4416-57-3

Usage

Uses

Used in Pharmaceutical Industry:
Testololactone is used as an antineoplastic agent for the treatment of advanced stage breast cancer. It functions by inhibiting the synthesis of sex hormones, which are often involved in the growth and progression of breast cancer cells. By limiting the availability of these hormones, testololactone helps to slow down or stop the growth of cancerous cells, providing a valuable therapeutic option for patients with advanced breast cancer.

InChI:InChI=1/C19H26O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h11,14-16H,3-10H2,1-2H3/t14-,15+,16+,18+,19+/m1/s1

Upstream product

• 57-83-0 Progesterone 
• 521-17-5 5-androstenediol 
• 145-13-1 Pregnenolone 
• 53-43-0 dehydroepiandrosterone 

Relevant academic research and scientific papers

Biotransformations of steroids to testololactone by a multifunctional strain Penicillium simplicissimum WY134-2

The biotransformations of a range of steroidal compounds, including 17α-hydroxy progesterone, progesterone, testosterone, androst-4-ene-3,17- dione (AD), pregnenolone, and dehydroepiandrosterone (DHEA), by Penicillium simplicissimum WY134-2 have been investigated. In all the cases, testolic acid and testololactone were detected, and the acid was converted to the lactone when pH was adjusted to 1, leading to isolation of testololactone in 25%-96% yields. Especially for progesterone and testosterone, the isolated yields were 93% and 96% with substrate concentration being 3 g/L, suggesting that P. simplicissimum WY134-2 may be used for the synthesis of testololactone. The results revealed the multi-functional catalytic activity of P. simplicissimum WY134-2 toward steroids for the first time. The possible reaction pathways of steroids promoted by this strain were discussed.

Synthesis of steroidal lactone by penicillium citreo-viride

The biotransformations of a series of steroids by the fungus penicillium citreo-viride A.C.C.C. 0402 have been investigated, and the conversion to the same product testolactone (1) was observed from progesterone (2), dehydroepiandrosterone (3), 4-androstene-3, 17-dione (4), 5-androstene-3, 17-diol (5) with the exception of pregnenolone (6) and 3β-hydroxy-5, 16-pregnadien-20-one (7). The possible metabolic pathways of the biotransformations were also discussed in the paper and the fungus penicillium citreo-viride A.C.C.C. 0402 was isolated during screening stains from samples collected from Zhengzhou, Henan province of China.

Studies on Baeyer-Villiger oxidation of steroids: DHEA and pregnenolone d-lactonization pathways in Penicillium camemberti AM83

Penicillium camemberti AM83 strain is able to carry out effective Baeyer-Villiger type oxidation of DHEA, pregnenolone, androstenedione and progesterone to testololactone. Pregnenolone and DHEA underwent oxidation to testololactone via two routes: through

Baeyer-villiger oxidation of some steroids by Aspergillus tamarii MRC 72400

Biotransformations of epiandrosterone (1), dehydroepiandrosterone (2), testosterone (3), progesterone (4) and pregnenolone (5) by Aspergillus tamarii MRC 72400 for 5 days have been reported and the results of these incubations have been compared with previously published data obtained with Aspergillus tamarii QM 1223. A. tamarii MRC 72400 showed higher Bayer-Villiger monooxygenase activities than A. tamarii QM 1223 did. Apart from pregnenolone (5), A. tamarii MRC 72400 metabolized these steroids in different ways. Incubation of epiandrosterone (1) afforded 3β,11β-dihydroxy-5α-androstan-17- one (6) (3%) and 3β-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (7) (9.5%). Incubation of dehydroepiandrosterone (2) afforded 3β-hydroxy-17a- oxa-D-homoandrost-5-en-17-one (8) (28%), testolactone (9) (6%), 3β,7β-dihydroxyandrost-5-en-17-one (10) (13%) and 3β,7α- dihydroxyandrost- 5-en-17-one (11) (24%). Incubation of testosterone (3) afforded testolactone (9) (58%). Incubation of progesterone (4) also afforded testolactone (9), however in higher yield (86%). Incubation of pregnenolone (5) afforded 3β-hydroxy-17a-oxa-D-homoandrost- 5-en-17-one (8) (25%) and testolactone (9) (27%).

Baeyer-Villiger oxidation of DHEA, pregnenolone, and androstenedione by Penicillium lilacinum AM111

The Baeyer-Villiger monooxygenase (BVMO) produced by Penicillium lilacinum AM111, in contrast to other enzymes of this group known in the literature, is able to process 3β-hydroxy-5-ene steroid substrates. Transformation of DHEA and pregnenolone yielded, as a sole or main product, 3β-hydroxy-17a-oxa-d-homo-androst-5-en-17-one, a new metabolite of these substrates; pregnenolone was transformed also to testololactone. Testololactone was the only product of oxidation of androstenedione by P. lilacinum AM111. Investigations of the time evolution of reaction progress have indicated that the substrates stimulate activity of BVMO(s) of P. lilacinum AM111.

Microbial side-chain degradation of progesterone I: Optimization of the transformation conditions

The microbial side-chain degradation of progesterone for the production of C-19 androgens was investigated. Thirty seven locally isolated fungal cultures were screened for their ability to degrade the side-chain of progesterone. Fusarium dimerum showed the greatest bioconversion efficiency and was selected for further studies. 50% of the substrate was converted to androstenedione after 24 hrs. 72 hrs old culture was able to produce maximum yields of testosterone, androstenedione and androstadienedione. The maximum conversion activities (90%) of progesterone were recorded at pH 7. The capacity of the fungus to degrade the side-chain of progesterone was greatly diminished on using high concentration of progesterone. The bioconversion estimates sharply decreased by using glucose syrup, corn steep liquor and glucose-corn steep media.