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Antifungal of Modified Neolignans from Mitrephora Wangii Hu

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Antifungal of Modified Neolignans from Mitrephora Wangii Hu Appl Biol Chem (2016) 59(3):385–389 Online ISSN 2468-0842 DOI 10.1007/s13765-016-0178-3 Print ISSN 2468-0834 ARTICLE Antifungal of modified neolignans from Mitrephora wangii Hu Saksri Sanyacharernkul1 . Sirinapa Nantapap1 . Kallaya Sangrueng2 . Narong Nuntasaen3 . Wilart Pompimon4 . Puttinan Meepowpan1 Received: 24 August 2015 / Accepted: 28 January 2016 / Published online: 15 February 2016 Ó The Korean Society for Applied Biological Chemistry 2016 Abstract Chromatographic separation of leaves and Introduction twigs from M. wangii had led to the isolation of cono- carpan (1) and 30-methoxyconocarpan (2). These structures The genus Mitrephora belongs to the Annonaceae family were assigned on the basis of spectroscopic methods. and comprises approximately 48 species distributed in Compound 1 was modified by organic reactions and the Asia (Deepralard et al. 2007; Rayanil et al. 2013)suchas modified compound 5 exhibited potent antifungal, Pyric- Philippines, Indonesia, Malaysia, Thailand, China, and ularia oryzae. The method used poisoned food technique Southern India. M. wangii is a small to medium size tree. with mycelial growth inhibition for 14 days, 57 % It has a smooth bark, devoid of patterns. The oblong (100 ppm). Compound 5 was stronger than mancozeb leaves are glossy from above, with the undersides cov- which the fungi toxicity drug used as a positive control. ered by fine hairs. The flowers possess a creamy yellow shade. The leaves and twigs of M. wangii were collected Keywords Annonaceae Á Conocarpan Á Mitrephora from Chiang Mai province, Thailand, in 2012. BKF no. wangii Á Neolignans Á Pyricularia oryzae 99291. It was identified by Mr. Narong Nuntasaen, The Forest Herbarium, Department of National Park Wildlife and Plant Conservation, Ministry of Natural Resources and Environment. The previous phytochemical investi- gations of Mitrephora species discovered diterpenoids (Zgoda-Pols et al. 2002;Deepralardetal.2007;Meng et al. 2007; Rayanil et al. 2013), polyacetylene car- boxylic acids/esters (Zgoda-Pols et al. 2001;Lietal. & Wilart Pompimon [email protected] 2009), lignans (Deepralard et al. 2007;Geetal.2008), sesquiterpenes (Deepralard et al. 2007;Geetal.2008), & Puttinan Meepowpan [email protected] and alkaloids (Deepralard et al. 2007). Among these compounds, the diterpenoids and alkaloids showed sig- 1 Department of Chemistry and Center for Innovation in nificant antimicrobial, antimalarial, and cytotoxic activ- Chemistry, Faculty of Science, Chiang Mai University, ities (Zgoda-Pols et al. 2002;Lietal.2005;Mueller Chiang Mai 50200, Thailand et al. 2009). M. wangii has revealed the presence of 2 Department of Chemistry, Faculty of Science and several alkaloids, phenolic amide, steroids, neolignans, Technology, Phranakhon Rajabhat University, Bangkok 10220, Thailand and allantoin. The neolignan derivative compounds, namely conocarpan (1)and30-methoxyconocarpan (2), 3 The Forest Herbarium, Department of National Park, Wildlife and Plant Conservation, Ministry of Natural Resources and exhibited significant cytotoxicities (Tanamatayara, 