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01.04.2012 | Note

In vitro antitrypanosomal activity of bis(bibenzyls)s and bibenzyls from liverworts against Trypanosoma brucei

verfasst von: Kazuhiko Otoguro, Aki Ishiyama, Masato Iwatsuki, Miyuki Namatame, Aki Nishihara-Tukashima, Hiroaki Kiyohara, Toshihiro Hashimoto, Yoshinori Asakawa, Satoshi Ōmura, Haruki Yamada

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2012

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Abstract

During the course of our screening program to discover new antitrypanosomal compounds, 17 known plant aromatic compounds [12 bis(bibenzyls)s and 5 bibenzyls] were evaluated for in vitro activity against Trypanosoma brucei brucei. Sixteen compounds were found to exhibit antitrypanosomal activity. In particular, three compounds, marchantin A (1), plagiochin A (5) and 2(R)-2-isopropenyl-6,7-dihydroxy-4-(2-phenylethyl)dihydrobenzofuran (16) demonstrated moderate selective and potent antitrypanosomal activities in vitro. We detail here the antitrypanosomal properties and cytotoxicities of the compounds in comparison with two commonly used therapeutic drugs, eflornithine and suramin. Our finding represents the first report of the promising trypanocidal activity of these compounds. The research also provides valuable insight into structure–activity relationships and the possible mode of action of the compounds.

Otoguro K, Ishiyama A, Namatame M, Nishihara A, Furusawa T, Masumam R, Shiomi K, Takahashi Y, Yamada H, Ōmura S (2008) Selective and potent in vitro antitrypanosomal activities of 10 microbial metabolites. J Antibiot 61:372–378PubMedCrossRef

Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Shiomi K, Takahashi Y, Ichimura M, Yamada H, Ōmura S (2008) In vitro and in vivo antitrypanosomal activities of two microbial metabolites, KS-505a and Alazopeptin. J Antibiot 61:627–632PubMedCrossRef

Toriizuka Y, Kinoshita E, Kogure N, Kitajima M, Ishiyama A, Otoguro K, Yamada H, Ōmura S, Takayama H (2008) New lycorine-type alkaloid from Lycoris traubii and evaluation of antitrypanosomal and antimalarial activities of lycorine derivatives. Bioorg Med Chem 16:10182–10189PubMedCrossRef

Abdel-Sattar E, Harraz FM, Al-ansari SM, El-Mekkawy S, Ichino C, Kiyohara H, Ishiyama A, Otoguro K, Ōmura S, Yamada H (2008) Acylated pregnane glycosides from Caralluma tuberculata and their antiparasitic activity. Phytochemistry 69:2180–2186PubMedCrossRef

Ishiyama A, Otoguro K, Iwatsuki M, Namatame M, Nishihara A, Nonaka K, Kinoshita Y, Takahashi Y, Masuma R, Shiomi K, Yamada H, Ōmura S (2009) In vitro and in vivo antitrypanosomal activities of three peptide antibiotics: leucinostatin A and B, alamethicin I and tsushimycin. J Antibiot 62:303–308PubMedCrossRef

Abdel-Satter E, Shehab NG, Ichino C, Kiyohara H, Ishiyama A, Otoguro K, Ōmura S, Yamada H (2009) Antitrypanosomal activity of some pregnane glycosides isolated from Caralluma species. Phytomedicine 16:659–664CrossRef

Iwatsuki M, Kinoshita Y, Niitsuma M, Hashida J, Mori M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Nonaka K, Masuma R, Otoguro K, Yamada H, Shiomi K, Ōmura S (2010) Antitrypanosomal peptaibiotics, trichosporins B-VIIa and B-VIIb, produced by Trichoderma polysporum FKI-4452. J Antibiot 63:331–333PubMedCrossRef

Hashida J, Niitsuma M, Iwatsuki M, Mori M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Nonaka K, Ui H, Masuma R, Otoguro K, Yamada H, Shiomi K, Ōmura S (2010) Pyrenocine I, a new pyrenocine analog produced by Paecilomyces sp. FKI-3573. J Antibiot 63:559–561PubMedCrossRef

Otoguro K, Ishiyama A, Iwatsuki M, Namatame M, Nishihara-Tsukashima A, Nakashima T, Shibahara S, Kondo S, Yamada H, Ōmura S (2010) In vitro and in vivo anti-Trypanosoma brucei activities of phenazinomycin and related compounds. J Antibiot 63:579–581PubMedCrossRef

10.

