Download PDF
Planta Med 2011; 77(17): 1939-1943
DOI: 10.1055/s-0031-1279995
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Glycosides from the Methanol Extract of Notopterygium incisum

Mei You1 , Juan Xiong2 , Yun Zhao1 , Lei Cao1 , Shi-Biao Wu1 , Gang Xia1 , Jin-Feng Hu1 , 2
  • 1Department of Natural Products for Chemical Genetic Research, Key Laboratory of Brain Functional Genomics, Ministry of Education (MOE), East China Normal University, Shanghai, P. R. China
  • 2Department of Natural Products Chemistry, School of Pharmacy, Fudan University, Shanghai, P. R. China
Further Information

Publication History

received April 8, 2011 revised May 17, 2011

accepted May 20, 2011

Publication Date:
15 July 2011 (online)

Also available at
    Permissions and Reprints

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

Supporting Information

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
    Search in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 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
    Thieme ConnectPubMedSearch in Google Scholar
  • 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
    Thieme ConnectPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 10 Yamauchi T, Hara M, Mihashi K. Pregnenolone glucosides of Nerium odorum.  Phytochemistry. 1972;  11 3345-3347
    CrossrefPubMedSearch in Google Scholar
  • 11 Kitajima J, Ishikawa T, Satoh M. Polar constituents of celery seed.  Phytochemistry. 2003;  64 1003-1011
    CrossrefPubMedSearch in Google Scholar
  • 12 Zou C, Pu X Y, Zhou J. Sesquiterpenoids from Kadsura ananosma.  Acta Bot Yunn. 1993;  15 196-200
    PubMedSearch in Google Scholar
  • 13 Kitajima J, Kimizuka K, Tanaka Y. Three new sesquiterpenoid glucosides of Ficus pumila fruit.  Chem Pharm Bull. 2000;  48 77-80
    CrossrefPubMedSearch in Google Scholar
  • 14 Kitajima J, Okamura C, Ishikawa T, Tanaka Y. Coumarin glycosides of Glehnia littoralis root and rhizoma.  Chem Pharm Bull. 1998;  46 1404-1407
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 20 Yoshimura T, Kisyuku H, Kamei T, Takabatake K, Shindo M, Shishido K. Enantiocontrolled synthesis of (+)-curcuquinone and (−)-curcuhydroquinone.  ARKIVOC. 2003;  VIII 247-255
    PubMedSearch in Google Scholar
  • 21 Klyne W. The configuration of the anomeric carbon atoms in some cardiac glycosides.  Biochem J. 1950;  47 xli-xlii
    PubMedSearch in Google Scholar
  • 22 Bonner W A, Craig J M. Derivatives of the anomeric glucopyranosylbenzenes.  J Am Chem Soc. 1950;  72 3480-3483
    CrossrefPubMedSearch in Google Scholar
  • 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
    Thieme ConnectPubMedSearch in Google Scholar
  • 24 Talapatra S K, Chaudhuri M K, Talapatra B. Coumarins of the root bark of Feronia elephantum.  Phytochemistry. 1973;  12 236-237
    CrossrefPubMedSearch in Google Scholar

Prof. Dr. Jin-Feng Hu

Department of Natural Products for Chemical Genetic Research
Key Laboratory of Brain Functional Genomics
Ministry of Education, East China Normal University

No. 3663 Zhongshan Road N

Shanghai 200062

P. R. China

Phone: +86 21 62 60 75 10

Fax: +86 21 62 60 67 91

Email: jfhu@brain.ecnu.edu.cn

Email: jfhu@fudan.edu.cn