2011). Environment, Bangkok 10900, Thailand However, there has been no reported either phytochem- 4 istry or biological activities of M. wangii prior to our Laboratory of Natural Products, Department of Chemistry, Faculty of Science, Center for Innovation in Chemistry, work. Lampang Rajabhat University, Lampang 52100, Thailand 123 386 Appl Biol Chem (2016) 59(3):385–389 K CO CH3 2 3 H C excess MeI 3 OCH3 acetone, room temp. O (3) (99%) 3'' 1'' CH3 3 eq. PhCOCl CH3 O H 4 2' 3' 3 3C 5 3a 3 H3C 4' 1.3 eq. NEt3 2'' 2 OH O 1' 6 O DCM, room temp. O 7 7a 6' 5' (54%) Conocarpan (1) (4) 3 eq. Ac2O CH3 O H C CH 1.3 eq. NEt3 3 3 O DCM, room temp. O (5) (93%) Fig. 1 Structural modification products of compounds 3–5 Materials and methods 24 h. The resulting mixture was filtrated, evaporated to dryness, and purified to methylation product by preparative Extraction and isolation thin-layer chromatography (EtOAc:hexane (2:8) as a developing solvent). Air-dried leaves and twigs of M. wangii (3 kg) (BKF no. Compound 4 (77.6 mg, 54 % yield) was prepared by 99291) were successively macerated with three organic benzoylation of conocarpan (1) (99.9 mg) which was dis- solvents such as hexane (7 L 9 5 time), ethyl acetate (7 L solved in CH2Cl2 and adding benzoyl chloride to the 9 7 time), and methanol (6 L 9 4 time), followed by fil- solution mixture. Then, Et3N was added to the reaction tration. The filtrates were evaporated to dryness under mixture and then stirred at room temperature for 24 h. The reduced pressure to afford 307.15, 296.83, and 190.00 g of resulting mixture was quenched with an aqueous saturated crude extracts, respectively. The hexane extract was sepa- solution of NaHCO3 (10 mL 9 3 times) and extracted with rated by silica gel column (No. 7734, 600 g), eluting with CH2Cl2 (10 mL 9 3 times). The combined organic layer gradient hexane and ethyl acetate (100:0 to 0: 100). Frac- was dried (MgSO4), filtered, and concentrated in vacuo. tions with similar pattern on TLC (10 % ethyl acetate in Purification of the residue by preparative thin-layer chro- hexane) were combined to yield 5 fractions (HA1-HA5). matography (EtOAc:hexane (2:8) as a developing solvent) The fraction HA3 was rechromatographed (silica gel) fol- gave benzoylation product. lowed by crystallization with EtOH to obtain a compound 1 Compound 5 (113.7 mg, in 93 % yield) was obtained by viz. conocarpan (1) (0.4959 g). Ethyl acetate extract was acetylation of conocarpan (1) (104.5 mg) when anhydrous isolated by column chromatography (CC) technique to give Ac2O was employed in the benzoylation mentioned above. 8 fractions (EA1-EA8). The fraction EA2 was rechro- matographed 3 times to achieve compound 2, to be precise 0 3 -methoxyconocarpan (2) (0.0042 g), and fraction EA5 Antifungal activity assay was also rechromatographed 3 times to afford compound 1 (0.9700 g). Identification of the isolated compounds was The antifungal activity of pure and modified compounds done by means of spectroscopic methods (1H, 13CNMR was evaluated against P. oryzae separately by the poisoned and 2D NMR, IR, EI-MS) and comparison with those food technique (Grover and Moore 1962). Treatment sets reports. comprise the concentration at 100, 200, and 300 ppm. Each concentration was aseptically poured into the petri plate Structural