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Antibacterial Activities of Pyrenylated Coumarins from the Roots of Prangos Hulusii

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Antibacterial Activities of Pyrenylated Coumarins from the Roots of Prangos Hulusii molecules Article Antibacterial Activities of Pyrenylated Coumarins from the Roots of Prangos hulusii Nur Tan 1,*, Seçil Yazıcı-Tütüni¸s 1, Merve Bilgin 2, Emir Tan 2 and Mahmut Miski 1,* 1 Department of Pharmacognosy, Faculty of Pharmacy, Istanbul University, Istanbul 34116, Turkey; [email protected] 2 Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Istanbul Yeni Yuzyil University, Istanbul 34110, Turkey; [email protected] (M.B.); [email protected] (E.T.) * Correspondences: [email protected] (N.T.); [email protected] (M.M.); Tel.: +90-530-491-6629 (N.T.); +90-545-550-4455 (M.M.) Received: 9 June 2017; Accepted: 28 June 2017; Published: 1 July 2017 Abstract: The dichloromethane extract of the roots of Prangos hulusii, a recently described endemic species from Turkey, has yielded nine known and one new prenylated coumarins. The structures were elucidated by spectroscopic methods and direct comparison with the reference compounds where available. The root extract and its prenylated coumarins exhibit antimicrobial activity against nine standard and six clinically isolated strains at a concentration between 5 and 125 µg/mL. In particular, the new coumarin, 40-senecioiloxyosthol (1), displayed 5 µg/mL MIC (Minimum Inhibitory Concentration) value against Bacillus subtilis ATCC 9372, murraol (4) and auraptenol (5) showed 63 µg/mL MIC value against Klebsiella pneumoniae ATCC 4352 and Bacillus subtilis ATCC 9372, and isoimperatorin (9) exhibited 16 µg/mL MIC value. Keywords: Prangos hulusii; pyrenylated coumarins; antibacterial activity 1. Introduction Prangos is an important genus of Apiaceae family, with 43 species known worldwide [1]. There are 17 species of Prangos in Turkey; nine of them are endemic [2]. Members of this genus have carminative, laxative, stomachic, stimulant, emmenagogue, antienflammatuar, antimicrobial, and antidiabetic properties, and are used for the treatment of burns, hemorrhoids, and wounds [3–6]. Many coumarin, alkaloid, flavonoid, and terpenoid derivatives were isolated from the roots, aerial parts, and fruits of Prangos species [7–10]. Prangos hulusii (S. G. ¸Senol,H. Yıldırım & Ö. Seçmen) is a newly identified endemic species from Flora of Turkey [11]. Preliminary biological activity studies on the extracts of the roots of P. hulusii showed the presence of antimicrobial and cytotoxic activities [12]. The dichloromethane extract of the roots of P. hulusii was subjected to a series of chromatographic separations to yield a new coumarin, 40-senecioiloxyosthol (1), along with nine known coumarins; osthol (3)[13], murraol (4)[14], auraptenol (5)[15], meranzin (6)[16], hydroxyosthol-epoxide (7)[17], meranzin hydrate (8)[16], isoimperatorin (9)[18], oxypeucedanin (10)[18], psoralen (11)[19], and two phytosterols; stigmasterol and β-sitosterol [20]. Structures of the isolated compounds (Figure1) were elucidated using spectroscopic techniques and chemical transformations as well as by direct comparison with the reference standards where available. Antimicrobial activities of the dichloromethane extract of the roots of P. hulusii and prenylated coumarins isolated from this extract were investigated against the standard and clinically isolated 15 bacterial strains. Molecules 2017, 22, 1098; doi:10.3390/molecules22071098 www.mdpi.com/journal/molecules Molecules 2017, 22, 1098 2 of 8 Molecules 2017, 22, 1098 2 of 8 Figure 1. Structures of prenylated coumarins 1–10. 2. Results and Discussion 40′‐-SenecioiloxyostholSenecioiloxyosthol ( (11)) was was obtained obtained as as a a colorless colorless gum. gum. The The HRESIMS HRESIMS spectrum spectrum of of1 1suggests suggests a a molecular formula of C20H22O5 with 10 degrees of unsaturation based on the [M ++ H]+ molecular molecular formula of C20H22O5 with 10 degrees of unsaturation based on the [M + H] molecular peak 1 atpeakm/ zat343.1544 m/z 343.1544 (calcd (calcdm/z 343.1545). m/z 343.1545). The 1 H-NMRThe H‐NMR spectrum spectrum (Table (Table1) of 1 1)was of very1 was similar very similar to that ofto ostholthat of [ 13osthol,16], with[13,16], the exceptionwith the exception of a missing of vinylica missing methyl vinylic group methyl signal group of the prenylsignal sideof the chain prenyl of osthol. side 1 Insteadchain of of osthol. two vinylic Instead methyl of two signals, vinylic the methyl1H-NMR signals, spectrum the H of‐1NMRdisplayed spectrum a vinylic of 1 methyldisplayed group a vinylic signal methyl