Abstract
Biotechnological methods producing artemisinin (ART) directly are limited because the final stages of the ART biosynthesis pathway remain elusive. Dihydro-epi-deoxyarteannuin B (DHEDB) is synthesized from dihydroartemisinic acid (DHAA) and used as a substrate at the present research. DHEDB was fed to cultured cells of Artemisia annua 10 days post subculture under light and dark conditions. The structures of the biotransformed products were elucidated by HR-ESI-MS and NMR analysis. Three hydroxylated products, 3α-hydroxy-dihydro-epi-deoxyarteannuin B (1), 9β-hydroxy-dihydro-epi-deoxyarteannuin B (2) and 14-hydroxy-dihydro-epi-deoxyarteannuin B (3), were obtained. Among them, compound 3 is a new compound. The autoxidation experiment of DHEDB indicated that three compounds were generated by enzymatic catalysis. The content of ART increased by 23.9 % compared to the control group under dark culture. Effects of DHEDB on the transcriptome of A. annua were determined under the optimal conditions. The genes HMGR, FPS, ADS, CYP71AV1, CPR, DBR2 and ALDH1 were involved in the process of biotransformation. qRT-PCR results showed that the increase in ART content was correlated with the increasing expression of the related genes. However, DHEDB and its biotransformed products are unlikely to be the intermediates of ART production because they showed no similarities in structure. Otherwise, the increase of ART content may due to the elicitor like effect of DHEDB as exogenous substance in A. annua cells.
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