Yıl 2018,
Cilt: 9 Sayı: 2, 117 - 125, 25.10.2018
Büşra Fendoğlu
Ayşe Kuruüzüm-uz
,
Didem Şöhretoğlu
Öz
Mushrooms (macrofungi) are
a part of the human diet as a source of both food and medicine for centuries
especially in East-Asia. The use of mushrooms and their extracts for medicinal
purposes became more popular due to increasing number of research conducting on
them recently. They predominantly contain polysaccharides, terpenes and
sterols. Alkaloids exhibits bioactive effects even in very small doses and
mainly distributed in Angiosperms. Their occurrences in macrofungi is very
limited and not very-well documented as much as other constituents like
polysaccharides or terpenes. In this review, we focused on distribution and
bioactivities of mushroom alkaloids.
Kaynakça
- Anke, T., Oberwinkler, F., Steglich, W., Schramm, G.J. The Strobilurins -New Antifungal Antibıotics From The Basidiomycete Strobilurus tenacellus (Pers. Ex Fr.) Sing, Antibiotics, 30(10)806−810(1977).
- Antunes, E. M., Copp, B.R., Davies-Coleman, M.T., Samaai, T., Pyrroloiminoquinone and related metabolites from marine sponges, Nat. Prod. Rep., 22(1)62-72(2005).
- Barros-Fihlo, B.A., de Oliveira, M.C., Mafezoli, J.; Barbosa, F.G., Rodrigues-Filho, E., Secondary metabolite production by the basidiomycete, Lentinus strigellus, under different culture conditions, Nat. Prod. Commun., 7(6)771−773(2012).
- Bogenschutz, M.P., Forcehimes, A.A., Pommy, J.A., Wilcox, C.E., Barbosa, P.C., Strassman, R.J., Psilocybin-assisted treatment for alcohol dependence: a proof-of-concept study, J Psychopharmacol, 29(3)289-299(2015).
- Bogenschutz M.P., Ross S., Therapeutic Applications of Classic Hallucinogens, Curr Top Behav Neurosci, (2017). doi: 10.1007/7854_2016_464.
- Carod-Artal, F.J., Hallucinogenic drugs in pre-Columbian Mesoamerican cultures, Neurologia, 30(1)42-9(2015).
- Chiu, C.H., Chyau, C.C., Chen, C.C., Lee, L.Y., Chen, W.P., Liu, J.L., Lin, W.H., Mong, M.C., Erinacine A-Enriched Hericium erinaceus Mycelium Produces Antidepressant-Like Effects through Modulating BDNF/PI3K/Akt/GSK-3β Signaling in Mice, Int. J. Mol. Sci., 19(2)341(2018).
- Dewick, P.M., Medicinal Natural Products: A Biosynthetic Approach, John Wiley & Sons Ltd., West Sussex(2002).
- Eyal, Z., Matzov, D., Krupkin, M., Paukner S., Riedl R., Rozenberg H., Zimmerman E., Bashan A., Yonath A., A novel pleuromutilin antibacterial compound, its binding mode and selectivity mechanism, Sci. Rep., 6,1−8(2016).
- Griffiths, R.R., Johnson, M.W., Carducci, M.A., Umbricht, A., Richards, W.A., Richards, B.D., Cosimano, M.P., Klinedinst, M.A., Psilocybin produces substantial and sustained decreases in depression and anxiety in patients with life-threatening cancer: A randomized double-blind trial, J. Psychopharmacol, 30(12)1181-1197(2016).
- Grob, C.S., Danforth, A.L., Chopra, G.S., Hagerty, M., McKay, C.R., Halberstadt, A.L., Greer, G.R., Pilot study of psilocybin treatment for anxiety in patients with advanced-stage cancer, Arch Gen Psychiatry., 68(1)71-78(2011).
- Heinrich, M., Barnes, J., Gibbons, S., Williamson, E., Fundamentals of Pharmacognosy and Phytotherapy, Second Ed., Elsevier, Livingstone(2012).
