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Journal articles on the topic 'Baccatin'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 September 2023

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1

Kim, Ki-Hyang, Chan-Su Park, Dong-Eun Park, Sun-A. Im, and Chong-Kil Lee. "Immune adjuvant and antitumor activity of baccatin III, a synthetic precursor of taxol (155.15)." Journal of Immunology 186, no. 1_Supplement (2011): 155.15. http://dx.doi.org/10.4049/jimmunol.186.supp.155.15.

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Abstract Baccatin III (BA-III), a precursor for the synthesis of taxol, is widely considered to be an inactive derivative of taxol. Here we show that baccatin III exerts immune adjuvant activity. When added to cultures of immature dendritic cells (DCs) generated from bone marrow cells with GM-CSF, baccatin III increased the expression of MHC II molecules and the allostimulatory activity of the DC. The immune adjuvant activity of baccatin III was examined in mice injected with a model antigen, OVA, emulsified with Freud’s incomplete adjuvant. Inclusion of baccatin III significantly increased th

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2

Ding, Qi, Dong-Mei Fang, Xiao-Huan Li, and Feng Gao. "Two New Taxane Diterpenoids From Taxus baccata." Natural Product Communications 15, no. 9 (2020): 1934578X2095328. http://dx.doi.org/10.1177/1934578x20953280.

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Two new diterpenoids named 13-oxo-wollifoliane-10,15-olide (1) and 19-acetoxy-7,9,10-deacetyl-baccatin VI (2), along with 14 known taxanes (3-16), were isolated from Taxus baccata. The structures of these compounds were elucidated by 1-dimensional and 2-dimensional nuclear magnetic resonance spectra, high-resolution electrospray ionization-mass spectrometry, and infrared spectroscopy. Structurally, 13-oxo-wollifoliane-10,15-olide (1) is the first taxane diterpenoid possessing an unusual carbonyl group at the C-13 position of the 11(15→1),11(10→9)bis- abeo-taxane structure (5/6/6/6/4 skeleton),

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3

Saicic, R. N., R. Matovic, and Z. Cekovic. "Semisynthesis of Taxol®: An improved procedure for the isolation of 10-deacetylbaccatin III." Journal of the Serbian Chemical Society 64, no. 9 (1999): 497–503. http://dx.doi.org/10.2298/jsc9909497s.

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From the needles of domestic yew, (Taxus baccata), 10-deacetylbaccatin III (10-DAB) can be isolated in quantities of up to 297 mg per kg of fresh needles. Additional quantities of 10-Dcan be obtained from the extract by NaBH4 mediated reductive hydrolysis of baccatin esters. A four-step procedure converts 10-Dinto taxol in 58% overall yield.

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4

Chiaroni, A., D. Guénard, F. Guéritte-Voegelein, et al. "A Baccatin III Derivative." Acta Crystallographica Section C Crystal Structure Communications 51, no. 3 (1995): 465–68. http://dx.doi.org/10.1107/s0108270194007341.

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5

Wang, Li, Ya-jun Li, and Zheng-wei Li. "Towards validating new enzymatic routes for synthetic conversion: 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetyl baccatin III–ethyl acetate–water (1/1/1)." Acta Crystallographica Section C Structural Chemistry 71, no. 3 (2015): 191–94. http://dx.doi.org/10.1107/s2053229614027399.

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The title compound, C34H38Cl6O14·C4H8O2·H2O, prepared by the reaction of 10-deacetyl baccatin III with 2,2,2-trichloroethyl chloroformate in pyridine, crystallizesviastrong intermolecular hydrogen bonds and noncovalent interactions between 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetyl baccatin III (7,10-di-Troc-DAB), water and ethyl acetate. A detailed comparison of the molecular conformation with those of related structures is presented.

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6

Shen, Ya-Ching, Kuang-Liang Lo, Chun-Ling Lin та Rupak Chakraborty. "Microbial transformation of baccatin VI and 1β-Hydroxy baccatin I by aspergillus niger". Bioorganic & Medicinal Chemistry Letters 13, № 24 (2003): 4493–96. http://dx.doi.org/10.1016/j.bmcl.2003.08.069.

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7

Dutta, Dinah, Apurba Datta, David Vander Velde, and Gunda Georg. "Oxidation of Baccatin III at C14: A Facile Rearrangement of the Baccatin III Core." Letters in Organic Chemistry 4, no. 3 (2007): 151–54. http://dx.doi.org/10.2174/157017807780737246.

