Production of biologically active taxoids by a callus culture of Taxus cuspidata.

Abstract

Ten known taxoids, paclitaxel, 7-epi-taxol, taxol C, baccatin VI, taxayuntin C, taxuyunnanine C and its analogues (2-5), and yunnanxane (6), and an abietane, taxamairin A, were produced in the callus culture of Taxus cuspidata cultivated on a modified Gamborg's B5 medium in the presence of 0.5 mg/L NAA. After stimulation with 100 microM methyl jasmonate, five more taxoids, cephalomannine, 1beta-dehydroxybaccatin VI, taxinine NN-11 (1), baccatin I, and 2alpha-acetoxytaxusin, and one more abietane, taxamairin C, were found in addition to the above-mentioned compounds. It was also observed that the content of the products increased over three times. Taxinine NN-11 (1) is a new taxane whose structure was assigned as 5alpha,13alpha-diacetoxy-9alpha-cinnamoyloxy-4(20),11-taxadien-10beta-ol by analysis of its spectral data. Taxinine NN-11 (1) exhibited significant MDR reversal activity toward 2780 AD tumor cells. The results of primary screening based on 39 human cancer cell lines suggest that 1 also belongs to a new mechanistic class. Efficient production of 1 was investigated using the callus culture of T. cuspidata.

• Authors: Jiao Bai, Mutumi Kitabatake, Kazuki Toyoizumi, Liwei Fu, Shujun Zhang, Jungui Dai, Junichi Sakai, Katutoshi Hirose, Takao Yamori, Akihiro Tomida, Takashi Tsuruo, Masayoshi Ando
• Journal: Journal of natural products (J Nat Prod) Vol. 67 Issue 1 Pg. 58-63 (Jan 2004) ISSN: 0163-3864 [Print] United States
• PMID: 14738387 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents, Phytogenic
• Paclitaxel

Topics

• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Drug Screening Assays, Antitumor
• Humans
• Japan
• Molecular Structure
• Paclitaxel (analogs & derivatives, chemistry, isolation & purification, pharmacology)
• Plants, Medicinal (chemistry)
• Taxus (chemistry)