolipids. Relative amount (molar ratio) of galactolipids was; mono-, di-, tri-, tetra-, 60:30:5:1 (Ref. 0197). Rice bran, 2.3% of the total lipid (Ref. 0160). Cassava tubers (tapioca), 7.3% (Ref. 0198).



Synthesized with chloroplast enzymes using UDP-galactose as a galactosedonor (Ref. 0197). The extractable lipids of the cassava tuber flour comprized about half thetotal flour lipid (2.5%) and consisted chiefly of galdags. These included tetra-galdag (7.3% of the total lipid) (Ref. 0198).
[0160] / [0197] / [0198]
60
1-O-Hexadecyl-2-O-hexadecanoyl-3-(a-rhamnopyrnosyl-1-4-b-galactopyranosyl-1-4-b-galactopyranosyl-1-4-b-galactopyranosyl)-sn-glycerol
 GGG0061
Ineo Ishizuka
Download ChemDraw structure file





Mung bean (Phaseolus mungo) sprout, 7-day mung bean, 0.2% of the total lipid (Ref. 0199).




[0199]
61
1,2(2,3)-Di-O-acyl-3(1)-(a-galactopyranosyl-1-2-a-galactopyranosyl-1-3-b-D-glycero-D-mannoheptopyranosyl-1-3-a-glucopyranosyl-1-2-a-glucopyranosyl-1-2-a-glucopyranosyl)-sn-glycerol
 GGG0062
Ineo Ishizuka
Download ChemDraw structure file





Acholeplasma modicum (Ref. 0200).




[0200]
62
a-Glucuronosyldiacylglycerol
1,2-Di-O-acyl-3-[a-glucuronopyranosyl]-sn-glycerol
 GGG0063
Ineo Ishizuka
Download ChemDraw structure file





Pseudomonas diminuta, 3.5% of the total lipid or 15 mg/g (Ref. 0149). Metabolism (Ref. 0201). Pseudomonas vesicularis (Ref. 0150).




[0149] / [0150] / [0201]
63
b-Glucuronosyldiacylglycerol
1,2-Di-O-acyl-3-[b-glucuronopyranosyl]-sn-glycerol
 GGG0064
Ineo Ishizuka
Download ChemDraw structure file





Alteromonas (pseudomonas) rubescens, 3.0% of the total lipid (Ref. 0158). Metabolism and the relation with growth phase (Ref. 0202). Pseudomonas vesicularis (Ref. 0150).




[0150] / [0158] / [0202]
64
1,2-Di-O-acyl-3-[b-glucopyranosyl-1-4-a-glucuronopyranosyl]-sn-glycerol
 GGG0065
Ineo Ishizuka
Download ChemDraw structure file





Pseudomonas diminuta, 4.1% of the total lipid (Ref. 0149). Pseudomonas vesicularis (Ref. 0150).




[0149] / [0150]
65
1,2-Di-O-acyl-3-[a-glucopyranosyl-1-4-a-galacturonopyranosyl]-sn-glycerol
 GGG0066
Ineo Ishizuka
Download ChemDraw structure file





Streptomyces LA 7071, 6% of the total lipid. Acylated at position-2 or -3 of galacturonic acid (Ref. 0203).




[0203]
66
1,2(2,3)-Di-O-acyl-3(1)-(a-N-acetylneuraminosyl-2-9-a-N-acetylneuraminosyl-2)-sn-diacylglycerol
 GGG0067
Ineo Ishizuka
Download ChemDraw structure file





Chemical synthesis (Ref. 0205).




[0205]
67
1,2(2,3)-Di-O-acyl-3(1)-(b-N-acetylneuraminosyl-2-9-a-N-acetylneuraminosyl-2)-sn-diacylglycerol
 GGG0068
Ineo Ishizuka
Download ChemDraw structure file





Chemical synthesis (Ref. 0205).




