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. 2011 Dec 19;16(12):10541-55.
doi: 10.3390/molecules161210541.

Biotransformation of (1S)-2-carene and (1S)-3-carene by Picea abies suspension culture

Marcela Dvorakova  1 , Irena Valterova, David Saman, Tomas Vanek
Affiliations

Biotransformation of (1S)-2-carene and (1S)-3-carene by Picea abies suspension culture

Marcela Dvorakova et al. Molecules. .

Abstract

Biotransformation of (1S)-2-carene and (1S)-3-carene by Picea abies suspension culture led to the formation of oxygenated products. (1S)-2-Carene was transformed slowly and the final product was identified as (1S)-2-caren-4-one. On the other hand, the transformation of (1S)-3-carene was rapid and finally led to the formation of (1S)-3-caren-5-one and (1S)-2-caren-4-one as equally abundant major products. The time-course of the reaction indicates that some products abundant at the beginning of the reaction (e.g. (1S, 3S, 4R)-3,4-epoxycarane and (1R)-p-mentha-1(7),2-dien-8-ol) were consumed by a subsequent transformations. Thus, a precise selection of the biotransformation time may be used for a production of specific compounds.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The relative abundance (in %) of (1S)-2-carene and its biotransformation products in time-course; Legend: □, (1S)-2-carene; ■, (1R)-p-menth-1(7),2-dien-8-ol; –, (1S,4R)-2-caren-4-ol; ×, p-cymen-8-ol; ○, (1S)-2-caranone; ●, (1S)-2-caren-4-one; +, (1S)-3-caren-2-one; ∆, (1R)-p-menth-2-en-7,8-diol; ▲, (1R,4R)-p-menth-2-en-1,8-diol.
Scheme 1
Scheme 1
(1S)-2-Carene (1) and its biotransformation products—(1S,4R)-2-caren-4-ol (3), (1S)-2-caren-4-one (5), (1S)-3-caren-2-one (9), (1S)-2-caranone (10), (1R)-p-mentha-1(7),2-dien-8-ol (4), (1R,4R)-p-menth-2-en-1,8-diol (6), (1R)-p-menth-2-en-7,8-diol (7), and p-cymen-8-ol (12).
Figure 2
Figure 2
The relative abundance (in %) of (1S)-3-carene and its biotransformation products in time-course; Legend: □, (1S)-3-carene; ◊, 1,4-cineole; ■, (1R)-p-menth-1(7),2-dien-8-ol; ∆, (1R)-p-menth-1,5-dien-8-ol; ▲, (1S,3S,4R)-3,4-epoxycarane; –, m-cymen-8-ol; ×, p-cymen-8-ol; ○, (1S)-2-caranone; ●, (1S)-2-caren-4-one; +, (1S)-3-caren-2-one; -, (1S)-3-caren-5-one.
Scheme 2
Scheme 2
(1S)-3-Carene (2) and its biotransformation products: 1,4-cineole (23) (1R)-p-mentha-1(7),2-dien-8-ol (4), (1R)-p-mentha-1,5-dien-8-ol (22), p-cymen-8-ol (12), m-cymen-8-ol (13), (1S,3S,4R)-3,4-epoxycarane (11), (1S)-2-caren-4-one (5), (1S)-3-caren-5-one (14), (1S)-3-caren-2-one (9), and (1S)-2-caranone (10).
Scheme 3
Scheme 3
Structures of (1S)-3-carene (2) biotransformation products formed by various organisms according to literature [8,9,10,11,13].
Scheme 4
Scheme 4
Structures of synthesized reference substances.
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