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Naturally Occurring Thiophenes: Isolation, Purification, Structural

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Naturally Occurring Thiophenes: Isolation, Purification, Structural Phytochem Rev (2016) 15:197–220 DOI 10.1007/s11101-015-9403-7 Naturally occurring thiophenes: isolation, purification, structural elucidation, and evaluation of bioactivities Sabrin R. M. Ibrahim • Hossam M. Abdallah • Ali M. El-Halawany • Gamal A. Mohamed Received: 26 December 2014 / Accepted: 17 March 2015 / Published online: 22 March 2015 Ó Springer Science+Business Media Dordrecht 2015 Abstract Thiophenes are a class of heterocyclic are generally composed of one to five thiophene rings aromatic compounds based on a five-membered ring that are coupled together through their a-carbons, and made up of one sulfur and four carbon atoms. The carry alkyl chains on their free ortho-positions. thiophene nucleus is well established as an interesting Thiophene-containing compounds possess a wide moiety, with numerous applications in a variety of range of biological properties, such as antimicrobial, different research areas. Naturally occurring thio- antiviral, HIV-1 protease inhibitor, antileishmanial, phenes are characteristic secondary metabolites nematicidal, insecticidal, phototoxic and anticancer derived from plants belonging to the family Aster- activities. This review focuses on naturally occurring aceae, such as Tagetes, Echinops, Artemisia, Bal- thiophene derivatives; their sources, physical and samorhiza, Blumea, Pluchea, Porophyllum and spectral data, and biological activities. Eclipta. Furthermore, naturally occurring thiophenes Keywords Thiophenes Á Biosynthesis Á NMR data Á Anti microbial Á Cytotoxic S. R. M. Ibrahim Department of Pharmacognosy and Pharmaceutical Chemistry, Faculty of Pharmacy, Taibah University, Al Madinah Al Munawwarah 30078, Kingdom of Saudi Arabia Introduction S. R. M. Ibrahim Department of Pharmacognosy, Faculty of Pharmacy, Thiophenes are a class of heterocyclic aromatic Assiut University, Assiut 71526, Egypt compounds based on a five membered ring containing one sulfur and four carbon atoms with a molecular H. M. Abdallah Á A. M. El-Halawany Á G. A. Mohamed Department of Natural Products and Alternative formula of C4H4S. The word ‘thiophene’ is derived Medicine, Faculty of Pharmacy, King Abdulaziz from the Greek words ‘theion’ and ‘phaino’, which University, Jeddah 21589, Kingdom of Saudi Arabia mean sulfur and shining, respectively. Thiophene derivatives make up a significant proportion of the H. M. Abdallah Á A. M. El-Halawany (&) Department of Pharmacognosy, Faculty of Pharmacy, organosulfur-containing compounds found in petro- Cairo University, Cairo 11562, Egypt leum, as well as several other products derived from e-mail: [email protected] fossil fuels, and are formed as the by-products of petroleum distillation (Chaudhary et al. 2012; Mishra G. A. Mohamed Department of Pharmacognosy, Faculty of Pharmacy, et al. 2011). Natural thiophenes are characteristic Al-Azhar University, Assiut Branch, Assiut 71524, Egypt secondary metabolites of plants belonging to the 123 198 Phytochem Rev (2016) 15:197–220 family Asteraceae, including the following genera: chemical shift values in d ppm), 13C NMR (spec- Tagetes, Echinops, Artemisia, Balsamorhiza, Blumea, trometer frequency, solvent, chemical shift in d