[0205]
68
Mycobacterial sulfolipid I
a,a'-Trehalose 2,3,6,6'-tetraester-2'-sulfate
 GGG0085
Ineo Ishizuka
Download ChemDraw structure file
Toxicity of intradermal injection (Ref. 0091).
[a]25/ =40.5 (Ref. 0091).
1400-1450 cm-1: NH of ammonium salt, 1660-1740 cm-1: acyl carbonyl, 1250 cm-1, SO; 824cm-1, SO; 808cm-1, type 3 (Ref. 0091).




Mycobacterium taberculosis (Ref. 0091/0092). Review (Ref. 0208).



Spontaneous desulfation (Ref. 0091)Deacylation to yield trehalose 2-sulfate (Ref. 0092)
Branched long-chain fatty acid (Ref. 0092)
[0091] / [0092] / [0208]
69
Glycolipid B
O-2-Acylamido-2-deoxy-b-D-glucopyranosyl pentacyclic tetrol
 GGG0086
Ineo Ishizuka
Download ChemDraw structure file
This strain, adapting to the environment of pH3, and 60degC, appears to utilize this unique membrne component (Ref. 0107).
1645cm-1, amide; 1545cm-1, amide (Ref. 0107).




Bacillus acidocaldarius (16.7% of total lipid or 26.0% of glycolipid) (Ref. 0107).




[0107]
70
Long-chain diglycerol tetraethers
 GGG0087
Ineo Ishizuka
Download ChemDraw structure file





Thermoplasma acidophilum (Ref. 0111).



This strain grows at 59degC Cand pH 2, and phylogenetically belongs to Mycoplasmatales (Ref. 0111).
C40 hydrocarbon chains (Ref. 0111).
[0111]
71
Gentiobiosyl caldarchaeol
Gentiobiosyl caldarchaeol
 GGG0088
Ineo Ishizuka
Download ChemDraw structure file

1100cm-1, C-O-C; 1035cm-1, C-OH (Ref. 0118).

Positive FAB-MS; m/z 1648.4, [M+Na]+; m/z 1649.0, [M+Na+1]+ (Ref. 0118).


Methanobacterium thermoautotrophicum (Ref. 0117/0118).




[0117] / [0118]
72
1-O-Acyl-2-b-Galactopyranosylethyleneglycol
 GGG0089
Ineo Ishizuka
Download ChemDraw structure file


EI-MS : TMS derivatives of glucosylethyleneglycol (comparison with glucosylglycerol) and its acetates (Ref. 0139).


Ripening (immature) corn seed, 1% of the total lipid (Ref. 0139). Chemical synthesis (Ref. 0139).




[0139]
73
1,2(2,3)-Di-O-acyl-3(1)-(a-N-acetylneuraminosyl-2-9-a-N-acetylneuraminosyl-2)-sn-phosphatidate
 GGG0090
Ineo Ishizuka
Download ChemDraw structure file
The presence of the hydrophobic end causes the polysaccharides to aggregate in a micellar form and may be the entity by which the polysaccharide remains attached to the outer membrane of the bacterium giving rise to the structure recognized as a capsule.


C-2 CARBOXYL OF NeuAc IS GLYCOSIDICALLY BOUND TO THE PHOSPHATEMONOESTER OF PHOSPHATIDIC ACID.

Meningococcus and E. coli K92 (Ref. 0204).