- Hellwig, V., Dasenbrock, J., Klostermeyer, D., Kroiß, S., Sindlinger, T., Spiteller, P., Steffan, B., Steglich, W., Engler-Lohr, M., Semar, S., Anke, T., New benzodioxepin type strobilurins from basidiomycetes. Structural revision and determination of the absolute configuration of strobilurin D and related β-methoxyacrylate antibiotics, Tetrahedron, 55(33)10101−10118(1999).
- Hofmann, A., Multidisciplinary Association for Psychedelic Studies (MAPS). LSD: My Problem Child. The Beckley Foundation Press, Oxford(2005).
- Homer, J.A. ve Sperry, J., Mushroom-Derived Indole Alkaloids, Journal of Natural Products, 80(7)2178-2187(2017).
- Jones, R.N., Fritsche T.R., Sader, H.S., Ross, J.E., Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci, Antimicrob. Agents Chemother., 50(7)2583−2586(2006).
- Kanokmedhakul, S., Kanokmedhakul, K., Phonkerd, N., Soytong, K., Kongsaeree, P., Suksamrarn, A., Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802, Planta Med., 68(9)834−836(2002).
- Kavanagh, F., Hervey, A., Robbins, W.J., Antibiotic Substances From Basidiomycetes: VIII. Pleurotus multilus (Fr.) Sacc. and Pleurotus passeckerianus Pilat, Proc. Natl. Acad. Sci. U. S. A., 37(9)570−574(1951).
- Khan, M.A., Tania, M., Liu, R., Rahman, M.M., Hericium erinaceus: an edible mushroom with medicinal values, J. Complement. Integr. Med., 10(1)(2013). doi: 10.1515/jcim-2013-0001.
- Liu, J., Lotesta, S.D., Sorensen, E.J., A Concise Synthesis of the Molecular Framework of Pleuromutilin, Chem. Commun., 47(5)1500−1502(2011).Nichols, D.E., Hallucinogens, Pharmacol. Ther., 101(2)131–181(2004).
- Novak, R., Are pleuromutilin antibiotics finally fit for human use?, Ann. N. Y. Acad. Sci., 1241,71−81(2011).
- Öztürk, M., Tel-Cayan, G., Muhammad, A.,Terzioglu, P., Duru, M.E., Mushrooms: A Source Of Exciting Bioactive Compounds, Studies in Natural Products Chemistry, 45(10)363−457(2015).
- Peters, S., Spiteller, P., Mycenarubins A and B, red pyrroloquinoline alkaloids from the mushroom Mycena rosea., Eur. J. Med. Chem., 2007(10)1571–1576(2007a).
- Peters, S., Spiteller, P., Sanguinones A and B, blue pyrroloquinoline alkaloids from the fruiting bodies of the mushroom Mycena sanguinolenta, Journal of Natural Products, 70(8)1274-7(2007b).
- Peters, S., Jaeger, R.J.R., Spiteller P., Red pyrroloquinoline alkaloids from the mushroom Mycena haematopus, European Journal of Organic Chemistry, 2008(2)319–23(2008).
- Poulsen, S.M., Karlsson, M., Johansson, L.B., Vester, B., The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome, Mol. Microbiol., 41(5)1091−1099(2001).
- Pulte, A., Wagner, S., Kogler, H., Spiteller, P., Pelianthinarubins A and B, Red Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena pelianthina, Journal of Natural Products, 79(4)873-8(2016).
- Quang, D.N., Spiteller, P., Porzel, A., Schmidt, J., Geissler, T., Arnold, N., Wessjohann, L., Alkaloids from the mushroom Pseudobaeospora pyrifera, pyriferines A-C, Journal of Natural Products, 71(9)1620-2(2008).
- Ross, S., Bossis, A., Guss, J., Agin-Liebes, G., Malone, T., Cohen, B., Mennenga, S.E., Belser, A., Kalliontzi, K., Babb, J., Su, Z,, Corby, P., Schmidt, B.L., Rapid and sustained symptom reduction following psilocybin treatment for anxiety and depression in patients with life-threatening cancer: a randomized controlled trial, J Psychopharmacol., 30(12)1165-1180(2016).