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8

Banik, Bimal K., Miguel Fernandez, and Clarissa Alvarez. "Sodium Bismuthate–Induced Oxidation of Baccatin." Synthetic Communications 35, no. 23 (2005): 3065–67. http://dx.doi.org/10.1080/00397910500278842.

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9

Danishefsky, Samuel J., John J. Masters, Wendy B. Young, et al. "Total Synthesis of Baccatin III and Taxol." Journal of the American Chemical Society 118, no. 12 (1996): 2843–59. http://dx.doi.org/10.1021/ja952692a.

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10

Tatini, Lakshmi Kumar, N. Someswara Rao, Muzaffar Khan, Krishna Sumanth Peraka, and K. V. S. R. Krishna Reddy. "Concomitant Pseudopolymorphs of 10-Deacetyl Baccatin III." AAPS PharmSciTech 14, no. 2 (2013): 558–68. http://dx.doi.org/10.1208/s12249-013-9940-6.

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11

Baldelli, Eleonora, Arturo Battaglia, Ezio Bombardelli та ін. "Diastereoselective 14β-Hydroxylation of Baccatin III Derivatives". Journal of Organic Chemistry 68, № 25 (2003): 9773–79. http://dx.doi.org/10.1021/jo0347112.

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12

Guéritte-Voegelein, F., V. Sénilh, B. David, D. Guénard, and P. Potier. "Chemical studies of 10-deacetyl baccatin III." Tetrahedron 42, no. 16 (1986): 4451–60. http://dx.doi.org/10.1016/s0040-4020(01)87285-9.

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13

Harper, James K., N. Kent Dalley, Anna E. Mulgrew, F. G. West, and David M. Grant. "10-Deacetyl baccatin III dimethyl sulfoxide disolvate." Acta Crystallographica Section C Crystal Structure Communications 57, no. 1 (2001): 64–65. http://dx.doi.org/10.1107/s0108270100011781.

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14

Battaglia, Arturo, Ralph J. Bernacki, Carlo Bertucci та ін. "Synthesis and Biological Evaluation of 2‘-Methyl Taxoids Derived from Baccatin III and 14β-OH-Baccatin III 1,14-Carbonate". Journal of Medicinal Chemistry 46, № 23 (2003): 4822–25. http://dx.doi.org/10.1021/jm034146v.

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15

AMINI, Sayed-Asadollah, Leila SHABANI, Ladan AFGHANI, Zohreh JALALPOUR, and Majid SHARIFI-TEHRANI. "Squalestatin-induced production of taxol and baccatin in cell suspension culture of yew (Taxus baccata L.)." TURKISH JOURNAL OF BIOLOGY 38 (2014): 528–36. http://dx.doi.org/10.3906/biy-1401-47.

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16

Cusidó, Rosa M., Javier Palazón, Mercedes Bonfill, Oscar Expósito, Elisabet Moyano, and M. Teresa Piñol. "Source of isopentenyl diphosphate for taxol and baccatin III biosynthesis in cell cultures of Taxus baccata." Biochemical Engineering Journal 33, no. 2 (2007): 159–67. http://dx.doi.org/10.1016/j.bej.2006.10.016.

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17

Baloglu, Erkan, and David G. I. Kingston. "A New Semisynthesis of Paclitaxel from Baccatin III." Journal of Natural Products 62, no. 7 (1999): 1068–71. http://dx.doi.org/10.1021/np990040k.

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18

Balogu, Erkan, and David G. I. Kinston. "A New Semisynthesis of Paclitaxel from Baccatin III." Journal of Natural Products 62, no. 8 (1999): 1214. http://dx.doi.org/10.1021/np9903200.

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19

ElSohly, Hala N., Edward M. Croom, Wlodzimierz J. Kopycki, Alpana S. Joshi, Mahmoud A. ElSohly, and James D. McChesney. "Taxane Contents of Taxus Cultivars Grown in American Nurseries." Journal of Environmental Horticulture 15, no. 4 (1997): 200–205. http://dx.doi.org/10.24266/0738-2898-15.4.200.