[0204]
74
Seminolipid, sulfogalactoglycerolipid
Galactosylalkylacylglycerol 3-sulfate
 GGG0091
Ineo Ishizuka
SGG, SM4g
 Download ChemDraw structure file
Inhibition of arylsulfatase activities (Ref. 0048); relation with sperm capacitation (Ref. 0072); labeled by intracranial injection of [35S]sulfate (Ref. 0061); labeled by intraperitoneal injection of [35S]sulfate(Ref. 0015/0066); not hydrolyzable by glycosulfatase (Ref. 0015) ; antigenicity against mice (monoclonal antibody) (Ref. 0043/0050); a component of myelin (Ref. 0069/0070).
[a]23/D = +2.78(C=1.44 IN C/M 1:1),[a]/D =0 (C=,0.39 IN C/M 1:1) (Ref. 0059).
Sol in pyridine insol in diethylether sol in hot methanol but precipitates on cooling to ambient temperature (Ref. 0058) Behavior in the Folch partition (Ref. 0027).
1735cm-1 ester carbonyl (Ref. 0058) 1240cm-1 C-O-S (Ref. 0058) ,820cm-1 equatorial C-O-S (Ref. 0058) 875cm-1 type 2b (b) (Ref. 0058) , diacyl species: 1720cm-1 is larger (Ref. 0061)
CDCl3/CD3OD, 2:1(v/v) 35 OR 60
Galactosyl-alkylGro (Ref. 0065) , SI-MS (Ref. 0036)
The visual color absorption of the Azure A complex (Ref. 0027)
Silicagel TLC <<>>
Review (Ref. 0208). Porcine testis sperm 0.3 and 1.0mmol/g respectively) (Ref. 0058/0063) rat testis (Ref. 0087/0068), Relation with age (Ref. 0073)rat brain (Ref. 0060/0061/0065/0066) male and female of 300g rat (190 nmol/g) (Ref. 0060) guinea pig testis (Ref. 0059), mouse testis (Ref. 0025), bovine testis and sperm (Ref. 0067) human testis (Ref. 0006). Nerve tissues of gadoid fishes (Ref. 0207)
(Ref. 0193/0210)

None
Mammalian sperm, 16:0 + 16:0 (Ref. 0208)
[0006] / [0015] / [0025] / [0027] / [0043] / [0048] / [0050] / [0058] / [0059] / [0060] / [0061] / [0063] / [0065] / [0066] / [0067] / [0068] / [0069] / [0070] / [0072] / [0073] / [0087] / [0193] / [0207] / [0208] / [0210]
75
6'-O-phosphocholine-a-glucopyranosyl-(1-3')-1,2-diacyl-sn-glycerol
 GGG0096
Ineo Ishizuka
Download ChemDraw structure file

FT-IR (Ref. 0218).
1H-NMR, DQF-COSY in phase-sensitive mode, determination of hexose configuration as a-glucose, coupling of H6 of glucose and OH of choline with phosphate (Ref. 0218).
Negative LSIMS and negative and positive tandem mass spectrometry (Ref. 0218).


Mycoplasma fermentans (Ref. 0218).
Stereo-specific synthesis with sn-1 configuration (Ref. 0219).


Major fatty acid, 16:0 (Ref. 0218).
[0218] / [0219]
76
1''-Phosphocholine-2''-amino-dihydroxypropane-3''-phospho-6'-a-glucopyranosyl-(1-3)-diacylglycerol
 GGG0097
Ineo Ishizuka
Download ChemDraw structure file

1H-DQF-COSY in phase-sensitive mode; 31P-NMR; 1H-31P-HMQC (Ref. 0220/0221).
Positive and negative LSIMS, CID (Ref. 0220).


Mycoplasma fermentans (Ref. 0220).




[0220] / [0221]
77
2,3-Diphytanyl-1-[2,6-sulfo-a-mannopyranosyl-1-2-a-glucopyranosyl]-sn-glycerol
 GGG0098
Naoko Tanaka
S2-DGD-1
 Download ChemDraw structure file
Increased depending on the salt concentration of the medium (Ref. 0102).
1230-1260 cm-1, S=O (Ref. 0222). 843 cm-1, C-O-S (Ref. 0222).
1H-NMR (Ref. 0222),
[Spectrum 0001](I.Ishizuka). 13C-NMR (Ref. 0222),
[Spectrum 0002](I.Ishizuka).
Negative FAB (NH4 SALT) (Ref. 0222) [M+Na-2H]- , 1227 (C20-C25-diether) and 1157 (C20-C20-diether) [M-SO3H]- , 1125 (C20-C25-diether) and 1055 (C20-C20-diether)


Natrialba asiatica JCM9576 (former strain 172) (Ref. 0222/0206)



2,3-di-O-phytanyl-sn-glycerol (C20-C20-diether) or 2-O-sesterterpenyl-3-O-phytanyl-sn-glycerol (C20-C25-diether) (Ref. 0222).
[0102] / [0206] / [0222]
78
1,2-diacyl-3-O-a-D-glucopyranosyl-(1-3)-O-amannopyranosyl)-glycerol
 GGG0099
Ineo Ishizuka
BF-7
 Download ChemDraw structure file
The bacteria induces nitrogen-fixing root nodules on the leguminous host, white clover (Trifolium repens). This glycolipid elicit various symbiosis-related morphological responses on white clover roots (Ref. 0224).




