Mammalian exocrine secretions XVI. Constituents of secretion of supplementary sacculi of dwarf hamster, Phodopus sungorus sungorus

Article abstract of DOI:10.1023/A:1010380315961

As a first step in a study of the role of the secretion of the supplementary sacculi (buccal secretion) of the dwarf hamster, Phodopus sungorus sungorus, almost complete chemical characterization of the secretion was achieved. The 35 compounds identified include carbon dioxide, hydrogen sulfide, a large number of carboxylic acids (representing the bulk of the organic volatile fraction of the secretion), phenol, 2-piperidone, indole, two long-chain hydroxyesters, cholestrol, desmosterol, and lanosterol. The position of the double bonds in γ-icosadienyl-γ-butyrolactone and γ-henicosadienyl-γ-butyrolactone could not be determined, and these two compounds remained only partially characterized. Large variations were found in the relative concentrations in which the short-chain carboxylic acids are present in the secretions of individual animals, and although this aspect was not investigated in sufficient detail in the present investigation, the difference in the carboxylic acid profiles of the secretions of individual animals could play a role in individual recognition in this animal.

Full text of DOI:10.1023/A:1010380315961

Journal of Chemical Ecology, Vol. 27, No. 6, 2001
MAMMALIAN EXOCRINE SECRETIONS XVI.
CONSTITUENTS OF SECRETION OF SUPPLEMENTARY
SACCULI OF DWARF HAMSTER, Phodopus sungorus sungorus
1,
1
1
2
2
B. V. BURGER, * D. SMIT, H. S. C. SPIES, C. SCHMIDT, U. SCHMIDT,
and A. Y. TELITSINA3
1Laboratory for Ecological Chemistry
Department of Chemistry, University of Stellenbosch
Stellenbosch 7600, South Africa
2Zoological Institute, University of Bonn
Poppelsdorfer Schloss, D-53115 Bonn, Germany
3Institute of Animal Evolutionary Morphology and Ecology, Russian Academy of Sciences
Leninsky 33, Moscow 117071, Russia
(Received January 3, 2000; accepted January 29, 2001)
Abstract—As a first step in a study of the role of the secretion of the supplemen-
tary sacculi (buccal secretion) of the dwarf hamster, Phodopus sungorus sun-
gorus, almost complete chemical characterization of the secretion was achieved.
The 35 compounds identified include carbon dioxide, hydrogen sulfide, a large
number of carboxylic acids (representing the bulk of the organic volatile fraction
of the secretion), phenol, 2-piperidone, indole, two long-chain hydroxyesters,
cholestrol, desmosterol, and lanosterol. The position of the double bonds in
�
-icosadienyl-� -butyrolactoneand� -henicosadienyl-� -butyrolactonecouldnot
be determined, and these two compounds remained only partially characterized.
Large variations were found in the relative concentrations in which the short-
chain carboxylic acids are present in the secretions of individual animals, and
although this aspect was not investigated in sufficient detail in the present in-
vestigation, the difference in the carboxylic acid profiles of the secretions of
individual animals could play a role in individual recognition in this animal.
Key Words—Phodopus sungorus sungorus, dwarf hamster, mammalian semio-
chemicals, mammalian pheromones, exocrine secretion, buccal gland secretion,
supplementary sacculi.
*
To whom correspondence should be addressed.
1
277
0
098-0331/01/0600-1277$19.50/0 �C 2001 Plenum Publishing Corporation

