135
IPACIIJFTI((;
§OlUTJHIWJEST
FORJE§T & RANGJE JEXJPJERlMlJENT §TATTI ON
1967
P .O . Box 245
Berkeley,
Monoterpene Composition of
some preliminary findings
RICHARD H.SMITH
Until recently, little was known
of the monoterpene and other resin
characteristics of pine hybrids. The
development of analytical procedures
using gas-liquid chromatography has
begun to fill this gap in knowledge.
Preliminary data from a study at
the Institute of Forest Genetics,
Placerville, Calif., indicates that
monoterpenes can be used to determine
the hybrid origin of a tree if the
composition of the parents is qualitatively different. But difficulty
may be encountered if only quantitative differences in monoterpene composition exist between the trees.
Early Studies
Data on the turpentine composition
of pines have been compiled by Mirov
(1961). These data were gathered by
Mirov and others by the analytical
procedures used at that time, largely
extraction and reaction; Mirov briefly
mentioned gas chromatography as a new
method. Williams and Bannister (1962)
update the information for 22 species
of pine grown in New Zealand, by the
use of gas chromatography. Since that
time gas-liquid chromatography has
been used for the analysis of other
pine species.
Little is known, however, about the
monoterpenes or other resin characteristics of pine hybrids. Mirov reports
that certain resin properties of the
Pinus contorta X banksiana hybrid
Service
-
U.
94701
ABSTRACT:
Pine Species and Hybrids
Forest
California
S.
Xylem resin samples, ?btained from 72 freshly cut
pine
stumps at the Institute of Forest
Genetics, Placerville, Calif., were
analyzed for monoterpenes by gasliquid chromatography. Very little
or no qualitative or quantitative
variation could be attributed to annual ring, time of securing sample,
and period of storage of sample up
to 1 year.
The 34 hybrids sampled
generally had resin properties that
were intermediate between those of
their parents. Several pines had
terpenes whose presence hitherto has
been unreported.
RETRIEVAL TERMS:
Intraspecific variation; geographic variation; chemotaxonomy; gas chromatography; monoterpenes;Pinus.
Line Project:2201.
(1956) and the P. ponderosa X jeffreyi
hybrid (1961) were intermediate between
the two parents. Zobel (1951) used
physical resin properties as one means
of determining the P. jeffreyi X coulteri hybrid in natural stands. Bannister et al. (1959) and Forde (1964)
studied the inheritance of monoterpenes
of the P. attenuata X radiata hybrid
by using gas-liquid chromatographic
analyses; they found a strong adherence to intermediacy in their studies.
.Most recently, Critchfield (1966) reports the use of gas chromatographic
analysis of monoterpenes to verify
hybrids of P. sabiniana X coulteri
and P. sabiniana X torreyana.
Study Site and Procedures
The opportunity to gather preliminary data on the monoterpene composition of many pine hybrids developed
during a partial thinning of a 10- to
25-year-old hybrid plantation at the
Institute of Forest Genetics. At the
same time, additional data could be
obtained on inter-ring constancy of
terpene composition that had been
found in P. ponderosa (Smith 1964a).
Many of the hybrids used were described by Little and Righter (1965).
Department
of
Agriculture
Each tree was cut to an 18-inch
stump in early February 1964. Resin
flow does take place then, though at a
greatly reduced rate . Each stump was
recut to a 12-inch stump within a day
or two to make the cut level . Each
cross section was carefully scraped
with a new razor blade to remove all
debris and to eliminate the smearing
effect of the saw.
thermal conductivity detector. The
column was stainless steel, 8 feet by
1/4 or 1/8 inch; the solid support was
60/80 or 80/100 Chromosorb W acidwashed, respectively, for the two diameters. The liquid support was 7-1/2 or
10 percent S, S' oxydipropionitrile.
Operational parameters were 130 to
140°C. on the injector, 55 to 65°C. on
the column, and 140 to 150°C. on the
detector, filaments at 200 ma., and
helium at 40 to SO mI . per min . Sample
size ranged from 0.2 to 0.6 ~l. for
distillates and 1.0 to 3.0 ~l, for pentane preparations. Variations in these
parameters did not alter the analysis.
By the next day resin was beginning to exude from the individual
annual rings. A small sample of
resin was obtained from the 1963 annual ring by carefully moving a thin
glass rod along the annual ring. The
rod with the drop of resin was immediately placed in a 2 mI . screwcap
vial . From 0.1 to 0.05 mI. of pentane (chromatographic quality) was
added to the vial and agitated to
dissolve the resin from the rod; the
vial was tightly sealed immediately
with a teflon-gasketed screwcap. This
procedure was repeated for the oldest
ring from which resin could be obtained. No effort was made to secure
both ring samples from the same radial segment.
Quantitative determinations were
made by normalizing peak areas obtained
with a disc integrator. Qualitative
determinations were made by comparing
relative retention times with knowns
and known mixtures and by the introduction of knowns into the sample. The
qualitative determinations were checked by analyzing at least one sample
from each tree on a LAC-446 column at
90°C. A further check on qualitative
determination was made by analyzing
the resin from trees which represented groups of trees on an Apiezon-L
column at 110°C. The qualitative
determination of both a-thujene and
terpinolene should be considered tentative because of the lack of relatively pure known standards. The distillate of P. muricata was used as a
standard for identifying the terpinolene peak (Blight and McDonald 1963).
There was agreement among the columns
in the relative retention time for the
peak described by Blight and McDonald
as terpinolene with and without this
distillate as a standard. The determination of a-thujene was based on
the agreement of relative retention
times .on the oxydipropionitrile and
Apiezon columns (Klouwen and ter Heide
1962).
The following day all resin that
had collected on the stump surfaces
was carefully scraped up and placed in
corked vials. These samples were held
at 35°F. until the resin could be distilled in a Hickman molecular still at
40°C. for 24 hr. at atmospheric pressure. If there was not enough resin
for distillation--usually less than 1
or 2 cC . --we added an approximate
equal volume of pentane. The pentane
preparation or the distillate was
transferred to the standard 2-ml.
screwcap vial. The distillations
were completed within 3 weeks after
the collection of the resin. All
prepared samples were held at 35°F.
until analyzed.
