Planta Med 2008; 74(15): 1812-1817
DOI: 10.1055/s-0028-1088326
Original Paper
Natural Products Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

New Guaiane Sesquiterpenes and Furanocoumarins from Notopterygium incisum

Shi-Biao Wu1 , Yun Zhao1 , Hui Fan1 , Ying-He Hu1 , Mark T. Hamann2 , Jiang-Nan Peng2 , Courtney M. Starks3 , Mark O’Neil-Johnson3 , Jin-Feng Hu1 , 3
  • 1Key Laboratory of Brain Functional Genomics, East China Normal University, Shanghai, P. R. China
  • 2Department of Pharmacognosy and National Center for the Development of Natural Products (NCNPR), School of Pharmacy, The University of Mississippi, University, MS, USA
  • 3Sequoia Sciences, Inc., Saint Louis, USA
Further Information

Publication History

Received: May 17, 2008 Revised: August 13, 2008

Accepted: August 28, 2008

Publication Date:
07 November 2008 (online)

Abstract

In addition to twenty-nine known compounds, two new guaiane sesquiterpenes and two new furanocoumarins were isolated from the chloroform extract of the rhizomes of Notopterygium incisum. The new structures were elucidated by means of spectroscopic methods including 2 D NMR techniques and mass spectrometry to be 8β-acetoxy-4α,6α-dihydroxy-1α,5α(H)-guai-9-ene (incisumdiol A, 1), 4α,6α-dihydroxy-1α,5α(H)-guai-9-ene (incisumdiol B, 2), 5-[(2E,5Z)-7-hydroxy-3,7-dimethyl-2,5-octadienoxy]psoralene (3) and 5-[(2,5)-epoxy-3-hydroxy-3,7-dimethyl-6-octenoxy]psoralene (4).