1
278
BURGER ET AL.
INTRODUCTION
Certain aspects of the biology of the dwarf hamster, Phodopus sungorus
sungorus, were summarized in the previous article in the series on mammalian
exocrine secretions (Burger et al., 2001). In addition to the ventral gland, both
male and female dwarf hamsters produce a buccal secretion from the supplemen-
tary sacculi situated at the opening of their cheek pouches. Very little information
is available on this subject. Functions attributed to this secretion include com-
munication of information about sex, identity, female breeding condition, and
even regulation of certain physiological functions in P. s. campbelli (Vasilieva and
Feoktistova, 1994). These authors reported the results of a study on the role of
the sacculi in the development of juveniles. It was found that surgical removal of
the sacculi did not influence development of the pups when they could consume
secretion from parents and littermates but that restriction or inability to consume
secretion led to a significant increase in the pup mortality, with conditions such as
nonspecific enterocolitis and disbacteriosis, and a significant delay in growth and
reproductive development. An increase in adrenal gland weight occurred in such
animals, and the effects of deprivation were found to be more pronounced in male
pups.
The buccal secretion thus appears to play an important role in the survival
and development of juvenile dwarf hamsters. Although polar involatile compounds
could be responsible for at least some of the functions attributed to the secretion,
it was decided to start with the investigation of the volatile organic fraction as a
first step towards the complete chemical characterization of the secretion. We now
report the identification of practically all its volatile organic constituents.
METHODS AND MATERIALS
General and Analytical Methods. The procedures and instrumentation used
in the identification of the constituents of the buccal secretion of the hamster were
described by Burger et al. (2001) in the previous paper in this series. In addition to
the column coated with 95%-dimethyl–5%-diphenylsiloxane copolymer used for
analysis of the ventral secretion of the male dwarf hamster, a glass capillary column
(
40 m � 0.3 mm) coated with 0.375 �m of OV-1701 was used for qualitative as
well as quantitative analyses of the buccal secretion of male and female dwarf
hamsters. The GC and GC-MS parameters used for analysis with the PS-089
column were also used for analyses on the OV-1701 column. These analyses were
done on both columns using extracts of the buccal secretions of individual animals
and the analyses were repeated using solventless sample introduction techniques.
Small quantities of the secretion (ca. 0.2 mg) were, for example, introduced into
the injector of the GC and the GC-MS instrument using a sample introduction

MAMMALIAN EXOCRINE SECRETIONS XVI
1279
probe (Burger et al., 1990), and similar sample sizes were also introduced as a
smear on the inside of a clean injector liner. When solventless sample introduction
was used, the volatile material was cryotrapped on the column with dry ice. For
quantitative analyses, the injector was operated in the splitless mode and the data
acquisition and processing software specified in the previous paper in this series
(Burger et al., 2001) were used.
Sample Collection and Preparation. The sticky, whitish secretion was col-
lected separately from the supplementary sacculi of males and females in their
summer state, i.e., with the day length exceeding 10 hr. Samples were collected
on a weekly basis. Grasping a hamster firmly by the scruff of the neck caused the
animal to open its mouth, and the waxy secretion was collected by scooping it from
the glandular area with the device used for the collection of the animal’s ventral
secretion (Burger et al., 2001). The material was transferred from the wire loops
to a Reacti-Vial containing dichloromethane using another piece of stainless-steel
wire, after which the contents of the vial were thoroughly mixed using a thin glass
rod. This caused the secretion to be spread out on the wall of the vial. The ma-
terial in the vial was sonicated for 10 min, centrifuged for 15 min at 2500 rpm,
and the dichloromethane extract containing the organic material transferred to a
clean Reacti-Vial with a 100-�l syringe. The extract was concentrated in an inert
atmosphere (Burger et al., 1999a) for GC and GC-MS analysis. Secretion intended
for quantitative analyses was collected on a wire loop as described above. A small
sample (ca. 0.2 mg) of the material was accurately weighed into a sample intro-
duction probe (Burger et al., 1990) or a clean glass liner and immediately analyzed
to avoid losing the more volatile constituents of the secretion. Hexadecanoic acid
was used as external standard in the quantitative analyses.
Reference Compounds. Some of the compounds identified in the secretion
are commercially available, while others were available from previous research
projects. The following compounds were synthesized during the present study.
3-Phenylpropanoic acid (19). Cinnamic acid (3.06 g, 20 mmol), dissolved
in degassed methanol (25 ml), was hydrogenated at room temperature and atmo-
spheric pressure in the presence of Pd on activated carbon (5%, 300 mg) until 1.02
equivalents of hydrogen had been taken up. The catalyst was filtered off and the
methanol removed on a rotary evaporator. The product containing some residual
catalyst was taken up in dichloromethane, the solution filtered through a layer
of silica gel, and the solvent evaporated to give 3-phenylpropanoic acid (2.66g,
5.8%). 13C NMR (CDCl3): � = 179.36 (s, C-1), 140.14 (s, C-1 ), 128.56 (d, C-3
0
8
and 5), 128.26 (d, C-2 and 6), 126.38 (d, C-4), 35.63 (t, C-2), 30.57 (t, C-3).
2-Hydroxyoctadec-1-yl acetate (31). A mixture of the hydroxyester (31) and
1-hydroxyoctadec-1-yl acetate was synthesized by the Al2O3-catalyzed reaction
of 1,2-epoxyoctadecane with acetic acid as described by Burger et al. (1999a). The
title compound (27) and 1-hydroxyoctadec-1-yl acetate were formed in a ratio of
+
1
: 3 (GC-MS). HR-MS (mixture of the two isomers): m /z M 255.262, calcd. for

