One unique steroidal sapogenin obtained through the microbial transformation of ruscogenin by Phytophthora cactorum ATCC 32134 and its potential inhibitory effect on tissue factor (TF) procoagulant activity.
With the aim to obtain more effective tissue factor (TF) inhibitors, the microbial transformation of three steroidal sapogenins, ruscogenin (1), diosgenin (2) and sarsasapogenin (3), was carried out and only ruscogenin was selectivity converted to 1-hydroxy-spirost-4-en-3-one (4) by Phytophthora cactorum ATCC 32134. The in vitro anti-TF procoagulant activity of this metabolite was enhanced almost 10 times to an IC(50) value of 0.29 microM. The chemical assignments of compound 4 were made unambiguously using ESI-MS, IR and 2D NMR spectroscopy.
Chen
Nai-Dong
ND
Department of Complex Prescription of Traditional Chinese Medicine, China Pharmaceutical University, #639 Long Mian Road, Nanjing 211198, China.
Yue
Lei
L
Zhang
Jian
J
Kou
Jun-Ping
JP
Yu
Bo-Yang
BY
D001711:Biotransformation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010838:Phytophthora / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013150:Spirostans / Q000378:metabolism*; D013256:Steroids / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology*; D013925:Thromboplastin / Q000037:antagonists & inhibitors*
D013150:Spirostans; D013256:Steroids; D013925:Thromboplastin; C012541:ruscogenin