Diesel Trees - Bioenergy Crop Plants - page 622

taBle 24.1
three major sesquiterpenes Present in the oleoresins of copaifera species

Percentage in
oleoresin species reference compound

Copaifera langsdorfii Gramosa and Silveira

2005

53.3
8.7
6.5

β-Caryophyllene
Germacrene B
β-Selinene

Copaifera martii Zoghbi et al. 2007 42.6 a

15.7 a
5.0 a

β-Caryophyllene
δ-Cadinene
β-Elemene

Copaifera multijuga Veiga Junior et al. 2007 57.5

8.3
2.6

β-Caryophyllene
δ-Humulene
β-Bergamotene

Copaifera cearensis Veiga Junior et al. 2007 19.7

8.2
8.2

β-Caryophyllene
δ-Copaene
β-Bisabolol

Copaifera reticulate Veiga Junior et al. 2007 40.9

6.0
4.1

β-Caryophyllene
δ-Humulene
β-Bergamotene

Copaifera trapezifolia Veiga Junior et al. 2006 33.5

11.0
7.6

β-caryophyllene
Germacrene D
Spathulenol

a Number represents an average of 11 sampling dates.

The cellular mechanisms involved in transport, storage, and secretion of oleoresin constituents
against the concentration gradient present in resin ducts are not well understood (Langenheim
2003; Keeling and Bohlmann 2006). Synthesis of terpenoids present in conifer oleoresins typically
involves TPSs and cytochrome P450 oxygenases (P450). A conifer diterpene synthase (PtTPS-LAS)
and the first diterpene P450 (PtAO) have been localized to plastids and the endoplasmic reticulum
(ER) using a green fluorescent protein in tobacco leaf cells (Ro and Bohlmann 2006). On the basis
of the lack of accumulation of diterpenes in cells, these authors suggest that a transport mechanism
must be in place to move the diterpenes into the ER or cytosol of cells.
Although Copaifera oleoresin exudes from resin ducts during tapping, no experiments have
confirmed which tissues are responsible for production of chemical constituents in the oleoresin.
Calvin (1980) hypothesized that the constituents in Copaifera oleoresin must be synthesized in the
canopy of the tree and seep down through the resin ducts. In Norway spruce, diterpene synthases
have been localized to epithelial cells surrounding resin ducts using protein-specific antibodies
(Keeling and Bohlmann 2006). Recently, we have found that the sesquiterpenes are present in
C. officinalis oleoresin in leaves and stem tissue of seedlings as well as leaves, stems, and roots
of 2-year-old saplings (Chen et al. 2009). The presence of sesquiterpenes in different tissues at
different ages could indicate transport or changes in regulation of TPS gene scripts signaled by
development. In addition, the terpenes detected in oleoresins also appear in other tissues such as
seeds (Gramosa and Silveira 2005). The seeds also have different sesquiterpenes that are not seen in
oleoresins such as γ-muurolene, perhaps suggesting that different TPSs function in different tissues.

24.4 BIoloGIcal FunctIons oF oleoresIn
The principal chemical constituents of Copaifera oleoresin are terpenoids. Therefore, understanding
the biological/ecological roles of terpenoids will allow us to understand the roles of Copaifera