1
280
BURGER ET AL.
13
C20H40O3 255.269. Major component: C NMR (CDCl3): � = 171.48 (s, C-1),
0
0
0
0
7
(
5.74 (d, C-2 ), 64.82 (t, C-1 ), 31.95 (t, C-16 ), 30.51 (t, C-3 ), 29.30–30.5
0
0
0
0
0
t, C-5 – C-15 ), 25.33 (t, C-4 ), 22.71 (t, C-17 ), 21.20 (q, C-2), 14.12 (q, C-18 ).
13
0
Minor component (31): C NMR (CDCl3): � = 171.20 (s, C-1), 69.99 (d, C-2 ),
0 0 0 0 0 0
6
2
8.81 (t, C-1 ), 33.37 (t, C-3 ), 25.38 (t, C-4 ) 29.30 (t, C-5 –C-15 ), 31.95 (t,C-16 ),
0
0
2.71 (t, C-17 ), 20.89 (q, C-2), 14.12 (q, C-18 ).
-Hydroxyicos-1-yl acetate (32). A mixture of the hydroxyester (32) and
-hydroxyicos-2-yl acetate was prepared from 1,2-epoxyicosane as described
2
1
above. The two isomers were present in the product in a ratio of 1 : 2 (GC-MS). HR-
+
MS (mixture of the two isomers): m/z M 356.332, calcd. for C22H44O3 356.329.
13
0
Major component: C NMR (CDCl3): � = 171.55 (s, C-1), 75.75 (d, C-2 ), 64.81
0 0 0 0 0 0
(
2
(
t, C-1 ), 31.95 (t, C-18 ), 30.52 (t, C-3 ), 29.3–30.5 (t, C-5 –C-17 ), 25.33 (t, C-4 ),
0
0
13
2.71 (t, C-19 ), 21.22 (q, C-2), 14.13 (t, C-20 ). Minor component (32): C NMR
0
0
0
CDCl3): � = 171.27 (s, C-1), 70.00 (d, C-2 ), 68.80 (t, C-1 ), 33.38 (t, C-3 ),
0 0 0 0 0
3
(
1.95 (t, C-18 ), 29.3–31.0 (t, C-5 –C-16 ), 29.18 (t, C-17 ), 25.39 (t, C-4 ), 22.71
0
0
t, C-19 ), 20.90 (q, C-2), 14.13 (q, C-20 ).
RESULTS AND DISCUSSION
A typical total ion chromatogram of an extract of the buccal secretion of a
male dwarf hamster is given in Figure 1. Tentative identification of the constituents
of the secretion was based on low-resolution mass spectral data, supported by
information obtained by their chemical ionization mass spectra, generated with
methane as reactant gas. Final confirmation of most of the proposed structures
was obtained by coinjection of an extract of the secretion with authentic synthetic
material.
Solventless sample introduction made it possible to identify even highly
volatile constituents of the secretion such as carbon dioxide (which was to be
expected in the material and is probably extracted from the animal’s breath),
hydrogen sulfide, and trimethylamine. The bulk of the volatile organic fraction of
the secretion consists of short-chain carboxylic acids. These compounds together
with the hydrogen sulfide and trimethyl amine are responsible for the unpleasant
odor of the animal’s breath.
A few diunsaturated compounds could not be fully characterized because
dimethyl disulfide (DMDS) derivatization did not yield informative mass spectral
data. This was probably due to the high molecular masses of the derivatives, which
are expected to elute as flat peaks in the upper isothermal part of the chromatogram
of the material subjected to DMDS derivatization. The interpretation of the mass
spectra of long-chain hydroxyesters has been discussed by Burger et al. (1996).
In the present study the identification of the hydroxyesters 31 and 32 was based

