Top

Published in:

01-01-2018 | Review

Immunomodulatory constituents from Ascomycetous fungi

Author: Haruhiro Fujimoto

Published in: Journal of Natural Medicines | Issue 1/2018

Abstract

Our screening project, namely, search for new immunomodulatory constituents from Ascomycetous fungi, was guided by the effects on mitogen-induced proliferations of mouse spleen lymphocytes. On the project, the defatted crude extracts from Gelasinospora multiforis, G. heterospora, G. longispora, G. kobi, Diplogelasinospora grovesii, Emericella aurantio-brunnea, Eupenicillium crustaceum, etc., submitted to the solvent partition followed by fractionation with repeated chromatography monitored by immunomodulatory activity to afford many active constituents, of which molecular structures including absolute configurations and immunomodulatory activities were elucidated. All of these immunomodulatory constituents isolated on the project were practically not immunostimulants but immunosuppressants.

Nakamura A, Nagai K, Suzuki S, Ando K, Tamura G (1986) A novel method of screening for immunomodulating substances, establishment of an assay system and its application to culture broths of microorganisms. J Antibiot 39:1148–1154CrossRef

Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63CrossRefPubMed

Tori K (1980) Application of ¹³C-NMR spectroscopy to natural product chemistry—triterpenes and their glycosides (in Japanese). Kagaku No Ryoiki Zokan 125:221–245

Fujimoto H, Satoh Y, Nakayama M, Takayama T, Yamazaki M (1995) Isolation of some immunosuppressive components from an Ascomycete, Gelasinospora multiforis. Chem Pharm Bull 43:547–552CrossRef

Nair MSR (1976) Biogenesis and revised structure of rosellisin; structure of rosellisin aldehyde. Phytochemistry 15:1090–1091CrossRef

Fujimoto Y, Tsunoda H, Uzawa J, Tatsuno T (1982) Structure of islandic acid, a new metabolite from Penicillium islandicum Sopp. J Chem Soc Chem Commun, pp 83–84

Fujimoto H, Satoh Y, Nakayama M, Takayama T, Yamazaki M (1995) New immunosuppressive components from Ascomycetes, Gelasinospora multiforis and G. kobi (in Japanese). The 37th Symposium on the Chemistry of Natural Products Symposium Papers, Tokushima, pp 625–630

Bouillant ML, Bernillon J, Favre-Bonvin J, Salin N (1989) New hexaketides related to sordariol in Sordaria macrospora. Z Naturforsch 44c:719–723CrossRef

Fujimoto H, Sumino M, Nagano J, Natori H, Okuyama E, Yamazaki M (1999) Immunomodulatory constituents from three Ascomycetes, Gelasinospora heterospora, G. multiforis, and G. longispora. Chem Pharm Bull 47:71–76CrossRef

10.

Kusumi T (1993) Determination of the absolute configuration of organic compounds by means of NMR spectroscopy–modified Mosher’s method (in Japanese). J. Synth Org. Chem (Yuki Gosei Kagaku Kyokai Shi) 51:462–470CrossRef

11.

Fujimoto H, Satoh Y, Yamazaki M (1998) Four new immunosuppressive components, kobiin and kobifuranones A, B, and C, from an Ascomycete, Gelasinospora kobi. Chem Pharm Bull 46:211–216 (Idem 2006 Errata for Chem. Pharm. Bull., 54:1745-1746) CrossRef

12.

Randazzo G, Fogliano V, Ritieni A, Mannina L, Rossi E, Scarallo A, Segre AL (1993) Proliferin, a new sesterterpene from Fusarium proliferatum. Tetrahedron 49:10883–10896CrossRef

13.

Turner WB, Aldridge DC (1983) Hexaketides, in “Fungal metabolites II”. Academic Press Inc. LTD, London, pp 109–115

14.

Sakurai I, Shimizu S, Yamamoto Y (1988) Studies on metabolites of Macrophoma commelinae. III. isolation of new metabolites and biosynthesis of macommelin group. Chem Pharm Bull 36:1328–1335CrossRef

15.

Grove JF, Speake RN, Ward G (1966) Metabolic products of Colletotrichum capsici: isolation and characterisation of acetylcolletotrichin and colletodiol. J Chem Soc C, pp 230–234

16.