A few stumps were resampled the
second day after cutting to determine
the effect of a I-day delay.
Each of the three samples from each
tree was analyzed at least once within
3 months after preparation on the 1/8inch oxydipropionitrile column.
At
least one sample from each tree was
The monoterpene analysis was made
by a gas-liquid chromatograph with a
-2-
analyzed on the LAC column within 6
months. One year after preparation
one sample from each tree was analyzed on the 1/4-inch oxydipropionitriIe column.
of full sibs; heptane was involved in
three out of the four which were not
intermediate (table 3).
Results and Di scussion
In interpreting these results it
should be emphasized that all data
pertain to the normalized monoterpene
composition of xylem resin; other
resin systems might be quite different. The term "monoterpene" has been
liberally applied to include aliphatic
hydrocarbons, such as heptane, nonane,
and undecane, which volatilize before
or along with the monoterpenes. In
most cases only the generalized monoterpene composition of species is considered, since the resin ·of the actual
parents was not obtained and in many
cases could not be obtained if so desired. The interpretation of the
analysis of hybrids must, therefore,
be considered preliminary. The results
from this study were as follows:
• No change occurred in the monoterpene samples during the I-year
period between the first and second
series of analyses.
• Evidence suggests that some of
the natural hybrids used in breeding
are not valid FI but apparently are the
result of one or more backcrosses to
one of the parents (table 3).
• Several terpenes, whose presence
had not yet been reported, were found
in some pines as follows (table 3): P.
engelmannii--camphene, myrcene, B-phellandrene; P. strobus--camphene, myrcene,
limonene; P. monticola--nonane, myrcene,
B-phellandrene; P. griffithii--undecane,
B-pinene, myrcene, limonene; P. flexili 0
--nonane, B-pinene, 3-carene, sabinene,
myrcene, limonene, B-phellandrene, terpinolene; P. strobiformis (reflexa)-camphene, sabinene, myrcene, limonene,
B-phellandrene; P. canariensis--camphene, B-pinene, 3-carene, myrcene, Bphellandrene; P. longifolia --myrcene,
limonene, B-phellandrene, y-terpinene.
Acknowledgment
This study would not have been possible without the untiring efforts of
many persons, particularly F. I. Righte~
who was responsible for developing most
of these hybrids; and the technical
staff of the Institute of Forest Genetics, who performed the work necessary
for producing them. Their efforts are
gratefully acknowledged.
• Good agreement was obtained in
comparing the first and second day's
sampling of the recut stump surface
(table 1). This finding indicates
that the I-day delay between stump
preparation and sample collection had
no apparent effect on the resin composition at this time of the year and
was, therefore, a valid procedure .
Literature Cited
Bannister, M. H., Brewerton, H. U. ,
and McDonald, I. R. C.
1959.
Vapour-phase chromatography
in a study of hybridism in Pi nus.
Svensk Papperstidn. 62(16):567573, illus.
• The three samples extracted
from the same tree ; i.e., the 1963
annual ring, the oldest ring with resin, and the total resin from the
stump in all trees studied did not
differ appreciably in monoterpene composition (table 2).
Bannist er, M. H. , Willi ams, A.L., M c D on a l ~
I. R. C., and Forde, M. B.
1962.
Variation of turpentine composition in five population samples
of Pinus radiata.
New Zeal. J.
Sci. 5(4):486-495.
• There was a general qualitative
intermediacy among all 34 hybrids
(table 3).
• There was quantitative intermediacy in three out of seven pairs
-3-
Blight, M. M., and McDonald, I.R.C.
1963.
Note on L-sabinene from
Pinus muricata. New Zeal. J. Bot.
6 (2): 229-231.
Mirov, N. T.
1956.
Composition of turpentine of
ZodgepoZe X jack pine hybrids. Can.
J. Bot. 34:443-457.
Critchfield, William B.
1966.
CrossabiZity and reZationships of the CaZifornia big-cone
pines. 2nd Genet. Workshop Soc.
Amer. Forest. and 7th Lake States
Forest Tree Impr. Conf . Proc. U.S .
Forest Servo Res. Pap. NC-6(1965).
N.Central Forest Exp. Sta. pp.
36-44, illus.
Forde, M. B.
1964.
Inheritance of turpentine
composition in Pinus attenuata X
radiata. New Zeal . J. Bot. 2(1):
53-59.
Mirov, N. T.
1961.
Composition of gum turpentines
of pines. U.S. Dep. Agr. Tech. Bull.
1239. 158 pp., illus.
Smith, R. H.
1963.
The monoterpenes of ZodgepoZe
pine oZeoresin. Phytochemistry 3
(2):259-262.
Smith, R. H.
1964a. PerenniaZ constancy of the
mono terpene synthesis in the wood
oZeoresin of pinus ponderosa. Nature 202(4927):107-108, illus.
Smith, R. H.
1964b. Variations in the monoterpene
composition of ponderosa pine wood
oZeoresin. U.S. Forest Serv.Res.
Pap . PSW-15. Pacific SW. Forest &
Range Exp. Sta. 17 pp., illus.
Forde, M.B., and Blight, M. M.
1964.
GeographicaZ variation in
the turpentine of bishop pine.
New Zeal J. Bot. 2(1):44-52.
Klouwen, M. H., and ter Heide, R.
Williams, A. L., and Bannister, M. H.
1962.
Studies on terpenes. I. A
1962.
Composition of gum turpentine
systematic anaZysis of monoterpene
from twenty-two species of pines
hydrocarbons by gas-Ziquid chromagrown in New ZeaZand. J. Pharmacol.
tography. J. Chromatogr. 7:297-310.
Sci. 51(10):970-975, illus.
Little, E. L., and Righter, F. I.
1965.
BotanicaZ description of forty artificiaZ pine hybrids. U.S.
Dep. Agr. Tech. Bull. 1345. 47 pp.,
illus.
Zobel, B.
1951 .
OZeoresin composition as a
determinant of pine hybridity.
Bot. Gaz. 113:221-227
The Author'_ _ _ _ _ _ _ _ _ _ _ __
RICHARD H . SMITH is in charge of th1s Sta'
tioh ' s r esearch on the b i ology , ecology ,
and control of destructive forest insects,
with headquarters 1n Berkeley . He holds
B. S . (1942) and M. S . (1947) degrees from
New York State University College of Forestry . and a Ph . D. degree (1961) from the
University of California , Berkeley .