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 Okuyama E, Nishimura S, Ohmori S, Ozaki Y, Satake M, Yamazaki M. Analgesic component of Notopterygium incisum Ting.  Chem Pharm Bull. 1993;  41 926-9
  • 3 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 2498-502.
  • 4 Kozawa M, Fukumoto M, Matsuyama Y, Baba K. Chemical studies on the constituents of the Chinese crude drug ”Quiang Huo”.  Chem Pharm Bull. 1983;  31 2712-7.
  • 5 Qiu Y Q, Lu X, Pang T, Zhu S K, Kong H W, Xu G W. Study of traditional Chinese medicine volatile oils from different geographical origins by comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GC × GC-TOFMS) in combination with multivariate analysis.  J Pharm Biomed Anal. 2007;  43 1721-7
  • 6 Mahmoud A A. 7-epi-Eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenes from Pluchea dioscoridis. .  Phytochemistry. 1997;  45 1633-8
  • 7 Bruno M, De la Torre M C, Rodriguez B, Omar A A. Guaiane sesquiterpenes from Teucrium leucocladum. .  Phytochemistry. 1993;  34 245-7
  • 8 Ahmed A A, Hegazy M EF, Hassan N M, Wojcinska M, Karchesy J, Pare P W. et al . Constituents of Chrysothamnus viscidiflorus. .  Phytochemistry. 2006;  67 1547-53
  • 9 Itokawa H, Morita H, Watanabe K, Takase A, Iitaka Y. Two new sesquiterpenoids (alpinolide and hanamyol) from Alpinia japonica (Thunb.) Miq. Chem Lett 1984: 1687-90
  • 10 Anh N H, Ripperger H, Sung T V, Adam G. Neolignans and a sesquiterpene from Caryodaphnopsis tonkinensis. .  Phytochemistry. 1996;  42 1167-9
  • 11 Malone J F, Parves M, Karim A, McKervey M A, Ahmad I, Bhatty M K. Isolation and crystal structure of grilactone, a new guaianolide from Ferula oopoda. J Chem Soc [Perkin II] 1980: 1683-5
  • 12 Casinovi C G, Tomassini L, Nicoletti M. A new guaianolide from Ferula arrigonii Bocchieri.  Gazz Chim Ital. 1989;  119 563-4
  • 13 Masuda T, Takasugi M, Anetai M. Psoralen and other linear furanocoumarins as phytoalexins in Glehnia littoralis. .  Phytochemistry. 1998;  47 13-6
  • 14 Adams M, Ettl S, Kunert O, Wube A A, Haslinger E, Bucar F. et al . Antimycobacterial activity of geranylated furocoumarins from Tetradium daniellii. .  Planta Med. 2006;  72 1132-5
  • 15 Talapatra S K, Chaudhuri M K, Talapatra B. Coumarins on the root bark of Feronia elephantum. .  Phytochemistry. 1973;  12 236-7.
  • 16 Liu R M, Sun Q H, Shi Y R, Kong L Y. Isolation and purification of coumarin compounds from the root of Peucedanum decursivum (Miq.) Maxim by high-speed counter-current chromatography.  J Chromatogr A. 2005;  1076 127-32
  • 17 Cassady J M, Ojima N, Chang C J, McLaughlin J L. An investigation of the antitumor activity of Micromelum integerrimum (Rutaceae).  J Nat Prod. 1979;  42 274-8
  • 18 Panichayupakaranant P, Noguchi H, De-Eknamkul W, Sankawa U. Naphthoquinones and coumarins from Impatiens balsamina root cultures.  Phytochemistry. 1995;  40 1141-3.
  • 19 Cardona L, Garcia B, Pedro J R, Pérez J. 6-Prenyloxy-7-methoxycoumarin, a coumarin-hemiterpene ether from Carduus tenuiflorus. .  Phytochemistry. 1992;  31 3989-91.
  • 20 Miyake Y, Murakami A, Sugiyama Y, Isobe M, Koshimizu K, Ohigashi H. Identification of coumarins from lemon fruit (Citrus limon) as inhibitors of in vitro tumor promotion and superoxide and nitric oxide generation.  J Agric Food Chem. 1999;  47 3151-7
  • 21 Murray R DH, Ballantyne M M, Hogg T C, McCabe P H. Claisen rearrangements – VI. Synthesis of the coumarins, sesibiricin and toddaculin.  Tetrahedron. 1975;  31 2960-5
  • 22 Nemoto T, Ohshima T, Shibasaki M. Enantioselective total syntheses of (+)-decursin and related natural compounds using catalytic asymmetric epoxidation of an enone.  Tetrahedron. 2003;  59 6889-97
  • 23 Zschocke S, Lehner M, Bauer R. 5-Lipoxygenase and cyclooxygenase inhibitory active constituents from Qianghuo (Notopterygium incisum).  Planta Med. 1997;  63 203-6.
  • 24 Zdero C, Jakupovic J, Bohlmann F. Diterpenes and other constituents from Pteronia species.  Phytochemistry. 1990;  29 1231-45
  • 25 Fuendjiep V, Wandji J, Tillequin F, Mulholland D A, Budzikiewicz H, Fomum Z T. et al . Chalconoid and stilbenoid glycosides from Guibourtia tessmanii. .  Phytochemistry. 2002;  60 803-6
  • 26 Szendi Z, Forgó P, Sweet F. Complete 1H and 13C NMR spectra of pregnenolone.  Steroids. 1995;  60 442-6
  • 27 Mayer S F, Steinreiber A, Orru R VA, Faber K. Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-panaxytriol and (R)- and (S)-falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction.  J Org Chem. 2002;  67 9115-21
  • 28 Bohlmann F, Rode K M. Polyacetylenverbindungen, 147. Die Polyine aus Oenanthe crocata L.  Chem Ber. 1968;  101 1163-75
  • 29 Bohlmann F, Zdero C. Polyacetylenverbindungen, 230. Ein neues Polyin aus Centella-Arten.  Chem Ber. 1975;  108 511-4

Prof. Dr. Jin-Feng Hu

Department of NaturalProducts for Chemical GeneticResearch

Key Laboratory of BrainFunctional Genomics

Ministry of Education &Shanghai Key Laboratory of BrainFunctional Genomics

East China Normal University

3663 Zhongshan Road N

Shanghai 200062

People’s Republic of China

Tel.: +86-21-6260-7510

Fax: +86-21-6260-6791

Email: jfhu@brain.ecnu.edu.cn


Lead Discovery and RapidStructure Elucidation Group

Sequoia Sciences, Inc.

1912 Innerbelt Business Center Drive

Saint Louis, MO 63114

USA

Phone: +1-314-373-5181

Fax: +1-314-373-5186

Email: jhu@sequoiasciences.com