See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/265632918 Studies on volatile organic compounds of some truffles and false truffles ARTICLE in NATURAL PRODUCT RESEARCH · AUGUST 2014 Impact Factor: 0.92 · DOI: 10.1080/14786419.2014.940942 CITATION READS 1 71 4 AUTHORS, INCLUDING: Maurizio D'Auria Università degli Studi della Basili… 367 PUBLICATIONS 2,789 CITATIONS SEE PROFILE Rocco Racioppi Università degli Studi della Basili… 115 PUBLICATIONS 736 CITATIONS SEE PROFILE Available from: Maurizio D'Auria Retrieved on: 05 February 2016 This art icle was downloaded by: [ 79.37.209.180] On: 15 Sept em ber 2014, At : 05: 55 Publisher: Taylor & Francis I nform a Lt d Regist ered in England and Wales Regist ered Num ber: 1072954 Regist ered office: Mort im er House, 37- 41 Mort im er St reet , London W1T 3JH, UK Natural Product Research: Formerly Natural Product Letters Publicat ion det ails, including inst ruct ions f or aut hors and subscript ion inf ormat ion: ht t p: / / www. t andf online. com/ loi/ gnpl20 Studies on volatile organic compounds of some truffles and false truffles a a b Maurizio D'Auria , Rocco Racioppi , Gian Luigi Rana & Alessandro Laurit a a a Dipart iment o di Scienze, Universit à degli St udi della Basilicat a, V. le At eneo Lucano, 10, 85100, Pot enza, It aly b Scuola di Scienze Agrarie, Forest ali, Aliment ari ed Ambient ali, Universit à degli St udi della Basilicat a, V. le At eneo Lucano, 10, 85100, Pot enza, It aly Published online: 07 Aug 2014. To cite this article: Maurizio D'Auria, Rocco Racioppi, Gian Luigi Rana & Alessandro Laurit a (2014) St udies on volat ile organic compounds of some t ruf f les and f alse t ruf f les, Nat ural Product Research: Formerly Nat ural Product Let t ers, 28: 20, 1709-1717, DOI: 10. 1080/ 14786419. 2014. 940942 To link to this article: ht t p: / / dx. doi. org/ 10. 1080/ 14786419. 2014. 940942 PLEASE SCROLL DOWN FOR ARTI CLE Taylor & Francis m akes every effort t o ensure t he accuracy of all t he inform at ion ( t he “ Cont ent ” ) cont ained in t he publicat ions on our plat form . However, Taylor & Francis, our agent s, and our licensors m ake no represent at ions or warrant ies what soever as t o t he accuracy, com plet eness, or suit abilit y for any purpose of t he Cont ent . Any opinions and views expressed in t his publicat ion are t he opinions and views of t he aut hors, and are not t he views of or endorsed by Taylor & Francis. 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Term s & Downloaded by [79.37.209.180] at 05:55 15 September 2014 Condit ions of access and use can be found at ht t p: / / www.t andfonline.com / page/ t erm sand- condit ions Natural Product Research, 2014 Vol. 28, No. 20, 1709–1717, http://dx.doi.org/10.1080/14786419.2014.940942 Studies on volatile organic compounds of some truffles and false truffles Maurizio D’Auriaa*, Rocco Racioppia, Gian Luigi Ranab and Alessandro Lauritaa a Dipartimento di Scienze, Università degli Studi della Basilicata, V.le Ateneo Lucano, 10, 85100 Potenza, Italy; bScuola di Scienze Agrarie, Forestali, Alimentari ed Ambientali, Università degli Studi della Basilicata, V.le Ateneo Lucano, 10, 85100 Potenza, Italy Downloaded by [79.37.209.180] at 05:55 15 September 2014 (Received 27 March 2014; final version received 30 June 2014) Results