Powell JW, Whalley WB (1969) The chemistry of fungi. part LVIII. structure of colletodiol a metabolite of Chaetomium funicola. J Chem Soc C, pp 911–912

17.

MacMillan J, Pryce RJ (1968) The structure of colletodiol, a macrocyclic dilactone from Colletotrichum capsici. Tetrahedron Lett 9:5497–5500CrossRef

18.

Amstutz R, Hungerbuhler E, Seebach D (1981) Revidierte struktur des makrodiolids colletodiol. Helv Chim Acta 64:1796–1799CrossRef

19.

Fujimoto H, Nagano J, Yamaguchi K, Yamazaki M (1998) Immunosuppressive components from an Ascomycete, Diplogerasinospora grovesii. Chem Pharm Bull 46:423–429CrossRef

20.

Hensens OD, Zink D, Williamson JM, Lotti VJ, Chang RSL, Goetz MA (1991) Variecolin, a sesterterpenoid of novel skeleton from Aspergillus variecolor MF138. J Org Chem 56:3399–3403CrossRef

21.

Takahashi H, Hosoe T, Nozawa K, Kawai K (1999) Two new sesterterpenes from the Ascomycetous fungus Emericella purpurea. J Nat Prod 62:1712–1713CrossRef

22.

Shimizu Y, Bando H, Chou H-N, Duyne G V, Clardy JC (1986) Absolute configuration of brevetoxins. J Chem Soc Chem Commun, pp 1656–1658

23.

Riche C, Pascard-Billy C, Devys M, Gaudemer A, Barbier M (1974) Structure cristalline et moleculaire de la phomenone, phytotoxine produite par le champignon Phoma exigua var. non oxydabilis. Tetrahedron Lett 15:2765–2766CrossRef

24.

Fujimoto H, Nakamura E, Okuyama E, Ishibashi M (2000) Immunomodulatory constituents from an Ascomycete, Emericella aurantio-brunnea. Chem Pharm Bull 48:1436–1441CrossRef

25.

Sassa T, Nukina M (1984) Macrophorin D, a new self-growth inhibitor of the causal fungus of Macrophoma fruit rot of apple. Agric Biol Chem 48:1923–1925

26.

Sassa T, Yoshikoshi H (1983) New terpene-linked cyclohexenone epoxides, macrophorin A, B and C, produced by the fungus caused Macrophoma fruit rot of apple. Agric Biol Chem 47:187–189

27.

Imahori K, Yamakawa T (eds) (1998) Mevalonic acid in “Dictionary of Biochemistry, Version 3” (in Japanese). Tokyo-Kagakudojin Co., Tokyo, p 1411

28.

Brown HC, Kim SC, Krishnamurthy S (1980) Selective reductions. 26. lithium triethylborohydride as an exceptionally powerful and selective reducing agent in organic synthesis. exploration of the reactions with selected organic compounds containing representative functional groups. J Org Chem 45:1–12CrossRef

29.

Hirai N, Koshimizu K (1981) Chirality of the acyl group of β-hydroxy-β-methylglutaryl-hydroxyabscisic acid. Phytochemistry 20:1867–1869CrossRef

30.

Ayer WA, Altena IV, Browne LM (1990) Three piperazinediones and a drimane diterpenoid from Penicillium brevi-compactum. Phytochemistry 29:1661–1665CrossRef

31.

Wang HJ, Gloer JB, Wicklow DT, Dowd PF (1995) Aflavinines and other antiinsectan metabolites from the ascostromata of Eupenicillium crustaceum and related species. Appl Environ Microbiol 61:4429–4435PubMedPubMedCentral

32.

Fujimoto H, Nakamura E, Kim Y-P, Okuyama E, Ishibashi M, Sassa T (2001) Immunomodulatory constituents from an Ascomycete, Eupenicillium crustaceum, and revised absolute structure of macrophorin D. J Nat Prod 64:1234–1237CrossRefPubMed

33.

Fujimoto H, Fujimaki T, Okuyama E, Yamazaki M (1999) Immunomodulatory constituents from an Ascomycete, Microascus tardifaciens. Chem Pharm Bull 47:1426–1432CrossRef

34.

