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Cerebrosides from Longan Arillus  

Ryu, Ji-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University)
Publication Information
Archives of Pharmacal Research / v.26, no.2, 2003 , pp. 138-142 More about this Journal
Abstract
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.
Keywords
Euphoria longana; Longan Arillus; Sapindaceae; Cerebroside; Isolation; Structure determination;
Citations & Related Records

Times Cited By Web Of Science : 7  (Related Records In Web of Science)
Times Cited By SCOPUS : 12
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1 Hsu, F-L., Lu, F.-H., and Cheng, J.-T., Influence of acetonylgeraniin, a hydrolyzable tannin from Euphoria longana, on orthostatic hypotension in a rat model. Planta Med., 60, 297-300 (1994)   DOI   ScienceOn
2 Kang, S. S., Kim, J. S., Son, K. H., Kim, H. P., and Chang, H. W., Cyclooxygenase-2 inhibitory cerebrosides from Phytolaccae radix. Chem. Pharm. Bull., 49, 321-323 (2001)   DOI   ScienceOn
3 Kim, J. S., Byun, J. H., and Kang. S. S., Isolation of soya-cerebroside from the roots of Trichosanthes kirilowii. Nat. Prod. Sci., 7, 27-32 (2001)
4 Mahato, S. B., Sahu, N. P., and Chakravarti, R. N., Chemical investiqation on the leaves of Euphoria longana. Phytochemistry, 10, 2847-2848 (1971)   DOI   ScienceOn
5 Ohnishi, M. and Fujino, Y., Chemical composition of ceramide and cerebroside in azuki bean seeds. Agric. Biol. Chem., 45, 1283-1284 (1981)   DOI
6 Voutquenne, L., Lavaud, C., Massiot, G., Sevenet, T., and Hadi, H. A., Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus. Phytochemistry, 50, 63-69 (1999)   DOI   ScienceOn
7 Inagaki, M., Harada, Y., Yamada, K., Isobe, R., Higuchi, R., Matsuura, H. and Itakura, Y., Isolation and structure determination of cerebrosides from garlic, the bulbs of Allium sativum L. Chem. Pharm. Bull., 46, 1153-1156 (1998)   DOI   ScienceOn
8 Xiao, Z.-Y, Chen, D.-H., and Si, J.-Y., Studies on the chemical constituents from Momordica charantia. Chin. Trad. Herbal Drugs (Zhongcaoyao), 31, 571-573 (2000)
9 Ohnishi, M. and Fujino, Y., Sphingolipids in immature and mature soybeans. Lipids, 17, 803-810 (1982)   DOI
10 Shibuya, H., Kawashima, K., Sakagami, M., Kawanishi, H., Shimomura, M., Ohashi, K., and Kitagawa, I., Sphingolipids and Glycerolipids. I. Chemical structures and ionophoretic activities of soya-cerebrosides I and II from soybean. Chem. Pharm. Bull., 38, 2933-2938 (1990)   DOI   PUBMED   ScienceOn
11 Okuyama, E. and Yamazaki, M., The principles of Tetragonia tetragonoides having anti-ulcerogenic activity. II. Isolation and structure of cerebrosides. Chem. Pharm. Bull., 31, 2209-2219 (1983)   DOI   PUBMED   ScienceOn
12 Jung, H. J., Kim, C.-O., Kim, Y. C., and Kang, S. S., New bioactive cerebrosides from Arisaema amurense. J. Nat. Prod., 59, 319-322 (1996)   DOI   ScienceOn
13 Kojima, M., Suzuki, H., Ohnishi, M., and Ito, S., Effects of growth temperature on lipids of adzuki bean cells. Phytochemistry, 47, 1483-1487 (1998)   DOI   ScienceOn
14 Yoshioka, A., Etoh, H., Yagi, A., Sakata, K., and Ina, K., Isolation of Flavonoids and cerebrosides from bark of Prunus jamasakura as repellents against the bule mussel, Mytilus edulis. Agric. Biol. Chem., 54, 3355-3356 (1990)   DOI
15 Achenbach, H., Lottes, M., Waibel, R., Karikas, G. A., Correa, M. D., and Gupta, M. P., Alkaloids and other compounds from Psychotria correae. Phytochemistry, 38, 1537-1545 (1995)   DOI   ScienceOn
16 Cheng, J.-T., Lin, T.-C., and Hsu, F.-L., Antihypertensive effect of corilagin in the rat. Can. J. Physiol. Pharmacol., 73, 1425-1429 (1995)   DOI   PUBMED   ScienceOn
17 Hara, S., Okabe, H., and Mihashi, K., Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates. Chem. Pharm. Bull., 35, 501-506 (1987)   DOI
18 Minakata, H., Komura, H., Tamura, S. Y., Ohfune, Y., Nakanishi, K., and Kata, T., Antimutagenic unusual amino acids from plants. Experientia, 41, 1622-1623 (1985)   DOI   PUBMED   ScienceOn
19 Inoue, T., Sakurai, N., Nagai, S., and Nagai, M., Studies on the constituents of Aceraceae Plants (X). Isolation of flavonoid glycosides and a cerebroside from the leaves of Acer negundo. Shoyakugaku Zasshi, 46, 261-264 (1992)
20 Kleiman, R., Earle, F. R., and Wolff, I. A., Dihydrosterculic acid, a major fatty acid component of Euphoria longana seed oil. Lipids, 4, 317-320 (1969)   DOI   ScienceOn
21 Kang, S. S., Kim, J. S., Xu, Y. N., and Kim, Y. H., Isolation of new cerebroside from the root bark of Aralia elata. J. Nat. Prod., 62, 1059-1060 (1999)   DOI   ScienceOn
22 Yasuhara, Y. and Yamaguchi, S., Determination of absolute configuration and enantiomeric purity of 2- and 3-hydroxycarboxylic acid ester. Tetrahedron Lett., 21, 2827-2830 (1980)   DOI   ScienceOn
23 Okuyama, E., Ebihara, H., Takeuchi, H., and Yamazaki, M., Adenosine, the anxiolytic-like principle of the arillus of Euphoria longana. Planta Med., 65, 115-119 (1999)   DOI   ScienceOn
24 Sung, M.-L., Fowden, L., Millington, D. S., and Sheppard, R. C., Acetylenic amino acids from Euphoria longan. Phytochemistry, 8, 1227-1233 (1969)   DOI   ScienceOn
25 Sahai, M., Manickam, M., Gupta, M., Srivastava, A., and Ray, A. B., Characterization of a cerebroside isolated from the leaves of Datura metel. J. Indian Chem. Soc., 76, 95-97 (1999)
26 Ito, S., Ohnishi, M., and Fujino, Y., Investigation of sphingolipids in pea seeds. Agric. Biol. Chem., 49, 539-540 (1985)   DOI
27 Bensky, D. and Gamble, A., Materia Medica, Revised Ed., Eastland Press, Seattle, p. 335, (1993)