of solid phase micro-extraction coupled to gas chromatography and mass spectrometry analyses, accomplished on sporophores of 11 species of truffles and false truffles, are reported. Volatile organic compounds (VOCs) found in Gautieria morchelliformis were dimethyl sulphide, 1,3-octadiene, 3,7-dimethyl-1,6-octadien-3-ol, amorphadiene, isoledene and cis-muurola-3,5-diene. In Hymenogaster luteus var. luteus, presence of 1,3-octadiene, 1-octen-3-ol, 3-octanone, 3-octanol and 4acetylanisole was revealed. Two VOCs, 4-acetylanisole and b-farnesene, constituted aroma of Hymenogaster olivaceus. Melanogaster broomeanus exhibited as components of its aroma 2-methyl-1,3-butadiene, 2-methylpropanal, 2-methylpropanol, isobutyl acetate, 3,7-dimethyl-1,6-octadien-3-ol, 3-octanone and b-curcumene. VOC profile of Octavianina asterosperma was characterised by the presence of dimethyl sulphide, ethyl 2-methylpropanoate, methyl 2-methylbutanoate and 3-octanone. Tuber rufum var. rufum and Pachyphloeus conglomeratus showed the presence of dimethyl sulphide only. Keywords: truffles; false truffles; volatile organic compounds; solid phase microextraction; gas chromatography; mass spectrometry 1. Introduction The odour is one of the main general characteristics of truffles (Ascomycetes) and false truffles (Basidiomycetes) is not easy to recognise in their different species. On the other hand, the description of the above scent is sometimes rather vague or can be a source of uncertainty (Montecchi & Sarasini 2000). Examples of the above incongruity, regarding sporophores of four false truffles, are hereafter reported: (1) Hymenogaster luteus Vittad. var luteus. They would have, according to Vittadini (1831), a strawberry smell which vice versa is described by other authors (Montecchi & Sarasini 2000) as very like fig leaves or, even, lavender. (2) Hymenogaster muticus Berkeley and Broome (1848). These would have a weak (or slender), not bad scent (which, however, remains indefinite) (Montecchi & Sarasini 2000). (3) Gautieria morchelliformis Vittad. Kuntze (Vittadini 1831) would be initially characterised by a pleasant smell of exotic fruits (without any specific detail). The same odour would then become nauseous. (4) Octavianina asterosperma (Vittad.) Kuntze would have a fruit or sweetmeat (i.e. candy like) smell (Vittadini 1831). *Corresponding author. Email: maurizio.dauria@unibas.it q 2014 Taylor & Francis 1710 M. D’Auria et al. Downloaded by [79.37.209.180] at 05:55 15 September 2014 As, in the past, some researches on volatile organic compounds (VOCs) of the main truffles and a false truffle naturally growing in Basilicata (southern Italy) were successfully carried out using solid phase micro-extraction (SPME) coupled to gas chromatography (GC) and mass spectrometry (MS) (Mauriello et al. 2004; D’Auria et al. 2012; D’Auria et al. 2013), it seemed worthy to study with the same technique other hypogeous fungi whose results were not included in the previous investigations and which were characterised by a not well-defined scent in the specific literature (Montecchi & Sarasini 2000; Riousset et al. 2001; Gori 2005). The aim of this work is to characterise the chemical components of the aroma of some uncommon truffles and false truffles whose chemical characterisation of the aroma cannot be found in the literature. Furthermore, we want to contribute to a more clear characterisation of the properties of these minor species discussing the correspondence between the chemical composition and the description of the scent as it is present in the specialised literature in this field. 