-4-
Table 1.- - Monoterpene composition of resin samples taken at 24 - hour intervals from cross section · of five fresh-cut stumps
IFG Hep -
Speci es or hybrid
of Pinus
No .
tane
No - a-pi - Unde - Camnane nene
cane phene
r3-pi nene
3-car - Sabi nene
ene
a-phellan ~
drene
Myr- Limo- r3-phellan .. y-terpi- Unknown
No . 2
cene nene drene
nene
iterpinoene)
Percent
ponderosa X ponderosa
var . scopulorum
161
ponderosa X engelmannii
18
~~5
---- ------ --
1.1
.5
28 . 0
29. 4
-----
0.7
.5
33.4
34.8
24. 2
23.1
--
--
---
3.4
3. 3
6. 7
6.2
1.1
1.0
---
1.5
1.0
39. 3
40 . 7
--
(~3
13.8
13. 2
35 . 6
35 .8
--
--
--
3. 7
4. 1
4.3
3.6
1.2
.5
gj5
2. 1
1.6
11.4
8. 2
2. 4
1.9
26 .8
26 .9
26 . 0
26 . 5
8;5
--
3 . 2 13.8
3 . 4 14. 6
16 . 2
17 . 2
2. 5
1.2
.9
2.1
---
.3
.6
4.2
4. 2
1.0
~~5
.3
.5
(!I)
--
6.3 0 /)
3.7
4. 7
3. 4
-------
(1I~
1.
1.4
2. 2
----
--
[jeffreyi X](jeffreyi X
coulteri) X ponderosa
12
j effreyi X (jeffreyi X
95
83 . 4
82 . 9
0. 1
1.6
4 .8
2. 6
-----
75
85 . 3
91.4
1.0
.9
1.3
.6
---
coulteri)
j effreyi X (jeffreyi X
coulteri)
(1/)
--
2. 5
2. 6
--
--
- - - - - - - - - - - -----
--
- - - - - - -- - - - -
------------
.. Ct4¥'·
----
1Trace.
I
~
Table 2 ,- -Monoterpene composition of resin of selected pines from three sources on fresh-cut stumps
I
Species or
hybrid of
IFG Source
Hep -
No .
tane
of sampIe!
No - a -pi - Unde - Camr3-pi nane nene
cane phene nene
3-car- Sabi - a-phel - Myr - Limo ene
nene
landrene cene nene
Pinus
r3-phely- terpi - Unkno'M1
No . 2
landrene nene
ite~~inoene
Percent
ponderosa X
wind
938
ponderosa var .
scopulorum X
engelmannii
25
(j effreyi X
13
ponderosa) X
jeffreyi
j effr?i X
( je freyi X
peuce)
1
10
S
94. 8
94.1
89 . 8
82
1
20
S
93.4
93.8
87 . 9
3
1
8
S
~5
2. 5
coul ted)
monticola X
(strows X
1
8
S
-------
1
12
S
See footnotes at end of table .
---------
6.4
6. 7
6. 1
-~~
--- (1/)
23 . 2
23. 1
21.9
43. 4
42 . 2
42 . 5
---
--
----
4.9
6.2
5. 9
19.6
17 . 7
20. 2
0.6
1.6
.7
--
---
---
1.0
.9
.5
.2
.4
.4
(.2/)
54 . 3
54 . 9
56 . 7
----
1.9
1.5
,8
13. 1
14. 6
13. 2
25.8
24.4
25 . 3
.8
2. 7
2. 7
3. 7
----
.2
.7
,3
.2
.5
1.2
1.2
1.2
2. 0
<r.i
1.4
.7
1.8
1.9
a;~
1.5
.4
1.5
~~5. 5
-1.3
52. 4
52 . 0
50. 3
-----
2. 8
2. 2
2. 5
42. 1
44. 0
39 . 6
(21)
(11)
--
.4
.4
1.4
.6
------
--
2. 0
1.3
1.4
----
.7
.7
.8
(21)
----
-------
1.1
1.5
2.1
(.21)
--
.3
2. 9
1.5
3. 1
.3
.7
1.2
.3
.4
1.0
.7
,7
1.6
----
--
.5
-.9
aj5
0. 1
1.8
1.9
2. 5
~~~
1.7
2. 0
1.6
---
---------
--
-(1/)
--
----
-.2
-
Table 2 ,--Monoterpene composition of resin of selected pines from three sources on fresh-cut stumps , COntinued
Hep - No - a .. pi - Unde cane
tane nane nene
IFG Source
Species or
hybrid of
No .
Pinus
of ~am pI e
Cam ~
phene
S-pi nene
Sabi - a -phe! - Myr - LimoI andr ene cene nene
nene
3-car ene
S~phe l -
landrene
y- terpi - Unknown
No . 2
nene
tterplno ene)
Percent
contorta var .
murrayana X
contorta var .
c ontorta
echinata X
taeda
14
caul teri X
300
wind
I
Q\
I
--
1
9
S
~~
1
20
S
-----
----
1
12
S
~~
.. ..
--
5
----
-
,
--
0. 5
.7
1.1
7. 5
11.2
15. 5
2. 3
4.2
4.8
1.9
1.7
3. 2
65 . 2
67 . 0
62. 7
---
1.1
.5
.6
30 . 1
29. 9
32 . 1
~5
.-.-4
-
-
-----
53 . 1
56 .6
60. 3
1.6
3. 5
1.4
1.5
2. 5
1.9
2. 8
2. 8
(1/ )
1.6
2.8
2. 3
(~~
6. 1
6. 6
10 . 7
---
(Y)
---
---
1.9
1.7
3.7
75 . 5
69 .8
57 . 8
--
--
--
----
.7
.5
1.0
2. 5
1.5
2. 7
.4
.5
.6
---
--=0
1.6
1.3
1.4
1.4
1.5
1.6
36 . 2
30. 3
29 . 4
----
1.4 2. 8
2. 1 2. 1
3.2
.3
1.0
1.0
.4
11 = 1963 annual ring
>1= year of ring prior to 1963
S = scrape sample from whole stump.
