Glycosides from the Methanol Extract of Notopterygium incisum

Abstract

Five new (1–5) and twelve known (6–17) different types of glycosides together with a known sesquiterpene triol (18) were isolated from the methanol extract of the rhizomes of Notopterygium incisum. The new structures were elucidated by means of spectroscopic and chemical methods to be pregn-5-en-3β,20(S)-diol-3-O-bis-β-D-glucopyranosyl-(l → 2,1 → 6)-β-D-glucopyranoside (1), oleuropeic aldehyde 8-O-β-D-glucopyranoside (2), 2(R)-(3,4-dimethoxyphenyl)-propane-1,3-diol-1-O-β-D-glucopyranoside (3), eudesman-3α,4α,11-triol-11-O-β-D-glucopyranoside (4), and marmesin-11-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside (5). The absolute configuration of the aglycone in compound 3 was assigned by application of Klyne's rule.

Key words

Notopterygium incisum - Umbelliferae - structure elucidation - glycosides

References

• 1 China Pharmacopoeia Committee .Pharmacopoeia of the P. R. C.. the first division of 2000 Edition (English). Beijing: Chemical and Technologic Press; 2000: 232
• 2 Gu Z M, Zhang D X, Yang X W, Hattori M, Namba T. Isolation of two new coumarin glycosides from Notopterygium forbesii and evaluation of a Chinese crude drug, Qiang-Huo, the underground parts of N. incisum and N. forbesii, by high-performance liquid chromatography.  Chem Pharm Bull. 1990;  38 2498-2502
• 3 Ma Z, Xu W, Liu-Chen L Y, Lee D Y W. Novel coumarin glycoside and phenethyl vanillate from Notopterygium forbesii and their binding affinities for opioid and dopamine receptors.  Bioorg Med Chem. 2008;  16 3218-3223
• 4 Zhang P, Yang X W. Studies on chemical constituents in roots and rhizomes of Notopterygium incisum.  Zhongguo Zhong Yao Za Zhi. 2008;  33 2918-2921
• 5 Liu Z G, Ren P P, Li F M. Chemical constituents from the water-soluble part of Notopterygium incisum Ting ex H. T. Chang.  J Shenyang Pharm Univ. 2006;  23 568-569
• 6 Sun Y F, Xiao Y Q, Liu X H. Chemical constituents of Notopterygium incisum Ting.  Zhongguo Zhong Yao Za Zhi. 1994;  19 357-358
• 7 Wu S B, Zhao Y, Fan H, Hu Y H, Hamann M T, Peng J N, Starks C M, O'Neil-Johnson M, Hu J F. New guaiane sesquiterpenes and furanocoumarins from Notopterygium incisum.  Planta Med. 2008;  74 1812-1817
• 8 Wu S B, Pang F, Wen Y, Zhang H F, Zhao Z, Hu J F. Antiproliferative and apoptotic activities of linear furocoumarins from Notopterygium incisum on cancer cell lines.  Planta Med. 2010;  76 82-85
• 9 Zhu W M, Zhao Q, Li S L, Hao X J. Sesquiterpenoids from Hedychium yunnanense and Porana discifera, and the structural revision of two sesquiterpenoids from Laggera pterodonta.  J Asian Nat Prod Res. 2007;  9 277-283
• 10 Yamauchi T, Hara M, Mihashi K. Pregnenolone glucosides of Nerium odorum.  Phytochemistry. 1972;  11 3345-3347
• 11 Kitajima J, Ishikawa T, Satoh M. Polar constituents of celery seed.  Phytochemistry. 2003;  64 1003-1011
• 12 Zou C, Pu X Y, Zhou J. Sesquiterpenoids from Kadsura ananosma.  Acta Bot Yunn. 1993;  15 196-200
• 13 Kitajima J, Kimizuka K, Tanaka Y. Three new sesquiterpenoid glucosides of Ficus pumila fruit.  Chem Pharm Bull. 2000;  48 77-80
• 14 Kitajima J, Okamura C, Ishikawa T, Tanaka Y. Coumarin glycosides of Glehnia littoralis root and rhizoma.  Chem Pharm Bull. 1998;  46 1404-1407
• 15 Ahluwalia V K, Boyd D R, Jain A K, Khanduri C H, Sharma N D. Furanocoumarin glucosides from the seeds of Apium graveolens.  Phytochemistry. 1988;  27 1181-1183
• 16 Liu R, Sun Q H, Sun A L, Cui J C. Isolation and purification of coumarin compounds from Cortex Fraxinus by high-speed counter-current chromatography.  J Chromatogr A. 2005;  1072 195-199
• 17 Angyal S J, Bethell G S. Conformational analysis in carbohydrate chemistry. III. The ¹³C N.M.R. spectra of the hexuloses.  Austrian J Chem. 1976;  29 1249-1265
• 18 Prawat H, Mahidol C, Ruchirawat S, Prawat U, Tuntiwachwuttikul P, Tooptakong U, Taylor W C, Pakawatchai C, Skelton B W, White A H. Cyanogenic and non-cyanogenic glycosides from Manihot esculenta.  Phytochemistry. 1995;  40 1167-1173
• 19 Itokawa H, Xu J P, Takeya K. Studies on chemical constituents of antitumor fraction from Periploca sepium Bge. I.  Chem Pharm Bull. 1987;  35 4524-4529
• 20 Yoshimura T, Kisyuku H, Kamei T, Takabatake K, Shindo M, Shishido K. Enantiocontrolled synthesis of (+)-curcuquinone and (−)-curcuhydroquinone.  ARKIVOC. 2003;  VIII 247-255
• 21 Klyne W. The configuration of the anomeric carbon atoms in some cardiac glycosides.  Biochem J. 1950;  47 xli-xlii
• 22 Bonner W A, Craig J M. Derivatives of the anomeric glucopyranosylbenzenes.  J Am Chem Soc. 1950;  72 3480-3483
• 23 Matano Y, Okuyama T, Shibata S, Hoson M, Kawada T, Osada H, Noguchi T. Studies on coumarins of a Chinese drug “Qian-Hu”; VII. Structures of new coumarin-glycosides of Zi-Hua Qian-Hu and effect of coumarin-glycosides on human platelet aggregation.  Planta Med. 1986;  2 135-138
• 24 Talapatra S K, Chaudhuri M K, Talapatra B. Coumarins of the root bark of Feronia elephantum.  Phytochemistry. 1973;  12 236-237