New ellagitannin and galloyl esters of phenolic glycosides from sapwood of Quercus mongolica var. crispula (Japanese oak)

Phytochemistry Letters

Volumn 6, Issue 3, 2013, Pages 486-490

  Omar, Mohamed ^a,b   Matsuo, Yosuke ^a   Maeda, Hajime ^c   Saito, Yoshinori ^a   Tanaka, Takashi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b Al Azhar University   (Egypt)

^c Nagasaki Agricultural and Forestry Technical Development Center   (Japan)

Author keywords

Ellagitannin; Fagaceae; Lignan glycoside; Polyphenol; Quercus mongolica; Sapwood

Indexed keywords

2ALPHA O GALLOYL LYONIRESINOL 3 APHA O BETA DEXTRO XYLOPYRANOSIDE; 4,5 DIMETHOXY 3 HYDROXYPHENOL 1 O BETA(6 O GALLOYL)GLUCOPYRANOSIDE; ELLAGITANNIN; EPIQUISQUALIN B; GLYCOSIDE; LIGNAN; PHENOL DERIVATIVE; PLANT EXTRACT; QUERCUS MONGOLICA EXTRACT; UNCLASSIFIED DRUG; VESCALAGIN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; JAPANESE OAK; MEDICINAL PLANT; NONHUMAN; OAK; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUERCUS MONGOLICA; SAPWOOD; WOOD;

FAGACEAE; LITHOCARPUS GLABER; QUERCUS MONGOLICA; QUERCUS MONGOLICA VAR. CRISPULA;

EID: 84880181447     PISSN: 18743900     EISSN: 18767486     Source Type: Journal    
DOI: 10.1016/j.phytol.2013.06.004     Document Type: Article

References (26)