Pluchea, Porophyllum, and Eclipta. Thiophene values), plant source (family), molecular formula, derivatives isolated from natural sources can be calculated molecular weight and reference(s). The 1H classified according to the number of thiophene rings and 13C NMR data have been rounded to two and one in their structure, including thiophenes (one ring), decimal places, respectively. The molecular weight bithiophenes (two rings), terthiophenes (three rings) data have been rounded to four decimal places. The and quinquethiophenes (five rings) (Fig. 1). Thio- NMR data have been listed on each structure because phene and its derivatives are produced as part of the of the differences in the systems used to number the chemical defense mechanism in numerous plant different structures. The principle aim of this review is species, which involve the manufacture and storage to provide a reference for researchers that they can use of organic substances in different parts of the plants. for the rapid identification of isolated thiophenes These compounds can behave as repellents, act as through a comparison of their physical and spectral toxic substances or have anti-nutritional effects on data. The highlighted bioactivities of these compounds herbivores (Gil et al. 2002). Natural thiophenes are may also be of interest to synthetic and medicinal derived from polyacetylenes, which can be stored in chemists for the design of new drugs using known plant tissues or released into the soil (Tang et al. 1987). thiophenes as raw materials. The thiophenes described These compounds can also act as toxins that are in this review have been arranged in five different activated by sunlight or UV irradiation (300–400 nm). groups according to the number of thiophene rings in These compounds are toxic towards numerous patho- their structure, including group I-thiophene, group II- gens, including nematodes, insects, fungi, and bacteria bithiophenes, group III-terthiophenes, group IV-quin- (Champagne et al. 1984; Gil et al. 2002). quethiophenes, and group V-miscellaneous thio- A recent review of the available literature revealed phenes (Tables 1, 2, 3, 4, 5). that there are currently no reviews pertaining to the biosynthesis, isolation and biological activity of naturally occurring thiophenes. Herein, we have listed Thiophene biosynthesis the thiophenes that have been reported in the literature over the past few decades and provided a summary of The first naturally occurring thiophene derivative, a- their biological activities, physical constants, spectral terthiophene, was isolated in 1947 from Tagetes erecta data, plant sources, and associated references. These (Zechmeister and Sease 1947). Since then, more than data have been listed in the following order for each 150 thiophene-based natural products comprising one, compound: name, structure, melting point (°C), opti- two or three thiophene rings and side chains bearing a cal rotation (concentration, solvent), UV (solvent, variable number of double or triple bonds (Bohlmann kmax nm, log e), IR (medium, absorption band in and Zdero 1985; Kagan 1991) had been characterized cm-1), 1H NMR (spectrometer frequency, solvent, from Asteraceae and fungi (Bohlmann 1988; Sorensen Fig. 1 Classes of naturally occurring thiophenes 123 Phytochem Rev (2016) 15:197–220 199 Table 1 Naturally occurring thiophene: group-I: thiophene 1. 