Iwatsuki M, Otoguro K, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Hashida J, Nakashima T, Masuma R, Takahashi Y, Yamada H, Ōmura S (2010) In vitro antitrypanosomal activity of 12 low-molecular-weight antibiotics and observations of structure/activity relationships. J Antibiot 63:619–622PubMedCrossRef

11.

Niitsuma M, Hashida J, Iwatsuki M, Mori M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Matsumoto A, Takahashi Y, Yamada H, Otoguro K, Shiomi K, Ōmura S (2010) Sinefungin VA and dehydrosinefungin V, new antitrypanosomal antibiotics produced by Streptomyces sp. K05-0178. J Antibiot 63:673–679PubMedCrossRef

12.

Inahashi Y, Iwatsuki M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Matsumoto A, Hirose T, Sunazuka T, Yamada H, Otoguro K, Takahashi Y, Ōmura S, Shiomi K (2011) Spoxazomicins A-C, novel antitrypanosomal alkaloids produced by an endophytic actinomycete, Streptosporangium oxazolinicum K07-0460^T. J Antibiot 64:303–307PubMedCrossRef

13.

Otoguro K, Iwatsuki M, Ishiyama A, Namatame M, Nishihara-Tukashima A, Kiyohara H, Hashimoto T, Asakawa Y, Ōmura S, Yamada H (2011) In vitro antitrypanosomal activity of plant terpenes against Trypanosoma brucei. Phytochemistry (in press)

14.

Asakawa Y (1995) Chemical costituents of the bryophytes. In: Herz W, Kirby GW, Moore RE, Steglich W, Tamm CH (eds) Progress in the chemistry of organic natural products, vol 65. Springer, Vienna, pp 1–562

15.

Taira Z, Takei M, Endo K, Hashimoto T, Sakiya Y, Asakawa Y (1994) Marchantin A trimethyl ether: its molecular structure and tubocurarine-like skeletal muscle relaxation activity. Chem Pharm Bull 42:52–56PubMedCrossRef

16.

Asakawa Y (1984) Phytochemistry of Hepaticae: isolation of biologically active aromatic compounds and terpenoids. Rev Latinoam Quim 14:109–114

17.

Hashimoto T, Tori M, Asakawa Y, Fukazawa Y (1987) Plagiochins A, B, C, and D, new types of macrocyclic bis(bibenzyls) having a biphenyl linkage between the ortho positions to the benzyl methylenes, from the liverwort Plagiochila acanthophylla subsp. Japonica. Tetrahedron Lett 28:6295–6298CrossRef

18.

Toyota M, Tori M, Takikawa K, Shiobara Y, Kodama M, Asakawa Y (1985) Perrottetins E, F, and G from Radula perrottetii (liverwort). Isolation, structure determination, and synthesis of perrottetin E. Tetrahedron Lett 26:6097–6100CrossRef

19.

Asakawa Y, Toyota M, Taira Z, Takemoto T, Kido M (1983) Riccardin A and riccardin B, two novel cyclic bis(bibenzyls) possessing cytotoxicity from the liverwort Riccardia multifida (L.) S. Gray. J Org Chem 48:2164–2167CrossRef

20.

Hashimoto T, Yoshida T, Kan Y, Takaoka S, Tori M, Asakawa Y (1994) Structures of four novel macrocyclic bis(bibenzyl) dimers, pusilatins A–D from the liverwort Blasia pusilla. Tetrahedron Lett 35:909–910CrossRef

21.

Hashimoto T, Ikeda H, Takaoka S, Tanaka M, Asakawa Y (1999) Ptychantols A–C, macrocyclic bis(bibenzyls), possessing a trans-stilbene structure from the liverwort Ptychanthus striatus. Phytochemistry 52:501–509CrossRef

22.

Hashimoto T, Kanayama S, Fukuyama Y, Takaoko S, Tori M, Asakawa Y (1994) Two novel macrocyclic bis(biphenyls), isoplagiochins A and B from the liverwort Plagiochila fruticosa. Tetrahedron Lett 35:911–912CrossRef

23.

