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Talarodiolide, a New 12-Membered Macrodiolide, and GC/MS Investigation of Culture Filtrate and Mycelial Extracts of Talaromyces Pinophilus

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Talarodiolide, a New 12-Membered Macrodiolide, and GC/MS Investigation of Culture Filtrate and Mycelial Extracts of Talaromyces Pinophilus molecules Article Talarodiolide, a New 12-Membered Macrodiolide, and GC/MS Investigation of Culture Filtrate and Mycelial Extracts of Talaromyces pinophilus Maria Michela Salvatore 1 ID , Marina DellaGreca 1, Rosario Nicoletti 2,3 ID , Francesco Salvatore 1, Francesco Vinale 4 ID , Daniele Naviglio 1 ID and Anna Andolfi 1,* 1 Department of Chemical Sciences, University of Naples ‘Federico II’, 80126 Naples, Italy; [email protected] (M.M.S.); [email protected] (M.D.); [email protected] (F.S.); [email protected] (D.N.) 2 Council for Agricultural Research and Agricultural Economy Analysis, 00184 Rome, Italy; [email protected] 3 Department of Agriculture, University of Naples ‘Federico II’, 80055 Portici, Italy 4 Institute for Sustainable Plant Protection, National Research Council, 80055 Portici (NA), Italy; [email protected] * Correspondence: andolfi@unina.it; Tel.: +39-081-2539179 Received: 23 March 2018; Accepted: 17 April 2018; Published: 19 April 2018 Abstract: Talarodiolide, a new 12-membered macrodiolide, was isolated and characterized from the culture filtrate of strain LT6 of Talaromyces pinophilus. The structure of (Z)-4,10-dimethyl-1,7-dioxa- cyclododeca-3,9-diene-2,8-dione was assigned essentially based on NMR and MS data. Furthermore, several known compounds were isolated and identified in the crude extract of the culture filtrate and mycelium of this strain. EI mass spectrum at 70 eV of all isolated metabolites was acquired and compiled in a custom GC/MS library to be employed to detect metabolites in the crude extracts. Keywords: Talaromyces pinophilus; talarodiolide; macrodiolides; GC/MS; secondary metabolites 1. Introduction With a widespread occurrence in very diverse environmental contexts, from the soil to the sea [1–3], the species Talaromyces pinophilus (=Penicillium pinophilum) (Eurotiales: Trichocomaceae) has received increasing attention in mycological research for its ability to act as a fungal antagonist and plant-growth promoter [1,4,5], and for possible biotechnological applications based on the production of enzymes [6,7] and bioactive metabolites [8–10]. Two strains (LT4 and LT6), possibly deriving from the same wild clone since they were both recovered from the rhizosphere of a tobacco plant cropped near Lecce (Apulia, Southern Italy), have been particularly studied in our laboratories after they were shown to produce a novel fungitoxic and cytostatic compound named 3-O-methylfunicone (OMF) [1,11]. OMF is part of a homogeneous family comprising about 20 structurally related secondary metabolites which have been mainly characterized from cultures of Talaromyces strains [12]. It has notable antitumor properties based on several biomolecular mechanisms of action resulting from a series of preclinical assays [13–17]. Although it represents the main extrolite produced by our strains, other funicone variants have been occasionally extracted [18,19], indicating that some factors act during the culturing cycle which may lead to the accumulation of intermediate or side products. Within our recent activity aiming at the standardization of OMF production, additional compounds were detected from cultures of strain LT6. Among them, a new product with an unusual structure for a natural compound, namely talarodiolide, was purified from its culture filtrates. Furthermore, the present paper reports findings from the Molecules 2018, 23, 950; doi:10.3390/molecules23040950 www.mdpi.com/journal/molecules Molecules 2018, 23, x 2 of 9 Molecules 2018, 23, 950 2 of 9 talarodiolide, was purified from its culture filtrates. Furthermore, the present paper reports findings fromfirst GC/MS-based the first GC/MS investigation-based investigation on secondary on secondary metabolites metabolites in culture in filtrate culture and filtrate mycelial and extracts mycelial of T.extracts pinophilus of T.. pinophilus. 2. Results 2.12.1.. Isolation and Identification Identification of M Metabolitesetabolites The crude crude CHCl CHCl33 extractextract from from the the culture culture filtrates filtrates of ofT. T.pinophilus pinophilus strainstrain LT6 LT6 was was purified purified by combinedby combined column column (CC)(CC) and thin and layer thin layerchromatography chromatography (TLC), (TLC),leading leading to isolation to isolation of one new of one (1, Figurenew (1 ,1) Figure and 1four) and known fourknown compounds compounds (2–5, Figure (2–5, Figure 1). Structures1). Structures of known of known compounds compounds were 1 13 wereconfirmed confirmed by comparison by comparison of data ofobtained data obtained from OR, from 1H and OR, 13CH-NMR and , andC-NMR ESI-TOF , and MS ESI-TOF with those MS withreported those in reported the literature in the literature for OMF for OMF[11], [11cyclo], cyclo-(S--(ProS-Pro--R-Leu),R-Leu), cyclocyclo-(S-(-ProS-Pro--S-Ile)S-Ile) [20 [20],], and cyclo-(-(S-Pro--Pro-S-Phe)-Phe) [2121](] (2–5).). 