2rrace .
Table 3 .--Data on the monoterpene compo s ition of the resin from the 1963 annua l rin g of pin e species and hybrids cut i n th e
Febru ary 1964 thinning at the In stitute of For est Genetics, Pl acerville, california
Species or
hybrid
1
of
P inus
.,
c
..,'"
.,0.
ci
Z
0
~
.....
::I:
.,
c
'C0"
Z
.,
.,c
....c
0.
,
<:3
N
.....
ci
Z
.:l
C
::>
.,
c
.,u'"
-0
C
::>
.,
.,c
..c:0.
e
u'"
.,
.,c
....c0.
crl
.,
.,c....
u
',"
'" 3
.,
.,c
...,c
.0
en'"
,
.,
.,c
C
'"
.,
.,..c:-o.,.... .,uC
.,
.....
..... c
0.
,
<:3
C
a
e
....
;>,
::;:
j
.,
,
.,C
C .,
.C..,
..c:-o
..,.,,
......,'" .,c....
0. '
en.
0.
N
N
ci
....
Z
>-
:i
c
::>
Remarks
Percent
1. j effreyi X jeffreyi
2. j effreyi X ponderosa var. scopulorum
885
96
1
1
-
1
-
*
1
+
-
1
-
1
-
-
4
Similar to that reported.
14
29
1
4
+
+
1
1
57
-
-
2
1
1
*
4
Qu a lity intermediate : heptane , nonane ,
and camphen e of jeffreyi ' 3 -carene
myrcene , limonen~ ~ and terpinolene of
var. scopulorum .
Remaining constituents in small amounts in both species .
Qu antity not intermediate ; heptane at
29 percent far below the expect ed 47
p ercent . while 3- carene at 57 percent
well above the expected 35-40 p ercent.
,
See footnotes at end of t able .
....
Table 3 .- - Data on the mono terpene composition of the resin from the 1963 annual ring of pine speci es and hybrids cut in the
February 1964 thinning at the Inst itute of For est Genetics, Pl acerville, California, continued
Sp ec ies or
hybrid 1
N
Q)
of
c::
0
Z
".....
~
Pinus
...'0."
Q)
::c
Q)
c::
c::
'"
0
z
,
....
Q)
Q)
Q)
c::
Q)
c::
c::
c::
Q)
c::
Q)
Q)
Q)
c::
Q)
c::
....
c::
c::
Z
u
..c
.:t
"0
E
0.
u
~
~
U
C!l
<"l
0.
,
c:3
0
c::
'"
Q)
c::
Q)
...
0.
'"
,
..
Q)
....
',"
.D
'"
Ul
Q)
c::
'" Q)
....
c::
Q)
c::
Q)
c::
Q;
. ..c::
,
:»
....
'"
Q)
Q)
..:::-0
u
0
....E
0.
;:;:
c:3
....l
c::
'" Q)
....
c::
....
Q)
Q)
..
c::
Q)
c::
....
.
0.
N
N
Remark s
0
Z
0.
...
.:t
C!2.
>-
~
..c"O
Q)
c::
Percent 3
5
32
-
2
+
+
*
2
45
+
-
12
1
1
-
4
Similarity to No . 2 not surprising,
since var . scopulorum was fo~nd to b e
qui te similar to washoensis ;
trace
amount of a -thujene may be found in
both var . scopulorum and washoensis .
4 . (a) (jeffreyi X ponderosa ) e X ponderosa
13
+
+
8
-
+
1
21
47
-
-
6
13
2
+
2
(b) (i effreyi X pon derosa ) e X ponderosa
8
4
1
10
-
-
*
21
39
-
-
7
15
1
+
Full siblings : the hybrid is a true
Fl '
Similar qualitative composition .
However, < 5 percent heptane is far
below expected 23 perc ent if there
was intermediacy ; y-terpinene f-ounrl
in ponderosa .
3
13
95
+
3
-
-
*
*
1
-
-
1
+
+
,
-
Half sib of No . 4; hybrid the common
parent. Heptane at 95 percent far
above the expected 71 percent . Note
effect of changing one parent.
20
72
1
12
-
+
+
1
1
+
-
2
1
11
-
-
Full si bs ; however, only (c) and (d)
are quantitatively similar; (a) and
(b) differ conSiderably in heptane ,
a -pinene , and -phellandrene .
Sm~l ~
3.
I
'-.I
I
jeffreyi X washoensis
5. ( j effreyi X ponder osa) e X jeffreyi
6. (a)
jeffreyi X ( jefrreyi X cou lt eri)O
amount of (X-pinene,
0 8-2 .
(b) jeffreyi X (jeffreyi X coulteri) 1
93
+
1
-
+
2
+
*
+
-
1
+
3
-
-
85
1
1
-
-
1
+
*
+
-
6
+
5
-
-
(c)
jeffreyi X (jef75
freyi X cou lteri )O
(d)
jeffreyi X (jef 95
freyi X coulteri)?
83
*
5
-
-
1
3
1
+
-
3
*
4
- -
1561
7 . (a) ieffreyi X (jeffreyi X coulteri)O
77
+
10
-
1
1
1
+
*
-
4
1
5
- -
I
I
See footnotes at end of table .
- _._-
myrcene,
anrl.
I
-
phellandrene, components generally
high in coulteri, suggests natural
hybrid is not a true Fl but has been
backcrossed one or more times to
jeffreyi.
Full si bs but not as similar as ex pected, differing appreciably in hep tane , 77 and 69 percent ; a- pinene , 10
and 16 p e rcent . No common par e ntag e
with No . 6 .
I
Table 3 . - -Data on the mono terpene composition of the resin from the 1963 annual ring of pine species and hybrids cut in
February 1964 thinning at th e Institute of Forest Genetics , Pla ce rville, California . continued
Species or
N
~
hybrid 1 of
.
0
Z
t.:l
fz..
Pinus
.,
C
II>
.,
til
C
..,til
0.
C
0
z
II>
C
C
...a. .;;.ob .,
II>
C
.
.
.
.....
II>
til
II>
.,C
Z
u
..c
C
-0
C
E
a.
til
u
II>
II>
II>
C
.,....C
0.
u
.,C
...