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Abstract The taxane content of the needles, stems and clippings of 92 cultivars obtained from ten nurseries in the United States is presented. The analysis of 10-desacetyl baccatin III (1), baccatin III (2), 10-desacetyl taxol (3) cephalomannie (4), 10-desacetyl-7-epi-taxol (5) and taxol (6) was carried out using a high performance liquid chromatographic method developed in our laboratory. The total ‘useful’ taxane content of the leaves, stems, and clippings in the studied cultivars ranged from 0.0135–0.1471%, 0.0055–0.0462% and 0.0121–0.1183%, respectively, with 1 and 6 being the most abundan

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20

Dalmaris, Eleftheria, Evangelia V. Avramidou, Aliki Xanthopoulou, and Filippos A. Aravanopoulos. "Dataset of Targeted Metabolite Analysis for Five Taxanes of Hellenic Taxus baccata L. Populations." Data 5, no. 1 (2020): 22. http://dx.doi.org/10.3390/data5010022.

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Novel primary sources of one of the world’s leading anticancer agent, paclitaxel, as well as of other antineoplastic taxanes such as 10-deacetylbaccatin-III, are needed to meet an increasing demand. Among the Taxus species the promise of Taxus baccata L. (European or English yew) has been documented. In this study, the metabolite analysis of two marginal T. baccata populations in Greece (Mt. Cholomon and Mt. Olympus), located at the southeastern edge of the species natural distribution, are being explored. A targeted liquid chromatography – mass spectrometry (LC-MS/MS) analysis was used to det

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21

Bonfill, M., O. Expósito, E. Moyano, R. M. Cusidó, J. Palazón, and M. T. Piñol. "Manipulation by culture mixing and elicitation of paclitaxel and baccatin III production in Taxus baccata suspension cultures." In Vitro Cellular & Developmental Biology - Plant 42, no. 5 (2006): 422–26. http://dx.doi.org/10.1079/ivp2006761.

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22

Palazón, Javier, Rosa M. Cusidó, Mercedes Bonfill, Carmen Morales, and M. Teresa Piñol. "Inhibition of paclitaxel and baccatin III accumulation by mevinolin and fosmidomycin in suspension cultures of Taxus baccata." Journal of Biotechnology 101, no. 2 (2003): 157–63. http://dx.doi.org/10.1016/s0168-1656(02)00318-8.

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23

Bonfill, M., S. Bentebibel, E. Moyano, et al. "Paclitaxel and baccatin III production induced by methyl jasmonate in free and immobilized cells of Taxus baccata." Biologia plantarum 51, no. 4 (2007): 647–52. http://dx.doi.org/10.1007/s10535-007-0137-2.

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24

Hoffman, Angela, Clinton Shock, and Erik Feibert. "Taxane and ABA Production in Yew under Different Soil Water Regimes." HortScience 34, no. 5 (1999): 882–85. http://dx.doi.org/10.21273/hortsci.34.5.882.

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Taxol® (paclitaxel), an important anticancer agent, is found in many species of yew. As the need for Taxol increases, sustainable sources must be found for this drug. Plants often respond to stress with increased production of terpenoid compounds such as Taxol and related taxanes or hormones such as abscisic acid (ABA). To determine whether water stress would enhance the production and recovery of Taxol from stem clippings, 100 young Taxu×media `Hicksii' shrubs were grown for sustainable production of Taxol from stem clippings for two seasons in the dry climate of the Malheur Experiment Statio

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25

Shiina, Isamu, Hayato Iwadare, Hiroki Sakoh, Masatoshi Hasegawa, Yu-ichirou Tani, and Teruaki Mukaiyama. "A New Method for the Synthesis of Baccatin III." Chemistry Letters 27, no. 1 (1998): 1–2. http://dx.doi.org/10.1246/cl.1998.1.

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26

Samaranayake, Gamini, Kurt A. Neidigh, and David G. I. Kingston. "Modified Taxols, 8. Deacylation and Reacylation of Baccatin III." Journal of Natural Products 56, no. 6 (1993): 884–98. http://dx.doi.org/10.1021/np50096a012.

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27

Margraff, Rodolphe, Daniel Bézard, Jean Dominique Bourzat, and Alain Commerçon. "Synthesis of 19-hydroxy docetaxel from a novel baccatin." Bioorganic & Medicinal Chemistry Letters 4, no. 2 (1994): 233–36. http://dx.doi.org/10.1016/s0960-894x(01)80120-7.

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28

Zhang, Jianfeng, and Zhigang Guo. "Effect of methyl jasmonic acid on baccatin III biosynthesis." Tsinghua Science and Technology 11, no. 3 (2006): 363–67. http://dx.doi.org/10.1016/s1007-0214(06)70201-2.

