Hitoyopodin A, 15-Hydroxy hitoyopodin A, 13-Hydroxy hitoyopodin A

Hitoyopodin A (1): NPEdia

15-Hydroxy hitoyopodin A (2): NPEdia
15-Hydroxy hitoyopodin A

13-Hydroxy hitoyopodin A (3): NPEdia
13-Hydroxy hitoyopodin A (3)

Producing organism
Coprinopsis cinerea (NBRC 100011)
Biological activity
Growth Inhibition
  • Hitoyopodin A (1): HL-60 cells (IC50 = 3.7 μM), Plasmodium falciparum (IC50 = 6.7 μM)
  • 15-Hitoyopodin A (2): HL-60 cells (IC50 = 16 μM),
  • 13-Hitoyopodin A (3): HL-60 cells (IC50 = 14 μM), Plasmodium falciparum (IC50 = 25 μM)
Three sesquiterpenoids, hitoyopodin A (1) and its hydroxy derivatives 2 and 3, were isolated from the culture broth of the mushroom Coprinopsis cinerea. Their absolute structures (1–3) with a benzoxabicyclo[3.2.1]octane core were determined by spectroscopy, X-ray crystallography, and total synthesis of 1. Compound 1 displays antiproliferative activity against HL-60 cancer cells and the malarial parasite Plasmodium falciparum.
  • Otaka J, Shimizu T, Futamura Y, Hashizume D, Osada H.: Structures and synthesis of hitoyopodins: bioactive aromatic sesquiterpenoids produced by the mushroom Coprinopsis cinerea.
    Org Lett, [Epub ahead of print] (2018) PMID: 30234313 [ doi: 10.1021/acs.orglett.8b02788 ]
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