- Sauter, H., Steglich, W., Anke, T., Strobilurins: Evolution of a New Class of Active Substances, Angewandte Chemie International Edition, 38(10)1328−1349(1999).
- Slack, G.J., Puniani, E., Frisvad, J.C., Samson, R.A., Miller, J.D., Secondary metabolites from Eurotium species, Aspergillus calidoustus and A. insuetus common in Canadian homes with a review of their chemistry and biological activities, Mycol. Res., 113(4)480−490(2009).
- Sullivan, R., Smith, J.E., Rowan, N.J., Medicinal Mushrooms and Cancer Therapy translating a traditional practice into Western medicine, Perspect. Biol. Med., 49(2)159-170(2006).
- Şöhretoğlu, D., Huang, S., Ganoderma lucidum Polysaccharides as An Anti-cancer Agent., Anticancer Agents Med Chem. 17,(2018). doi: 10.2174/1871520617666171113121246
- Tylš, F., Páleníček, T., Horáček, J., Psilocybin-summary of knowledge and new perspectives, Eur. Neuropsychopharmacol, 24(3)342-56(2014).
- Wang, K., Bao, L., Ma, Ke., Liu, N., Huang, Y., Ren, J., Wang, W., Liu H., Eight new alkaloids with PTP1B and α-glucosidase inhibitory activities from the medicinal mushroom Hericium erinaceus, Tetrahedron, 71(51)9557-9563(2015).
- Wasser, P. S., Current findings, future trends, and unsolved problems in studies of medicinal mushrooms, Appl Microbiol Biotechnol, 89(5)1323–1332(2011).
- Wachtel-Galor, S.,Yuen, J., Buswell, J.A., Benzie, I.F.F., Herbal Medicine: Biomolecular and Clinical Aspects, CRC Press/Taylor & Francis, Boca Raton(2011).
Mantarlardan Elde Edilen Alkaloitler
Yıl 2018,
Cilt: 9 Sayı: 2, 117 - 125, 25.10.2018
Büşra Fendoğlu
Ayşe Kuruüzüm-uz
,
Didem Şöhretoğlu
Öz
Mantarlar (makrofunguslar) besin kaynağı ve ilaç
olarak özellikle Doğu Asya’da yüzyıllardır diyetin bir parçasıdır. Son
zamanlarda üzerlerinde yapılan çalışmaların sayısının artması nedeniyle
mantarların ve ekstrelerinin tıbbi amaçla kullanımı daha popüler hale
gelmiştir. Mantarlar çoğunlukla polisakkaritler, terpenler ve steroller
taşımaktadır. Alkaloitler çok düşük dozlarda bile biyoaktif etki gösterirler ve
genellikle Angiospermlerde bulunurlar. Bu grup bileşiklerin makrofunguslarda
bulunuşları oldukça sınırlıdır ve haklarında polisakkaritler ya da terpenler
gibi diğer bileşiklerin mantarlarda yayılışları kadar detaylı bilgi yoktur. Bu
derlemede, mantarlarda bulunan alkaloitlerin dağılımı ve biyoaktivitelerine
odaklandık.
Kaynakça
- Anke, T., Oberwinkler, F., Steglich, W., Schramm, G.J. The Strobilurins -New Antifungal Antibıotics From The Basidiomycete Strobilurus tenacellus (Pers. Ex Fr.) Sing, Antibiotics, 30(10)806−810(1977).
- Antunes, E. M., Copp, B.R., Davies-Coleman, M.T., Samaai, T., Pyrroloiminoquinone and related metabolites from marine sponges, Nat. Prod. Rep., 22(1)62-72(2005).
- Barros-Fihlo, B.A., de Oliveira, M.C., Mafezoli, J.; Barbosa, F.G., Rodrigues-Filho, E., Secondary metabolite production by the basidiomycete, Lentinus strigellus, under different culture conditions, Nat. Prod. Commun., 7(6)771−773(2012).
- Bogenschutz, M.P., Forcehimes, A.A., Pommy, J.A., Wilcox, C.E., Barbosa, P.C., Strassman, R.J., Psilocybin-assisted treatment for alcohol dependence: a proof-of-concept study, J Psychopharmacol, 29(3)289-299(2015).