MAMMALIAN EXOCRINE SECRETIONS XVI
1281
FIG. 1. Total ion chromatograms of the secretion of the supplementary sacculi (buccal
secretion ) of the dwarf hamster, Phodopus sungorus sungorus: (A) Analysis of unprocessed
secretion on a relatively polar column (OV-1701) using solventless sample introduction;
(B) Extract of the secretion analized on an apolar column (PS-089).
mainly on their coelution with the synthetic hydroxyesters because they are present
in the secretion in such low concentrations that some of the less abundant ions
were not visible in the high-molecular-weight range of their mass spectra. The two
unsaturated � -lactones, 33 and 36, which are also present in the ventral secretion
of the dwarf hamster (Burger et al., 2001), remained incompletely characterized
in the present investigation. The compounds identified in the buccal secretion are
listed in Table 1 together with information on the analytical techniques employed
in their identification, and some quantitative data on the constituents present in
male and female secretions. Several compounds identified in the animal’s buccal
secretion are also present in its ventral secretion. In addition to the structures of
representative examples of these compounds given in the paper on the ventral
secretion (Burger et al., 2001), the structures of some of the compounds that are
not common to both secretions are given in Figure 2.
Typically about 1–4 mg of secretion could be collected from one animal, but
some of the animals from our colony consistently produced almost no secretion.
The quantitative determination of the volatile organic constituents of the secretion
posed a problem because polar compounds such as the short-chain carboxylic acids
were not quantitatively extracted with small quantities of dichloromethane from
the mucoid material in which they are produced. The highly volatile constituents
are lost during concentration of extracts when larger quantities of solvent are used.

1
282
BURGER ET AL.

MAMMALIAN EXOCRINE SECRETIONS XVI
1283

1
284
BURGER ET AL.

MAMMALIAN EXOCRINE SECRETIONS XVI
1285
FIG. 2. Structures of some representative examples of the compounds identified in the
buccal secretion of the dwarf hamster, P. s. sungorus.
Solventless sample introduction, on the other hand, discriminates to a certain ex-
tent against the heavy constituents of the secretion. Furthermore, the FID in GC
analyses and the mass spectrometer in GC-MS analyses both have different quanti-
tative responses to small and large molecules, while CO2 and H2S are not detected
by FID. Ideally the volatile organic constituents present in the headspace gas of
the secretion should be determined at temperatures corresponding to the hamster’s
body temperature in their summer and winter states. Furthermore, the extreme
polarity differences between highly polar compounds such as ethanoic acid and
the less polar long-chain constituents of the secretion, make it difficult to suggest
an universal stationary phase for sample enrichment. Headspace analysis of the
buccal secretion was not done in the present investigation. The quantitative data in
Table 1 were obtained by combining the results of analyses using different capillary
columns and sample introduction techniques in GC as well as GC-MS analyses.
Although the quantitative results probably represent a relatively accurate picture
of the quantitative composition of the secretion analyzed, the data are considered
to be somewhat preliminary at this stage and are given merely as a guideline for
biologists planning behavioral studies on the dwarf hamster. Nevertheless, the re-
sults do give quite a reliable picture of the ratio in which compounds within limited
volatility ranges are present in the secretion. Some of the largest quantitative dif-
ferences among the buccal secretions from individual animals were found among
the short-chain carboxylic acids, and the role of these compounds in individual
and sexual recognition in P. sungorus should be investigated in more detail.
The highly volatile compounds, carbon dioxide (1), hydrogen sulfide (2),
and trimethylamine (3) were detected in the secretion because solventless sample
introduction techniques were employed in GC and GC-MS analyses in addition
to conventional analysis of extracts. These compounds are almost completely lost
from an extract if the solvent has to be evaporated to concentrate an extract for anal-
ysis. The presence of carbon dioxide in the secretion is to be expected because it is

