Planta Med 2011; 77(5): 477-481
DOI: 10.1055/s-0030-1250464
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

New Phenylpropanoids and In Vitro α-Glucosidase Inhibitors from Balanophora japonica

Tong Zhou1 , Xiao-hui Zhang1 , Shu-wei Zhang1 , Shan-shan Liu1 , Li-jiang Xuan1
  • 1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, P. R. China
Further Information

Publication History

received June 4, 2010 revised September 26, 2010

accepted September 29, 2010

Publication Date:
26 October 2010 (online)

Abstract

Five new phenylpropanoids, named balajaponins A–E (15), were isolated from Balanophora japonica, along with 24 known compounds. Among them, three hydrolysable tannins (68) showed specific in vitro α-glucosidase inhibition, with IC50 values in the range of 1–4 µM. Kinetic analysis revealed that they all acted in a noncompetitive mode.

References

  • 1 Zhonghua Bencao Editorial Committee of the State Administration of Traditional Chinese Medicine .Zhonghua Bencao, Vol. 2. Shanghai; Scientific and Technical Publishers 1999: 1265
  • 2 Wang K J, Zhang Y J, Yang C R. New phenolic constituents from Balanophora polyandra with radical-scavenging activity.  Chem Biodivers. 2006;  3 1317-1324
  • 3 Jiang Z H, Tanaka T, Iwata H, Sakamoto S, Hirose Y, Kouno I. Ellagitannins and lignan glycosides from Balanophora japonica (Balanophoraceae).  Chem Pharm Bull. 2005;  53 339-341
  • 4 Hosokawa A, Sumino M, Nakamura T, Yano S, Sekine T, Ruangrungsi N, Watanabe K, Ikegami F. A new lignan from Balanophora abbreviata and inhibition of lipopolysaccharide (LPS)-induced inducible nitric oxide synthase (iNOS) expression.  Chem Pharm Bull. 2004;  52 1265-1267
  • 5 Jiang Z, Wen X, Tanaka T, Wu S, Liu Z, Iwata H, Hirose, Wu S, Kouno I. Cytotoxic hydrolyzable tannins from Balanophora japonica.  J Nat Prod. 2008;  71 719-723
  • 6 Jiang Z H, Hirose Y, Iwata H, Sakamoto S, Tanaka T, Kouno I. Caffeoyl, coumaroyl, galloyl, and hexahydroxydiphenoyl glucoses from Balanophora japonica.  Chem Pharm Bull. 2001;  49 887-892
  • 7 Gallagher B D, Taft B R, Lipshutz B H. Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives.  Org Lett. 2009;  11 5374-5377
  • 8 Zhang Z, Ma Y, Zhao Y F. Microwave-assisted one-pot synthesis of dihydrocoumarins from phenols and cinnamoyl chloride.  Synlett. 2008;  7 1091-1095
  • 9 Haruna M, Koube T, Ito K, Murata H. Balanophonin, a new neo-lignan from Balanophora japonica Makino.  Chem Pharm Bull. 1982;  30 1525-1527
  • 10 Ludwig C H, Nist B J, McCarthy J L. Lignin XII. The high resolution nuclear magnetic resonance spectroscopy of protons in compounds related to lignin.  J Am Chem Soc. 1964;  86 1186-1196
  • 11 Zhu Y, Lü Z P, Xue C B, Wu W S. New triterpenoid saponins and neolignans from Morina kokonorica.  Helv Chim Acta. 2009;  92 536-545
  • 12 Harada N, Nakanishi K. A method for determining the chiralities of optically active glycols.  J Am Chem Soc. 1969;  91 3989-3991
  • 13 Dillon J, Nakanishi K. Absolute configurational studies of vicinal glycols and amino alcohols. II. With Pr(dpm)3.  J Am Chem Soc. 1969;  97 5417-5422
  • 14 Jiang Z H, Hirose Y, Iwata H, Sakamoto S, Tanaka T, Kouno I. Caffeoyl, coumaroyl, galloyl, and hexahydroxydiphenoyl glucoses from Balanophora japonica.  Chem Pharm Bull. 2001;  49 887-892
  • 15 Bassey S A, Acharavadee P, Okon D E, Udofot J E, Chulabhorn M, Prasat K. α-Glucosidase inhibitory, aromatase inhibitory, and antiplasmodial activities of a biflavonoid GB1 from Garcinia kola stem bark.  Planta Med. 2010;  76 276-277
  • 16 Boonmee A, Reynolds C D, Sangvanich P. α-Glucosidase inhibitor proteins from Sesbania grandiflora flowers.  Planta Med. 2007;  73 1197-1201
  • 17 Lineweaver H, Burk D. The determination of enzyme dissociation constants.  J Am Chem Soc. 1934;  56 658-666
  • 18 Mathews S T, Kim T, Zhang A J, Fish W J, Rimando A M, Mentreddy S R. Anti-diabetic properties of serviceberry (Amelanchier alnifolia).  Planta Med. 2008;  74 70
  • 19 Deacon C F, Hughes T E, Holst J J. Dipeptidyl peptidase IV inhibition potentiates the insulinotropic effect of glucagon-like peptide 1 in the anesthetized pig.  Diabetes. 1998;  47 764-769

Prof. Li-jiang Xuan

State Key Laboratory of Drug Research
Shanghai Institute of Materia Medica
Chinese Academy of Sciences

555 Zuchongzhi Road

Zhangjiang Hi-Tech Park

Shanghai 201203

People's Republic of China

Phone: +86 21 20 23 10 00 23 11

Fax: +86 21 50 80 70 88

Email: ljxuan@mail.shcnc.ac.cn

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