Antibacterial Compounds from Mushrooms I: A Lanostane-Type Triterpene and Prenylphenol Derivatives from Jahnoporus hirtus and Albatrellus flettii and Their Activities Against Bacillus cereus and Enterococcus faecalis

Abstract

Antibacterial bioassay-guided fractionation of two American mushroom species, Jahnoporus hirtus and Albatrellus flettii, led to the isolation and identification of their major antibacterial constituents: 3,11-dioxolanosta-8,24(Z)-diene-26-oic acid (1) from J. hirtus and confluentin (2), grifolin (3), and neogrifolin (4) from A. flettii. Compound 1 is a new lanostane-type triterpene. All purified compounds were evaluated for their ability to inhibit the growth of Bacillus cereus and Enterococcus faecalis using standard MIC assays. Compounds 1–4 demonstrated MIC values of 40, 20, 10, and 20 µg/mL, respectively, against B. cereus and MIC values of 32, 1.0, 0.5, and 0.5 µg/mL, respectively, against E. faecalis. Thus, one novel compound and three others were shown to possess antimicrobial activities against these gram-positive bacteria employed as surrogates for more virulent and dangerous pathogens.

Key words

Jahnoporus hirtus - Albatrellus flettii - Scutigeraceae - triterpene - prenylphenol - antibacterial

References

• 1 Kabir M S, Engelbrecht K, Polanowski R, Rott M A, Schwan W R, Stemper M, Reed K, Sherman D, Cook J M, Monte A. New classes of gram-positive antibacterials: inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis.  Bioorg Med Chem Lett. 2008;  18 5745-5749
• 2 Helgason E, Okstad O A, Caugant D A, Johansen H A, Fouet A, Mock M, Hegna I, Kolstø A B. Bacillus anthracis, Bacillus cereus, and Bacillus thuringiensis – one species on the basis of genetic evidence.  Appl Environ Microbiol. 2000;  66 2627-2630
• 3 Huycke M M, Sahm D F, Gilmore M S. Multiple-drug resistant enterococci: the nature of the problem and an agenda for the future.  Emerg Infect Dis. 1998;  4 239-249
• 4 Quang D N, Hashimoto T, Arakawa Y, Kohchi C, Nishizawa T, Somab G-I, Asakawa Y. Grifolin derivatives from Albatrellus caeruleoporus, new inhibitors of nitric oxide production in RAW 264.7 cells.  Bioorg Med Chem. 2006;  14 164-168
• 5 Koch B, Steglich W. Meroterpenoid pigments from Albatrellus flettii (Basidiomycetes).  Eur J Org Chem. 2007;  10 1631-1635
• 6 Kawagishi H, Tanaka A, Sugiyama K, Mori H, Sakamoto H, Ishiguro Y, Kobayashi K, Uramato M. A pyradine-derivative from the mushroom Albatrellus confluens.  Phytochemistry. 1996;  42 547-548
• 7 Nukata M, Hashimoto T, Yamamoto I, Iwasaki N, Tanaka M, Asakawa Y. Neogrifolin derivatives possessing anti-oxidative activity from the mushroom Albatrellus ovinus.  Phytochemistry. 2002;  59 731-737
• 8 Luo D Q, Shao H J, Zhu H J, Liu J K. Activity in vitro and in vivo against plant pathogenic fungi of grifolin isolated from the basidiomycete Albatrellus dispansus.  Z Naturforsch. 2005;  60 50-56
• 9 Qing C, Liu M H, Yangl W M, Zhang Y L, Wang L, Liu J K. Effects of albaconol from the basidiomycete Albatrellus confluens on DNA topoisomerase II-mediated DNA cleavage and relaxation.  Planta Med. 2004;  70 792-796
• 10 Shim S H, Ryu J, Kim J S, Kang S S, Xu Y, Jung S H, Lee Y S, Lee S, Shin K H. New lanostane-type triterpenoids from Ganoderma applanatum. .  J Nat Prod. 2004;  67 1110-1113
• 11 Wang L Y, Wang N L, Yao X S, Miyata S, Kitanaka S. Euphane and tirucallane triterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of Xenopus. .  J Nat Prod. 2003;  66 630-633
• 12 Makino M, Motegi T, Fujimoto Y. Tirucallane-type triterpenes from Juliania adstringens.  Phytochemistry. 2004;  65 891-896
• 13 Hellwig V, Nopper R, Mauler F, Freitag J, Liu J K, Ding Z H, Stadler M. Activities of prenylphenol derivatives from fruit bodies of Albatrellus spp. on the human and rat vanilloid receptor 1 (VR1) and characterisation of the novel natural product, confluentin.  Arch Pharm. 2003;  336 119-126
• 14 Mahiou V, Roblot F, Hocquemiller R, Cavé A. Piperogalin, a new prenylated diphenol from Peperomia galioides.  J Nat Prod. 1995;  58 324-328
• 15 Nukata M, Hashimoto T, Yamamoto I, Iwasaki N, Tanaka M, Asakawa Y. Neogrifolin derivatives possessing anti-oxidative activity from the mushroom Albatrellus ovinus.  Phytochemistry. 2002;  59 731-737
• 16 Keller A C, Maillard M P, Hostettmann K. Antimicrobial steroids from the fungus Fomitopsis pinicola.  Phytochemistry. 1996;  41 1041-1046
• 17 Rösecke J, König W A. Steroids from the fungus Fomitopsis picicola.  Phytochemistry. 1999;  52 1621-1627
• 18 Keller C, Maillard M, Keller J, Hostettmann K. Screening of European fungi for antibacterial, antifungal, larvicidal, molluscicidal, antioxidant and free-radical scavenging activities and subsequent isolation of bioactive compounds.  Pharm Biol. 2002;  40 518-525
• 19 Clinical and Laboratory Standards Institute .Performance standards for antimicrobial susceptibility testing; 16th informational supplement. M100-S16. Wayne; Clinical and Laboratory Standards Institute 2006
• 20 Hathaway W E, Newby L A, Githens J H. The acridine orange viability test applied to bone marrow cells. I. Correlation with trypan blue and eosin dye exclusion and tissue culture transformation.  Blood. 1964;  23 517-525