Skip to main content
SpringerLink
Log in

New penicillide derivatives isolated from Penicillium simplicissimum

  • Original Paper
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

Two new penicillide derivatives, secopenicillides A (3) and B (4), were isolated along with penicillide (1) and purpactin A (2), and altenusin (5) and dehydroaltenusin (6), the antifungal substances of this fungus, from the extract of Penicillium simplicissimum IFM 53375. The absolute structures of 3 and 4 were determined by spectroscopic investigation and chemical correlation to penicillide (1). The absolute configuration of purpactin A (2) was determined by the chemical method.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Pitt JI (2000) A laboratory guide to common Penicillium species. Food Science Australia, North Ryde, pp 74–75, 100–101

  2. Komai S, Hosoe T, Itabashi T, Nozawa K, Okada K, de Campos Takaki GM, Yaguchi T, Takizawa K, Fukushima K, Kawai K (2005) Two new meroterpenoids, penisimplicin A and B, isolated from Penicillium simplicissimum. Chem Pharm Bull 53:1114–1117

    Article  CAS  PubMed  Google Scholar 

  3. Komai S, Hosoe T, Itabashi T, Nozawa K, Yaguchi T, Fukushima K, Kawai K (2005) New vermistatin derivatives isolated from Penicillium simplicissimum. Heterocycles 65 (in press)

  4. Sassa T, Niwa G, Unno H, Miura Y (1974) Structure of penicillide, a new metabolite produced by a Penicillium species. Tetrahedron Lett 15:3941–3942

  5. Nishida H, Tomoda H, Cao J, Okuda S, Omura S (1991) Purpactins, new inhibitors of acyl-CoA: cholesterol acyltransferase produced by Penicillium purpurogenum. II. Structure elucidation of purpactins A, B and C. J Antibiot 44:144–151

    Article  CAS  PubMed  Google Scholar 

  6. Rossett T, Sankhala RH, Stickings CE, Taylor MEU, Thomas R (1957) Studies in the biochemistry of micro-organisms 103. Metabolites of Alternaria tenuis Auct.: culture filtrate products. Biochem J 67:390–400

    Article  Google Scholar 

  7. Suzuki K, Nozawa K, Udagawa S, Nakajima S, Kawai K (1991) Penicillide and dehydroisopenicillide ferom Talaromyces derxii. Phytochemistry 30:2096–2098

    Article  CAS  Google Scholar 

  8. Tomoda H, Nishida H, Masuma R, Cao J, Okuda S, Omura S (1991) Purpactins, new inhibitors of acyl-CoA:cholesterol acyltransferase produced by Penicillium purpurogenum. I. Production, isolation and physico-chemical and biological properties. J Antibiot 44:136–143

    Article  CAS  PubMed  Google Scholar 

  9. Proska B, Uhrin D, Adamcova J, Fuska J (1992) Vermixocins A and B, two novel metabolites from Penicillium vermiculatum. J Antibiotic 45:1268–1272

    Article  Google Scholar 

Download references

Acknowledgements

We are grateful to Dr. H. Kasai and Miss N. Kobayashi of Hoshi University for NMR and MS spectral measurements. This study was supported in part by Hoshi University Science/Technology Frontier Research Base from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and by a cooperative research program of the Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University (2004-22).

Author information

Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

    Shin-ichirou Komai, Tomoo Hosoe, Takeshi Itabashi & Ken-ichi Kawai

  2. School of Pharmaceutical Sciences, Ohu University, 31-1 Misumido, Tomita-machi, Koriyama, Fukushima 963-8611, Japan

    Koohei Nozawa

  3. Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, Chuo-ku, Chiba 260-8673, Japan

    Takashi Yaguchi & Kazutaka Fukushima

Authors
  1. Shin-ichirou Komai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tomoo Hosoe
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Takeshi Itabashi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Koohei Nozawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Takashi Yaguchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Kazutaka Fukushima
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ken-ichi Kawai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ken-ichi Kawai.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Komai, Si., Hosoe, T., Itabashi, T. et al. New penicillide derivatives isolated from Penicillium simplicissimum . J Nat Med 60, 185–190 (2006). https://doi.org/10.1007/s11418-005-0028-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-005-0028-9

Keywords

Search

Navigation