Tarennane and Tarennone, Two Novel Chalcone Constituents from Tarenna attenuata

Abstract

Two novel chalcone constituents, tarennane (1) and tarennone (2), together with nine known compounds, were isolated from the whole plant of Tarenna attenuata. By analysis of physical and spectroscopic data, the structures of new compounds were elucidated as (E)-4-[3-(4-hydroxy-3-methoxyphenyl)-acryl]-3,4,5-trimethoxycyclohexa-2,5-dienone (1) and 1,2-bis(3,5-dimethoxy-4-hydroxyphenyl)-3-hydroxypropan-1-one (2). These two compounds were tested for antioxidant activities in the MTT and DPPH assays. Compound 1 revealed potent antioxidant activities against H₂O₂-induced impairment in PC12 cells, but neither of them showed DPPH radical-scavenging activity with IC₅₀ values of 181.1 and 210.3 μM, respectively.

References

• 1 Lynn D G, Steffens J C, Kamut V S, Graden D W, Shabanowitz J, Riopel J L. Isolation and characterization of the first host recognition substance for parasitic angiosperms.  J Am Chem Soc. 1981;  103 1868-70.
• 2 El-Feraly F S, Hufford C D. Synthesis and carbon-13 nuclear magnetic resonance assignments of xenognosin.  J Org Chem. 1982;  47 1527-30.
• 3 Zhao W, Xu R, Qin G, Wu H, Jiang S, Yang G. A new phenolic glycoside from Mussaenda pubescens .  Nat Prod Sci. 1996;  2 14-8.
• 4 Wu T S, Yeh J H, Wu P L. The heartwood constituents of Tetradium glabrifolium .  Phytochemistry. 1995;  40 121-4.
• 5 Luo X R, Gao Y Z, Chen W Q, Xu X , Wu H. Flora Reipublicae Popularis Sinicae.  Beijing: Science. Press;  1999 382-3.
• 6 Board of Health of Revolution Committee in Region. Guangxi Zhuang Autonomous Guangxi herbal selections. Nanning; Guangxi People's Publishing House 1974: 1798-9.
• 7 Yang X W, Ma Y L, He H P, Wang Y H, Di Y T, Zhou H. et al . Iridoid constituents of Tarenna attenuata .  J Nat Prod. 2006;  69 971-4.
• 8 Kayser O, Kolodziej H. Highly oxygenated coumarins from Pelargonium sidoides .  Phytochemistry. 1995;  39 1181-5.
• 9 Bano S, Ahmad V U, Perveen S, Bano N, Shafiuddin M, Shameel M. Marine natural Products; II. Chemical constituents of the red alga Botryocladia leptopoda .  Planta Med. 1987;  53 117-8.
• 10 Li C H, Zhou H J, Yang X D, Zhao J F, Li L. The chemical study on Cleidion brevipetiolatum .  Nat Prod Res Dev. 2004;  16 514-5.
• 11 Shimomura H, Sashida Y, Oohara M, Tenma H. Phenolic glucosides from Parabenzoin praecox .  Phytochemistry. 1988;  27 644-6.
• 12 Manchand P S, Belica P S, Wong H S. Synthesis of 3,4,5-trimethoxybenzaldehyde.  Synth Commun. 1990;  20 2659-66.
• 13 Hanke F J, Kubo I. Assigning ¹³C-NMR resonances of natural products.  J Nat Prod. 1989;  52 1237-45.
• 14 Li Y S, Luo S D, Zhang M, Chen J J, Wang Z T. Constituents of Liguliria veilerea (Franch.) Hand-Mazz.  China J Chin Mater Med. 2001;  26 835-7.
• 15 Scott K N. Carbon-13 nuclear magnetic resonance of biologically important aromatic acids. I. Chemical shifts of benzoic acid and derivatives.  J Am Chem Soc. 1972;  94 8564-8.
• 16 Li X D, Wu L J, Zang X Y, Zhang J. Studies on chemical constituents of Sorbaria sorbifolia .  China J Chin Mater Med. 2002;  27 841-3.
• 17 Wang M, Kikuzaki H, Zhu N, Sang S, Nakatani N, Ho C T. Isolation and structural elucidation of two new glycosides from sage (Salvia officinalis L.)  J Agric Food Chem. 2000;  48 235-8.
• 18 Harrison L J, Sia G L, Yeow S K, Tan H TW, Connolly J D, Lavaud C. et al . A ferulic acid ester of sucrose and other constituents of Bhesa paniculata .  Phytochemistry. 1995;  38 1497-500.
• 19 Yang N Y, Duan J A, Qian S H, Tian L J. Studies on the chemical constituents of Tagetes erecta L .  J Shenyang Pharm Univ. 2003;  20 258-9.
• 20 Wang R, Zhou J, Tang X C. Tacrine attenuates hydrogen peroxide-induced apoptosis by regulating expression of apoptosis-related genes in rat PC12 cells.  Mol Brain Res. 2002;  107 1-8.
• 21 Alley M C, Scudiero D A, Monks A, Hursey M L, Czerwinski M J, Fine D L. et al . Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay.  Cancer Res. 1988;  48 589-601.
• 22 Blois M S. Antioxidant determinations by the use of a stable free radical.  Nature. 1958;  181 1199-200.