.,C
.
til
ell
C
til II>
-< C
-< .,
II>
...
....
..c-o
.,uC
til
CIl
<:3
:;:
C
.D
.,
a.
II>
C
C
II>
..
0
....
».
.E
....l
N
N
til II>
...
.
+'
.
.;;.
>-
::>
.,C ....-<C
., .,....
C
II>
the
..c-o
0.
C
....0.
II>
0
Z
Remarks
C
.....
:z:
559
69
1
16
-
1
+
3
2
1
+
2
1
3
-
1
589
88
+
5
-
1
+
*
1
+
-
1
1
3
-
-
No common parent age with Nos. 6 and
7 . shows e xpected differences and
similarities between nonsibs. Considerable similarity among all six
individuals of this hybrid pr esented
in Nos . 6 . 7. and 8 of this table.
<:3
::>
::>
'" 3
err
P ercent
7. (b) jeffreyi X (jeffreyi X coulteri)
°
8.
jeffreyi X (jeffreyi
X coulteri) O
9.
[jeffreyi X (1effreyi
X coulteri O) X pont,.
derosa
12
-
+
11
-
2
+
27
26
+
-
3
14
16
-
4
Lack of heptane notable. since about
35 perc ent expe c ted ; 16 p e rcen t Bphel1andrene c onsiderably above expected 7-9 per~ent .
Amounts of
other components within expect ed
range.
10 .
[jeffr eyi X (1effteyi
X coul ted O )
X jeffreyi X ponderosa
25
20
1
12
-
1
-
40
5
+
-
Z
8
12
-
-
Little can be s aid about this complex hybrid . Compos ition wi thin
the exp ected limits. since both
parents are or contain a natural
hybrid which may not be a valid Fl '
11. (a) cou lt e ri X wind
300
+
+
53
-
2
2
2
+
2
+
2
1
36
-
1
Compos4 tion falls within reported
range.
( b) coulteri X wind
57
1
1
43
-
4
+
3
+
+
+
15
5
28
-
-
12 . (a) ponderosa X wind
483
-
-
5
+
-
-
15
51
+
-
9
16
1
+
3
( b ) ponderosa X wind
938
-
-
6
+
-
+
23
43
-
-
5
20
1
+
2
13 . (a) ponderosa X wind
654
+
-
15
-
-
*
64
+
-
-
3
16
1
-
-
(b ) Ponderosa X wind
401
+
-
12
-
-
*
62
1
-
-
7
18
1
-
-
I
00
I
°
-
Half sibs through female parent.
Compositions similar and within
expect ed range. since great r ange
has been found for !his pine (Mirov
1961 ; Smith 1964b) .
Simil a r ity a coincidence. since derived from two different wind-pollinated p arents .
I nteresting to note
tha t both essenti ally l ack 3 -carene.
--
See footnot e s at end of table .
Table 3. - - Data on the monoterpene composition of the resin From the 1963 annual ring of pine species and hybrids cut in the
February 196+ thinning at the Institute of Forest Genetics, Placerville, California, continued
N
Species or
hybrid
1
Q)
.;
of
Pinus
Q)
c:
Q)
0.
c:
l1I
c:
:x:
z
Z
.,l1I
~
....
Q)
0
c:Q)
....c:
0.
,
<::l
,
....
.;
Q)
Z
.:l
c:
::>
Q)
c:
l1I
c:
Q)
u
Q)
.<:
0.
el1I
"0
c:
u
::>
OJ
Q)
Q)
c:Q)
.c:...
...
c:Q)
c:
u
:0l1I
c:Q)
l1I
0.
M
cO
Percen t
CJl
OJ
c:
.... c:
l1I OJ
.... OJ
OJ ...
'<:"0
0.
,
<::l
Q)
Q)
c:Q)
u
...
:>0
::;;
c:Q)
c:
0
e
::l
c: Q)
.... c:
l1I
....
Q)
Q)
...
.<:"0
0.
cD
c:
....c:
N
N
Q)
0.
...
.,,
Q)
.;
Z
:i
Remarks
c:
>-
::>
3
14. (a) Ponderosa X
(jeffreyi X
coulteri)o
28
69
2
13
-
2
+
2
1
1
-
3
+
8
..
-
(b) ponderosa X
(jeffreyi X
coulteri)o
32
66
2
15
-
+
1
1
1
1
-
4
1
10
-
-
(c) ponderosa X
(jeffreyi X
coulteri)o
2
80
1
8
-
1
1
1
1
*
-
3
1
5
-
4
5
5
41
-
3
-
26
-
-
-
4
16
1
-
-
Composition somewhat as expected
- - heptane and large amount of apinene fro~ montezumae (Mirov
1961) and - pinene, myrcene, and
limonene from ponderosa ; nonane
and undecane probably from monte zumae ~ce neither found in the
hundreds of ponderosa examined ;
composition of montezumae based
on just a few trees . Lack of 3 carene of note , since lacking in
wind-pollinated offspring of this
same ponderosa (see No. 13a) . Reported composition of montezumae
quite variable, falling into two
types - - high a- pinene (Mirov 1961 )
and high 3-carene (Williams and
Bannister 1962) .
6
-
-
11
-
-
-
40
26
-
-
11
9
1
+
2
Composition lell within range
anticipated .
115
-
-
5
+
-
+
27
50
-
-
7
7
1
*
4
Nonsibs ; differ considerably but
fall within expected limits , since
both parent species very variable .
161
1
+
28
-
-
1
33
24
-
..
3
7
1
+
2
Full sibs ; (a) and (b) are quite
similar, whi Ie (c) differs in the
~ount of heptane, a-pinene, and
- phellandrene . Heptan e, > 66
percent , far above expected 25
percent , suggests nonapplicability
of quantitative intermediacy or
- \ natural not true F.
Same' suggestion made for a different jeffreyi
X coulteri in No . 6 . Also some
uncertainty about the ponderosa
parent ; in area where natural
hybrids of jeffreyi X ponderosa
are suspected .
I
<.D
I
15 . Ponderosa X montezumae
16. Ponderosa X washoensis
17 . (a) ponderosa X ponderosa var .
scopulorum
(b) Ponderosa X pon derosa var.
scopulorum
---
-
----
See footnotes at end of table .