- Bogenschutz M.P., Ross S., Therapeutic Applications of Classic Hallucinogens, Curr Top Behav Neurosci, (2017). doi: 10.1007/7854_2016_464.
- Carod-Artal, F.J., Hallucinogenic drugs in pre-Columbian Mesoamerican cultures, Neurologia, 30(1)42-9(2015).
- Chiu, C.H., Chyau, C.C., Chen, C.C., Lee, L.Y., Chen, W.P., Liu, J.L., Lin, W.H., Mong, M.C., Erinacine A-Enriched Hericium erinaceus Mycelium Produces Antidepressant-Like Effects through Modulating BDNF/PI3K/Akt/GSK-3β Signaling in Mice, Int. J. Mol. Sci., 19(2)341(2018).
- Dewick, P.M., Medicinal Natural Products: A Biosynthetic Approach, John Wiley & Sons Ltd., West Sussex(2002).
- Eyal, Z., Matzov, D., Krupkin, M., Paukner S., Riedl R., Rozenberg H., Zimmerman E., Bashan A., Yonath A., A novel pleuromutilin antibacterial compound, its binding mode and selectivity mechanism, Sci. Rep., 6,1−8(2016).
- Griffiths, R.R., Johnson, M.W., Carducci, M.A., Umbricht, A., Richards, W.A., Richards, B.D., Cosimano, M.P., Klinedinst, M.A., Psilocybin produces substantial and sustained decreases in depression and anxiety in patients with life-threatening cancer: A randomized double-blind trial, J. Psychopharmacol, 30(12)1181-1197(2016).
- Grob, C.S., Danforth, A.L., Chopra, G.S., Hagerty, M., McKay, C.R., Halberstadt, A.L., Greer, G.R., Pilot study of psilocybin treatment for anxiety in patients with advanced-stage cancer, Arch Gen Psychiatry., 68(1)71-78(2011).
- Heinrich, M., Barnes, J., Gibbons, S., Williamson, E., Fundamentals of Pharmacognosy and Phytotherapy, Second Ed., Elsevier, Livingstone(2012).
- Hellwig, V., Dasenbrock, J., Klostermeyer, D., Kroiß, S., Sindlinger, T., Spiteller, P., Steffan, B., Steglich, W., Engler-Lohr, M., Semar, S., Anke, T., New benzodioxepin type strobilurins from basidiomycetes. Structural revision and determination of the absolute configuration of strobilurin D and related β-methoxyacrylate antibiotics, Tetrahedron, 55(33)10101−10118(1999).
- Hofmann, A., Multidisciplinary Association for Psychedelic Studies (MAPS). LSD: My Problem Child. The Beckley Foundation Press, Oxford(2005).
- Homer, J.A. ve Sperry, J., Mushroom-Derived Indole Alkaloids, Journal of Natural Products, 80(7)2178-2187(2017).
- Jones, R.N., Fritsche T.R., Sader, H.S., Ross, J.E., Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci, Antimicrob. Agents Chemother., 50(7)2583−2586(2006).
- Kanokmedhakul, S., Kanokmedhakul, K., Phonkerd, N., Soytong, K., Kongsaeree, P., Suksamrarn, A., Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802, Planta Med., 68(9)834−836(2002).
- Kavanagh, F., Hervey, A., Robbins, W.J., Antibiotic Substances From Basidiomycetes: VIII. Pleurotus multilus (Fr.) Sacc. and Pleurotus passeckerianus Pilat, Proc. Natl. Acad. Sci. U. S. A., 37(9)570−574(1951).
- Khan, M.A., Tania, M., Liu, R., Rahman, M.M., Hericium erinaceus: an edible mushroom with medicinal values, J. Complement. Integr. Med., 10(1)(2013). doi: 10.1515/jcim-2013-0001.
- Liu, J., Lotesta, S.D., Sorensen, E.J., A Concise Synthesis of the Molecular Framework of Pleuromutilin, Chem. Commun., 47(5)1500−1502(2011).Nichols, D.E., Hallucinogens, Pharmacol. Ther., 101(2)131–181(2004).
