• Natural Product Sciences
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• 제12권4호
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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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• 제26권2호
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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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• 제14권3호
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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.

• 생약학회지
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• 제37권3호
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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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• 한국생물공학회 2000년도 추계학술발표대회 및 bio-venture fair
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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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• 제34권7호
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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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• 제26권2호
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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.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.202.3-202.3
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• 2002

• 한국식품영양과학회지
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• 제31권2호
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• pp.177-183
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• 2002

대두 및 대두발효식품인 청국장과 된장의 cerebroside 구성성분인 지방산, 당 및 장쇄 sphingoid base들을 GC-MS로 분석하였다. Cerebroside 산-가수분해물의 지방산들을 O-TMS methylester 유도체로 만들어 분석하였으며 대두 및 청국장의 경우 2-hydroxyhexadecanoic acid(16 : 0h)가 각각 52.2% 및 62.0%로 가장 많았고 2-hydroxydocosanoic acid(22 : 0h) 및 2-hydroxytetracosanoic acid(24 : 0h)도 15.0~17.6%이었다. 그러나 된장의 경우 16 : 0h는 10.2%로 많은 감소를 보인 반면 24 : 0h는 40.9%, 22 : 0h는 23.4% 었으며 23 : 0h, 25 : 0h 및 26 : 0h도 대두 및 청국장에 비하여 많았다. Cerebroside 산-가수분해물의 장쇄 sphingoid base들은 N-acetyl-O-TMS 유도체로 분석하였으며 대두 및 청국장에서 4- trans, 8-trans-sphingadienine (d18 : 2 $\Delta$$^{4trans, 8trans}$) 는 59.9% 및 44.5%이었으며 4-hydroxy-8-trans, cis-sphingening (t18 : 1$\Delta$$^{8trans or cis}$)는 20.9% 및 35.9% 이었고 된장 cerebroside 역시 dl8 : 2$\Delta$$^{4trans, 8trans}$가 가장 많았다. 그러나 phytosphingosine(t18 : 0) 및 sphingosine 이 성질체(d18 : 1)들은 거의 보이지 않았다. 또한 된장의 경우 오랜 기간 미생물들에 의하여 발효되었지만 Aspergillus 속들의 cerebroside가 가지는 것으로 알려진 2-hydroxyoxtadec-3-enoic acid(18 : 1h) 및 9-methyl-4,8-sphingadienine 등은 발견되지 않았다. 대두, 청국장 및 된장 cerebroside의 당유도체 mass spectrum 분석 결과 99%이상이 glucose 1번 탄소가 ceramide backbone에 결합된 monoglucocerebroside 인 것으로 나타났다.

• 분석과학
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• 제6권3호
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• pp.335-343
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• 1993

Fast atom bombardment mass spectrometer(FAB-MS), gas chromatography mass spectrometer(GC-MS), TLC 등을 이용하여 대두 배아 추출 cerebroside의 구조를 분석하였다. Cerebroside를 이루고 있는 각각의 구성 성분은 화학적인 산분해 후 GC-MS로 분석하였다. Cerebroside의 분자량 분포는 LiOH로 포화된 3-nitrobenzyl alcohol(3-NBA)를 matrix로 한 양이온 검출 FAB-MS법으로 측정하였다. FAB-MS와 GC-MS 결과를 종합하여 cerebroside의 구조를 해석함으로써 기존의 분석법이 가지고 있던 문제점을 개선하였다. 대두 배아로부터 추출한 cerebroside의 대부분은 N-2'-hydroxy palmitoyl-sphingadienine에 당이 한 분자 결합된 형태로 존재하였으며 그 조성이 매우 단순하였다.