• Natural Product Sciences
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• v.12 no.4
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• pp.193-196
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• 2006

A mixture of cerebrosides (1) and four triterpenoids (2 - 5) have been isolated from the hexane- and EtOAc-soluble fractions of the roots of Synurus deltoides (Ait.) Nakai (Compositae). Triterpenoid structures were determined as lupeol (2), $\beta-amyrin$ (3), $\alpha-amyrin$ (4), and ursolic acid (5). Synurus cerebrosides (1) were characterized as a common long chain base (2S,3S,4R,8E)-2-amino-8-octadecene-1,3,4-triol and fatty acyl chains; palmitic acid, (2R)-2-hydroxybehenic acid, (2R)-2-hydroxytricosanoic acid, (2R)-2-hydroxylignoceric acid, (2R)-2-hydroxypentacosanoic acid, and (2R)-2-hydroxyhexacosanoic acid. The synurus cerebrosides (1) were the first isolation from a natural source.

• Archives of Pharmacal Research
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• v.26 no.2
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• pp.138-142
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• 2003

From the pulp of Euphoria longana (Longan Arillus), three cerebroside molecular species have been isolated. Six known cerebrosides, soyacerebrosides I and II, 1-Ο-$\beta$-D-glucopyranosyl-(2S,3R,4E,8E)-2-(2 -lignoceroylamino)-4,8-octadecadiene-1,3-diol (long an cerebroside I) and its 8Z isomer (Iongan cerebroside II), momor-cerebroside I, and phytolacca cerebroside, were identified as major components of these cerebroside molecular species. All the cerebrosides were shown to be a mixture of geometrical isomers (8E and 8Z) of sphingosine-type or phytosphingosine-type glucocerebrosides possessing 2-hydroxy fatty acids. The structures of these cerebrosides have been determined on the basis of chemical and spectroscopic evidence.

• Natural Product Sciences
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• v.14 no.3
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• pp.161-166
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• 2008

A mixture of sixteen cerebrosides, which comprised four cerebroside molecular species (PL-1 ${\sim}$ PL-4) was separated from the roots of Paeonia lactiflora. The structures of cerebrosides were characterized as $1-O-{\beta}$-D-glucopyranosides of phytosphingosines, which comprised a common long-chain base, (2S,3S,4R,8E/Z)-2-amino-8-octadecene-1,3,4-triol with eight fatty acids or 2-hydroxy fatty acids of varying chain lengths ($C_{16}$, $C_{18}$, $C_{20-26}$) linked to the amino group. Aralia cerebroside and its 8Z isomer (PL-1), $1-O-{\beta}$-D-glucopyranosyl-(2S,3S, 4R,8E/Z)-2-[(2'R)-2'-hydroxytetracosanoylamino]-8-octadecene-1,3,4-triol (PL-2), $1-O-{\beta}$-D-glucopyranosyl-(2S,3S,4R, 8E/Z)-2-[(2'R)-2'-hydroxydocosanoylamino]-8-octadecene-1,3,4-triol (PL-3), and $1-O-{\beta}$-D-glucopyranosyl-(2S,3S,4R, 8E/Z)-2-[(2'R)-2'-hydroxytricosanoylamino]-8-octadecene-1,3,4-triol (PL-4) were identified as major components of these cerebroside molecular species. All the major cerebrosides were shown to be a mixture of geometrical isomers (8E and 8Z) of phytosphingosine-type glucocerebrosides possessing 2R-hydroxy fatty acids. In addition, three ${\beta}-sitosterol$ derivatives and adenosine were also separated. The structures of these isolates have been determined on the basis of chemical and spectroscopic evidence.

• Korean Journal of Pharmacognosy
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• v.37 no.3
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• pp.125-129
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• 2006

The chromatographic separation of n-BuOH extract of the aerial parts of Prunus padus (Rosaceae) led to the isolation of two cerebrosides, and six phenolic compounds. Their structure were identified to be pinelloside (1), soyacebroside I (2), $quercetin-3-O-{\beta}-D-galactopyranoside$ (3), nudiposide (4), (+)-isolarisiresinol $9'-O-{\beta}-D-xylopyroanoside$ (5), khaephuoside A (6) and icariside F2(7) by physicochemical and spectroscopic methods. The compounds $1,5{\sim}7$ are first isolated from the genus Prunus.

• 한국생물공학회:학술대회논문집
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• 2000.11a
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• pp.765-766
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• 2000

Cerebrosides were isolated from soybean, deunjang and chungkukjang and their constituents were investigated. The principal fatty acid of soybean cerebroside was 2-hydroxy-palmitic acid but chungkukjang cerebroside consisted palmitic acid, elaidic acid(trans 18:1), oleic acid and stearic acid. The only sugar in cerebrosides was glucose. TLC analysis of cerebroside hydrolysate elucidated soybean and chungkukjang had same sphingold bases, mainly dihydroxy bases, trans-4, trans-sphingadienine. But, alkali stable glycolipid fractions of chungkukjang and deunjang had $2{\sim}3$ different primary amines.