1
286
BURGER ET AL.
extracted from expired breath of the animal by the moisture-containing secretion.
Hydrogen sulfide does not feature in reports on mammalian exocrine secretions,
probably because it is not detected by FID. It will also not be registered in the total
ion chromatogram if the mass spectra are scanned from a mass higher than m/z
34. Hydrogen sulfide, trimethylamine, and the short-chain fatty acids, of which
almost all the unbranched, iso- and anteiso-branched members from C2 to C6 are
present in the buccal secretion, are probably responsible for the obnoxious smell
of the dwarf hamster’s breath and the secretion. A mixture of similar volatile
fatty acids has been identified in many mammalian secretions, such as, for exam-
ple, the interdigital secretion of the reindeer (Brundin et al., 1978), the perineal
scent gland of guinea pigs (Wellington et al., 1979), and human vaginal secretion
(Huggins and Preti, 1976). The microbial production of trimethylamine, indole
(18), other amines, organosulfur compounds, and fatty acids from amino acids
in mammalian exocrine secretions has been reviewed and discussed by Albone
1984). The occurrence of long-chain saturated and unsaturated fatty acids, 2-
(
piperidone (16), and 3-phenylpropanoic acid (19) in mammalian exocrine secre-
tions was discussed briefly in the previous paper in this series (Burger et al., 2001).
Long-chain acetates are not common in mammalian secretions. Several have,
however, been identified in the male abdominal scent gland of the jird, Meriones
tristrami (Kagan et al., 1983), the preputial secretion of the mouse, Mus musculus
(
(
Spener et al., 1969), and the preorbital secretion of the male oribi, Ourebia orebi
Mo et al., 1995).
Phenol (13) and its derivatives, such as the three isomeric cresols, other alkyl-
substituted phenols, and phenolic acids, are present in many mammalian secre-
tions. Phenol and p-cresol were found in human vaginal secretions (Huggins and
Preti, 1976); p-ethylphenol, p-propylphenol, and pyrocatechol in castoreum of the
beaver, Castor fiber, (Lederer, 1946, 1949); phenol, m- and p-cresol, and m- and
p-propylphenol in aged urine of some African Bovidae (Madubunyi et al., 1996);
and phenol, m-cresol, m-ethylphenol, and m-propylphenol in the interdigital secre-
tions of the bontebok, Damaliscus dorcas dorcas, and the blesbok, D. d. phillipsi
(Burger et al., 1999a). The preorbital secretions of the antelope we have so far in-
vestigated do not contain phenols and phenolic compounds. As far as mammalian
exocrine secretions are concerned, phenol and phenolic compounds are apparently
found in glandular structures in which the conditions are favorable for survival of
microorganisms and the accumulation of the secretions of the gland and/or the
products of microbial activity.
Oxindole (21) as its steroid conjugate has been identified in the urine of
children (Voeltler et al., 1971). Acetophenone has been identified in the urine of
the red fox, Vulpes vulpes (Jorgenson et al., 1978), and p-hydroxyacetophenone in
castoreum of the beaver (Lederer, 1946, 1949).
Hexanal (7) is a potent odor with a threshold value to the human nose slightly
lower than that of limonene (Ohloff, 1978), which has been identified in human

