Bicyclononane Aldehydes and Antiproliferative Constituents from Amomum tsao-ko

Abstract

A racemic mixture of a new bicyclononane aldehyde, (1RS,5SR,6RS)-5-hydroxybicyclo[4.3.0]non-2-ene-2-carbaldehyde (1) was isolated from the fruits of Amomum tsao-ko, together with 12 known compounds (2–13). The structure of 1 was determined on the basis of extensive spectroscopic analysis, including 1D and 2D NMR data. The antiproliferative activity of compounds 1–13 was assessed in the murine neuroblastoma cell line N2a.

Key words

Amomum tsao‐ko - Zingiberaceae - bicyclic aldehydes - antiproliferative activity

References

• 1 Nanjing University for Chinese Medicine .Dictionary of Traditional Chinese Medicine. Shanghai; Shanghai Science and Technique Publishing House 2006: 2124
• 2 Lee K Y, Kim S H, Sung S H, Kim Y C. Inhibitory constituents of lipopolysaccharide-induced nitric oxide production in BV2 microglia isolated from Amomum tsao-ko.  Planta Med. 2008;  74 867-869
• 3 Song Q S, Teng R W, Liu X K, Yang C R. Tsaokoin, a new bicyclic nonane from Amomum tsao-ko.  Chin Chem Lett. 2001;  12 227-230
• 4 Moon S S, Lee J Y, Cho S C. Isotsaokoin, an antifungal agent from Amomum tsao-ko.  J Nat Prod. 2004;  67 889-891
• 5 Starkenmann C, Mayenzet F, Brauchli R, Wunsche L, Vial C. Structure elucidation of a pungent compound in black cardamon: Amomum tsao-ko Crevost et Lemarie (Zingiberaceae).  J Agric Food Chem. 2007;  55 10902-10907
• 6 Moon S S, Cho S C, Lee J Y. Tsaokoarylone, a cytotoxic diaryheptanoid from Amomum tsao-ko fruits.  Bull Korean Chem Soc. 2005;  26 447-450
• 7 Martin T S, Kikuzaki H, Hisamoto M, Nakatani N. Constituents of Amomum tsao-ko and their radical scavenging and antioxidant activities.  J Am Oil Chem Soc. 2000;  77 667-673
• 8 Dawson G W, Pickett J A, Smiley D WM. The aphid sex pheromone cyclopentanoids: synthesis in the elucidation of structure and biosynthetic pathways.  Bioorg Med Chem. 1996;  4 351-361
• 9 Ji R, Chen Z X, Corvini P FX, Kappler A, Brune A, Haider, Schaffer A. Synthesis of [¹³C]- and [¹⁴C]-labeled phenolic humus and lignin monomers.  Chemosphere. 2005;  60 1169-1181
• 10 Mayer S F, Steinreiber A, Orru R VA, Faber K. Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-panaxytriol and (R)- and (S)-falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction.  J Org Chem. 2002;  67 9115-9121
• 11 Mino T, Hasegawa T, Shirae Y, Sakamoto M, Fujita T. N,O-ligand accelerated zinc-catalyzed transesterification of alcohols with vinyl esters.  J Organomet Chem. 2007;  692 4389-4396
• 12 Yoshida T, Murai M, Abe M, Ichimaru N, Harada T, Nishioka T, Miyoshi H. Crucial structural factors and mode of action of polyene amides as inhibitors for mitochondrial NADH-ubiquinone oxidoreductase (Complex I).  Biochemistry. 2007;  46 10365-10372
• 13 Cory A H, Owen T C, Barltrop J A, Cory J G. Use of an aqueous soluble tetrazolium/formazan assay for cell growth assay in culture.  Cancer Commun. 1991;  3 207-212