Iridoid Esters from Tabebuia avellanedae and Their In Vitro Anti-inflammatory Activities

Li Zhang; Isao Hasegawa; Tomihisa Ohta

doi:10.1055/s-0042-110322

Planta Medica, Inhaltsverzeichnis

Planta Med 2017; 83(01/02): 164-171
DOI: 10.1055/s-0042-110322

Natural Product Chemistry and Analytical Studies

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Iridoid Esters from Tabebuia avellanedae and Their In Vitro Anti-inflammatory Activities

Li Zhang

¹College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa City, Japan

²Faculty of Pharmaceutical Sciences, Henan University of Chinese Medicine, Zhengzhou City, China

,

Isao Hasegawa

¹College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa City, Japan

,

Tomihisa Ohta

¹College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa City, Japan

› Institutsangaben

Abstract

A phytochemical investigation of the inner bark of Tabebuia avellanedae Lorentz ex Griseb was carried out by various chromatographic techniques, resulting in the isolation and characterization of eight new iridoid esters, namely Avelladoids A–H (1-8). Their chemical structures were elucidated on the basis of extensive spectroscopic analyses, especially 2D NMR experiments and HRMS data. The anti-inflammatory effects of 1–8 were determined on an LPS-stimulated RAW 264.7 cell line. Among them, compounds 1, 2, and 3 exhibited anti-inflammatory activities by inhibition of NO and PGE₂ production in a dose-dependent manner, without altering cell viability.

Key words

Bignoniaceae - Tabebuia avellanedae - iridoid esters - RAW 264.7 cells - anti-inflammatory - NO - PGE₂

Volltext

Referenzen

References
1 Castellanos JRG, Prieto JM, Heinrich M. Red Lapacho Tabebuia impetiginosa–a global ethnopharmacological commodity. J Ethnopharmacol 2009; 121: 1-13
2 Suo MR, Hasegawa I, Kato H, Takano F, Ohta T. Anti-inflammatory constituents from Tabebuia avellanedae . Fitoterapia 2012; 83: 1484-1488
3 Suo MR, Ohta T, Takano F, Jin S. Bioactive phenylpropanoid glycosides from Tabebuia avellanedae . Molecules 2013; 18: 7336-7345
4 Machado T, Pinto A, Pinto M, Leal I, Silva M, Amaral A, Kuster R, Netto-dosSantos K. In vitro activity of Brazilian medicinal plants, naturally occurring naphthoquinones and their analogues, against methicillin-resistant Staphylococcus aureus . Int J Antimicrob Ag 2003; 21: 279-284
5 Zhang L, Tatsuno T, Hasegawa I, Ohta T. Furanonaphthoquinones from Tabebuia avellanedae induce cell cycle arrest and apoptosis in the human non-small cell lung cancer cell line A549. Phytochem Let 2015; 11: 9-17
6 Choi WH, Um MY, Ahn J, Jung CH, Park MK, Ha TY. Ethanolic extract of Taheebo attenuates increase in body weight and fatty liver in mice fed a high-fat diet. Molecules 2014; 19: 16013-16023
7 Freitas AE, Moretti M, Budni J, Balen GO, Fernandes SC, Veronezi PO, Heller M, Micke GA, Pizzolatti MG, Rodrigues AL. NMDA receptors and the L-arginine-nitric oxide-cyclic guanosine monophosphate pathway are implicated in the antidepressant-like action of the ethanolic extract from Tabebuia avellanedae in mice. J Med Food 2013; 16: 1030-1038
8 Kim MG, Jeon JH, Lee HS. Larvicidal activity of the active constituent isolated from Tabebuia avellanedae bark and structurally related derivatives against three mosquito species. J Agric Food Chem 2013; 61: 10741-10745
9 Byeon SE, Chung JY, Lee YG, Kim BH, Kim KH, Cho JY. In vitro and in vivo anti-inflammatory effects of taheebo, a water extract from the inner bark of Tabebuia avellanedae . J Ethnopharmacol 2008; 119: 145-152
10 Lee MH, Choi HM, Hahm D, Her E, Yang H, Yoo MC, Kim KS. Analgesic and anti-inflammatory effects in animal models of an ethanolic extract of Taheebo, the inner bark of Tabebuia avellanedae . Mol Med Rep 2012; 6: 791-796
11 Awale S, Kawakami T, Tezuka Y, Ueda JY, Tanaka K, Kadota S. Nitric oxide (NO) production inhibitory constituents of Tabebuia avellanedae from Brazil. Chem Pharm Bull 2005; 53: 710-713
12 Zhang L, Hasegawa I, Ohta T. Anti-inflammatory cyclopentene derivatives from the inner bark of Tabebuia avellanedae . Fitoterapia 2016; 109: 217-223
13 Güllük E, Bogdan E, Christl M. 3-Substituted cyclopenta[c]pyrans: synthesis and electrophilic Substitutions. Eur J Org Chem 2006; 2006: 531-542
14 Garcez FR, Garcez WS, Mahmoud TS, Figueiredo PO, Resende UM. New constituents from the trunk bark of Tabebuia heptaphylla . Química Nova 2007; 30: 1887-1891
15 von Poser GL, Schripsema J, Henriques AT, Jensen SR. The distribution of iridoids in Bignoniaceae . Biochem Syst Ecol 2000; 28: 351-366
16 Warashina T, Nagatani Y, Noro T. Constituents from the bark of Tabebuia impetiginosa . Phytochemistry 2004; 65: 2003-2011
17 Warashina T, Nagatani Y, Noro T. Further constituents from the bark of Tabebuia impetiginosa . Phytochemistry 2005; 661: 589-597
18 Piaz FD, Vassallo A, Temraz A, Cotugno R, Belisario MA, Bifulco G, Chini MG, Pisano C, Tommasi ND, Braca A. A chemical-biological study reveals C9-type iridoids as novel heat shock protein 90 (Hsp90) inhibitors. J Med Chem 2013; 56: 1583-1595
19 Qian J, Hunkler D, Rimpler H. Iridoid-related aglycone and its glycosides from Scrophularia ningpoensis . Phytochemistry 1992; 31: 905-911
20 Cavill GWK, Hinterberger H. The chemistry of ants. V. Structure and reactions of dolichodial. Aust J Chem 1961; 14: 143-149
21 Berdini R, Bianco A, Guiso M, Marini E, Nicoletti M, Passacantilli P, Righi G. Isolation and partial synthesis of 7, 8-dehydro-6β, 10-dihydroxy-11-noriridomyrmecin, a methylcyclopentanoid monoterpene from Scrophularia canina . J Nat Prod 1991; 54: 1400-1403
22 Nakano K, Maruyama K, Murakami K, Takaishi Y, Tomimatsu T. Iridoids from Tabebuia avellanedae . Phytochemistry 1993; 32: 371-373
23 Kinne RW, Brauer R, Stuhlmuller B, Palombo-Kinne E, Burmester GR. Macrophages in rheumatoid arthritis. Arthritis Res 2000; 2: 189-202
24 Gracie JA, Forsey RJ, Chan WL, Gilmour A, Leung BP, Greer MR, Kennedy K, Carter R, Wei XQ, Xu D, Field M, Foulis A, Liew FY, McInnes IB. A proinflammatory role for IL-18 in rheumatoid arthritis. J Clin Invest 1999; 104: 1393
25 Michaelssony E, Holmdahl M, Engström A, Burkhardt H, Scheynius A, Holmdahl R. Macrophages, but not dendritic cells, present collagen to T cells. Eur J Immunol 1995; 25: 2234-2241

Zusatzmaterial

Supporting Information