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. 2012 Apr;8(30):124-8.
doi: 10.4103/0973-1296.96555.

Biotransformation of furannoligularenone by transgenic crown galls of Panax quinquefolium

Chunyan Yan  1 , Jue Wang, Guoyan Duan, Rongmin Yu
Affiliations

Biotransformation of furannoligularenone by transgenic crown galls of Panax quinquefolium

Chunyan Yan et al. Pharmacogn Mag. 2012 Apr.

Abstract

Background: Transgenic plant suspension cultures could be used as an effective tool for the biotransformation of exogenous compounds.

Objective: To investigate the biotransformation of furannoligularenone (1) by transgenic crown galls of Panax quinquefolium.

Materials and methods: Compound 1 was administered into the crown gall cultures and co-cultured for 6 days. The cultures were dried and extracted with methanol for HPLC analyses. The extract was separated on column chromatography, and biotransformation products' structures were elucidated by the physicochemical properties and the data of NMR and MS. Moreover, three flasks were randomly chosen each day to establish time-course during the period for co-culturing.

Results: Co-culturing compound 1 with crown galls yielded two compounds, 3-oxo-eremophila-1,7(11)-dien-12,8-olide (2) and 3-oxo-8-hydroxy-eremophila-1,7(11)-dien-12,8-olide (3), which were obtained by biotransformation using P. quinquefolium crown galls for the first time. Time-course investigation revealed that the mole conversion ratio reached the highest level of 45.5% and 33.9% on fourth and fifth day after substrate administration, respectively. Furthermore, a proposal biosynthesis pathway was given from compound 1 to compounds 2 and 3.

Conclusion: This was the first example of compound 1 being successfully converted into compounds 2 and 3 by transgenic crown galls of P. quinquefolium.

Keywords: Biotransformation; Panax quinquefolium; furannoligularenone; transgenic crown galls.

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Conflict of interest statement

Conflict of Interest: None declared.

Figures

Figure 1
Figure 1
Time–course curve of the biotransformation of 1 in the medium and the transgenic crown galls of P. quinquefolium. (–■–)The yield of 2 in the culture; (–◊–) the yield of 3 in the culture; (–▲–) the yield of 2 in the medium; and (–◦–) the yield of 3 in the medium
Figure 2
Figure 2
A proposal biosynthesis pathway of furannoligularenone (1)
Figure 3
Figure 3
The comparison of time-course curve of compounds 2 and 3 from 1 in crown galls of P. quinquefolium and hairy roots of P. multiflorum. (–Δ–) The yield of 2 in hairy roots; (–◦–) the yield of 3 in hairy roots; (–▲–) the yield of 2 in crown galls; and (–■–) the yield of 3 in crown galls
Figure 4
Figure 4
HPLC chromatograms of the biotransformation compound of 1 by crown galls of P. quinquefolium and hairy roots of P. multiflorum
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