Production of biologically active taxoids by a callus culture of Taxus cuspidata.
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.
Bai
Jiao
J
Graduate School of Science and Technology and Department of Chemistry and Chemical Engineering, Niigata University, 2-8050 Ikarashi, Niigata 950-2181, Japan.
Kitabatake
Mutumi
M
Toyoizumi
Kazuki
K
Fu
Liwei
L
Zhang
Shujun
S
Dai
Jungui
J
Sakai
Junichi
J
Hirose
Katutoshi
K
Yamori
Takao
T
Tomida
Akihiro
A
Tsuruo
Takashi
T
Ando
Masayoshi
M
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007564:Japan; D015394:Molecular Structure; D017239:Paclitaxel / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D020946:Taxus / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D017239:Paclitaxel