• Bulletin of the Korean Chemical Society
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• v.34 no.7
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• pp.2143-2147
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• 2013

Matrix assisted laser desorption/ionization (MALDI) mass spectrometry (MS) is a very effective method for lipid mass fingerprinting. However, MALDI MS suffered from spectral complexities, differential ionization efficiencies, and poor reproducibility when analyzing complex lipid mixtures without prior separation steps. Here, we aimed to find optimal MALDI sample preparation methods which enable selective or class-wide mass fingerprinting of two totally different lipid classes. In order to achieve this, various matrices with additives were tested against the mixture of phosphatidylcholine (PC) and cerebrosides (Cers) which are abundant in animal brain tissues and also of great interests in disease biology. Our results showed that, from complex lipid mixtures, 2,4,6-trihydroxyacetophenone (THAP) with $NaNO_3$ was a useful MALDI matrix for the class-wide fingerprinting of PC and Cers. In contrast, THAP efficiently generated PC-focused profiles and graphene oxide (GO) with $NaNO_3$ provided Cer-only profiles with reduced spectral complexity.

• Archives of Pharmacal Research
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• v.26 no.2
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• pp.132-137
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• 2003

Three cerebrosides 2, 3, and 5 and two terpene glycosides 1 and 4 have been isolated from the methanol extract of the root of Aster scaber. Their structures were determined as 3-Ο-$\beta$-D-glucuronopyranosyl-oleanolic acid methyl ester (1), (2S, 3S, 4R, 2 R, 8Z, 15 Z)-N-2 -hydroxy-15 -tetracosenoyl-1-Ο-$\beta$-D-glucopyranosyl-4-hydroxy-8-sphingenine (2), (2S, 3S, 4R, 8Z)-N-octadecanoyl-1-Ο-$\beta$-D-glucopyranosyl-4-hydroxy-8-sphingenine (3), 1$\alpha$-hydroxy-6$\beta$-Ο-$\beta$-D-glucosyl-eudesm-3-ene (4), and (2S, 3S, 4R, 2 R, 8Z)-N-2 -hydroxy-hexadecanoyl-1-Ο-$\beta$-D-glucopyranosyl-4-hydroxy-8-sphingenine (5) on the basis of spectroscopic methods.

• Proceedings of the PSK Conference
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• 2002.04a
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• pp.202.3-202.3
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• 2002

• Journal of the Korean Society of Food Science and Nutrition
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• v.31 no.2
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• pp.177-183
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• 2002

Cerebroside fatty acids, sugars and long-chain sphingoid bases in raw soybean and soybean fermented foods (chongkukjang and deunjang) were analyzed using gas chromatography-mass spectrometry (GC-MS) and high-pH anion exchange chromatography with pulsed amerometric detection (HPAEC-PAD). Fatty acids of acid-hydrolyzed cerebrosides were derivatized to O-TMS methylester and analysed. The major fatty acids in raw soybean and chongkukjang cerebrosides were identified as 2-hydroxyhexadecanoic acid (16 : 0h), 2-hydroxydocosanoic acid (22 : 0h) and 2-hydroxytetracosanoic acid (24 : 0h). In the case of deunjang cerebroside, 24 : 0h (40.9%) and 22 : 0h (23.4%) were major fatty acids, but 16 : 0h, 23 : 0h, 25 : 0h and 26 : 0h were also detected. Long-chain sphingoid bases of acid-hydrolyzed cerebrosides from raw soybean, chongkukjang and deunjang consisted primarily of 4-tracts, 8-tracts-sphingadienine (dihydroxy base, d18 : 2$\Delta$$^{4trans, 8trans}$) and sis-tracts isomers of 4-hydroxy-sphingenine (trihydroxy base, tl8:1$\Delta$$^{4trans or cis}$) with much less amounts of phytosphingosine (tl8: 0) and isomers of sphingenine (d18 : 1). Although deunjang is a soybean food fermented by fungi and microorganisms for a long period, 2-hydroxyoctadec-3-enoic acid (18 : 1h) and branched 9-methyl-4,8-sphingadienine known as compositional cerebroside fatty acids in Aspergillus species were not detected. Mass spectrum for sugar derivatives in cerebrosides of soybean foods including raw soybean and fermented soybean showed that C-1 of glucose moiety was linked to ceramide backbone as like a monoglucosylceramide.

• Analytical Science and Technology
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• v.6 no.3
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• pp.335-343
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• 1993

The structure of cerebrosides from soybean embryo was determined using fast atom bombardment mass spectrometer (FAB-MS), gas chromatography mass spectrometer (GC-MS) and TLC. The components of cerebroside were determined by GC-MS after acid hydrolysis. The molecular weight distribution of cerebroside was measured by positive mode FAB-MS with LiOH saturated 3-nitrobenzylalcohol(3-NBA) matrix. Structures of individual components of complex mixtures can be determined easily by this process. The major constituent of soybean extracted cerebroside was determined as the glucoside of N-2'-hydroxypalmitoyl-sphingadienine.