Planta Med 2012; 78(6): 625-629
DOI: 10.1055/s-0031-1298322
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Carboline Alkaloids from Psammosilene tunicoides and Their Cytotoxic Activities

Junmian Tian1 , 3 , Yunheng Shen1 , Huiliang Li1 , Runhui Liu1 , Lei Shan1 , Jinming Gao3 , Weidong Zhang1 , 2
  • 1Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China
  • 2King Saud University, Riyadh, Saudi Arabia
  • 3College of Science, Northwest A & F University, Yangling, P. R. China
Further Information

Publication History

received October 20, 2011 revised January 22, 2012

accepted February 6, 2012

Publication Date:
12 March 2012 (online)

Abstract

Five new carboline alkaloids, tunicoidines A–E (15), and two known carboline alkaloids, 1-acetyl-β-carboline-3-carboxylic acid (6) and 1-acetyl-3-carbomethoxyl-β-carboline (7), were isolated for the first time from the root of Psammosilene tunicoides. The structures of the new carboline alkaloids were established on the basis of 1D- and 2D-NMR, and HR-MS spectroscopic analyses. The seven compounds were evaluated for cytotoxicity against A549, HCT116, ZR-75-30, and HL-60 cell lines. However, only compound 7 had potent cytotoxic activity against the HCT116 cell line with an IC50 value of 9.67 µg/mL, while the others showed no cytotoxic activities against the four tested cell lines.

Supporting Information

References

  • 1 Zhong H M, Ni W, Hua Y, Chen Y Z, Chen C X. A new tritepenoid saponin from Psammosilene tunicoides.  Acta Bot Yunn. 2002;  24 781-786
  • 2 Tian J M, Shen Y H, Yang X W, Liang S, Tang J, Shan L, Zhang W D. Tunicyclin A, the first plant tricycle ring cyclopeptide from Psammosilene tunicoides.  Org Lett. 2009;  11 1131-1133
  • 3 Nemet I, Varga-Defterdarovic L. Methylglycoxal-derived β-carbolines formed from tryptophan and its derivates in the Maillard reaction.  Amino Acids. 2007;  32 291-293
  • 4 Faini F, Castillo M, Torres R. A new β-carboline alkaloid from Vestia lycioides.  Phytochemistry. 1978;  17 338
  • 5 Ravinder K, Vijender Reddy A, Krishnaiah P, Ramesh P, Ramakrishna S, Laatsch H, Venkateswarlu Y. Isolation and synthesis of a novel β-carboline guanidine derivative tiruchanduramine from the Indian ascidian Synoicum macroglossum.  Tetrahedron Lett. 2005;  46 5475-5478
  • 6 Tian J M, Yang X W, Di Y T, Ma Y L, Li L, Li L, He H P, Hao X J. Antioxidant lignans from Manathes patentiflora.  Planta Med. 2009;  75 534-537
  • 7 Tan N H, Zhou J. Plant cyclopeptides.  Chem Rev. 2006;  106 840-895
  • 8 Li H Z, Nakashima T, Tanaka T, Zhang Y J, Yang C R, Kouno I. Two new maltol glycosides and cyanogenic glycosides from Elshioltzia rugulosa Hemsl.  J Nat Med. 2008;  62 75-78
  • 9 Xiao S L, Lin W, Wang C, Yang M. Synthesis and biological evaluation of DNA targeting flexible side-chain substituted β-carboline derivatives.  Bioorg Med Chem Lett. 2001;  11 437-441
  • 10 Zhao M, Bi L R, Wang W, Wang C, Baudy-Floch M, Ju J F, Peng S Q. Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates.  Bioorg Med Chem Lett. 2006;  14 6998-7010

Dr. Weidong Zhang

Department of Phytochemistry
School of Pharmacy
Second Military Medical University

325# Guohe Rd.

Shanghai 200433

P. R. China

Phone: +86 21 81 87 12 44

Fax: +86 21 81 87 12 44

Email: wdzhangy@hotmail.com

Dr. Yunheng Shen

Department of Phytochemistry
School of Pharmacy
Second Military Medical University

325# Guohe Rd.

Shanghai 200433

P. R. China

Phone: +86 21 81 87 12 45

Fax: +86 21 81 87 12 45

Email: shenyunheng9217018@yahoo.com.cn