MAMMALIAN EXOCRINE SECRETIONS XVI
1287
breast milk (Stafford et al., 1976). It has also been found in interdigital and pre-
orbital secretions of the bontebok, Damaliscus dorcas dorcas and blesbok, D. d.
phillipsi (Burger et al., 1999a,b), and in the preorbital secretions of the steenbok,
Raphicerus campestris (Burger et al., 1999c). In the interdigital secretions of the
bontebok and blesbok, this aldehyde is accompanied by another nine saturated and
unsaturated C7 –C10 aldehydes. The origin of aldehydes in mammalian secretions
has not been established, but in addition to the possibility that they are produced
by the exocrine glands of the mammals or by microbial action, short- to medium-
chain aldehydes are also produced by the autoxidation of unsaturated lipids such
as, for example, unsaturated triglycerides.
Unbranched short- to intermediate-chain alkanes have been identified in
human effluvia (Ellin et al., 1974). The alkanes found in some mammalian ex-
ocrine secretions are mostly unbranched with intermediate to long chain lengths
consisting of even as well as odd numbers of carbon atoms (Burger et al., 1990,
1999a–c). It has to be accepted that these compounds are produced by the glands
or by microflora present in the glandular structures because there does not seem to
be evidence that their presence can be ascribed to contamination of the secretions
with, for example, petroleum products. The two � -lactones (33 and 36) that are
also present in the ventral secretion of the male dwarf hamster remained uniden-
tified in this investigation. 2-Hydroxyicos-1-yl acetate (32) was also found in the
male ventral secretion, but instead of 2-hydroxyoctadec-1-yl acetate (31), present
in the buccal sectretion, the ventral secretion contains the 1-hydroxyhexadec-2-yl
and 2-hydroxyhexadec-1-yl pentanoates and their hydroxyheptadecyl analoges.
The presence of these � -lactones, hydroxyesters, and the steroidal compounds
cholesterol (34), desmosterol (37), and lanosterol (38) in the dwarf hamster was
briefly referred to in the article on the ventral secretion of the animal (Burger
et al., 2001).
REFERENCES
ALBONE, E. S. 1984. Mammalian Semiochemistry, The Investigation of Chemical Signals Between
Mammals. Wiley-Interscience, Chichester, UK, pp. 135–162.
BRUNDIN, A., ANDERSSON, G., ANDERSSON, K., MOSSING, T., and KA¨LLQUIST, L. 1978. Short-chain
aliphatic acids in the interdigital gland secretion of reindeer (Rangifer tarandus), and their dis-
crimination by reindeer. J. Chem. Ecol. 4:613–622.
BURGER, B. V., MUNRO, Z., SMIT, D., SCHMIDT, U., WU, C.-L., and TIEN, F.-C. 1990. Sample intro-
duction in gas chromatography: Simple method for the solventless introduction of crude samples
of biological origin. J. Chromatogr. 518:207–214.
BURGER, B. V., TIEN, F.-C., le ROUX, M., and MO, W.-P. 1996. Mammalian exocrine secretions X.
Constituents of the preorbital secretion of grysbok, Raphicerus melanotis. J. Chem. Ecol. 22:739–
7
64.
BURGER, B. V., NELL, A. E., SPIES, H. S. C., LE ROUX, M., BIGALKE, R. C., and BRAND, P.
A. J. 1999a. Mammalian exocrine secretions XII: Constituents of interdigital secretions of