2. Results and discussion The species/varieties of hypogeous fungi studied are listed in Table 1. The species selected for study in this work depends on those found in the autumn –winter 2013 –2014 in Basilicata (southern Italy). Environmental scanning electron microscopy (ESEM) images of basidiospores of only O. asterosperma and H. luteus var. luteus are included in the Supplementary materials. The chromatograms of each fungal species showed the presence of some VOCs; the identified compounds are collected in Table 1. In G. morchelliformis, dimethyl sulphide, 1,3-octadiene, 3,7dimethyl-1,6-octadien-3-ol, g-muurolene, amorphadiene, isoledene and cis-muurola-3,5-diene have been found. H. luteus var. luteus showed the presence of 1,3-octadiene, oct-1-en-3-ol, 3octanone, 3-octanol and 4-acetylanisole. Melanogaster broomeanus Berk. apud Tul. & C. Tul. has as VOCs 2-methyl-1,3-butadiene, 2-methylpropanal, isobutyl acetate, 2-methylpropan-1-ol, 3octanone, 3,7-dimethyl-1,6-octadien-3-ol, octyl acetate and b-curcumene. Unfortunately, the main component of the aroma of M. broomeanus could not be identified (Table 1). The GC – MS spectrum of M. variegatus (Vittad.) Tul. & C. Tul. showed that in this species the VOCs were 2methyl-1,3-butadiene, 2-methylpropanal, 2-methylpropan-1-ol, ethyl 2-methylpropanoate, isobutyl acetate, 2-methypropyl propanoate, 2-methylpropyl 2-methyl-2-butenoate, 3-phenylpropyl acetate and 2-methylpropyl propanoate. In O. asterosperma, dimethyl sulphide, methyl 2propenoate, methyl 2-methylpropanoate, ethyl propanoate, methyl butanoate, methyl 2methylbutanoate, ethyl methacrylate, methyl 2-methyl-3-oxobutanoate and 3-octanone were found. Tuber rufum Pico: Fr. var. rufum, Montecchi & Lazzari 1993 and Pachyphloeus conglomeratus Berkeley & Broome 1846 showed the presence of only dimethyl sulphide. The main component of G. morchelliformis aroma was amorphadiene (Komatsu et al. 2010) which is an important precursor of the antimalarial drug artemisinin. The aroma of this species is probably a mixture of dimethyl sulphide and terpenes which confer the enough pleasant camphoric smell which could be like that of exotic fruit (i.e. immature mango fruit) reported in the literature. The main components of the aroma of H. luteus resulted in 1,3-octadiene (36.89%) and 3-octanone (21.56%), whereas 1-octen-3-ol (10.71%) is a minor constituent. 1,3-Octadiene is usually associated with a fungal aroma while 1-octen-3-ol and 3-octanone are responsible of a cheesy odour. 4-Acetylanisole, another component of scent of this false truffle, exhibits a butter, caramel, fruity, vanilla aroma. Mixture of the above VOCs in H. luteus var. luteus could explain in part why the description of its scent in previous literature results is quite complex and variable, ranging from mushroom-like aroma to those of strawberry, fig leaves and even lavender. The second main component of M. broomeanus aroma (2-methylpropanal) shows a fresh aldehydic floral odour. Isobutyl acetate also has a fruity