Rhizobium leguminosarum Bivar trifolii (Ref. 0224). Wild type Rhizobium cells accumulate this glycolipid in response to 4'7-dihydroxyflavone.



1,2-di-O-acyl-sn-glycerol. The major fatty acids are iso-hexadecanoic and anteiso-heptadecanoic (Ref. 0225)
[0224] / [0225]
79
2,3-Diphytanyl-sn-glycerol
 GGG0100
Ineo Ishizuka
Download ChemDraw structure file

1H-NMR (Ref. 0226).



Halobacterium halobium (Ref. 0226)
(+)-a-methoxy-a-trifluoromethyl-phenylacetic acid ester (Ref. 0226).


2,3-di-O-phytanyl-sn-glycerol (Ref. 0226).
[0226]
80
Monogalactosylmonoglyceride, galactosylmnoacylglycerol, lyso-galactosyldiglyceride
1-O-acyl-3-[b-galactopyranosyl]-sn-glycerol
 GGG0101
Ineo Ishizuka
GalDAG
 Download ChemDraw structure file

-25.7
1740
1H-NMR, 13C-NMR (Ref. 0227/0233).
FAB-MS


Treatment with lipase of monogalactosyldiacylglycerol from Cyanobacterium Phormidium tenue(Ref. 0227). Storage of the cyanobacterium, Phormidium tenue at -20C (Ref. 0233).



1-O-acyl-sn-glycerol(Ref. 0227).
[0227] / [0233]
81
Monogalactosylmonoglyceride, galactosylmnoacylglycerol, lyso-galactosyldiglyceride
2-O-acyl-3-[b-galactopyranosyl]-sn-glycerol
 GGG0102
Ineo Ishizuka
GalDAG
 Download ChemDraw structure file

-7.1
1730
1H-NMR, 13C-NMR (Ref. 0227).
FAB-MS


Treatment with lipase of monogalactosyldiacylglycerol from Cyanobacterium Phormidium tenue(Ref. 0227).



2-O-acyl-sn-glycerol(Ref. 0227).
[0227]
82
Digalactosylmonoglyceride, digalactosylmonoacylglycerol, lyso-digalactosyldiglyceride
1-O-acyl-3-[a-galactopyranosyl-(1-6)-b-galactopyranosyl]-sn-glycerol
 GGG0103
Ineo Ishizuka
GalDAG
 Download ChemDraw structure file

+17.0
1740
1H-NMR, 13C-NMR (Ref. 0227/0233).
FAB-MS


Treatment with lipase of digalactosyldiacylglycerol from Cyanobacterium Phormidium tenue(Ref. 0227). Storage of the cyanobacterium, Phormidium tenue at -20C (Ref. 0233).



Fatty acid 1-O-acyl-glycerol(Ref. 0227).
[0227] / [0233]
83
Digalactosylmonoglyceride, digalactosylmonoacylglycerol, lyso-digalactosyldiglyceride
2-O-acyl-3-[a-galactopyranosyl-b-galactopyranosyl]-sn-glycerol
 GGG0104
Ineo Ishizuka
GalDAG
 Download ChemDraw structure file

+5.3
1735
1H-NMR, 13C-NMR (Ref. 0227).
FAB-MS


Treatment with lipase of digalactosyldiacylglycerol from Cyanobacterium Phormidium tenue(Ref. 0227).