------
Table 3.--Data on the monoterpene composition of the resin from the 1963 annual ring of pine species and hybrids cut in the
February 1964 thinning at the Institute of Forest Genetics, Placerville, California, continued
hybrid
1
,
N
Species or
.-<
OJ
of
Pinus
OJ
0
Z
c:
OJ
'"
0.
C
:I:
Z
~
~
....
OJ
~
0
c:
OJ
c:
0.
....
~
OJ
OJ
c:
c:
z
u
..c:
,,;,
'0
C
0
C
~
OJ
'"
OJ
0.
a
U
~
OJ
OJ
OJ
c:
OJ
c:
c:
...
c:
OJ
c:
0.
,
cr
u,
E
OJ
....
'"
'"
""
en
,
c:
'" c:
OJ
-<
-< OJ
OJ ...
..c:'O
,
0.
OJ
OJ
c:
OJ
...u;>,
:;;
~
c:
OJ
C
0
E
.-<
....l
OJ
c:
'" c:
OJ
-<
-< OJ
OJ ...
..c:'O
0.
cO
c:
OJ
c:
.-<
0.
...
OJ
N
N
0
Z
,
>-
,,;,
c
~
Remarks
~
Percent 3
18 . (a) ponderosa X pon derosa var .
scopulorum
153
+
-
32
-
-
(b) ponderosa X ponderosa var .
scopulorum
147
+
..
35
-
-
19 . (a) ponderosa X
engelmannii
18
-
-
40
-
(b) ponderosa X
engelmannii
16
-
-
40
(a) Ponderosa X
engelmannii
119
1
-
(b) ponderosa X
engelmannii
110
+
21. (a) ponderosa var,
scopulorum X
engelmannii
25
(b) ponderosa var.
scopulorum X
engelmannii
1
26
26
-
-
6
6
2
+
2
1
28
24
-
-
2
8
1
+
1
-
+
14
36
-
-
4
4
1
+
2
-
-
*
18
25
..
-
4
10
1
*
1
29
-
-
*
28
29
-
-
4
5
1
-
2
-
32
-
-
1
17
34
-
-
6
7
1
*
3
+
-
54
-
-
2
13
26
-
-
2
1
*
+
2
29
+
-
51
-
-
1
15
28
-
-
1
1
1
+
2
22. ponderosa var .
scopulorum X
ponderosa
8
+
-
32
-
-
1
7
35
..
-
11
12
1
+
2
Half sib of No. 21.
Change to
ponderosa male parent in No. 22
readily apparent ; decrease in apinene and increase in 3- carene ,
myrcene, and limonene.
S- pinen e
could go either way , depending on
ponderosa parent used.
23 . ponderosa var.
arizonica X
ponderosa
12
-
-
28
-
-
*
22
39
-
-
3
4
1
+
2
Composition within sxpected
range (Mirov 1961) .
.t
Full sibs and quite similar .
Ponderosa parent wi thout 3 - car ene, noted wi th Nos. 13(a) and
15 . Thus, the 3 - ca rene JJ\ .. No. 18
came from var . ,scopulorum .
'.
'"
I
t-'
o
At least half sibs and could be
full sibs with a common female
parent and a pollen mixture . Q..Ii te
similar except between 25 and 35
percent in 3 - carene. High a - pinene expected, since about 80 per cent reported for engelmannii
(Mirov 1961) .
I
20.
See footnotes at end of table .
Nonsibs, and nonsibs to No. 19 .
Composition within expected
range .
Source of small amount
heptane probably engelmannii,
since slight traces of it rarely
found in ponderosa .
Full sibs ; composition nearly
identical and well within anticipated range.
"
Tab l e 3 . --~a ta on the monot e rpene composition of the r e sin from t h e 19n3 ann ual ri n g of p i n e species a n d h ybr ids cut in t h e
Fehruary 196 4 thi n nin g at the I nstit u te of Fo r est Gen etics , Pl ace r vi ll e, Ca l ifornia, c on t i nu ed
Sp e ci e s or
,
N
.-<
Q)
c
Q)
hybrid 1 of
Z
P inus
~
....
ci
Q)
c
ci
C
Q)
Q)
C
C
.-<
0.
0
'C0"
Z
0.
.>l
<:3
~
-0
C
...'"
Q)
:z::
z
'"
Q)
C
~
Q)
Q)
cQ)
..c
0.
c
Q)
c
. -<
E
U
'"
0.
,
co.
Q)
c
Q)
...
'",
Q)
cQ)
c
. -<
0
.D
0')
r/l
'"
,
C
.....'" Q)c
.....
Q)
Q)
...
..c-o
0.
,
Q)
Q)
C
Q)
...0
;.,
::;;
<:3
Q)
C
C
Q)
cQ)
'" Q)
.....
C
C
0
..c-o
E
j
.....
Q)
Q)
...
0.
<D
C
.-<
0.
...
...,
Q)
>-
N
N
ci
Z
Remarks
d
c
~
P ercent 3
V3 1
-
-
95
-
-
2
2
-
-
-
1
*
+
-
-
Compo s it ion sim il ar t o tha t repo rted by Mi r ov . How.ever t small
~mo u n ts o f camp he n e, my r cene , and
- ph e ll a nd rene n o t r e p o rt ed.
2 5. e n gelmannii X p onde r osa var. sco pu lorum
11
-
-
17
-
-
+
1
73
-
-
2
1
1
*
4
a- p i n e n e c onside r ab l y l ower than
e xp ected and 3 -ca r ene c onsiderably
h igh e r , if t wo p are nt s typ ical.
Howeve r t c onside r able 3 -carene
variati o n f o und in va r . sco pul orum,
and enge lmann ii not extensively
analyzed.
26 . ( a ) washoensis X
wind
35
-
-
17
-
-
+
27
37
-
-
12
4
2
+
2
Half sibs throu gh female p arent ;
exhibit cons i de r ab l e similarity .
(b) wa s hoensis X
wind
36
-
-
9
-.