- Novak, R., Are pleuromutilin antibiotics finally fit for human use?, Ann. N. Y. Acad. Sci., 1241,71−81(2011).
- Öztürk, M., Tel-Cayan, G., Muhammad, A.,Terzioglu, P., Duru, M.E., Mushrooms: A Source Of Exciting Bioactive Compounds, Studies in Natural Products Chemistry, 45(10)363−457(2015).
- Peters, S., Spiteller, P., Mycenarubins A and B, red pyrroloquinoline alkaloids from the mushroom Mycena rosea., Eur. J. Med. Chem., 2007(10)1571–1576(2007a).
- Peters, S., Spiteller, P., Sanguinones A and B, blue pyrroloquinoline alkaloids from the fruiting bodies of the mushroom Mycena sanguinolenta, Journal of Natural Products, 70(8)1274-7(2007b).
- Peters, S., Jaeger, R.J.R., Spiteller P., Red pyrroloquinoline alkaloids from the mushroom Mycena haematopus, European Journal of Organic Chemistry, 2008(2)319–23(2008).
- Poulsen, S.M., Karlsson, M., Johansson, L.B., Vester, B., The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome, Mol. Microbiol., 41(5)1091−1099(2001).
- Pulte, A., Wagner, S., Kogler, H., Spiteller, P., Pelianthinarubins A and B, Red Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena pelianthina, Journal of Natural Products, 79(4)873-8(2016).
- Quang, D.N., Spiteller, P., Porzel, A., Schmidt, J., Geissler, T., Arnold, N., Wessjohann, L., Alkaloids from the mushroom Pseudobaeospora pyrifera, pyriferines A-C, Journal of Natural Products, 71(9)1620-2(2008).
- Ross, S., Bossis, A., Guss, J., Agin-Liebes, G., Malone, T., Cohen, B., Mennenga, S.E., Belser, A., Kalliontzi, K., Babb, J., Su, Z,, Corby, P., Schmidt, B.L., Rapid and sustained symptom reduction following psilocybin treatment for anxiety and depression in patients with life-threatening cancer: a randomized controlled trial, J Psychopharmacol., 30(12)1165-1180(2016).
- Sauter, H., Steglich, W., Anke, T., Strobilurins: Evolution of a New Class of Active Substances, Angewandte Chemie International Edition, 38(10)1328−1349(1999).
- Slack, G.J., Puniani, E., Frisvad, J.C., Samson, R.A., Miller, J.D., Secondary metabolites from Eurotium species, Aspergillus calidoustus and A. insuetus common in Canadian homes with a review of their chemistry and biological activities, Mycol. Res., 113(4)480−490(2009).
- Sullivan, R., Smith, J.E., Rowan, N.J., Medicinal Mushrooms and Cancer Therapy translating a traditional practice into Western medicine, Perspect. Biol. Med., 49(2)159-170(2006).
- Şöhretoğlu, D., Huang, S., Ganoderma lucidum Polysaccharides as An Anti-cancer Agent., Anticancer Agents Med Chem. 17,(2018). doi: 10.2174/1871520617666171113121246
- Tylš, F., Páleníček, T., Horáček, J., Psilocybin-summary of knowledge and new perspectives, Eur. Neuropsychopharmacol, 24(3)342-56(2014).
- Wang, K., Bao, L., Ma, Ke., Liu, N., Huang, Y., Ren, J., Wang, W., Liu H., Eight new alkaloids with PTP1B and α-glucosidase inhibitory activities from the medicinal mushroom Hericium erinaceus, Tetrahedron, 71(51)9557-9563(2015).
- Wasser, P. S., Current findings, future trends, and unsolved problems in studies of medicinal mushrooms, Appl Microbiol Biotechnol, 89(5)1323–1332(2011).
- Wachtel-Galor, S.,Yuen, J., Buswell, J.A., Benzie, I.F.F., Herbal Medicine: Biomolecular and Clinical Aspects, CRC Press/Taylor & Francis, Boca Raton(2011).