modification followed by the addition of melted PDA and was swirled gently to achieve thorough mixing of the contents. In Compound 3 (94.1 mg, 99 % yield) was prepared by control sets, requisite amounts of sterile water were added methylation of conocarpan (1) (101.1 mg) which was dis- to the medium. After the solidification of the media, the solved in acetone (20 mL) and adding K2CO3 to the mycelia of 10 mm diameter of fungus (taken from a 7-day- solution mixture. Then, the excess MeI was added to the old culture) were put into the center of each plate. The reaction mixture and then stirred at room temperature for treatment and control sets were incubated at 25 ± 2 °C for 123 Appl Biol Chem (2016) 59(3):385–389 1 13 Table 1 H (400 MHz) and C 100 (MHz) NMR spectroscopic data for 3–5 in CDCl3 3'' 1'' CH3 CH3 CH O 6''' 5''' CH3 O H C 4 2' 3' 3 3 5 3a 3 H3C H C H3C CH 4' 3 1''' 4''' 3 2'' 2 OH OCH O 1''' 1' 3 O 6 O O 2''' 3''' O 7 7a 6' 5' O Conocarpan (1) Compound 3 Compound 4 Compound 5 Position Conocarpan (1) Compound (3) Compound (4) Compound (5) d13C (DEPT) d1H(mult, J Hz) d13C (DEPT) d1H(mult, J Hz) d13C (DEPT) d1H(mult, J Hz) d13C (DEPT) d1H(mult, J Hz) 1 –– –– –– –– 2 92.70 (CH) 5.11 (1H, d, 8.9) 92.82(CH) 5.08 (1H, d, 8.9) 92.13 (CH) 5.17 (1H, d, 8.6) 92.07 (CH) 5.12 (1H, d, 8.6) 3 45.01 (CH) 3.43 (1H, m) 45.15(CH) 3.39 (1H, m) 45.57 (CH) 3.41 (1H, m) 45.49 (CH) 3.36 (1H, m) 3a 132.31 (C) – 132.53 (C) – 133.66 (C) – 133.47 (C) – 4 120.73 (CH) 7.17 (1H, s) 120.73 (CH) 7.12 (1H, obsc.) 120.81 (CH) 7.22 (1H, obsc.) 120.79 (CH) 7.09 (1H, obsc.) 5 131.34 (C) – 131.25 (C) – 131.44 (C) – 131.42 (C) – 6 126.26 (CH) 7.16 (1H, d, 8.2) 126.28 (CH) 7.12 (1H, obsc.) 126.37 (CH) 7.22 (1H, obsc.) 126.35 (CH) 7.09 (1H, obsc) 7 109.24 (CH) 6.81 (1H) 109.21 (CH) 6.76 (1H) 109.33 (CH) 6.79 (1H) 109.30 (CH) 6.76 (1H) 7a 157.96 (C) – 159.73 (C) – 158.25 (C) – 158.21 (C) – 8 17.68 (CH3) 1.41 (3H, d, 6.8) 17.92(CH3) 1.38 (3H, d, 6.8) 18.13 (CH3) 1.43 (3H, d, 6.8) 18.10 (CH3) 1.39 (3H, d, 6.8) 10 132.43 (C) – 132.53 (C) – 132.09 (C) – 132.09(C) – 20,60 127.86 (2CH) 7.29 (2H, d, 8.5) 127.60 (2CH) 7.34 (2H, obsc.) 127.14 (2CH) 7.49 (2H, obsc.) 127.14 (2CH) 7.40 (2H, obsc.) 30,50 115.49 (2CH) 6.81 (2H, d, 6.6) 114.06 (2CH) 6.90 (2H, obsc.) 121.76 (2CH) 7.13 (2H, obsc.) 121.76 (2CH) 7.09 (2H, obsc.) 40 155.66 (C) – 158.35(C) – 150.51 (C) – 150.51 (C) – 40-O-Sub - (OH) 5.85 (1H, s) 55.32 (C) 3.80 (3H, s) 165.15 (C) – 169.48 (C) – 1’’’ – – – – 138.52 (C) – 21.16 (CH3) 2.26 (3H, s) 2’’’, 6’’’ – – – – 130.20 (CH) 8.20 (1H, obsc.) – – 3’’’, 5’’’ – – – – 128.59 (CH) 7.49 (1H, obsc.) – – 4’’’, – – – – 129.44 (CH) 7.62 (1H, obsc.)– – 100 130.68 (CH) 6.41 (1H, dd, 15.7, 1.5) 130.79 (CH) 6.36 (1H, dd, 15.7, 1.6) 130.69 (CH) 6.36 (1H, dd, 15.7, 1.6) 130.67(CH) 6.35 (1H, dd, 15.7, 1.6) 200 123.08 (CH) 6.13 (1H, dq, 15.7, 6.6) 124.56 (CH) 6.09 (1H, m) 123.17 (CH) 6.09 (1H, m) 123.17 (CH) 6.08 (1H, m) 00 3 18.34 (CH3) 1.90 (3H, dd, 6,6, 1.6) 18.88 (CH3) 1.85 (3H, dd, 6.6, 1.6) 18.43 (CH3) 1.85 (3H, dd, 6.6, 1.6) 18.43 (CH3) 1.84 (3H, dd, 6.6, 1.6) Sub substituent group, obsc obscure signal 123 387 388 Appl Biol Chem (2016) 59(3):385–389 Table 2 Mycelial growth Compounds Concentrations (ppm) Percentage inhibition of mycelial growth inhibition (P.
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