8', 9'-Dehydroascochlorin 
  1. Finding, producing organism and structure1)


    2. 8',9'-Dehydroascochlorin was found as testosterone 5a-reductase inhibitor from the 

    culture broth of a fungal strain FO-2787.
IMAGE imgs/dehascochlorine-ƒŒƒCƒ„01.gif
OHC


H3C
Cl


8', 9'-Dehydroascochlorin
Verticilliumsp. FO-2787

Bar:20 µm
  1. Biological activity1)


    2. 5a-Dihydrotestosterone (DHT) plays a key role in the growth and maintenance of 

    the mammalian prostate. Prostate hyperplasia and prostate cancer have been 

    associated with an overproduction of DHT which is converted from testosterone by 

    testosterone 5a-reductase (T-5a-reductase). Therefore T-5a-reductase inhibitor 

    has been expected as antiprostate cancer drug.

1) Teststerone 5a-reductase inhibitory activities

IMAGE imgs/dehascochlorine-ƒŒƒCƒ„02.gif
Compound
 

IC50(M)

IMAGE imgs/dehascochlorine-ƒŒƒCƒ„02.gif

LL-Z 1272b

LL-Z 1272d

LL-Z 1272e

LL-Z 1272g

LL-Z 1272z3.6 x 10-4
3.7 x 10-4

3.7 x 10-4

3.4 x 10-4

3.4 x 10-4(ascochlorin)

8',9'-Dehydroascochlorin1.4 x 10-3

Riboflavin1.3 x 10-3

IMAGE imgs/dehascochlorine-ƒŒƒCƒ„02.gif


2) These compounds showed no antimicrobial activities against Gram-positive and

-negative bacteria, fungi or yeast at a concentration of 500 µg/ml.

  1. Reference
  2. [539] S. Takamatsu et al., Chem. Pharm. Bull., 42, 953-956 (1994)