2-O-acyl-sn-glycerol(Ref. 0227).
[0227]
84
6-Sulfoquinovosylmonoacylglycerol, lyso-sulfoquinovosyldiglyceride
6-Sulfo-a-D-quinovopyranosyl-(1-3')-2'-O-acyl-sn-glycerol
 GGG0105
Ineo Ishizuka
Download ChemDraw structure file
Antitumour activity (Ref. 0242).
1H-NMR (2D) (Ref. 0242).
FAB-MS (Ref. 0242).
Absorption of the anthrone sulfuric acid assay, 592 nm (Ref. 0107)
Silicic acid column (Ref. 0227).
Treatment with lipase of 6-sulfoquinovosyldiacylglycerol from Cyanobacterium Phormidium tenue(Ref. 0227). Review (Ref. 0208). Sea urchin, Stronglylocentrotus intermedius (Ref. 0242)



2-Linolenyl (Ref. 0227)
[0107] / [0208] / [0227] / [0242]
85
6-O-acyl-b-glucosyldiacylglycerol
1,2(2,3)-Di-O-acyl-3-(6-O-acyl-b-glucopyranosyl)-sn-glycerol
 GGG0106
Ineo Ishizuka
Download ChemDraw structure file

(Ref. 0236).
1H-NMR (Ref. 0236).


Sephadex, silicic acid columns (Ref. 0228).
Acholeplasma laidlawii (Ref. 0228).
Chemical synthesis (Ref. 0236).



[0228] / [0236]
86
6-O-acyl-b-galactosylmonoacylglycerol
1-O-acyl-3-(6-O-acyl-b-galactopyranosyl)-sn-glycerol
 GGG0109
Ineo Ishizuka
Download ChemDraw structure file

Ester carbonyl (Ref. 0232).
1H-NMR (DQF-COSY), 13C-NMR, HMBC (Ref. 0232).


Silicic acid columns (Ref. 0232).
Nitrogen-fixing cyanobacterium Anabaena flos-aquae f. flos-aquae (Ref. 0232).



Fatty acid 1-Acyl-sn-glycerol (Ref. 0232)
[0232]
87
6-O-acyl-b-galactosylmonoacylglycerol
2-O-acyl-3-(6-O-acyl-b-galactopyranosyl)-sn-glycerol
 GGG0110
Ineo Ishizuka
Download ChemDraw structure file

Ester carbonyl (Ref. 0232).
1H-NMR (DQF-COSY), 13C-NMR, HMBC (Ref. 0232).


Silicic acid columns (Ref. 0232).
Nitrogen-fixing cyanobacterium Anabaena flos-aquae f. flos-aquae (Ref. 0232).



2-Acyl-sn-glycerol (Ref. 0232).
[0232]
88
a-glucosaminyl-a-iduronosyldiacylglycerol
1,2-diacyl-3-O-[a-2-amino-2-deoxy-glucopyranose-(1-4)-O-a-iduronopyranuronic acid]-glycerol
 GGG0112
Ineo Ishizuka
Download ChemDraw structure file

1H-NMR, 13C-NMR, HMBC, NOESY (Ref. 0239).



A marine bacterium Deleya marina (Ref. 0239).



C16:0, 16:1, 17cyc, 18:1 (Ref. 0239).
[0239]
89
1-O-(6'-sulfo-a-D-glucopyranosyl)-2,3-di-O-phytanyl-sn-glycerol
 GGG0115
Naoko Tanaka
Download ChemDraw structure file
Inhibited DNA polymerase a, b and reverse transcriptase (Ref. 0245)
IR data (CHCl3) (Ref. 0244).
1H-NMR (Ref. 0244).
Positive and Negative FABMS (Ref. 0244).



from 1-bromo-2-phytene and 1,2-O-Isopropylidene-L-threitol (Ref. 0244)



[0244] / [0245]
90
5-mycolony-arabinofuranosyl(1-1
 GGG0116
Naoko Tanaka
Download ChemDraw structure file





Mycobacterium avium-Mycobacterium intracellulare complex (Ref. 0247).




[0247]
91
Glycerophosphoryl phosphatidyl kojibiosyl diacylglycerol
3(1)-O-[6
 GGG0117
Naoko Tanaka
Download ChemDraw structure file





Streptococcus faecalis (Ref. 0248).