3-(4,8,12,16-Tetramethylheptadeca-3,7,11,15-tetraenyl)-thiophene-1-oxide -1 Pale yellowish oil; UV kmax (CH3OH) (log e): 218 (4.42) nm; IR (Nujol) cmax: 2925, 1642, 1230, 1025 cm ; EIMS m/z (rel. int.): 386 [M]? (10), 371 (17), 315 (18), 293 (7), 285 (15), 272 (5), 217 (8), 204 (15), 175 (10), 161 (12), 149 (17), 147 (10), 135 (27), 123 (22), 95 (27), 81 (94), 69 (100); HREIMS m/z: 386.2643 (calcd. for C25H38OS, 386.2645); NMR data (CDCl3, 500 and 125 MHz); The marine sponge Xestospongia sp. (Pedpradab and Suwanborirux 2011) 2. Xanthopappin A; 2-(E)-Hept-5-ene-1,3-diynylthiophene diol ? ? Brown oil; UV kmax (CH3OH) (log e): 206 (4.31), 252 (4.22), 313 (4.08) nm; EIMS m/z (rel. int.): 172 [M] (47), 171 [M–H] (34), ? ? 144 [M–C2H4] (32); HRTOFMS m/z: 173.0428 [M?H] (calcd. for C11H9S, 173.0424); NMR data (CDCl3, 500 and 125 MHz); The stems and roots of Xanthopappus subacaulis C. Winkl (family: Asteraceae) (Tian et al. 2006) 3. 10,11-Threo-xanthopappin D; 2-Hept-5,6-threo-dihydroxy-1,3-diynylthiophene Colourless oil; [a]D -20 (c 0.5, acetone); UV kmax (CH3OH): 306, 290, 232 nm; IR (KBr) cmax: 3367 (OH), 2924 (CH3), 2233 -1 ? (C:C) cm ; HRESIMS m/z: 229.0292 [M?Na] (calcd. for C11H10O2SNa, 229.0294); NMR data (CDCl3, 600 and 150 MHz); Whole plant of Xanthopappus subacaulis C. Winkl (family: Asteraceae) (Zhang et al. 2014) 4. 10,11-Erythro-xanthopappin D; 2-Hept-5,6-erythro-dihydroxy-1,3-diynylthiophene Colourless oil; [a]D ?20 (c 0.5, acetone); UV kmax (CH3OH): 304, 289, 232 nm; IR (KBr) cmax: 3345 (OH), 2924 (CH3), 2219 -1 ? (C:C) cm ; HRESIMS m/z: 435.0687 [2M?Na] (calcd. for 2(C11H10O2S) Na, 435.0695); NMR data (CDCl3, 600 and 150 MHz); Whole plant of Xanthopappus subacaulis C. Winkl (family: Asteraceae) (Zhang et al. 2014) 123 200 Phytochem Rev (2016) 15:197–220 Table 1 continued 5. N-Isobutyl-6-(2-thiophenyl)-2,4-hexadienamide ? HRESIMS m/z: 272.1072 ([M?Na] , (calcd. for C14H19NOS); NMR (CDCl3, 300 and 75 MHz); Leaves of Chrysanthemum coronarium L. (family: Asteraceae) (Ragasa et al. 1997) 6. Amplectol; (3,4-Dihydroxy-8-[50-methyl-thiophen-20-yl]-1,5-octadien-7-yne) -1 ? Colorless oil; UV kmax (CH3OH): 295 nm; IR mmax: 3620, 3565 (OH), 2200 (C:C) cm ; HREIMS m/z (rel. int.): 234.072 [M] ? ? (calcd. for C13H14O2S, 234.073) (6), 216 [M–H2O] (9), 177 [(M–CH(OH)CH=CH2)] ; NMR data (CDCl3, 400 MHz); Aerial parts of Blumea amplectens DC var. arenaria (family: Asteraceae) (Pathak et al. 1987) 7A. Echinoynethiophene A; 7,10-Epithio-7,9-tridecadiene-3,5,11-triyne-1,2-diol Yellow needles (acetone), mp. 122–123 °C; IR (KBr) cmax: 3328 (br), 3104, 2956, 2923, 2872, 2150, 1778, 1451, 1322, 1186, 1080 -1 ? (s), 1022, 946, 864, 805, 688 cm ;C13H10O2S; EIMS m/z (rel. int.): 230 [M] (90), 199 (100), 171 (33), 170 (32), 169 (33), 145 (22), 139 (20), 127 (50); NMR data (Acetone-d6, 500 and 125 MHz); Roots of Echinops grijissii Hance (family: Asteraceae) (Liu et al. 2002) 7B. Echinoynethiophene A; 7,10-Epithio-7,9-tridecadiene-3,5,11-triyne-1,2-diol Yellow amorphous powder; [a]D ?92.2 (c 0.1 CH3OH); UV kmax (e): 237 (7682), 245 (10,293), 251 (10,293), 273 (7728), 275 -1 (7935), 280 (8556), 324 (17,917), 341 (15,755) nm; IR mmax: 3321, 2912, 2863, 2222, 1634, 1446, 1416, 1385, 1090, 798 cm ; EIMS m/z (rel. int.): 230 [M]? (53), 212 (10), 199 (100), 183 (6), 170 (30), 169 (24), 149 (6), 139 (9), 127 (18), 93(9); HREIMS 123 Phytochem Rev (2016) 15:197–220 201 Table 1 continued m/z: 230.0403 (calcd.
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