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29

Py, Sandrine, and Françoise Khuong-Huu. "Reactivity of Baccatin III Derivatives towards Samarium II reagents." Tetrahedron Letters 36, no. 10 (1995): 1661–64. http://dx.doi.org/10.1016/0040-4039(95)00100-q.

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30

Magri, Neal F., David G. I. Kingston, Chote Jitrangsri, and Thomas Piccariello. "Modified taxols. 3. Preparation and acylation of baccatin III." Journal of Organic Chemistry 51, no. 16 (1986): 3239–42. http://dx.doi.org/10.1021/jo00366a043.

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31

Appendino, Giovanni, Luciano Barboni, Pierluigi Gariboldi, Ezio Bombardelli, Bruno Gabetta, and Davide Viterbo. "Revised structure of brevifoliol and some baccatin VI derivatives." Journal of the Chemical Society, Chemical Communications, no. 20 (1993): 1587. http://dx.doi.org/10.1039/c39930001587.

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32

DANISHEFSKY, S. J., J. J. MASTERS, W. B. YOUNG, et al. "ChemInform Abstract: Total Synthesis of Baccatin III and Taxol." ChemInform 27, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199630227.

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33

Harper, James K., N. Kent Dalley, Anna E. Mulgrew, F. G. West, and David M. Grant. "ChemInform Abstract: 10-Deacetyl Baccatin III Dimethyl Sulfoxide Disolvate." ChemInform 32, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.200122129.

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34

Navia-Osorio, Alberto, Hermann Garden, Rosa M. Cusidó, Javier Palazón, A. Wilhelm Alfermann, and M. Teresa Piñol. "Taxol® and baccatin III production in suspension cultures of Taxus baccata and Taxus wallichiana in an airlift bioreactor." Journal of Plant Physiology 159, no. 1 (2002): 97–102. http://dx.doi.org/10.1078/0176-1617-00576.

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35

Zocher, Rainer, Wolfram Weckwerth, Christine Hacker, Bettina Kammer, Till Hornbogen, and Dietrich Ewald. "Biosynthesis of Taxol: Enzymatic Acetylation of 10-Deacetylbaccatin-III to Baccatin-III in Crude Extracts from Roots ofTaxus baccata." Biochemical and Biophysical Research Communications 229, no. 1 (1996): 16–20. http://dx.doi.org/10.1006/bbrc.1996.1751.

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36

Kingston, David G. I., Ashok G. Chaudhary, A. A. Leslie Gunatilaka, and Mark L. Middleton. "Synthesis of taxol from baccatin III via an oxazoline intermediate." Tetrahedron Letters 35, no. 26 (1994): 4483–84. http://dx.doi.org/10.1016/s0040-4039(00)60706-2.

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37

Chatterjee, Sabarni K., Donna M. Barron, Sarah Vos, and Susan Bane. "Baccatin III Induces Assembly of Purified Tubulin into Long Microtubules†." Biochemistry 40, no. 23 (2001): 6964–70. http://dx.doi.org/10.1021/bi002816i.

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38

Cusidó, Rosa M., Javier Palazón, Alberto Navia-Osorio, et al. "Production of Taxol® and baccatin III by a selected Taxus baccata callus line and its derived cell suspension culture." Plant Science 146, no. 2 (1999): 101–7. http://dx.doi.org/10.1016/s0168-9452(99)00093-x.

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39

Katkovčinová, Zuzana, Martina Lázárová, Katarína Bruňáková, Ján Košuth, and Eva Čellárova. "Expression of dbat and dbtnbt Genes Involved in Paclitaxel Biosynthesis during the Growth Cycle of Taxus baccata L. Callus Cultures." Zeitschrift für Naturforschung C 63, no. 9-10 (2008): 721–30. http://dx.doi.org/10.1515/znc-2008-9-1018.

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The time-course of expression of dbat and dbtnbt genes involved in the later steps of paclitaxel biosynthesis and the intracellular taxane accumulation were investigated through a 64-day subculture interval of VI/M1 and VI/M2 Taxus baccata callus cultures. HPLC proved traces of baccatin III and an intracellular content of paclitaxel up to 90 μg/g DW. The steadystate of the respective gene transcripts was measured by quantitative real-time RT-PCR. The expression profile of dbat and dbtnbt genes was slightly different and varied within the subculture. The highest level of dbat expression was det

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40

Berkowitz, W. F., and A. S. Amarasekara. "An approach to the d-ring of baccatin III (taxol, cephalomannine)." Tetrahedron Letters 26, no. 31 (1985): 3663–64. http://dx.doi.org/10.1016/s0040-4039(00)89217-5.