Asakawa Y, Takikawa K, Toyota M, Takemoto T (1982) Chemosystematics of the bryophytes. Part 12. Novel bibenzyl derivatives and ent-cuparene-type sesquiterpenoids from Radula species. Phytochemistry 21:2481–2490CrossRef

24.

Asakawa Y, Hashimoto T, Takikawa K, Tori M, Ogawa S (1991) Prenyl bibenzyls from the liverworts Radula perrottetii and Radula complanata. Phytochemistry 30:235–251CrossRef

25.

Asakawa Y, Kondo K, Tori M, Hashimoto T, Ogawa S (1991) Prenyl bibenzyls from the liverwort Radula kojana. Phytochemistry 30:219–234CrossRef

26.

Otoguro K, Kohana A, Manabe C, Ishiyama A, Ui H, Shiomi K, Yamada H, Ōmura S (2001) Potent antimalarial activities of polyether antibiotic, X-206. J Antibiot 54:658–663PubMedCrossRef

27.

Asakawa Y (2001) Recent advances in phytochemistry of bryophytes-acetogenins, terpenoids and bis(bisbenzyl)s from selected Japanese, Taiwanese, New Zealand, Argentinean and European liverworts. Phytochemistry 56:297–312PubMedCrossRef

28.

Asakawa Y (2007) Biologically active compounds from bryophytes. Pure Appl Chem 79:557–580CrossRef

29.

Harinantenaina L, Quang DN, Nishizawa T, Hashimoto T, Kohchi C, Soma G, Asakawa Y (2005) Bis(bibenzyls) from liverworts inhibit lipopolysaccharide-induced inducible NOS in RAW 264.7 cells: a study of structure–activity relationships and molecular mechanism. J Nat Prod 68:1779–1781PubMedCrossRef

30.

Asakawa Y, Toyota M, Hashimoto T, Tori M, Nagashima F, Harinantenaina L (2008) Marchantiophyta (liverworts): rich sorces of macrocyclic bis(bibenzyls). Heterocycles 76:99–127CrossRef

31.

Suzuki T, Tamehiro N, Sato Y, Kobayashi T, Ishii-Watabe A, Shinozaki Y, Nishimaki-Mogami T, Hashimoto T, Asakawa Y, Inoue K, Ohno Y, Yamaguchi T, Kawanishi T (2008) The novel compounds that activate Farnesoid X receptor: the diversity of their effects on gene expression. J Pharmacol Sci 107:285–294PubMedCrossRef

32.

Shi YQ, Zhu CJ, Yuan HQ, Li BQ, Gao J, Qu XJ, Sun B, Cheng YN, Li S, Li X, Lou HX (2009) Marchantin C, a novel microtubule inhibitor from liverwort with anti-tumor activity both in vivo and in vitro. Cancer Lett 276:160–170PubMedCrossRef

33.

Simard F, Legault J, Lavoie S, Mshvildadze V, Pichette A (2008) Isolation and identification of cytotoxic compounds from the wood of Pinus resinosa. Phytother Res 22:919–922PubMedCrossRef

34.

Dodo K, Aoyama A, Noguchi-Yachida T, Makishima M, Miyachi H, Hashimoto Y (2008) Co-existence of α-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development. Bioorg Med Chem 16:4272–4285PubMedCrossRef

35.

Morita H, Tomizawa Y, Tsuchiya T, Hirasawa Y, Hashimoto T, Asakawa Y (2009) Antimitotic activity of two macrocyclic bis(bibenzyls), isoplagiochins A and B from the liverwort Plagiochila fruticosa. Bioorg Med Chem Lett 19:493–496PubMedCrossRef

Titel: In vitro antitrypanosomal activity of bis(bibenzyls)s and bibenzyls from liverworts against Trypanosoma brucei
verfasst von: Kazuhiko Otoguro
Aki Ishiyama
Masato Iwatsuki
Miyuki Namatame
Aki Nishihara-Tukashima
Hiroaki Kiyohara
Toshihiro Hashimoto
Yoshinori Asakawa
Satoshi Ōmura
Haruki Yamada
Publikationsdatum: 01.04.2012
Verlag: Springer Japan
Erschienen in: Journal of Natural Medicines / Ausgabe 2/2012
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-011-0587-x

Springer Medizin

Abstract

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