[0248]
92
Glucosylated diphosphatidylglycerol
2'-O-a-D-glucopyranosyl-1',3'-bis-(1,2-diacyl-sn-glycero-3-phospho)-glycerol
 GGG0118
Naoko Tanaka
Download ChemDraw structure file





group B streptococci (Ref. 0249)




[0249]
93
glycerophosphoglycolipids
1,2-di-O-acyl-3-O-[6-(sn-glycero-1-phospho-3-sn-glycero-1-phospho)-a-D-glucopyranosyl-(1-2)-(6-O-acyl-a-D-glucopyranosyl)]-glycerol
 GGG0119
Naoko Tanaka
Download ChemDraw structure file





Streptococcus lactis (Ref. 0250).




[0250]
94
lipoteichoic acid, poly(3-O-galabiosyl-2-galactosyl-sn-glycero-1-phosphate)
{-6Gal-a-(1-6)-Gal-a-(1-3)-[Gal-a-(1-2)]-sn-Gro-1-phospho-}n-6-Glc-a-(1-2)-[acyl-6-]Glc-a-(1-3)-1,2diacylglycerol
 GGG0120
Naoko Tanaka
Download ChemDraw structure file





Sreptococcus lactis Kiel 42172 (Ref. 0252).




[0252]
95
Gro-phospho-6-Glc-a-(1-2)-[acyl-6Glc-a]-(1-3)-1,2diacylglycerol
 GGG0121
Naoko Tanaka
Download ChemDraw structure file





Sreptococcus lactis Kiel 42172 (Ref. 0251).




[0251]
96
Gal-a-(1-2)-sn-Gro-1-phospho-6-Glc-a-(1-2)-[acyl-6Glc-a]-(1-3)-1,2diacylglycerol
 GGG0122
Naoko Tanaka
Download ChemDraw structure file





Sreptococcus lactis Kiel 42172 (Ref. 0251).




[0251]
97
Gal-a-(1-3)-sn-Gro-1-phospho-6-Glc-a-(1-2)-[acyl-6Glc-a]-(1-3)-1,2diacylglycerol
 GGG0123
Naoko Tanaka
Download ChemDraw structure file





Sreptococcus lactis Kiel 42172 (Ref. 0251).




[0251]
98
Di-[Gal-a]-(1-2,3)-sn-Gro-1-phospho-6-Glc-a-(1-2)-[acyl-6Glc-a]-(1-3)-1,2diacylglycerol
 GGG0124
Naoko Tanaka
Download ChemDraw structure file





Sreptococcus lactis Kiel 42172 (Ref. 0251).




[0251]
99
Gal-a-(1-6)-Gal-a-(1-3)-sn-Gro-1-phospho-6-Glc-a-(1-2)-[acyl-6Glc-a]-(1-3)-1,2diacylglycerol
 GGG0125
Naoko Tanaka
Download ChemDraw structure file





Sreptococcus lactis Kiel 42172 (Ref. 0251).




[0251]
100
Gal-a-(1-6)-Gal-a-(1-3)-[Gal-a-(1-2)]-sn-Gro-1-phospho-6-Glc-a-(1-2)-[acyl-6-]Glc-a-(1-3)-1,2diacylglycerol
 GGG0126
Naoko Tanaka
Download ChemDraw structure file





Sreptococcus lactis Kiel 42172 (Ref. 0251).




[0251]
101
Gal-a-(1-6)-Gal-a-(1-6)-Gal-a-(1-3)-[Gal-a-(1-2)]-sn-Gro-1-phospho-6-Glc-a-(1-2)-[acyl-6-]Glc-a-(1-3)-1,2diacylglycerol
 GGG0127
Naoko Tanaka
Download ChemDraw structure file





Sreptococcus lactis Kiel 42172 (Ref. 0251).