and floral smell. Furthermore, 3,7dimethyl-1,6-octadien-3-ol is known for its floral, sweet, woody odour, whereas b-curcumene is not known for its use as a fragrance due to its ‘peppery-saffron-sulphuric’ scent. All the above Downloaded by [79.37.209.180] at 05:55 15 September 2014 Table 1. GC– MS identified compounds from some truffle and false-truffle sporophores of hypogeous fungal species. Basidiomycetes KI KI lit. KI Ref. 2-Methyl-1,3-butadiene Dimethyl sulphide 2-Methylpropanal Methyl 2-propenoate 2-Methylpropan-1-ol 3-Methylbutanal Methyl 2-methylpropanoate Ethyl propanoate Methyl butanoate Dimethyldisulfide 3-Methyl-1,3,5-hexatriene 2-Methylpropyl acetate Methyl 2-methylbutanoate Ethyl 2-methylpropenoate 1-Octene 1,3-Octadiene Ethyl 2-butenoate Xylene 2-n-Butylfuran 2-Methylpropyl propanoate Methyl 2-methyl-3-oxobutanoate 2-Methylnonane Oct-1-en-3-ol 3-Octanone 3-Octanol 4-Methyldecane D-limonene Eucalyptol Trans-b-Ocimene 516 526 557 610 645 653 681 712 724 751 762 770 772 780 784 817 841 864 884 902 911 957 969 975 983 1005 1015 1019 1024 520 526 558 607 645 650 685 713 723 751 – 767 776 775 785 – 833 864 886 870 – 960 975 985 985 1005 1022 1020 1026 Helmig et al. (1996) Insausti et al. (2005) Carrapiso et al. (2002) Blazso et al. (1980) Brander et al. (1980) Morteza-Semnani et al. (2005) Blank and Grosch (1991) Schieberle (1991) Rychlik et al. (1998) Miller and Bruno (2003) – El – Sayed et al. (2005) Schieberle et al. (1990) Ong and Acree (1998) Takeoka et al. (1996) – Morales and Duque (1987) Hayes et al. (2002) Hartvigsen et al. (2000) Jordan et al. (2001) – Sun and Stremple Engel et al. (2002) Tzakou and Couladis (2001) VCF (2014) Jiang and Kubota (2004) Marin et al. (1992) Senatore and de Feo (1999) Choi (2003) H. luteus var. luteus Area (%) M. broomeanus Area (%) O. asterosperma Area (%) 4.87 ^ 0.01 6.23 ^ 0.02 10.98 ^ 0.02 7.33 ^ 0.01 4.35 ^ 0.01 4.20 ^ 0.01 0.45 ^ 0.01 1.00 ^ 0.01 28.32 ^ 0.03 5.16 ^ 0.01 4.26 ^ 0.01 0.12 ^ 0.01 0.09 ^ 0.01 10.08 ^ 0.02 18.76 ^ 0.02 1.80 ^ 0.01 0.72 ^ 0.01 7.17 ^ 0.01 36.89 ^ 0.03 0.52 ^ 0.01 0.16 ^ 0.01 0.43 ^ 0.01 0.31 ^ 0.01 1.88 ^ 0.01 0.11 ^ 0.01 0.15 ^ 0.01 7.28 ^ 0.02 21.56 ^ 0.03 10.71 ^ 0.03 7.56 ^ 0.02 9.49 ^ 0.03 0.19 ^ 0.01 0.30 ^ 0.01 0.05 ^ 0.01 0.08 ^ 0.01 Natural Product Research Compound G. morchelliformis Area (%) 0.09 ^ 0.02 1711 (Continued) Downloaded by [79.37.209.180] at 05:55 15 September 2014 1712 Table 1. (Continued) Basidiomycetes Compound KI KI lit. KI Ref. Cis-Linaloloxide (E)-1,4-Undecadiene 4-Carene 1-Undecene 3,7-Dimethyl-1,6-octadien-3-ol Oct-1-en-3-yl acetate 1,4-Dimethoxybenzene a-Terpineol Octyl acetate 3-Phenyl-2-propenal Methyl 3,5-dimethylbenzoate 4-Acetylanisole a-Copaene Diepi-a-cedrene Longifolene Octahydro-3,8,8-trimethyl-6methylene-1H-3a,7-metanoazulene Epi-bicyclosesquiphellandrene Cis-Thujopsene Unknown compound Amorphadiene b-Curcumene Cis-a-Bisabolene Epizonarene b-Bisabolene 1,2,3,5,6,8a-Hexahydro-4,7dimethyl-1-(1-methylethyl)naphthalene 8,9-Dehydroneoisolongifolene Hexadecane 1062 1073 1076 1077 1086 1096 1165 1185 1198 1276 1351 1355 1377 1384 1411 1429 1072 – 1079 1087 1084 1094 1163 1185 1198 1273 – 1348 1376 1382 1416 1424 Leffingwell and Alford (2005) – Hu et al. (2010) Ohnishi and Shibamoto (1984) Kuiate et al. (1999) Cavaleiro et al. (2002) Adams (1995) Choi (2003) Zarazir et al. (1970) Mondello et al. (2008) – Aligiannis et al. (2001) Adams (1995) Palá-Paúl et al. (2002) Hognadottir and Rouseff (2003) Asuming et al. (2005) 1437 1439 1482 1431 Cheng et al. (2005) Adams et al. (2005) 0.56 ^ 0.01 1468 1476 1505 1508 1513 1529 – 1483 1505 1501 1511 1528 – Moyler and Clery (1997) Javidnia et al. (2006) Adams and Nguyen (2005) Asuming et al. (2005) Asuming et al. (2005) 40.72 ^ 0.03 1571 1600 1558 1600 Sharififar et al. (2007) 0.14 ^ 0.01 H. luteus var. luteus Area (%) 0.04 ^ 0.01 M. broomeanus Area (%) O. asterosperma Area (%) 0.19 ^ 0.01 0.15 ^ 0.01 0.37 ^ 0.01 2.17 ^ 0.01 1.05 ^ 0.01 0.21 ^ 0.01 7.89 ^ 0.02 0.29 ^ 0.01 0.31 ^ 0.01 0.16 ^ 0.01 1.20 ^ 0.01 0.17 ^ 0.01 9.33 ^ 0.02 0.24 ^ 0.01 1.55 ^ 0.01 0.14 ^ 0.01 0.24 ^ 0.01 0.91 ^ 0.01 0.39 ^ 0.01 22.80 ^ 0.03 3.63 ^ 0.01 0.15 ^ 0.01 3.87 ^ 0.01 0.81 ^ 0.01 5.19 ^ 0.02 0.14 ^ 0.01 0.09 ^ 0.01 M. D’Auria et al. G. morchelliformis Area (%) Downloaded by [79.37.209.180] at 05:55 15 September 2014 1632 1700 1706 – 1700 1707 1735 – Compound Dimethyl sulphide Dimethyldisulfide Toluene 1-Methoxy-3-methylbenzene D -Limonene 1-Undecene 2-Nonanone 2-Undecanone Total KI 526 751 764 1005 1015 1077 1093 1287 Note: KI, Kovats index. KI lit. 526 751 762 1006 1022 1087 1093 1292 – 0.07 ^ 0.01 0.11 ^ 0.01 0.10 ^ 0.01 Kenig et al. (2005) – KI Ref. Insausti et al. (2005) Miller and Bruno (2003) Engel et al. (2002) Splivallo et al. (2007) Marin et al. (1992) Ohnishi and Shibamoto (1984) Nishimura (1995) Adams (2000) 70.22 Ascomycetes T. rufum var. rufum Area (%) 93.05 ^ 0.04 0.05 ^ 0.01 89.62 94.71 85.61 P. conglomeratus Area (%) 65.30 ^ 0.03 3.58 ^ 0.02 0.84 ^ 0.01 0.49 ^ 0.01 0.33 ^ 0.01 73.33 2.84 ^ 0.01 4.50 ^ 0.02 4.41 ^ 0.02 80.63 Natural Product Research 1-Methylethyl dodecanoate Heptadecane 2,6,10,14-Tetramethylpentadecane 1-Butyloctylbenzene Total 1713 1714 M. D’Auria et al. VOCs could explain why a ‘weak, pleasant, aromatic and fruity’ aroma for this Melanogaster species is reported in the literature (Montecchi & Sarasini 2000). The main components of O. asterosperma VOCs, i. e. ethyl 2-methylpropanoate (28.32%) and methyl 2-methylbutanoate (18.76%), both characterised by a fruity aroma, match the definition of ‘fruit-scented or candy-like’ aroma reported for this species (Montecchi & Sarasini 2000). Dimethyl sulphide (10.98%), perhaps along with 3-octanone (fournished a cheesy odour), completes the above described definition of aroma. Downloaded by [79.37.209.180] at 05:55 15 September 2014 3. Experimental The species/varieties of hypogeous fungi studied are listed in Table 1. In particular, besides three of the four false truffles mentioned in the Introduction, the following others were analysed: T. rufum varr. rufum, M. broomeanus and P. conglomeratus. Dogs used to search the hypogeous fungi object of the article belonged to ‘Lagotto romagnolo’ breed. Identification of species and varieties of collected fungi was mainly based on spore morphology and dimensions observed/measured on mature specimens. An optical microscope ‘Axioscop’ (Karl Zeiss, Jena, Germany) equipped with a digital camera mod. DS-U1 (Nikon, Tokyo, Japan) was generally employed. In some instances, a Philips XL 30 ESEM (scansion electronic microscope) (Philips, Amsterdam, Netherlands) for environmental