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 Volume 7. Issue 7. Pages 815-970. 2012
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 2012
NPC Natural Product Communications Vol. 7
No. 7
Search for Bioactive Compounds from Cantharellus cibarius 917 - 918
Włodzimierz Maria Daniewskia, Witold Danikiewiczb , W. Marek Gołębiewskic,* Mirosław Gucmac,
Agnieszka Łysikc, Jacek Grodnerc and Elżbieta Przybyszc
a
Professor emeritus
b
Institute of Organic Chemistry, Polish Academy of Science, Kasprzaka 44/52, 01-224 Warsaw, Poland
c
Institute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, Poland

golebiewski@ipo.waw.pl

Received: September 27th, 2011; Accepted: May 18th, 2012

Ground fruit bodies of Cantharellus cibarius (chanterelle) were extracted with dichloromethane and subjected to CC followed by preparative HPLC, which led
to the isolation of glycerol 1,2- and 1,3-dilinoleates and glycerol tridehydrocrepenynate. Extraction of C. cibarius fruit bodies with ethanol or methanol
afforded fatty acid ethyl or methyl esters as a result of esterification/transesterification reactions. Insecticidal activity of the isolated glycerides and esters was
much lower than that of the crude extracts and chromatographic fractions suggesting a synergistic effect of some of the compounds present in the mixture.

Keywords: Cantharellus cibarius, Cantharellaceae, Chanterelle, Isolation, Acylglycerols.

Cantharellus cibarius (Cantharellaceae family), chanterelle, is a very H H H H

MeO2C(CH2)7C CCH2C CC C(CH2)3CH3
popular edible mushroom of low caloric value. The fruit bodies of 1
chanterelle contain a plethora of organic and inorganic compounds 1 2 3
2, R = R = R = 14,15-dehydrocrepenynoyl
OR1
[1a,b]. The isolated organic metabolites include proteins, fats and 1 3
3, R = R = linoleoyl, R = H
1 2
2
3
fatty acids [1c,2a], carbohydrates, carotenes, vitamins, and sterols OR2 4, R = R = linoleoyl, R = H
1 2 3
5, R = R = R = linoleoyl
[2b]. A striking feature of chanterelle is that it is not infested by OR3 6, R = dilinoleoyl, oleoyl
7, R = linoleoyl, dioleoyl
pests, which suggests the presence of a chemical defense system
activated by damage to the fruit bodies. From the powdered fruit Table 1: NMR data for compounds 3 and 4 in CDCl3.
bodies of C. cibarius a new compound, named cibaric acid, was Posi- 3 4
isolated, but this was absent from the intact mushrooms [2a,c]. tion H mult. (J in Hz) HSQC C H mult. (J in Hz) HSQC C
Unfortunately, cibaric acid showed only very weak antimicrobial 2 2.35 t (4H, 8.0) 34.1 2.35 t (2H, 7.5) 34.1
2.32 t (2H, 7.0)
and nematicidal activity [2d]. 3 1.63 m (4H) 25.0 1.62 m (4H) 24.8
4 1.31 m 29.2 1.31 m 29.2
5 1.31 m 29.8 1.31 m 29.6
Investigation of ethyl acetate extracts of C. cibarius fruit 6 1.31 m 29.2 1.31 m 29.2
bodies have been carried out before revealing insecticidal and 7 1.31 m 29.8 1.31 m 30.2
8 2.02 m (4H) 27.0 2.03 m (4H) 27.0
fungicidal activity [2e]. In continuation of this work we tried 9 5.35 m (1H) 130.2 5.36 m (1H) 130.0
first to find biological activity in the volatile fraction isolated 10 5.35 m (1H) 128.2 5.36 m (1H) 127.9
11 2.77 t (4H, 6.5) 25.7 2.77 t (4H, 6.5) 25.6
from the mushrooms. The sample obtained from the damaged 12 5.35 m (1H) 128.2 5.36 m (1H) 127.9
chanterelle contained small quantities of about 20 compounds. 13 5.35 m (1H) 130.2 5.36 m (1H) 130.0
14 2.04 m (4H) 27.0 2.03 m (4H) 27.0
Several aralkanes, such as 2-phenylundecane, 5-phenylundecane, 15 1.31 m 29.8 1.31 29.6
2-phenyldodecane, 5- and 6-phenyldodecane, 1-octen-3-ol and 16 1.31 m 31.8 1.31 31.3
17 1.31 m 22.5 1.31 22.4
undecanal were detected. This fraction was not active against 18 0.89 t (6H, 6.5) 13.9 0.89 t (6H, 6.5) 13.9
Musca domestica (house fly) and Blatta orientalis (cockroach) and 1-Gly 4.17 dd (1H, 11.5; 4.5) 65.2 4.32 dd (1H, 11.8; 4.5) 61.9
4.16 dd (1H, 11.5; 5.8) 4.24 dd (1H, 11.8; 5.5)
was not further analyzed. The volatile fraction from chanterelle was 2-Gly 4.09 m (1H) 68.4 5.08 quint (1H, 5.0) 71.9
isolated before by steam distillation [3a]. 3-Gly 4.17 dd (1H, 11.5; 4.5) 65.2 3.73 d (2H, 3.5) 61.5
4.16 dd (1H, 11.5; 5.8)
OH 2.48 m 2.27 m
Searching for non-volatile metabolites from the ethanol extract we
first isolated linoleic, palmitic, oleic, and stearic acid ethyl esters,
Extracts, fractions and pure compounds were tested for their activity
which was in good agreement with our earlier finding [1c]. Another
against Musca domestica and Blatta orientalis (Table 2).
compound detected was the ester of 14-dehydrocrepenyic acid (1).
Fractionation of the ethanolic extract showed that insecticidal activity
The corresponding acid was isolated before from C. cibarius [2a].
occurred mostly in the non-polar compounds present in the ethyl
Then we isolated six further compounds by a combination of CC
acetate layer. Further separation of the ethyl acetate fraction, which
and HPLC, none of which has been found before in chanterelle;
exhibited 100% activity, showed only low activity, not exceeding
these are diglycerides 3 and 4, the triglyceride 2, and the
33.3% mortality of the house fly; this result could suggest a
inseparable mixture of triglycerides 5-7. Structures were established
synergistic effect of the substances present in the chanterelle.
by NMR spectroscopy and ESI MS. When extraction of the ground
fruit bodies was carried out with methanol the methyl esters were
Experimental
formed. This result indicated that the esters were artifacts, products
of enzyme catalyzed esterification or transesterification during the General: UV, UV-1700 Shimadzu spectrometer; NMR, Varian 500
isolation of the metabolites from chanterelle. UNITY plus-500 and Varian VNMRS 600 spectrometers in CDCl3;
918 Natural Product Communications Vol. 7 (7) 2012 Daniewski et al.

