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   10-DEACETYL BACCATIN III (10-DAB-III) C23H36O10 Molecular Formula C23H36O10

   Molecular Weight 544.60

   Description: White to off white crystalline powder

   Taxan-derivatives have gained great attention because of their partly excellent anti-cancer properties.

   10-Deacetyl-baccatin-III (10-DAB) can be gained from the leaves of yew trees and it is used as starting materials for numerous partial syntheses.

   the esterification of 10-DAB with longchain fatty acids can also generate an important enhancement of their kinetics and consequently their pharmacological action pattern

   Taxol? is the best-selling cancer drug in the history of our fight against cancer. It works by preventing cells from sub-dividing rapidly, a fundamental characteristic of all cancerous cells. This unique anti-mitotic (prevents mitosis or division of cells) works on a cellular and molecular level, and should have generic applicability to different cancers. The marketplace for Taxol? exceeds $2 billion, and is expected to increase with its approval for new cancer indications and clinical use for non-cancer related diseases.

   Taxol? is primarily manufactured by the Bristol-Myers Squibb Company in a multi-step (9-step) semi-synthetic process from a precursor taxoid, 10-deacetyl baccatin III (10-DAB). 10-DAB is an intermediate, which is isolated and purified from yew species such as Taxus baccata in a second but primary multi-step process. Historically developed by the National Cancer Institute and Hauser Chemical Company, Taxol? was first isolated and manufactured from the bark of the slow-growing Pacific yew, Taxus brevifolia.

   Aphios isolates and manufactures an all-natural Taxol? in a 4-step process that is cost-effective and environmental-friendly. The process also produces precursor taxoids, 10-DAB and cephalomannine which can be semi-synthetically converted to Taxol? in a 3-step process, as by-products. The process uses near-critical and supercritical fluids with or without polar co-solvents (SuperFluids?). These fluids are normally gases, which when compressed, exhibit enhanced thermodynamic properties. SuperFluids? are used for the selective extraction and chromatographic purification (CXP) of taxoids from the bark, roots and renewable needles of the yew tree. The CXP process has proven to be rapid (isolation times between 40 minutes and 4 hours), efficient (yields of more than 90 %), cost-effective (as much as 75 % lower in costs than organic phase techniques), and environmental-friendly (eliminates use of toxic organic solvents and utilizes renewable leaves/needles).

   10-deacetlybaccatin III in transformed roots of Taxus x media var. Hicksii Rehd.

   The diterpenoid, paclitaxel, is being used as a chemotherapeutic agent against various cancers. Paclitaxel was originally obtained by extraction of bark of Taxus brevifolia with the yield 0.01%. Currently this compound and its analogue docetaxel are being produced semi-synthetically through acylation of 10-deacetylbaccatin III (10-DAB III) isolated from the needles of different Taxus species. The latter compound was extracted from needles of T.baccata with the yield 0.1% of F.W. An alternative source of taxanes are cells and tissues of yew plant cultivated in vitro. The highest accumulation of paclitaxel (0.6%) was obtained in suspension culture of Taxus x media after elicitation with 100 mM of methyl jasmonate. Currently there is only one patent on transformation of yew plants with Agrobacterium rhizogenes by Palut-Carcasson (1994). No details on taxane production and determination in hairy root cultures of Taxus species were given by the patentee.

   In this work hairy root cultures of Taxus x media var. Hicksii were established by infection of the plantlets with Agrobacterium rhizogenes strain LBA 9402. The transformed roots were cultivated in hormone-free DCR liquid medium. The content of 10-deacetybaccatin III was determined using HPLC method in 28-day-old "hairy" roots before (control) and after elicitation with methyl jasmonate, vanadyl sulphate and chitosan. These roots were elicited for 48 hours, 1 week, 2 and 3 weeks.

   The 10-DAB III content in control was 82.79 mg/g D.W. The highest content of 10-DAB III (153.49 mg/g D.W.) was determined in roots cultivated for 1 week in the medium containing 10 mM of vanadyl sulphate. After the longer time of elicitation with all applied doses of vanadyl sulphate (1, 10, 100 mM) a significant decrease in 10-DAB III content was observed. The 10-DAB III accumulation diminished in "hairy" roots elicited with chitosan which was added to the medium in three concentrations: 0.2, 2 and 10 mg/dm3. Also the treatment with 100 mM of methyl jasmonate caused the decrease in 10-DAB III content.


   Scientific References:
    
    1.10-deacetlybaccatin III in transformed roots of Taxus x media var. Hicksii Rehd.Miros?awa Furmanowa, K. Syk?owska-Baranek. Department of Biology and Pharmaceutical Botany, Medical University, Banacha 1, 02-097 Warsaw, Poland
    2.Aphios Corporation granted Chinese Patent For Isolation of Taxol? from Yew Needles
    3.Taxol? ?what is 10-Deacetyl Baccatin III HPLC ?10-deacetlybaccatin III in transformed roots of Taxus x media var. Hicksii Rehd.Via Michael Derrida

   Amanuensis&Symbol trace Calligrapher: Michael Derrida