Dendrazawaynes A and B, Antifungal Polyacetylenes from Dendranthema zawadskii (Asteraceae)

Abstract

Two new C₁₄ polyacetylenes dendrazawayne A (7) and dendrazawayne B (9) together with known C₁₃ polyacetylenes (2, 3), C₁₄ polyacetylenes (1, 4, and 8) and polyacetylene amides (5 and 6) were isolated from the roots of Dendranthema zawadskii. The structures of 7 and 9 were elucidated based on spectroscopic methods including 2D-NMR, HR-TOF-MS, IR, and UV. Compounds 1, 2, 3, 5, and 6 showed moderate activity against tumor cell lines (human small lung cancer cell line A549, melanoma SK-Mel-2, and mouse melanoma B16F1) with IC₅₀ values in the range of 7.4 - 30 μg/mL. Compounds 7 and 9, including other polyacetylenes, showed strong activity against the fungus Trichophyton (MIC: 5 - 10 μg/mL).

Antifungal - Dendranthema zawadskii - Asteraceae - dendrazawayne A - dendrazawayne B - cytotoxicity - polyacetylenes

References

• 1 Kim J S, Im K S, Jung J H, Kim Y L, Kim J, Shim C J. et al . New bioactive polyacetylenes from the marine sponge Petrosia sp.  Tetrahedron. 1998;  54 3151-8.
• 2 Isaacs S, Kashman Y, Loya S, Hizi A. Petrosynol and petrosolic acid, two novel natural inhibitors of the reverse transcriptase of human immunodeficiency virus from Petrosia sp.  Tetrahedron. 1993;  49 10 435-8.
• 3 Li H Y, Matsunaga S, Fusetani N. Corticatic acids A - C, antifungal acetylenic acids from the marine sponge, Petrosia corticata .  J Nat Prod. 1994;  57 1464-7.
• 4 Hallock Y F, Cardellina J H, Balaschak M S, Alexander M R, Prather T R, Shoemaker R H. et al . Antitumor activity and stereochemistry of acetylenic alcohols from the sponge Cribrochalina vasculum .  J Nat Prod. 1995;  58 1801-7.
• 5 Christensen L P, Brandt K. Bioactive polyacetylenes in food plants of the Apiaceae family: Occurrence, bioactivity, and analysis.  J Pharm Biomed Anal. 2006;  41 683-93.
• 6 Wrang P A, Lam J. Polyacetylenes from Chrysanthemum leucanthemum .  Phytochemistry. 1975;  14 1027-35.
• 7 Pellati F, Calo S, Benvenuti S. High-performance liquid chromatography analysis of polyacetylenes and polyenes in Echinacea pallida by using a monolithic reversed-phase silica column. J Chromatogr A, in press.
• 8 Macdonald H G. A dictionary of natural products. Medford, New Jersey; Plexus Publishing Inc 1997: 185.
• 9 Han S, Sung K H, Yim D, Lee S, Lee C K, Ha N J. et al . The effect of linarin on LPS-induced cytokine production and nitric oxide inhibition in murine macrophages cell line RAW264.7  Arch Pharm Res. 2002;  25 170-7.
• 10 Lee Y N. Flora of Korea. Korea; Kyo-Hak Publishing Co 1996: 827
• 11 Samy R P, Ignacimuthu S. Antibacterial activity of some folklore medicinal plants used by tribals in Western Ghats of India.  J Ethnopharmacol. 2000;  69 63-71.
• 12 Bauer A W, Kirby W MM, Sherris J C, Turck M. Antibiotic susceptibility testing by a standardized single disc method.  Am J Clin Pathol. 1966;  45 493-6.
• 13 Nair M G, Mishra S K, Putnam A R. Antifungal anthracycline antibiotics, spartanamicins A and B from Micromonospora spp.  J Antibiot. 1992;  45 1738-45.
• 14 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D. et al . New colorimetric cytotoxicity assay for anticancer-drug screening.  J Natl Cancer Inst. 1990;  82 1107-12.
• 15 Bohlmann F, Burckhardt T, Zdero C. Naturally occurring acetylenes.  New York and London: Academic. Press;  1973 427-35.
• 16 Bohlmann F, Zdero C. Weitere Inhaltsstoffe der Gattung Dendranthema .  Chem Ber. 1975;  108 735-8.
• 17 Zeisberg R, Bohlmann F. ¹³C-NMR-Spektren von Polyinen.  Chem Ber. 1974;  107 3800-5.
• 18 Saadali B, Boriky D, Blaghen M, Vanhaelen M, Talbi M. Alkamides from Artemisia dracunculus .  Phytochemistry. 2001;  58 1083-6.
• 19 Dale J A, Mosher H S. Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters.  J Am Chem Soc. 1973;  95 512-9.