14 COOCH3 O O O O H 10 12 NH 2 O OCH3 O N 4 6 8 13 H CO O O 3 OCH3 O 1 2 3 O O O O H H O NH NH N H N O O O O O 4 5 6 O O O O O O H O O O O OH OH 7 8 O HO O OH 9 Figure 1. 1.Structures Structures of talarodiolide, of talarodiolide, 3-O-methylfunicone, 3-O-methylfunicone,cyclo-(S-Pro-R-Leu), cyclocyclo-(S--(ProS-Pro--R-Leu),S-Ile), cyclo-(-(SS-Pro--ProS-S-Phe),-Ile), vermistatin,cyclo-(S-Pro-S penisimplicissin,-Phe), vermistatin, penicillide, penisimplicissin, and 1-glycerol-linoleate penicillide, (1and–9), 1compounds-glycerol-linoleate produced ( by1–Talaromyces9), compounds pinophilus producedLT6, isolated by Talaromyces by preparative pinophilus chromatographic LT6, isolated methods by preparativeand identified chromatographic by spectroscopic and methods MS techniques. and identified by spectroscopic and MS techniques. Compound 1, isolated as amorphous solid, has aa molecularmolecular weightweight ofof 224224 mm//z accounting for a molecular formula of C12H16O4 and the index of hydrogen deficiency is five as deduced from molecular formula of C12H16O4 and the index of hydrogen deficiency is five as deduced from ESI-TOF 1 ESIMS.-TOF The 1 MS.H-NMR The spectrumH-NMR spectrum (Table1 and (Table Figure 1 and S1) revealed Figure S1) one revealed broad singlet one broad methyl, singlet one broad methyl, triplet one broadand one triplet triplet and in aliphaticone triplet region, in aliphatic and a broad region, singlet and of a olefinic broad signals.singlet of In theolefinic13C-NMR signals spectrum. In the 13 (TableC-NMR1 and spectrum Figure S5), (Table only 1 sixand carbon Figure signals S5), only were six presentcarbon indicatingsignals were a highly present symmetric indicating molecule. a highly 1 13 symmetricThe 1H and molecule.13C resonances The H ofand1 were C resonances assignedby of combination1 were assigned of COSY by combination and HSQC of experiments. COSY and HSQCThe COSY experiments. experiment The showed COSY homocorrelationsexperiment showed among homocorrelations the olefinic proton among at theδ 5.84 olefinic with proton the methyl at δ 5.84at δ 2.03withand the methylenemethyl at δat 2.03δ 2.40, and themethylene latter of at which δ 2.40, was the alsolatter correlated of which withwas also methylene correlated at δ with4.40. methyleneThe HSQC at (Figure δ 4.40. S3) The spectrum HSQC (Figure showed S3) correlations spectrum ofshowed methyl correlations at δ 2.03 with of methyl carbon at at δδ 2.0322.4, with two carbonmethylenes at δ 22.4, at δ 2.40two andmethylenes 4.40 with atcarbons δ 2.40 and at δ 4.4029.2 with and carbons 65.8, respectively, at δ 29.2 and and 65.8, one respectively, methine at δ 5.84and one methine at δ 5.84 with carbon 116.8. The carbons at δ 164.6 and 157.7 were assigned to a carboxyl Molecules 2018, 23, 950 3 of 9 with carbon 116.8. The carbons at δ 164.6 and 157.7 were assigned to a carboxyl group and substituted 2 sp carbon, respectively. According to the structure in the HMBC (Figure S4) spectrum, the H2-6/H2-12 protons were correlated to the C-8/C-2 at 164.4, C-4/C-10 at 157.7 and C-5/C-11 at 29.2. Furthermore, the H3-13/H3-14 protons were correlated to C-3/C-9, C-4/C-10 and C-5/C-11 carbons. The analysis of NOESY (Figure S6) spectrum evidenced NOE of the methyl at δ 2.03 and olefinic H-3 proton indicating a Z configuration at double bond. Table 1. NMR data and HMBC correlations for talarodiolide (1) recorded in CDCl3. Position δC δH (J in Hz) HMBC 2, 8 164.6 C - 3, 9 116.8 CH 5.84, brs 4,10 157.7 C - 5, 11 29.2 CH2 2.40, brt, 6.3 6, 12 65.8 CH2 4.40, t, 6.3 C-8/C-2,C-4/C-10, C-5/C-11 13, 14 22.4 CH3 2.03, brs C-3/C-9, C-4/C-10, C-5/C-11 These results and the molecular formula of C12H16O4 suggest that 1 is a symmetrical macrodiolides, (Z)-4,10-dimethyl-1,7-dioxa-cyclododeca-3,9-diene-2,8-dione. This structure was confirmed by data from ESI-TOF MS recorded in positive mode. The spectrum showed the sodiated dimeric, dimeric, sodiated and pseudomolecular ions [2M + Na]+, [2M + H]+, [M + Na]+, and [M + H]+ at m/z 471, 449, 247, and 225, respectively. Symmetric macrodiolides have been reported from many natural sources, and displayed some interesting effects, such as antibacterial, antifungal and cytotoxic activities ([22] and literature therein). However, in the light of the current knowledge, no 12-membered macrodiolide has been isolated from natural sources so far. In addition, the production of secondary metabolites by T. pinophilus LT6 was investigated after extraction of mycelium.
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