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41

Roth, Gregory P., Daniel R. Marshall, and Shu-Hui Chen. "Reaction of paclitaxel and 10-desacetyl baccatin III with diethylamino sulfurtrifluoride." Tetrahedron Letters 36, no. 10 (1995): 1609–12. http://dx.doi.org/10.1016/0040-4039(95)00133-w.

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42

Almqvist, Fredrik, Sophie Manner, Viveca Thornqvist, Ulf Berg, Margareta Wallin, and Torbj�rn Frejd. "Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol)." Organic & Biomolecular Chemistry 2, no. 21 (2004): 3085. http://dx.doi.org/10.1039/b409678a.

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43

Masters, John J., David K. Jung, Samuel J. Danishefsky, et al. "Eine neuartige, intramolekulare Heck-Reaktion: Synthese eines Cholesterin-Baccatin-III-Hybrids." Angewandte Chemie 107, no. 4 (1995): 495–98. http://dx.doi.org/10.1002/ange.19951070414.

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44

APPENDINO, G., L. BARBONI, P. GARIBOLDI, E. BOMBARDELLI, B. GABETTA, and D. VITERBO. "ChemInform Abstract: Revised Structure of Brevifoliol and Some Baccatin VI Derivatives." ChemInform 25, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199409280.

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45

MARGRAFF, R., D. BEZARD, J. D. BOURZAT, and A. COMMERCON. "ChemInform Abstract: Synthesis of 19-Hydroxy Docetaxel from a Novel Baccatin." ChemInform 25, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199426229.

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46

SHIINA, I., H. IWADARE, H. SAKOH, M. HASEGAWA, Y. TANI, and T. MUKAIYAMA. "ChemInform Abstract: A New Method for the Synthesis of Baccatin III." ChemInform 29, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199820231.

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47

Gunda I, Georg, Cheruvallath Zacharia S, Richard H. Himes, and Magdalena R. Mejillano. "Semisynthesis and biological activity of taxol analogues: baccatin III 13-(N-benzoyl-(2′R,3′S)-3′-(p-tolyl)isoserinate), baccatin III 13-(N-(p-toluoyl)-2′R,3′S)-3′-phenylisoserinate), baccatin III 13-(N-benzoyl-(2′R,3′S)-3′-(p-trifluoromethylphenyl)isoserinate), and baccatin III 13-(N-(p-trifluoromethylbenzoyl)-(2′R,3′S)-3′-phenylisoserinate)." Bioorganic & Medicinal Chemistry Letters 2, no. 12 (1992): 1751–54. http://dx.doi.org/10.1016/s0960-894x(00)80469-2.

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48

Barycki, Rafał, Maria Gumułka, Marek Masnyk, Włodzimierz M. Daniewski, Mirosław Kobus, and Mirosław Łuczak. "Synthesis of N-Acetyl-3-phenylisoserinates of Sesquiterpenoid Alcohols of Lactarius Origin." Collection of Czechoslovak Chemical Communications 67, no. 1 (2002): 75–82. http://dx.doi.org/10.1135/cccc20020075.

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Important biological properties of Taxol i.e. 13-N-benzoyl-(2R,3S)-3-phenylisoserinate of baccatin III and also N-benzoyl-(2R,3S)-3-phenylisoserinates of several sesquiterpenoid alcohols of Lactarius origin prompted us to synthesize N-acetyl-3-phenylisoserinates of latter alcohols in order to check and compare their biological properties. Suitably protected phenylisoserine 5 when reacted with sesquiterpenoid alcohols in the presence of DCC gave appropriate esters 7. These, after catalytic hydrogenation deprotection produced aminols 8, which were acetylated and gave the required N-acetyl-3-phe

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49

Cusido, R. M., J. Palazon, M. Bonfill, A. Navia-Osorio, C. Morales, and M. T. Pinol. "Improved Paclitaxel and Baccatin III Production in Suspension Cultures of Taxus media." Biotechnology Progress 18, no. 3 (2002): 418–23. http://dx.doi.org/10.1021/bp0101583.

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50

Chen, Shu-Hui, Stella Huang, Qi Gao, Jerzy Golik, and Vittorio Farina. "The Chemistry of Taxanes: Skeletal Rearrangements of Baccatin Derivatives via Radical Intermediates." Journal of Organic Chemistry 59, no. 6 (1994): 1475–84. http://dx.doi.org/10.1021/jo00085a040.

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