Taxusecone, a Novel Taxane with an Unprecedented 11,12-Secotaxane Skeleton, from<i>Taxus cuspidata</i>Needles

Yu, Shu; Ni, Zhi Yu; Zhang, Jing; Dong, Ming; Sauriol, Françoise; Huo, Chang Hong; Shi, Qing; Gu, Yu‐Cheng; Kiyota, Hiromasa; Cong, Bin

doi:10.1271/bbb.80698

Cited by 4 publications

(3 citation statements)

References 8 publications

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“…A novel 11,12-secotaxane was isolated from the needles of T. cuspidata , and it did not display in vitro cytotoxicity against human breast cancer MCF-7 cell line. As shown below (Scheme ), this unique framework would be biosynthesized from decinnamoyltaxinine B 11,12-oxide ( 186 ) …”

Section: Taxanes Isolated From Yew Treesmentioning

confidence: 99%

Natural Taxanes: Developments Since 1828

et al. 2011

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Section: Taxanes Isolated From Yew Treesmentioning

confidence: 99%

Natural Taxanes: Developments Since 1828

et al. 2011

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“…This result indicated that a high temperature may increase the extraction rate of 10-DAB from needles but is not conducive to further acetylation. This is primarily determined by the thermal sensitivity of TcDBAT, and may also be related to the diverse metabolite composition and the complex structure of plant cells [ 32 , 33 , 34 ]. Although the catalytic efficiency needs to be further improved, this result can prove that the integration of the extraction of 10-DAB and the biotransformation synthesis of baccatin III can be achieved by directly using Taxus needles as a substrate.…”

Section: Resultsmentioning

confidence: 99%

An Integrated Strategy Based on 10-DAB Extraction and In Situ Whole-Cell Biotransformation of Renewable Taxus Needles to Produce Baccatin III

Kou,

Yu,

Wang

et al. 2024

Molecules

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Baccatin III is a crucial precursor in the biosynthesis pathway of paclitaxel. Its main sources are extraction from Taxus or chemical synthesis using 10-deacetylbaccatin III (10-DAB) as substrate. However, these preparation approaches exhibit serious limitations, including the low content of baccatin III in Taxus and the complicated steps of chemical synthesis. Heterologous expression of 10-deacetylbaccatin III-10-O-acetyltransferase (TcDBAT) in microbial strains for biotransformation of 10-DAB is a promising alternative strategy for baccatin III production. Here, the promotion effects of glycerol supply and slightly acidic conditions with a low-temperature on the catalysis of recombinant TcDBAT strain were clarified using 10-DAB as substrate. Taxus needles is renewable and the content of 10-DAB is relatively high, it can be used as an effective source of the catalytic substrate 10-DAB. Baccatin III was synthesized by integrating the extraction of 10-DAB from renewable Taxus needles and in situ whole-cell catalysis in this study. 40 g/L needles were converted into 20.66 mg/L baccatin III by optimizing and establishing a whole-cell catalytic bioprocess. The method used in this study can shorten the production process of Taxus extraction for baccatin III synthesis and provide a reliable strategy for the efficient production of baccatin III by recombinant strains and the improvement of resource utilization rate of Taxus needles.

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“…Further examination of T. cuspidata yielded 315 13-oxobaccatin III from the leaves and an 11,12-secotaxane, taxusecone 104 from the needles. 316 An 11(15/1),1l(10/9)-diabeotaxane, sumataxin A 105 has been obtained 317 from the Taiwanese yew, T. sumatrana. This compound was formulated as the acetonide but it is worth pointing out that the plant was extracted with acetone.…”

Section: Taxanesmentioning

confidence: 99%