• 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.

• 대한화장품학회지
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• 제46권2호
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• pp.105-117
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• 2020

신령버섯(Agaricus blazei Murill)은 항암, 면역력 개선, 항비만 등 다양한 효능이 알려져 있으며, 피부 효능으로는 항산화, 항염, 미백 등에 대하여 보고되었다. 이러한 효능을 뒷받침하기 위하여, 신령버섯의 성분 연구가 진행되었다. 따라서 본 연구에서는 신령버섯 추출물의 피부 효능을 재확인하고 유용한 효능성분을 밝혀내어 이를 화장품 소재로서 이용하고자 하였다. 신령버섯 추출물은 100 ㎍/mL에서 멜라닌 합성 저해, 콜라겐 합성 증진, 보습과 관련된 유전자(hyaluronan synthase-2, 3와 aquaporin-3) 발현 증가를 나타내었다. 이들 화합물은 분광학적 데이터와 문헌값을 비교하여 ergosterol (1), 5-dihydroergosterol (2), cerevisterol (3), cerebroside B (4), cerebroside D (5), adenosine (6), 및 benzoic acid (7)로 동정하였다. 이들 중 비교적 효능이 알려지지 않은 3종의 sterol (1-3)과 2종의 glucosylceramide (4, 5)에 대하여 피부효능을 평가하였으며, 그 결과 5-dihydroergosterol (2)이 마우스 흑색종 세포에서 멜라닌 생성을 억제하였으며, 또한 인간 진피 섬유아세포 세포에서 콜라겐 생합성 촉진하였다. 그리고 cerevisterol (3), cerebroside B (4), cerebroside D (5)는 마우스 대식세포에서 NO 생성을 억제하였으며, 특히 cerebroside D (5)는 인간각질형성세포에서 hyaluronan synthase-2와 aquaporin-3 유전자 발현을 증가시켰다. 따라서 신령버섯 추출물과 분리 화합물은 화장품 소재로 활용 가능 할 것으로 생각된다.

• 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.

• 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.

• 생약학회지
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• 제37권2호통권145호
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• pp.81-84
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• 2006

A mixture of cerebrosid was purified from the roots of Panax notogiseng (Araliaceae) and characterized as 1-O-{\beta}-D-glucopyranosyl-(2S,3S,4R,8E)-2-[(2'R)-2‘-hydroxypalmitoylamino]-8-octadecene-1,3,4-triol (Aralia cerebroside) and its 8Z-isomer (1-O-{\beta}-D-glucopyranosyl-(2S,3S,4R,8E)-2-[(2'R)-2’-hydroxypalmitoylamino]-8-octadecene-1,3,4-triol, a major component of poke-weed cerebroside) by means of spectroscopic methods.

• Archives of Pharmacal Research
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• 제27권6호
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• pp.593-599
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• 2004

From the EtOAc fraction of the MeOH extract of Albizzia julibrissin (Leguminosae）, a rare 5-deoxyflavone (geraldone, 1）, isookanin (2）, luteolin (3）, an isoflavone (daidzein, 4）, five prenylated flavonoids ［soph6f1avescenol (5）, kurarinone (6）, kurarinol (7）, kuraridin (8） and kuraridinol (9）］, a cerebroside (soya-cerebroside I, 10）, and $(-)-syringaresinol-4-O-{\beta}-D-glucopyranoside$ (11） were isolated and characterized on the basis of spectral data. Compounds 2, 3, and 11, showed 1, 1-diphenyl-2-picrylhydrazyl radical scavenging activity.

• 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.

• Archives of Pharmacal Research
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• 제27권6호
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• pp.604-609
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• 2004

A new indolinepeptide (3） was isolated, together with two known compounds, a cerebroside (1） and an alloxazine (2）, from silkworm larvae infected with Paecilomyces sp. J300. On the basis of spectroscopic data, their structures were elucidated as (4E, 8E, 25, 2＇R, 3R ）-N-2＇-hydroxy-hexadecanoyl-1-O-$\beta$-D-glucopyranosyl-9-methyl-4, 8-sphingadienine (1）, 7,8-dimethylalloxazine (2） and 3$\beta$,5-dihydroxy-1-N-methyl-indoline-2$\beta$-carbonyl amino-D-alanyl-erythro-$\beta$-hydoxyiso-leucinyl-glycine (3）.

• Archives of Pharmacal Research
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• 제27권7호
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• pp.742-750
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• 2004

This paper for the first time reports the isolation of 5 compounds from Phellinus linteus. A sphingolipid (1) and two tyrosinase inhibitory compounds (2, 3) along with two carboxylic acids (4, 5), were isolated from the fruiting body of Phellinus linteus (Berk ＆ Curt) Aoshima. The structure of compound 1 was identified as 1-O-$\beta$-D-glucopyranosyl-(2S, 3R, 4E, 8E)-2-[(2R)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol, known as cerebroside B, based on spectroscopic methods such as 1D and 2D NMR as well as by acid hydrolysis. Compounds 2-5 were identified as protocatechualdehyde (2), 5-hydroxymethyl-2-furaldehyde (HMF) (3), succinic acid (4), and fumaric acid (5) based on the spectroscopic evidence. Compounds 2 and 3 inhibited the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with an $IC_{50}$ of 0.40 and 90.8 $\mu\textrm{g}$/mL, respectively. The inhibitory kinetics, which were analyzed by the Lineweaver-Burk plots, were found to be competitive and noncompetitive inhibitors with a $K_{j}$ of 1.1 $\mu\textrm{m}$ and 1.4 mM, respectively.

• 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.