Table 2: Insecticidal activity representing percentage mortality of fractions and (5-7). Finally elution with n-hexane/diethyl ether (6:4) afforded the
compounds isolated from Cantharellus cibarius.
diglycerides 3 and 4 and ergosterol.
Musca domestica Blatta orientalis
Fractions
10a g 30 g 10 g 30 g
50% Ethanol layerb
2.2 43.2 0 2.2 1,3-Di-O-linoleoylglycerol (3)
Ethyl acetate layerb 60 100 82.2 100 Colorless oil, 38.3 mg, by HPLC of CH2Cl2 extract, Rt 7.5 min.
Chromatography fraction 1c 2.2 33.3 3.3 0
Chromatography fraction 2c 0 8.9 0 0 UV MeOHmax (nm) (log ): 227 (3.22), 272 (2.41).
Chromatography fraction 3c 0 2.2 0 0 1
Chromatography fraction 4c 2.2 8.9 0 0
H NMR (CDCl3, 500 MHz) and HSQC: Table 1.
Neutral fractiond 10 40 0 3.3 ESI-MS 639 [M+Na]+, 616 [M]+; HR ESI MS (m/z) 639.4956
Acidic fractione
Glycerol tridehydrocrepenynate 2f
0
0
3.3
16.7
6.7
0
3.3
6.7
[M+Na]+ (calc. for C39H68O5Na, 639.4964).
Glycerol 1,3-dilinoleate 3f 0 16.7 0 0
Ergosterolf 0 10 0 0
Fipronilg 100 100 100 100
1,2-Di-O-linoleoylglycerol (4)
Control 0 0 0 0 Colorless oil, 15.0 mg, by HPLC of CH2Cl2 extract, Rt 10.2 min.
UV MeOHmax (nm) (log ): 280 (2.99), 335 (2.93).
a
dose applied per insect; b from the first method; c from the above acetate layer
chromatography; d CH2Cl2 extract from the second method without fatty acids; efatty 1
acids from the second method; f isolated from CH2Cl2 extract treated with diazomethane
H NMR (CDCl3, 500 MHz) and HSQC: Table 1.
from the second method; g reference insecticide active ingredient. ESIMS 639 [M+Na]+, 616 [M]+; HR ESI MS (m/z) 639.4963
[M+Na]+ (calc. for C39H68O5Na, 639.4964).
1
CI and EI mass spectra on AMD M-40, ESI mass spectra on LCT H NMR of 3 and 4 are very similar to the published data [3d].
(Micromass) and Mariner (Applied Biosystems).
Mixture of 1,2,3-tri-O-glycerides (5, 6,7)
Fungal material extraction and isolation: Fruit bodies of Colorless oil, 28.2 mg by HPLC from fraction 5, Rt.8.73 min.
1
Cantharellus cibarius were collected in the vicinity of Warsaw, H NMR (CDCl3, 600 MHz)  glycerol part; 5.26 (tt, J = 6.0; 4.3
Poland, identified by a mycologist, and a sample deposited (voucher Hz, 1H), 4.29 (dd, J = 11.9; 4.3 Hz, 2H), 4.14 (dd, J = 11.9; 6.0 Hz,
specimen number WA 0000017775) at the Herbarium Universitatis 2H), acyl part: 5.30 (m, 7.5 Hz), 2.76 (t, J = 6.5 Hz, 3.8H), 2.30 (t, J
Varsoviensis. For isolation of non-volatile metabolites, 2 extraction = 7.3 Hz, 6H), 2.04 (m, 5.4H), 2.01 (m, 5.4H), 1.6 (m, 6.1H), 1.3
methods were applied. In the first, the fruit bodies (ca 1.8 kg) were (m, 55.4H), 0.89 (t, J = 7.0 Hz, 9H);
ground, left for 30 min., stirred in ethanol (ca 800 mL) for 7 h at a. HR-ESI-MS (m/z) 901.7340 [M+Na]+ (calc. for C57H98O6Na,
room temperature and left overnight. The mixture was filtered and 901.7256) - six double bonds.
the mushrooms extracted twice in the same way. The combined b. HR-ESI-MS (m/z) 903.7454 [M+Na]+ (calc. for C57H100O6Na,
extracts were concentrated under vacuum, dissolved in 50% ethanol 903.7412) - five double bonds.