1
288
BURGER ET AL.
bontebok, damaliscus dorcas dorcas, and blesbok, D. d. phillipsi. J. Chem. Ecol. 25:2057–
084.
2
BURGER, B. V., NELL, A. E., SPIES, H. S. C., LE ROUX, M., and BIGALKE, R. C. 1999b. Mammalian
exocrine secretions XIII: Constituents of preorbital secretions of bontebok, Damaliscus dorcas
dorcas, and blesbok, D. d. phillipsi. J. Chem. Ecol. 25:2085–2097.
BURGER, B. V., GREYLING, J., and SPIES, H. S. C. 1999c. Mammalian exocrine secretions XIV: Con-
stituents of preorbital secretion of steenbok, Raphicerus campestris. J. Chem. Ecol. 25:2099–2108.
BURGER, B. V., SMIT, D., SPIES, H. S. C., SCHMIDT, C., SCHMIDT, U., TELITSINA, A. Y., and GRIERSON,
G. R. 2001. Mammalian exocrine secretions XV. Constituents of secretion of ventral gland of
male dwarf hamster, Phodopus sungorus sungorus. J. Chem. Ecol. 27:1259–1276.
ELLIN, R. I., FARRAND, R. L., OBERST, F. W., CRAUSE, C. L., BILLUPS, N. B., KOON, W. S., MUSSELMAN,
N. P., and SIDELL, F. R. 1974. An apparatus for the detection and quantitation of volatile human
effluents. J. Chromatogr. 100:137–152.
HUGGINS, G. R., and PRETI, G. 1976. Volatile constituents of human vaginal secretions. Am. J. Obstet.
Gynecol. 126:129–136.
JORGENSON, J. W., NOVOTNY, M., CARMACK, M., COPLAND, G. B., WILSON, S. R., KATONA, S., and
WHITTEN, W. K. 1978. Chemical constituents in the urine of the red fox (Vulpes vulpes L.) during
the winter season. Science 199:796–798.
KAGAN, R., IKAN, R., and HABER, O. 1983. Characterization of a sex pheromone in the jird (Meriones
tristrami). J. Chem. Ecol. 9:775–783.
LEDERER, E. 1946. Chemistry and biochemistry of the scent glands of the beaver, Castor fiber. Nature
1
57:231–232.
LEDERER, E. 1949. Chemistry and biochemistry of some mammalian secretions and excretions. J.
Chem. Soc. 1949:2115–2125.
MADUBUNYI, L. C., HASSANALI, A., OUMA, W., NYARANGO, D., and KABII, J. 1996. Chemoecological
role of mammalian urine in host location by tsetse, Glossina spp.(Diptera: Glossinidae). J. Chem.
Ecol. 22:1187–1199.
MO, W.-P., BURGER, B. V., LE ROUX, M., and SPIES, H. S. C. 1995. Mammalian exocrine secretions
IX: Constituents of preorbital secretion of oribi, Ourebia orebi. J. Chem. Ecol. 21:1191–1215.
OHLOFF, G. 1987. Resent developments in the field of naturally occurring aroma compounds. Fortsch.
Chem. Organ. Naturst. 35:431–527.
SPENER, F., MANGOLD, H. K., SANSONE, G., and HAMILTON, J. G. 1969. Long-chain alkyl acetates in
the preputial gland of the mouse. Biochim. Biophys. Acta 192:516–521.
STAFFORD, M., HORNING, M. G., and ZLATKIS, A. 1976. Profiles of volatile metabolites in body fluids.
J. Chromatogr. 126:495–502.
VASILIEVA, N. Y., and FEOKTISTOVA, N. Y. 1994. Unusual function of integumentary glandular complex
in Djungarian hamsters (Phodopus campbelli). Chemical Signals in Vertebrates V11, T u¨ bingen,
Germany, Proceedings, p. 49.
VOELTLER, D., JUNG, G., BREITMAIER, E., KO¨NIG, W., GUPTA, D., and BREITMAIER, G. 1971. Isolierung
von Oxindol aus Urin von Kindern. Z. Naturforsch. 26b:1380–1381.
WELLINGTON, J. L., BYRNE, K. J., PRETI, G., BEAUCHAMP, G. K., and SMITH, A. B. 1979. Perineal
scent gland of wild and domestic guinea pigs. A comparative chemical and behavioral study. J.
Chem. Ecol. 5:737–751.