17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7',6'-j]bispyrano[2',3':6,7]indolo[2,3-d:3',2'-g]carbazole-21,23,30,32-tetrone, 1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-, 14-oxide, (7cS,7dR,15aS,16aS,21aR,21bR,2...
- CAS No.
- 360765-75-9
- Chemical Name:
- 17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7',6'-j]bispyrano[2',3':6,7]indolo[2,3-d:3',2'-g]carbazole-21,23,30,32-tetrone, 1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-, 14-oxide, (7cS,7dR,15aS,16aS,21aR,21bR,2...
- Synonyms
- Stephacidin B;17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7',6'-j]bispyrano[2',3':6,7]indolo[2,3-d:3',2'-g]carbazole-21,23,30,32-tetrone, 1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-, 14-oxide, (7cS,7dR,15aS,16aS,21aR,21bR,2...;(7cS,7dR,15aS,16aS,21aR,21bR,22R,22aR,27aS,28aS)-1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7′,6′-j]bispyrano[2′,3′:6,7]indolo[2,3-d:3′,2′-g]carbazole-21,23,30,32-tetrone, 14-oxide;17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7′,6′-j]bispyrano[2′,3′:6,7]indolo[2,3-d:3′,2′-g]carbazole-21,23,30,32-tetrone, 1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-, 14-oxide, (7cS,7dR,15aS,16aS,21aR,21bR,22R,22aR,27aS,28aS)-
- CBNumber:
- CB89019032
- Molecular Formula:
- C52H54N6O8
- Molecular Weight:
- 891.04
- MDL Number:
- MOL File:
- 360765-75-9.mol
17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7',6'-j]bispyrano[2',3':6,7]indolo[2,3-d:3',2'-g]carbazole-21,23,30,32-tetrone, 1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-, 14-oxide, (7cS,7dR,15aS,16aS,21aR,21bR,2... Properties
Density | 1.66±0.1 g/cm3(Predicted) |
---|---|
storage temp. | -20°C |
solubility | DMSO: soluble; Methanol: soluble |
form | A solid |
pka | 12.09±0.70(Predicted) |
17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7',6'-j]bispyrano[2',3':6,7]indolo[2,3-d:3',2'-g]carbazole-21,23,30,32-tetrone, 1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-, 14-oxide, (7cS,7dR,15aS,16aS,21aR,21bR,2... Chemical Properties,Uses,Production
Biological Activity
Stephacidin B is a fungal metabolite that has been found in A. ochraceus.1 Dimeric stephacidin B is rapidly converted to a monomer, avrainvillamide , in vitro.2 Stephacidin B is cytotoxic to a variety of cancer cells, including testosterone-independent PC3 and -sensitive LNCaP prostate cancer cells (IC50s = 0.37 and 0.06 μM, respectively) and estradiol-independent SK-BR-3 and -sensitive MCF-7 breast cancer cells (IC50s = 0.32 and 0.27 μM, respectively).1 It induces apoptosis in HepG2 and Huh7 hepatocellular carcinoma cells when used at a concentration of 4 μM.3
References
1.Qian-Cutrone, J., Huang, S., Shu, Y.-Z., et al.Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cellsJ. Am. Chem. Soc.124(49)14556-14557(2002) 2.Wulff, J.E., Herzon, S.B., Siegrist, R., et al.Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell cultureJ. Am. Chem. Soc.129(16)4898-4899(2007) 3.Hu, L., Zhang, T., Liu, D., et al.Notoamide-type alkaloid induced apoptosis and autophagy via a P38/JNK signaling pathway in hepatocellular carcinoma cellsRSC Adv.9(34)19855-19868(2019)
17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7',6'-j]bispyrano[2',3':6,7]indolo[2,3-d:3',2'-g]carbazole-21,23,30,32-tetrone, 1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-, 14-oxide, (7cS,7dR,15aS,16aS,21aR,21bR,2... Preparation Products And Raw materials
Raw materials
Preparation Products
17H,21H,21bH,25H-21a,16a-(Iminomethano)-22,27a-methano-23H-diindolizino[6,7-a:7',6'-j]bispyrano[2',3':6,7]indolo[2,3-d:3',2'-g]carbazole-21,23,30,32-tetrone, 1,4,7c,11,15,15a,16,18,19,26,27,28,28a,29-tetradecahydro-1-hydroxy-4,4,11,11,15,15,29,29-octamethyl-, 14-oxide, (7cS,7dR,15aS,16aS,21aR,21bR,2... Suppliers
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