[0251]
102
Glc-b-(1-3)-Glc-a-(1-2)-Glc-a-(1-1)-2,3diacylglycerol
 GGG0128
Naoko Tanaka
Download ChemDraw structure file





Acholeplasma granularum (Ref. 0253)




[0253]
103
blaberoside
Acyl-6-Glc-b-(1-6)-Glc-b-(1-2)-(acyl-1,alkyl-3)Gro
 GGG0129
Naoko Tanaka
Download ChemDraw structure file

O-H stretching (3700-3100 cm-1), C-H streching (2970-2935 cm-1), ester C=O streching (1755 cm-1), trans C=C streching (1650 cm-1), C-O streching of a primary alchol (1050 cm-1), C-O streching of an alkyl ether (1080 cm-1) (Ref. 0254).
1H- and 13C-NMR, in Me2SO-d6, 1H COSY (Ref. 0254)

Laser desorption mass spectrometry (LDMS), plasma desorption mass spectrometry (PDMS), fast atom bombardment mass spectrometry (FAB-MS) (Ref. 0254)

Giant cockroach, Blaberus colosseus (Ref. 0254)



Acyl, 20h:1(3-hydroxy-11-eicosenoyl); Alkyl, 16:0, 16:1 (Ref. 0254)
[0254]
104
Acyl-6-Glc-b-(1-6)-Glc-b-(1-2)-(alkyl-3)Gro
 GGG0130
Naoko Tanaka
Download ChemDraw structure file

O-H stretching (3700-3100 cm-1), C-H streching (2970-2935 cm-1), ester C=O streching (1755 cm-1), trans C=C streching (1650 cm-1), C-O streching of a primary alchol (1050 cm-1), C-O streching of an alkyl ether (1080 cm-1) (Ref. 0254).
1H- and 13C-NMR, in Me2SO-d6, 1H-1H COSY (Ref. 0254)

Laser desorption mass spectrometry (LDMS), plasma desorption mass spectrometry (PDMS), fast atom bombardment mass spectrometry (FAB-MS) (Ref. 0254)

Giant cockroach, Blaberus colosseus (Ref. 0254)



Acyl, 20h:1(3-hydroxy-11-eicosenoyl); Alkyl, 16:0, 16:1 (Ref. 0254)
[0254]
105
Gal-b-(1-1)-2,3-di-O-phytanyl-sn-glycerol
 GGG0131
Naoko Tanaka
Download ChemDraw structure file

isopropyl doublet (CH3 deformations at 1376 and 1362 cm-1) (Ref. 0255).
13C-NMR, in benzene-d6/methanol-d4 (7:1) (Ref. 0255)

Positive FAB-MS (Ref. 0255)

the aceticlastic methanogen, Methanothrix concilii GP6 (Ref. 0255)



Alkyl, phytanyl(C20), 3-hydroxy-phytanyl(C20h); (Ref. 0255)
[0255]
106
Gal-b-(1-6)-[Glc-b-(1-3)]Gal-b-(1-1)-2,3-di-O-phytanyl-sn-glycerol
 GGG0132
Naoko Tanaka
Download ChemDraw structure file

isopropyl doublet (CH3 deformations at 1376 and 1362 cm-1) (Ref. 0255).
13C-NMR, in benzene-d6/methanol-d4 (7:1) (Ref. 0255)

Positive FAB-MS (Ref. 0255)

the aceticlastic methanogen, Methanothrix concilii GP6 (Ref. 0255)



Alkyl, 3-hydroxy-phytanyl(C20h); (Ref. 0255)
[0255]
107
Glc-a-(1-4)-(decanoyl-6)Glc-a-(1-3(1))-1(3),2-diaclyglycerol
 GGG0133
Naoko Tanaka
Download ChemDraw structure file

13C-NMR, in CHCl3-d/CH3OH-d6 (70:30) (Ref. 0256)

Negative FAB-MS (Ref. 0256)

a hyperthermophilic microorganism, Thermotoga maritima (Ref. 0256)



16:0 (Ref. 0256)
[0256]
108
Glc-a-(1-4)-Glc-a-(1-3(1))-1(3),2-diaclyglycerol
 GGG0134
Naoko Tanaka
Download ChemDraw structure file

13C-NMR, in CHCl3-d/CH3OH-d6 (70:30) (Ref. 0256)

Negative FAB-MS (Ref. 0256)





16:0 (Ref. 0256)
[0256]
109
phosphoglucolipid
glycerophosphoryl-6-Glc-a-(1-2)-Glc-a-(1-3)-1,2-diacylglycerol
 GGG0135
Naoko Tanaka
Download ChemDraw structure file

1H-NMR, 13-NMR, 31P-NMR in DMSO-d6/D2O, TOCSY, 31P-1H COSY, ROESY (Ref. 0257)



Acholeplasma laidlawii strain A-EF22 (Ref. 0257). Streptococcus faecalis (Ref. 0248).




