6850-30-2

Basic information

• Product Name: 4-dehydrowithaferin A
• Synonyms: 4-dehydrowithaferin A
• CAS NO: 6850-30-2
• Molecular Formula: C₂₈H₃₆O₆
• Molecular Weight: 468.58184
• Mol File: 6850-30-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 660.5°C at 760 mmHg
• Flash Point: 219.9°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 2.94E-20mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 4-dehydrowithaferin A(CAS DataBase Reference)
• NIST Chemistry Reference: 4-dehydrowithaferin A(6850-30-2)
• EPA Substance Registry System: 4-dehydrowithaferin A(6850-30-2)

Safety Data

• Hazardous Substances Data: 6850-30-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C28H36O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,24,29H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,24+,26+,27-,28+/m0/s1

Upstream product

• 5119-48-2 withaferin-A 
• 1392820-18-6 withaferin A 27-tert-butyldimethylsilyl ether 
• 1214886-31-3 27-O-(tert-butyldimethylsilyl)-4-dehydroxy-4-oxo-withaferin A 

Relevant articles and documents

Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells

Six new withanolides (1-6) along with eleven known ones (7-17) were isolated from the leaves of Withania aristata. Their structures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques. Semisynthesis of the minority metabolites 7 and 15 from compounds 6 and 9, respectively, as starting material, was performed. The isolated compounds as well as three derivatives (7a, 9a and 9b) of withaferin A were evaluated for cytotoxicity against HeLa (carcinoma of the cervix), A-549 (lung carcinoma) and MCF-7 (breast adenocarcinoma) human cancer cell lines, and against normal Vero cells (African green monkey kidney). Five compounds from this series (8, 9a, 9b, 11 and 13) exhibited potent antiproliferative effects on the tumor cells, even higher than the well known anticancer agent, withaferin A (9). Phosphatidylserine externalization, chromatin condensation, and caspase-3 activation clearly indicated apoptosis as a mechanism of action. The structure-activity relationship revealed valuable information on the pharmacophore for withanolide-type compounds.

Structure-activity relationships for withanolides as inducers of the cellular heat-shock response

To understand the relationship between the structure and the remarkably diverse bioactivities reported for withanolides, we obtained withaferin A (WA; 1) and 36 analogues (2-37) and compared their cytotoxicity to cytoprotective heat-shock-inducing activity (HSA). By analyzing structure-activity relationships for the series, we found that the ring A enone is essential for both bioactivities. Acetylation of 27-OH of 4-epi-WA (28) to 33 enhanced both activities, whereas introduction of β-OH to WA at C-12 (29) and C-15 (30) decreased both activities. Introduction of β-OAc to 4,27-diacetyl-WA (16) at C-15 (37) decreased HSA without affecting cytotoxicity, but at C-12 (36), it had minimal effect. Importantly, acetylation of 27-OH, yielding 15 from 1, 16 from 14, and 35 from 34, enhanced HSA without increasing cytotoxicity. Our findings demonstrate that the withanolide scaffold can be modified to enhance HSA selectively, thereby assisting development of natural product-inspired drugs to combat protein aggregation-associated diseases by stimulating cellular defense mechanisms.