Fujimoto H, Fujimaki T, Okuyama E, Yamazaki M (2000) Immunosuppressive constituents from an Ascomycete, Sordaria gondaensis. Mycotoxins 50:93–99CrossRef

35.

Fujimoto H, Sumino M, Okuyama E, Ishibashi M (2004) Immunomodulatory constituents from an Ascomycete, Chaetomium seminudum. J Nat Prod 67:98–102CrossRefPubMed

36.

Fujimoto H, Nakamura E, Okuyama E, Ishibashi M (2004) Six immunosuppressive features from an Ascomycete, Zopfiella longicaudata, found in a screening study monitored by immunomodulatory activity. Chem Pharm Bull 52:1005–1008CrossRef

37.

Fujimoto H, Asai T, Kim Y-P, Ishibashi M (2006) Nine constituents including six xanthone-related compounds isolated from two Ascomycetes, Gelasinospora santi-florii and Emericella quadrilineata, found in a screening study focused on immunomodulatory activity. Chem Pharm Bull 54:550–553CrossRef

38.

Tomikawa T, Shin-ya K, Furihata K, Kinoshita T, Miyajima A, Seto H, Hayakawa Y (2000) Rasfonin, a new apoptosis inducer in ras-dependent cells from Talaromyces sp. J Antibiot 53:848–850CrossRef

39.

Akiyama K, Kawamoto S, Fujimoto H, Ishibashi M (2003) Absolute stereochemistry of TT-1 (rasfonin), an α-pyrone-containing natural product from a fungus, Trichurus terrophilus. Tetrahedron Lett 44:8427–8431CrossRef

40.

Akiyama K, Yamamoto S, Fujimoto H, Ishibashi M (2005) Total synthesis of TT-1 (rasfonin), an α-pyrone-containing natural product from a fungus Trichurus terrophilus. Tetrahedron 61:1827–1833CrossRef

41.

Fujimoto H, Okamoto Y, Sone E, Maeda S, Akiyama K, Ishibashi M (2005) Eleven new 2-pyrones from a Fungi Imperfecti, Trichurus terrophilus, found in a screening study guided by immunomodulatory activity. Chem Pharm Bull 53:923–929CrossRef

42.

Yoganathan K, Rossant C, Glover RP, Cao S, Vittal JJ, Ng S, Huang Y, Buss AD, Butler MS (2004) Inhibition of the human chemokine receptor CCR5 by variecolin and variecolol and isolation of four new variecolin analogues, emericolins A-D, from Emericella aurantiobrunnea. J Nat Prod 67:1681–1684CrossRefPubMed

43.

Yoganathan K, Yang L-K, Rossant C, Huang Y, Ng S, Butler MS, Buss AD (2004) Cochlioquinones and epi-cochlioquinones: antagonists of the human chemokine receptor CCR5 from Bipolaris brizae and Stachybotrys chartarum. J Antibiot 57:59–63CrossRef

44.

Liu H, Chen S, Liu W, Liu Y, Huang X, She Z (2016) Polyketides with immunosuppressive activities from mangrove endophytic fungus Penicillium sp. ZJ-SY₂. Mar Drugs 14:217CrossRefPubMedCentral

Title: Immunomodulatory constituents from Ascomycetous fungi
Author: Haruhiro Fujimoto
Publication date: 01-01-2018
Publisher: Springer Singapore
Published in: Journal of Natural Medicines / Issue 1/2018
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-017-1162-x

Keynote webinar | Spotlight on sleep in brain health

Springer Medicine

Immunomodulatory constituents from Ascomycetous fungi

Abstract

Keynote webinar | Spotlight on sleep in brain health

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 1/2018

Correction to: Enzyme-linked immunosorbent assay for the quantitative/qualitative analysis of plant secondary metabolites

Sansoninto as evidence-based remedial medicine for depression-like behavior

In Memoriam

Evodiamine ameliorates liver fibrosis in rats via TGF-β1/Smad signaling pathway

Production of an emericellin and its analogues as fungal biological responses for Shimbu-to extract

New cyclic sulfides extracted from Allium sativum: garlicnins P, J2, and Q