1. Dad, G., Corbani, A., Manitto, P., Speranza, G., Lunazzi, L., 1989. Lignan glycosides from the heartwood of European oak Quercus petraea. J. Nat. Prod. 52, 1327-1330. (Pubitemid 20101790)
2. Fernandez de Simón, B., Sanz, M., Cadahía, E., Poveda, P., Broto, M., 2006. Chemical characterization of oak heartwood from Spanish forests of Quercus pyrenaica (Wild.): ellagitannins, low molecular weight phenolic, and volatile compounds. J. Agric. Food Chem. 54, 8314-8321. (Pubitemid 44785420)
3. Glabasnia, A., Hofmann, T., 2007. Identification and sensory evaluation of dehydroand deoxy-ellagitannins formed upon toasting of oak wood (Quercus alba L.). J. Agric. Food Chem. 55, 4109-4118. (Pubitemid 46867422)
4. HervéDu Penhoat, C.L.M., Michon, V.M.F., Ohassan, A., Peng, S., Scalbert, A., Gage, D., 1991a. Roburin A, a dimeric ellagitannin from heartwood of Quercus robur. Phytochemistry 30, 329-332.
5. HervéDu Penhoat, C.L.M., Michon, V.M.F., Peng, S., Viriot, C., Scalbert, A., Gage, D., 1991b. Structural elucidation of new dimeric ellagitannins from Quercus robur L. roburins A-E. J. Chem. Soc., Perkin Trans. 1, 1653-1660.
6. Hirano, Y., Kondo, R., Sakai, K., 2003. 5a-Reductase inhibitory tannin-related compounds isolated from Shorea laeviforia. J. Wood Sci. 49, 339-3432.
7. Hosoi, S., Shimizu, E., Ohno, K., Yokosawa, R., Kuninaga, S., Coskun, M., Sakushima, A., 2006. Structural studies of zoospore attractants from Trachelospermum jasminoides var. pubescens: taxifolin 3-O-glycosides. Phytochem. Anal. 17, 20-24. (Pubitemid 43141393)
8. Ishimaru, K., Nonaka, G., Nishioka, I., 1987. Tannins and related compounds. LV. Isolation and characterization of acutissimins A and B, novel tannins from Quercus and Castanea species. Chem. Pharm. Bull. 35, 602-610.
9. Ishimaru, K., Ishimatsu, M., Nonaka, G., Mihashi, K., Iwase, Y., Nishioka, I., 1988a. Tannins and related compounds. LXXI. Isolation and characterization of mongolicins A and B, Novel flavono-ellagitannins from Quercus mongolica var. grosseserrata. Chem. Pharm. Bull. 36, 3312-3318.
10. Ishimaru, K., Ishimatsu, M., Nonaka, G., Mihashi, K., Iwase, Y., Nishioka, I., 1988b. Tannins and related compounds. LXXII. Isolation and characterization of mongolicanin (procyanidino-ellagitannin), mongolinin A, acutissimin C and vescalagin carboxylic acid, novel tannins from Quercus mongolica var. grossesserrata. Chem. Pharm. Bull. 36, 3319-3327.
11. Ishimatsu, M., Tanaka, T., Nonaka, G., Nishioka, I., 1989. Tannins and related compounds: part 78. Alnusnins A and B from the leaves of Alnus sieboldiana. Phytochemistry 28, 3179-3184.
12. Lampire, O., Mila, I., Raminosoa, M., Michon, V., Penhoat, H.C., Faucheur, N., Laprevote, O., Scalbert, A., 1998. Polyphenols isolated from the bark of Castanea sativa Mill. Chemical structures and auto-association. Phytochemistry 49, 623-631. (Pubitemid 28415143)
13. Li, L., Seeram, N.P., 2010. Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds. J. Agric. Food Chem. 58, 11673-11679.
14. Lin, T., Ma, Y., Wu, J., Hsu, F., 1997. Tannins and related compounds from Quisqualis indica. J. Chin. Chem. Soc. 44, 151-155. (Pubitemid 127441991)
15. Nonaka, G., Ishimaru, K., Azuma, R., Ishimatsu, M., Nishioka, I., 1989. Tannins and related compounds. LXXXV. Structures of novel C-glycosidic ellagitannins, grandinin and pterocarinins A and B. Chem. Pharm. Bull. 37, 2071-2077.
16. Nonaka, G., Sakai, T., Tanaka, T., Mihashi, K., Nishioka, I., 1990. Tannins and related compounds. XCVII. Structure revision of C-glycosidic ellagitannins, castalagin, vescalagin, casuarinin and stachyurin, and related hydrolyzable tannins. Chem. Pharm. Bull. 38, 2151-2156. (Pubitemid 20338170)
17. Ohashi, K., Watanabe, H., Okumura, Y., Uji, T., Kitagawa, I., 1994. Indonesian medicinal plants. XII. Four isomeric lignan-glucosides from the bark of Aegle marmelos (Rutaceae). Chem. Pharm. Bull. 42, 1924-1926. (Pubitemid 24315513)
18. Okuda, T., Yoshida, T., Hatano, T., Koga, T., Toh, N., Kuriyama, K., 1982. Circular dichroism of hydrolyzable tannins: I. Ellagitannins and gallotannins. Tetrahedron Lett. 23, 3937-3940.
19. Peng, S., Scalbert, A., Monties, B., 1991. Insoluble ellagitannins in Castanea sativa and Quercus petraea woods. Phytochemistry 30, 775-778.
20. Saijo, R., Nonaka, G., Nishioka, I., 1989. Tannins and related compounds: part 82. Phenol glucoside gallates from Mallotus japonicas. Phytochemistry 28, 2443-2446.
21. Taguri, T., Tanaka, T., Kouno, I., 2004. Antimicrobial activity of 10 different plant polyphenols against bacteria causing food-borne disease. Biol. Pharm. Bull. 27, 1965-1969. (Pubitemid 41701572)
22. Takara, K., Matsui, D., Wada, K., Ichiba, T., Nakasone, Y., 2002. New antioxidative phenolic glycosides isolated from Kokuto non-centrifuged cane sugar. Biosci. Biotechnol. Biochem. 66, 29-35. (Pubitemid 39251084)
23. Tanaka, T., Ueda, N., Shinohara, H., Nonaka, G., Fujioka, T., Mihashi, K., Kouno, I., 1996. C-glycosidic ellagitannin metabolites in the heartwood of Japanese chestnut tree (Castanea crenata Sieb. et Zucc.). Chem. Pharm. Bull. 44, 2236- 2242. (Pubitemid 27036379)
24. Tanaka, T., Nakashima, T., Ueda, T., Tomii, K., Kono, I., 2007. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem. Pharm. Bull. 55, 899-901. (Pubitemid 46890090)
25. Viriot, C., Scalbert, A., Penhoat, C., Moutounet, M., 1994. Ellagitannins in woods of sessile oak and sweet chestnut: dimerization and hydrolysis during wood aging. Phytochemistry 36, 1253-1260. (Pubitemid 2118491)
26. Yoshida, T., Ohbayashi, H., Ishihra, K., Ohwashi, W., Haba, K., Okano, Y., Shingu, T., Okuda, T., 1991. Tannins and related polyphenols of melastomataceous plants: I. Hydrolyzable tannins from Tibouchina semidecandra. Cogn. Chem. Pharm. Bull. 39, 2233-2240.