-
31
46
-
-
7
5
1
+
3
27 . (a) con torta var.
murra y ana X
wind
39
+
-
7
-
-
+
11
2
2
1
1
1
75
-
-
75
-
-
6
+
-
*
14
16
3
1
3
1
55
-
1
28 . ( a ) con t or ta var.
mur r ayana X contorta va r . contorta
5
+
-
6
+
-
1
8
2
2
1
3
2
76
-
*
( b) con to r ta var.
murrayana X cont orta var . eo n tor t a
3
+
-
8
+
-
1
4
18
2
1
3
2
59
-
1
V11
-
-
9
-
-
1
4
5
2
1
2
2
73
-
1
24 . engelmannii X wind
/
I
......
......
I
( b ) conto r ta var .
murr li¥ a tit! X .'
wi nd
29 . c ontorta va r . contorta X wind
,.
I.
-----
See footnot e s a t end of t a bl e.
·Half sibs th r os gh female p aren t ,
but giffer i n . - pi nen e , 3 -ca r ene,
and - phe ll a ndr ene . Howeve r ,compo si t i on with in e xp ec t ed range
( Mir o v 1961 ; Sm i th 1963 ) .
Half sibs t hr ou gh fema l e p arent ;
ma l e a poll en mi ~ .
Qu ite di ff e r en t
in 3 -care n e and -phel l andrene , but
genera l comp ositi on about as exp ec t ed.
Half sibs of No . 2 7 ; r ela t ed
p airs quite s imilar.
Similar to var . murrayana ,' disti n ct
ter p ene diffe r ences un l ikely between
var . murrayan a and vaT . contor t a .
Table 3. - -Data on the monoterpene composition of the resin from the 1963 annual ring of pine species and hybrids cut in the
February 1964 thinning at the Institute of Forest Genetics , Placerville , California , continued
Species or
hybrid
1
of
Pinus
.,
c
.,'"
.,C>.
ci
Z
~
.....
:I:
.,
c
'C0"
Z
.,
.,c
.,.c
,
C>.
<::l
N
....
ci
Z
.:1
:5
.,
c
.,u'"
.,
.,
.,
.c
.,.c
1-0
.,.C
E
C>.
,
.,c
u
',"
.,
U
CQ
(Y)
.,c
C>.
'0
c
'"
;:>
.,c
.,c
.....'" .,
.....
.,c
.,
,Q
.coo
C>.
,
u
'"
en
Percent
,
C
., 1-0
.,
.,c
.,c
C
0
1-0
;>,
::E
<::l
E
j
.,
,
C
.....'" .,
.....
.,c
.,
1-0
.coo
C>.
,
CD
.,C
.,.C
C>.
N
N
ci
.,.,,
.:1
:>-
;:>
1-0
Remarks
Z
C
3
12
-
-
55
-
-
1
23
2
+
+
2
1
18
-
-
Half sib of Nos . 27 and 28 ; a pinene and B- pinene of banksiana
~Williams and Bannister 1962 ) ;
- phellandrene of v~r . murrayana .
Quantitative intermediacy not
strong ; a-§inene a nd B- pin ene
high. and . - phellandrene low.
General intermediacy in resin
prop erties of thi s hybrid noted
some time ago by Mirov ( 1956 ).
7
-
-
75
-
-
2
9
-
-
-
4
2
9
-
-
Compos ition generally intermediate between two parent spec ies (Williams and Bannister
1962 ) .
14
-
-
65
- -"
-
1
30
+
-
-
1
3
*
-
-
Large percentage a - pinene expect ed ; however. amount of S- pinene
far exceeds that r e port ed for
either parent (Williams and Ban nister 1962 ) .
33 . attenuata X radiata
89
-
-
59
-
-
2
38
+
-
-
1
1
1
-
-
Compo sition similar to tha t reported ( Bann ister e t al. 1962 ;
Forde 1964) .
34 . attenuata X remorata
10
-
-
44
-
-
1
3
+
34
-
1
1
1
+
16
(a) nigra var. ceben nensis X ni g ra
1
-
-
92
-
-
2
2
-
-
-
1
2
*
-
-
(b) nigra var . ceben nensis X var .. ,#
8
-
-
95
-
-
2
2
-
-
-
1
1
-
-
-
1
-
-
93
-
-
2
3
+
*
-
1
1
+
-
-
30. contorta var . murrayana X banksiana
31.
rigida X taeda
32 .
echinata X taeda
I
~
N
I
35.
cebennensis
(c) nigra var . ce oennensis X va r ,l",calabrica
See footnotes a t end of table .
.
Has expec t ed compositi on -- high
a - pinene from attenuata and high
sabinene and terpinolene from
remorata (Forde and Blight 1964 ) .
Composition of these. all hybr ids
of nigra and two of its varieties
- -cebennensis and calabrica -- nearly
identical and practically the same
as that reported (Williams and Ban nister 1962) .
First three half
sibs , and last two half sibs . Only
point of not e is trace of 3 - carene
and sabinene in last three ; indicates var . calabrica as source ,
since neither reported in nigra .
Table 3.- - Data on the monoterpene composition of the resin from the 1 9~3 annual ring of pine species and hybrids cut in the
February 1961 thinnin g at the Institute of Forest Genetics, Placerville, California, continued
N
Species or
Q)
Q)
C
0
hybrid 1 of
Z
Pinus
ft
'"
0.
+'
Q)
::I:
H
Q)
c
'C0"
Z
C
....
ci
,
Q)
Q)
c
cQ)
c
Z
()
.<:
0.
,
~
'"
-0
E
;:J
;:J
Q)
. 0<
~
C
Q)
0.
C
'"
U
Q)
Q)
...
c
Q)
c
. 0<
()
.0
',"
'"
' 0<
0.
CD
Percen t
I
f-'
tN
I
35 . (d) nigra var . calabrica X nigra
var . calabrica
35
(e) nigra var . cala brica X nigra
1
Q)
cQ)
c
Q)
c
'"
Ul
Q)
C
'"
-<
-<
Q)
Q)
cQ)
C
cQ)
()
0
Q)
Q)
...
Q)
'<:-0
...;>,
0.
,
~
~
C
E
j
N
Q)
'" Q)
-<
C
-< Q)
Q)
N
C
C
...
'<:-0
0.
