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

Abstract

Five new phenylpropanoids, named balajaponins A–E (1–5), were isolated from Balanophora japonica, along with 24 known compounds. Among them, three hydrolysable tannins (6–8) 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.

Balanophora japonica - Balanophoraceae - phenylpropanoids - hydrolysable tannins - α‐glucosidase inhibitors

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