and extracted with ethyl acetate. The EtOAc fraction was subjected c. HR ESI MS (m/z) 905.7602 [M+Na]+ (calc. for C57H102O6Na,
to CC on silica gel using CH2Cl2, mixtures with acetone, and 905.7569 - four double bonds.
methanol. In the second method, the mushrooms were extracted
with CH2Cl2 to avoid esterification. The combined extracts were Biological assays: Bioassays were performed with 4-5 day old
concentrated in vacuo, dissolved in 50% ethanol and extracted with females of the domestic fly, Musca domestica, and 21 day old
CH2Cl2, which was treated with an excess of CH2N2 to transfer nymphs of cockroach, Blatta orientalis. The active ingredients were
quantitatively all the free fatty acids into their methyl esters. The applied in aqueous acetone (1% by volume) to the dorsal plate (2.5
CH2N2 treated extract (2.1 g) was first chromatographed on neutral L, per fly and 5 L per cockroach). Treated insects were placed in
alumina (50 g) using CH2Cl2 as eluent and then fractionated into groups of 15 in Petri dishes and provided with nutrient medium.
several fractions on a silica gel column. Fraction 3 contained Each test was repeated 3 times and mortality percentage was
compound 1 (6 mg), methyl 14,15-dehydrocrepenynate (methyl recorded after 24 h.
octadeca-9Z,14Z-dien-12-ynoate [3b], which was isolated by
preparative-HPLC using a normal-phase column (5  Kromasil Acknowledgments - This work was supported by the Polish State
SiO2, 20 mm x 300 mm); diethyl ether/n-hexane 1:10. Preparative- Committee for Scientific Research, grant No. 20503032/1852,
HPLC (7% of diethyl ether in n-hexane) of fraction 4 led to the which is gratefully acknowledged. The authors thank Dr Marta
isolation of glycerol tridehydrocrepenynate (2) [3c]. Further elution Wrzosek, University of Warsaw, Department of Biology, Warsaw,
with diethyl ether/n- hexane (1:9) afforded a mixture of triglycerides Poland for identifying the fruiting bodies of Cantharellus cibarius.

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 Natural Product Communications Vol. 7 (7) 2012
Published online (www.naturalproduct.us)

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 Natural Product Communications
2012
Volume 7, Number 7
Contents
Original Paper Page

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Improved Method for Isolation of Lycopsamine from Roots of Comfrey (Symphytum officinale)
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Quality Control and Analytical Test Method for Taxus baccata Tincture Preparation
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Chalcones in Bioactive Argentine Propolis Collected in Arid Environments
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Phytopathogenic Fungal Inhibitors from Celery Seeds
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Synthesis and Antimicrobial Activities of Some Sulphur Containing Chromene Derivatives
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