Acetogenin and Prenylated Flavonoids from Helminthostachys zeylanica with Inhibitory Activity on Superoxide Generation and Elastase Release by Neutrophils

Abstract

One new acetogenin, 6-hydroxy-8-pentadecyloxocane-2,7-dione (1), and four new prenylated flavonoids, 4′′a,5′′,6′′,7′′,8′′,8′′a-hexahydro-5,3′,4′-trihydroxy-5′′,5′′,8′′a-trimethyl-4H-chromeno[2′′,3′′:7,6]flavone (2), 4′′a,5′′,6′′,7′′,8′′,8′′a-hexahydro-5,3′,4′,‐trihydroxy-5′′,5′′,8′′a-trimethyl-4H-chromeno[2′′,3′′:7,8]flavone (3), 2-(3,4-dihydroxyphenyl)-6-((2,2-dimethyl-6-methylenecyclohexyl)methyl)-5,7-dihydroxy-chroman-4-one (4), and 2-(3,4-dihydroxy-2-[(2,6,6-trimethylcyclohex-2-enyl)methyl]phenyl)-3,5,7-trihydroxy-4H-chromen-4-one (5), together with six known compounds, were isolated and purified from the rhizomes of Helminthostachys zeylanica by column chromatography and high performance liquid chromatography (HPLC) via bioactivity-guided fractionation isolation. The structures of the new isolates were elucidated by spectroscopic methods. Compounds 1, 3, and 5 showed inhibitory activities on either superoxide anion generation or elastase release by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (FMLP/CB).

Key words

Helminthostachys zeylanica - Ophioglossaceae - acetogenin - prenylated flavonoids - superoxide generation - elastase release

References

• 1 Chiu N Y, Chang K H. The illustrated medicinal plants of Taiwan, Vol. 3. Taipei; SMC Publishing, Inc. 1992: 18
• 2 Suja S R, Latha P G, Pushpangadan P, Rajasekharan S. Evaluation of hepatoprotective effects of Helminthostachys zeylanica (L.) Hook against carbon tetrachloride-induced liver damage in Wistar rats.  J Ethnopharmacol. 2004;  92 61-66
• 3 Chen C C, Huang Y L, Yeh P Y, Ou J C. Cyclized geranyl stilbenes from the rhizomes of Helminthostachys zeylanica.  Planta Med. 2003;  69 964-967
• 4 Murakami T, Hagiwara M, Tanaka K, Chen C M. Chemical investigation of the contents of Helminthostachys zeylanica. I.  Chem Pharm Bull. 1973;  21 1849-1851
• 5 Murakami T, Hagiwara M, Tanaka K, Chen C M. Chemical investigation of the contents of Helminthostachys zeylanica. II.  Chem Pharm Bull. 1973;  21 1851-1852
• 6 Huang Y L, Yeh P Y, Shen C C, Chen C C. Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica.  Phytochemistry. 2003;  64 1277-1283
• 7 Su B N, Park E J, Mbwambo Z H, Santarsiero B D, Mesecar A D, Fong H H S, Pezzuto J M, Kinghorn A D. New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient mosher ester procedure carried out in NMR tubes.  J Nat Prod. 2002;  65 1278-1282
• 8 Liaw C C, Chang F R, Chen S L, Wu C C, Lee K H, Wu Y C. Novel cytotoxic monotetrahydrofuranic annonaceous acetogenins from Annona montana.  Bioorg Med Chem. 2005;  13 4767-4776
• 9 Hwang T L, Li G L, Lan Y H, Chia Y C, Hsieh P W, Wu Y H, Wu Y C. Potent inhibition of superoxide anion production in activated human neutrophils by isopedicin, a bioactive component of the Chinese medicinal herb Fissistigma oldhamii.  Free Radic Biol Med. 2009;  46 520-528
• 10 Shen Y C, Chen S Y, Kuo Y H, Hwang T L, Chiang M Y, Khalil A T. Chemical transformation and biological activities of Ambrein, a major product of Ambergris from Physeter macrocephalus.  J Nat Prod. 2007;  70 147-153
• 11 Makishima M, Kanatani Y, Yamamoto-Yamaguchi Y, Honma Y. Enhancement of activity of 1alpha, 25-dihydroxyvitamin D3 for growth inhibition and differentiation induction of human myelomonocytic leukemia cells by tretinoin tocoferil, an alpha-tocopherol ester of all-trans retinoic acid.  Blood. 1996;  87 3384-3394
• 12 Ishiyama M, Tominaga H, Shiga M, Sasamoto K, Ohkura Y, Ueno K, Watanabe M. Novel cell proliferation and cytotoxicity assays using a tetrazolium salt that produces a soluble formazan dye.  In Vitro Toxicol. 1995;  8 187-190
• 13 Huang K F, Yen Y F. Constituents of Erythrina cariegata.  J Chin Pharm. 1995;  47 493-500
• 14 Pradhan B P, Chakraborty G C, Subba A. Triterpenoid lactone from Leucas aspera.  Phytochemistry. 1990;  29 1693-1695
• 15 Sasaki S. Handbook of proton-NMR spectra and data, 1st edition. New York; Academic Press 1985: 190
• 16 Sasaki S. Handbook of proton-NMR spectra and data, 1st edition. New York; Academic Press 1985: 289
• 17 Encarnación D R, Nogueiras C L, Salinas V H A, Anthoni U, Nielsen P H, Christophersen C. Isolation of eriodictyol identical with Huazhongilexone from Solanum hindsianum.  Acta Chem Scand. 1999;  53 375-377
• 18 Seo E K, Silva G L, Chai H B, Chagwedera T E, Farnsworth N R, Cordell G A, Pezzuto J M, Kinghorn A D. Cytotoxic prenylated flavanones from Monotes engleri.  Phytochemistry. 1997;  45 509-515
• 19 Chen Q, Powell D W, Rane M J, Singh S, Butt W, Klein J B, McLeish K R. Akt phosphorylates p 47 ^phox and mediates respiratory burst activity in human neutrophils.  J Immunol. 2003;  170 5302-5308
• 20 Sadhu C, Dick K, Tino W T, Staunton D E. Selective role of PI3K delta in neutrophil inflammatory responses.  Biochem Biophys Res Commun. 2003;  308 764-769