[0248] / [0257]
110
phosphoglucolipid
glycerophosphoryl-6-Glc-a-(1-2)-(monoacyl-glycerophosphoryl-6)Glc-a-(1-3)-1,2-diacylglycerol
 GGG0136
Naoko Tanaka
Download ChemDraw structure file

1H-NMR, 13-NMR, 31P-NMR in DMSO-d6/D2O, TOCSY, 31P-1H COSY, ROESY (Ref. 0257)



Acholeplasma laidlawii strain A-EF22 (Ref. 0257).




[0257]
111
3(1)-O-[6'-(1,2-diacyl-sn-glycerol-3-phosphoryl)-2'-O-(a-D-glucopyranosyl)-a-D-glucopyranosyl]-1(3),2-diacylglycerol
 GGG0137
Naoko Tanaka
Download ChemDraw structure file





Streptococcus faecalis (Ref. 0248).




[0248]
112 No image
Galactosylglucosyldiacylglycerol
1,2-Di-O-acyl-3-(a-galactopyranosyl-1-2-a-glucopyranosyl)-sn-glycerol
 GGG0138
Naoko Tanaka

13C-spectrum.
[Spectrum 0001](I.Ishizuka)



Streptococcus pneumoniae, 64% (mol%) (Ref. 0258)




[0258]
113 No image
1,2-Di-O-acyl-3-(a-galactopyranosyl-1-2-(6-O-acyl)-a-glucopyranosyl)-sn-glycerol
 GGG0139
Naoko Tanaka

1H-13C COSY spectrum.
[Spectrum 0001](I.Ishizuka)



Streptococcus pneumoniae, 5% (mol%) (Ref. 0258)




[0258]
114
6'-O-Phosphocholine-a-Glcp-(1'-3)-1,2-diacyl-sn-glycerol
 GGG1041
Kazuo Nakamura
Download ChemDraw structure file

400MHz 1H-NMR (Ref. 1063)
LSIMS TANDEM MS (COLLISION-ACTIVATED DISSOCIATION MS) (Ref. 1063)


Mycoplasma Fermentans (Ref. 1063)




[1063]
115
1,2-Diacyl-1-3a-D-glucuronopyranosyl-sn-glycerol-taurineamide
 GGG1070
Kazuo Nakamura
Download ChemDraw structure file





Hyphomonas jannaschiana VP-2T (ATCC 33883T, Budding seawater bacterium) (Ref. 1077)



n-14:0, 2mol%; n-15:0,3%; n-16:0,19%; cis-16:1w7,6%; n-17:0,4%; n-18:0,15%; cis-18:w7,44%; n-19:0,7% (Ref. 1077)
[1077]
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TITLE:Quantitative thin-layer chromatography of glycolipids in animal tissues. PubMed ID:5031779
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TITLE:Comparison of the cerebroside sulphatase and the arylsulphatase activity of human sulphatase a in the absence of activators. PubMed ID:235289
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TITLE:Levels of cerebrosides, sulfatides, and galactosyl diglycerides in different regions of rat brain - change during maturation and distributionin subcellular fractions of gray and white matter of sheep brain. PubMed ID:435504
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TITLE:Tamai,Y.,Kojima,H.,Abe,K.,And Saito,S. (1982) Glycolipid composition of fish brains and its bearing on the phylogeny in New Vistas in Glycolipid Research (Makita,A., Handa,S.,Taketomi, T., and Nagai,Y.,eds.), pp315-323.
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TITLE:Polar lipids of an extremely halophilic bacterial strain (r-4) isolated from salt ponds in spain.
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