analysis of ‘Grandi Attrezzature’ Centre (CIGAS) of University of Basilicata was also used. Collected fungal sporophores (basidiomata or ascomata) were superficially cleaned with a little brush, put in small glass containers furnished with screw caps. The samples were stored at 48C for 24 –48 h if the analyses could not be performed immediately. Some 2-mm thin slices were cut with sterile bistouries from each specimen and then kept in SPME vials at the low temperature mentioned above before being subjected to VOCs analysis. A 100-mm PDMS-SPME module (57300-U, Supelco, Milan, Italy) was employed to determine VOCs. SPME fibre was maintained over the sample in a 20 mL vial at 368C for 20 min. Analyses were accomplished with an HP 6890 Plus gas chromatograph equipped with a Phenomenex Zebron ZB-5 MS capillary column (30 m £ 0.25 mm i.d. £ 0.25 mm FT) (Agilent, Milan, Italy). A HP 5973 mass selective detector (Agilent) was utilised with helium at 0.8 mL/ min as the carrier gas. A splitless injector was maintained at 2508C and the detector at 2308C. The oven was held at 408C for 2 min, then gradually warmed, 88C/min, up to 2508C and held for 10 min. Tentatively identification of aroma components was based on mass spectra and Wiley 6 and NITS 98 library comparison. Single VOC peak was considered as identified when its experimental spectrum matched with a score over 90% that is present in the library. When present, the Kovats Retention Index was used to identify the aroma components. Amorphadiene was not present in our library and it was identified by comparison of the obtained mass spectrum with that reported in the literature (Komatsu et al. 2010). Some other compounds such as methyl butanoate, 3-methylbutyl acetate, xylene, anisole, acetophenone, 1,2-dimethoxybenzene and 1,4-dimethoxybenzene were identified by comparison of the retention time and the mass spectrum with those of authentic samples. Some terpenes (D -limonene, eucalyptol, terpineol, bocimene, 4-carene and isoledene) were determined by comparison with authentic samples (Sigma-Aldrich, Milan, Italy). All the analyses were performed in triplicate. 4. Conclusions In conclusion, this study showed that the VOCs found in the different species of truffles and false truffles allowed a better characterisation of their respective aromas. Some of the analysed species contained dimethyl sulphide as the main scent component, allowing to explain their particular aromas; other species showed relevant amount of unsaturated and aromatic Natural Product Research 1715 compounds, which could give their sporophores various pleasant odours; sporophores of some other species, characterised by the presence of aliphatic esters, had a fruity aroma, and finally, others species are characterised by the presence of relevant amounts of mono and sesquiterpenes. So far VOCs of truffle and false truffle species and varieties subjected to SPME – GC – MS analyses in this investigation were unknown. This gap of knowledge rendered difficult to exaustively indicate their sometimes complex aromas which remained unclear or undefinite. Supplementary material Supplementary Figures S1 –S2 are available online. Downloaded by [79.37.209.180] at 05:55 15 September 2014 References Adams RP. 1995. 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