group signal at δH 1.72 (3H) and a methylene singlet at δH 4.87 (2H), indicating that the at δH 1.72 (3H) and a methylene singlet at δH 4.87 (2H), indicating that the second vinylic methyl group of ostholsecond side vinylic chain methyl was replaced group withof osthol an acyloxy side chain bearing was methylene replaced group. with an Furthermore, acyloxy bearing the typical methylene vinylic group. Furthermore, the typical vinylic narrow quintet proton signal observed at δH 5.72 (J = 1.3 Hz) narrow quintet proton signal observed at δH 5.72 (J = 1.3 Hz) along with the two vinylic methyl group along with the two vinylic methyl group doublets at δH 2.19 and 1.90 (each 3H, J = 1.3 Hz) suggest the doublets at δH 2.19 and 1.90 (each 3H, J = 1.3 Hz) suggest the presence of a senecioil group as the acyl group.presence The of 2D-ROESY a senecioil spectrum group as of the1 exhibitedacyl group. interactions The 2D‐ROESY between spectrum C-50 methyl of 1 group exhibited protons interactions and H-20 protonbetween of C the‐5′ prenylatedmethyl group side protons chain of and osthol H‐ (Figure2′ proton2) as of well the prenylated as displayed side interactions chain of betweenosthol (Figure H-6 and 2) theas well methoxy as displayed group protons interactions at C-7, andbetween H-200 Hproton‐6 and and the H-4 methoxy00 methyl group protons protons of the at senecioiloxy C‐7, and H acyl‐2″ group,proton which and H clearly‐4″ methyl confirms protons the presence of the senecioiloxy of a senecioiloxy acyl group, acyl group which at the clearly C-40 confirmsmethyl group the presence of osthol 13 inof 1a. senecioiloxy Furthermore, acyl13C-NMR group (Tableat the1 C),‐ 2D4′ methyl COSY, group UV and of IR osthol spectroscopic in 1. Furthermore, data (see experimental C‐NMR (Table section 1), 2D COSY, UV and IR spectroscopic data (see experimental section and supplemental data) of 1 corroborated the structure as 4′‐senecioiloxyosthol. Previously, 4′‐angeloiloxy derivative of osthol (2) Molecules 2017, 22, 1098 3 of 8 Molecules 2017, 22, 1098 3 of 8 0 0 (i.e.,and supplementalmacrocarpin) data) was of reported1 corroborated from theLomatium structure macrocarpum as 4 -senecioiloxyosthol. (Hook. & Arn.) Previously, C. & 4 R.,-angeloiloxy another Apiaceaenderivative of plant osthol [21]. (2) (i.e.,The macrocarpin)1H‐NMR spectroscopic was reported data from reportedLomatium for macrocarpum macrocarpin(Hook. (2) were & Arn.) similarC. & to R., 1 thatanother of 1 Apiaceaenwith the exception plant [21]. of The the H-NMRpresence spectroscopic of angeloiloxy data acyl reported group for signals macrocarpin [i.e., δH (6.042) were (1H, similar br t), 1.97to that (3H) of 1andwith 1.88 the (3H)] exception instead of the of a presence senecioiloxy of angeloiloxy acyl group acyl signals. group signals [i.e., δH 6.04 (1H, br t), 1.97 (3H) and 1.88 (3H)] instead of a senecioiloxy acyl group signals. Table 1. 1H‐NMR and 13C‐NMR data of Compound 1. Table 1. 1H-NMR and 13C-NMR data of Compound 1. Positions ΔH (J in Hz) ΔC, Type 2 161.14, C Positions DH (J in Hz) DC, Type 3 6.23 d (9.8), 1H 116.08, CH 2 161.14, C 4 7.60 d (9.8), 1H 143.65, CH 3 6.23 d (9.8), 1H 116.08, CH 5 7.30 d (8.4), 1H 126.46, CH 4 7.60 d (9.8), 1H 143.65, CH 6 5 7.306.82 dd (8.4),(8.4), 1H1H 126.46,107.3, CH CH 7 6 6.82 d (8.4), 1H 107.3, CH160.09, C 8 7 160.09,116.66, C C 9 8 116.66,152.86, C C 10 9 152.86,112.92, C C ‐OCH3 103.89 s, 3H 112.92,56.01, C CH3 -OCH3 3.89 s, 3H 56.01, CH3 1′ 0 3.62 d (7.9), 2H 21.45, CH2 2′ 1 5.503.62 br d (7.9),t (7.9), 2H 1H 21.45, CH113.04,2 CH 20 5.50 br t (7.9), 1H 113.04, CH 3′ 131.24, C 30 131.24, C 4′ 0 4.87 s, 2H 62.40, CH2 4 4.87 s, 2H 62.40, CH2 5′ 0 1.72 br s, 3H 21.61, CH3 5 1.72 br s, 3H 21.61, CH3 1″ 100 166.8, C166.8, C 2″ 200 5.725.72 quintquint (1.3),(1.3), 1H1H 126.51,126.51, CH CH 3″ 300 156.41,156.41, C C 00 4″ 4 1.901.90 brbr dd (1.3),(1.3), 3H3H 27.39, CH27.39,3 CH3 00 5″ 5 2.172.17 brbr dd (1.3),(1.3), 3H3H 20.2, CH20.2,3 CH3 Figure 2. Interactions observed in the ROESY spectrum of 40-Senecioiloxyosthol. Figure 2. Interactions observed in the ROESY spectrum of 4′‐Senecioiloxyosthol. The antimicrobial activity of extracts and isolated coumarins of Prangos hulusii was evaluated against Gram‐positive and Gram‐negative nine reference standards and six clinically isolated microorganism strains. The results of minimum inhibition concentration (MIC, in μg/mL) values are summarized in Table 2. The best antimicrobial activity was observed against Escherichia coli with the dichlormethane (DCM) extract (i.e., MIC at 156 μg/mL), followed by the petroleum ether (PE) and methanol (MeOH) extracts (i.e., each MIC at 313 μg/mL).
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