7-Epi 10-Desacetyl Paclitaxel

The barks of Taxus wallichiana.

Paclitaxel impurity. Paclitaxel is a compound extracted from the Pacific yew tree with antineoplastic activity. Paclitaxel binds to tubulin and inhibits the disassembly of microtubules, thereby resulting in the inhibition of cell division. Paclitaxel also induces apoptosis by binding to and blocking the function of the apoptosis inhibitor protein Bcl-2 (B-cell Leukemia 2). Paclitaxel inhibits DNA synthesis and stimulates the release of tumor necrosis factor-α. Paclitaxel induces apoptosis in murine mammary carcinoma MCA-4 and ovarian carcinoma OCA-1 tumors.

alpha-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana.[Pubmed:28240909]

J Nat Prod. 2017 Apr 28;80(4):1087-1095.

From a CH2Cl2 extract of the bark of Taxus wallichiana, six new taxoids, wallitaxanes A-F (1-6), were isolated, together with 29 known compounds. The structures of the new compounds were elucidated on the basis of spectroscopic data interpretation. Wallitaxane D (4) was identified as an opened oxetane-type taxoid having the first naturally occurring C(H)-20 acetal group, while wallitaxanes E (5) and F (6) are representative of the rare abeo-taxoid class. The isolated compounds were evaluated for their alpha-glucosidase inhibitory activity and for cytotoxicity against the HeLa human cervical cancer cell line. In the present work, taxanes were found to exhibit alpha-glucosidase inhibitory activity for the first time, and wallitaxane A (1) showed the most potent effect, with an IC50 value of 3.6 muM. In turn, 7-epi-taxol (16) and 7-epi-10-deacetyltaxol (17) showed IC50 values of 0.05 and 0.085 nM, respectively, against HeLa cells.

Simultaneous determination of main taxoids in Taxus needles extracts by solid-phase extraction-high-performance liquid chromatography with pentafluorophenyl column.[Pubmed:18816506]

Biomed Chromatogr. 2009 Jan;23(1):63-70.

A simple and accurate RP-HPLC method with pentafluorophenyl (PFP) column was developed for the simultaneous determination of six taxoids, i.e. paclitaxel, 10-deacetylbaccatin III (10-DAB III), 7-xylosyl-10-deacetyltaxol (7-xyl-10-DAT), 10-deacetyltaxol (10-DAT), cephalomannine and 7-epi-10-deacetyltaxol (7-epi-10-DAT), in the extracts from the needles of three Taxus species. The mobile phase consisted of acetonitrile (A) and water (B), and the extracts were separated using gradient elution program: 30% A at the first 7 min, and then ramped to 42% A at 8 min, held until 38 min. The developed method was validated with satisfactory precision (RSD < 2.61%), repeatability (RSD < 2.92%) and recovery (95.19-104.47%). The above taxoids in the extracts of Taxus cuspidata, T. chinensis and T. media were analyzed with the developed RP-HPLC method, and the results showed that the contents of different taxoids in three mentioned species were distinct. Maximal amounts of 10-DAB III, 7-xyl-10-DAT and 7-epi-10-DAT appeared in T. chinensis, while T. media possessed the highest content of 10-DAT, cephalomannine and paclitaxel. The developed method is accurate and efficient. It can be reliably used in the improved determination of taxoids for the quality control of Taxus species.

7-Epi 10-desacetyl paclitaxel (7-epi-10-deacetyltaxol), a taxol derivative, exhibits cytotoxicity against HeLa cells with an IC50 of 85 μM.

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