C
. 0<
0.
Z
+'
~
>-
CD
ci
...
Q)
Remarks
C
;:J
3
-
-
94
-
-
1
3
+
1
-
1
1
*
-
*
-
-
92
-
-
3
3
+
*
-
1
1
+
-
-
36 . strobus X wind
89
-
+
47
-
-
2
48
-
-
-
1
1
1
-
-
Composition resembles existing
data only remotely (Mi rov 1961 ).
Camphene, myrcene , and limonene
not reporte g; proportions of a pinene and -pinene quite different.
37 . ( a) strobus X
montico la
12
-
+
48
-
-
1
48
-,
-
-
1
1
1
-
-
28
-
+
57
-
+
5
36
-
-
-
1
+
+
-
-
Both about as expect ~d ; large
amount a- pinene and -pinene and
smaller amount camphene , myrcene,
limonene, and S- ph ellandrene .
Terpenes not too suitable in
determining hybridity of so ft
pines because of simila ri ty
between species .
38 . monticola X monti cola
136
+
*
81
-
-
4
12
-
-
-
1
1
*
-
-
Mirov's ( 1961 ) data show much
diff e rent proportions of a - pin ene
and . - pinene and do n § t report
nonane . myrcene . and -phellandrene.
39. (a) monticola )(
strobus
175
-
+
52
-
-
3
43
-
-
-
1
*
*
-
-
(b) monticola X
strobus
122
-
-
52
-
1
1
41
-
-
-
1
1
1
+
1
3
+
+
52
-
-
3
42
1
-
-
*
*
1
..
-
(d) monticola X
griffithii
49
-
+
61
-
5
+
31
4
-
-
+
+
+
+
+
These four hybrids of monticola
somewhat simi l ar and about as expected ; large amounts of a- p inene
and 8-p inene. small amounts of
§amphene, myrcene, limonene. and
- phellandrene . Two have measurable amounts of undecane ; two
others have measurable amounts of
3 -carene .
(e) monticola X
peuce
6
-
+
67
-
-
2
28
-
-
-
1
1
1
-
-
( b) strobus X
gd ffi thi i
(c) monticola l(
( peuce X strobus)ql
See footnotes a t end of table .
Table 3 .--Data on the monoterpene comp osition of the resin from the 1 963 annual ring of pine species and hybrids cut in the
February 1 96 4 thi nning . at the I nstitute of Forest Genetics , P lacerville , California , c ontinu ed
OJ
N
Species or
OJ
hYbrid
l
OJ
c:i
of
C
Z
fZ
.....
Pinus
OJ
"'0-
c
::t:
Z
+'
OJ
"'
C
0
....
C
OJ
...c
,
0-
~
0
Z
OJ
OJ
C
C
C
()
.J:
...
OJ
"'
OJ
.Yo
-C
:>
:>
C
C
OJ
0E
u"'
OJ
OJ
C
C
C
.
0-
()
OJ
en
OJ
OJ
...
C
"'
.D
0
'"
"
en"'
0
0
C
C
"'
....
....
OJ
OJ
C
OJ
..
.J:-C
00
OJ
OJ
c:
..»
C
0
c:
OJ
u
:::;;
~
OJ
E
:3
C
OJ
.... c:
"' OJ
.... OJ
OJ ..
.J: -C
,
0-
CD
...
N
N
C
..
0-
OJ
+'
,
0
Z
.
Remarks
~
C
>-
:>
Percent 3
40 . griffithii X grif£i thi i
41.
f1exi1is X f1exi1is
-
1
1
+
-
+
Undecane , B -pinene, myrcen e, and
limonene have not been p reviously
repo rted (Mirov 1961 ) .
13
-
2
1
1
-
6
Quite different from reported (Mirov
196 1 ) ; a - p inene only ter p ene recorded.
Th is is eirst r epor t ing of n o nane, undecane ,
- pinene f 3 -ca r ene . sabinene ,
myr cene, li monene , S- phel l andrene ,
and ter p inol e n e. Large amou nt 3 carene sugges t s with i n-species varia·
tion . Mirov did n o t repo r t it, and
would have if it had bee n there.
26
+
+
93
-
4
+
2
-
-
12
+
4
28
-
8
+
5
35
,
I
f-'
-
+>42 .
4
+
+
85
-
8
+
2
+
3
-
1
*
+
-
1
Somewha t exp ec t ed compo sition ; large
amou nt a. p i n ene and smal l er amounts
of other te rpenes .
,\113
-
+
69
.
+
2
10
-
17
-
+
+
+
-
3
\75 5
-
-
18
-
-
-
18
56
-
-
3
1
1
+
4
81
-
-
90
-
-
2
7
+
-
-
1
1
*
-
-
Onl y data o n th ese s p ec i es (Mirov
1961 ) does not report a numbe r of
terpenes : f or strobiformis no cam~henel sabinene, myrcene, 1 imonene ,
.phellandrene ; for 10ngifo1ia no
myrcene , limonene, B . phelland r ene ,
y - t erpinene , terpinolene ; fo r can ·
ariensis no camph ~ne , 6-p inene, 3 carene , myrcene, ( - phellandrene.
flexilis X gri f .
t..hi i
-:~' £-i
43 . (a) strobi f ormis
J( wind
(b) longi f o1 i a X
wind
(c) canarien sis X
wind
~
~;
1 . • '" T rue .F1 hybrid.
0= Natura l ly occu r ring hybrid .
~ = Origin of hybrid uncertain .
2Tentatively identified as
a -thujene and terpinolene,
res p ec t ive l y .
3.
+
fr om 0. 1 to 0 . 4 percent .
trace .
zero .
May not equal 100 percent for
each t r ee b ecause of r o u n di n g
of decimals .
4 Smith , R .£ . VaIiations i n the
monote r pene "'~'oinposition of
P inus j effreyi, P . washoensis ,
P . co u1teri , P . conto r ta . 1967' .
(MS . submitted to Forest Sci . )
Geog r ap hic variation of the mo n oterpenes o f
P inus p onderosa. 1964 . (Onpubl .
5peloqui n , R . L .
master's thesis on f i l e at
Stanf ord Univ'1 P alo Al t o , Cal if.)
ol