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Four New Chromone Derivatives from Mangrove Endophytic Fungus Phomopsis Sp

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Four New Chromone Derivatives from Mangrove Endophytic Fungus Phomopsis Sp marine drugs Article Phomopsichin A–D; Four New Chromone Derivatives from Mangrove Endophytic Fungus Phomopsis sp. 33# Meixiang Huang 1,†, Jing Li 2,3,†, Lan Liu 2,4,*, Sheng Yin 1, Jun Wang 1,* and Yongcheng Lin 3,4,5 1 School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China; [email protected] (M.H.); [email protected] (S.Y.) 2 School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China; [email protected] 3 Key Laboratory of Functional Molecules from Oceanic Microorganisms (Sun Yat-sen University), Department of Education of Guangdong Province, Guangzhou 510080, China 4 South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Guangzhou 510006, China 5 School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China; [email protected] * Correspondence: [email protected] (L.L); [email protected] (J.W.); Tel.: +86-208-411-4834 (L.L.); +86-203-994-3090 (J.W.) † These authors contributed equally to this work. Academic Editor: Russell Kerr Received: 9 September 2016; Accepted: 8 November 2016; Published: 22 November 2016 Abstract: Four new chromone derivatives, phomopsichins A–D (1–4), along with a known compound, phomoxanthone A (5), were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp. 33#. Their structures were elucidated based on comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction or theoretical calculations of electronic circular dichroism (ECD). They feature a tricyclic framework, in which a dihydropyran ring is fused with the chromone ring. Compounds 1–5 showed weak inhibitory activities on acetylcholinesterase as well as α-glucosidase, weak radical scavenging effects on 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as OH, and weak antimicrobial activities. Compounds 1–4 showed no cytotoxic activity against MDA-MB-435 breast cancer cells. Their other bioactivities are worthy of further study, considering their unique molecular structures. Keywords: mangrove endophytic fungi; Phomopsis sp.; secondary metabolites; chromone derivatives 1. Introduction The chromone family of natural products exhibit a range of biological activities including anticancer, anti-inflammatory, antibacterial, antiviral, atypical antipsychotic, and anti-platelet properties [1–9]. In our continuous investigation of new bioactive secondary metabolites from the mangrove endophytic fungi in the South China Sea, four new chromone derivatives, phomopsichin A–D (1–4), along with a known compound, phomoxanthone A (5), were isolated from the metabolic products of endophytic fungus Phomopsis sp. 33# from the bark of the mangrove plant Rhizophora stylosa. Compounds 1–3 (Figure1) featured a tricyclic framework in which a dihydropyran ring is fused at C-3 and C-4 of the chromone ring. To our knowledge, the compounds with this type skeleton number approximately 10, which were reported to exhibit the activity attenuating resistin-induced adhesion of HCT-116 colorectal cancer cells to endothelial cells [10], the activity interrupting the dimer formation of Aβ17–42 peptide associated to Alzheimer’s disease [11], inhibitory activity against metallo-β-lactamases [12], moderate antibacterial activity and weak cytotoxic activity [13–15]. In this study, we report the isolation, structural elucidation, and exploration on the biological activities of compounds 1–5. Mar. Drugs 2016, 14, 215; doi:10.3390/md14110215 www.mdpi.com/journal/marinedrugs Mar. Drugs 2016, 14, 215 2 of 11 InMar. this Drugs study,2016, 14 we, 215 report the isolation, structural elucidation, and exploration on the biological2 of 11 activities of compounds 1–5. Figure 1. TheThe chemical structures of compounds 1–5. 2. Results Results 2.1. Structure Elucidation Phomopsichin A A ( 1,, Figure 11)) waswas obtainedobtained asas aa whitewhite solidsolid andand hadhad aa molecularmolecular formulaformula ofof C16HH1616OO7 7asas determined determined by by its its datum datum of of high high resolution resolution electrospray electrospray ionization mass spectroscopy (HRESIMS) (observed(observedm /mz 319.08184/z 319.08184 M− , calculatedM−, calculated 319.08233), 319.08233), requiring requiring nine degrees nine of unsaturation.degrees of unsaturation.The 13C-NMR The and 13C distortionless‐NMR and distortionless enhancement enhancement by polarization by polarization transfer (DEPT) transfer spectra (DEPT) (Table spectra1) 3 (Tableindicated 1) indicated the presence the ofpresence two carbonyl of two groups carbonyl (dc 169.5groups and (δc 173.2), 169.5 and eight 173.2), olefinic eight carbons, olefinic two carbons, sp CH 3 3 3 1 1 1 1 twogroups, sp CH one groups, sp CH 2onegroup, sp CH two2 methoxygroup, two groups, methoxy and groups, one methyl and one group. methyl The group.H-NMR The and H‐NMRH- H andcorrelation 1H‐1H correlation spectroscopy spectroscopy (COSY) (Table (COSY)1 and (Table Figure 1 2and) showed Figure the 2) showed signals ofthe two signalsm-hydrogens of two m‐ hydrogensof phenol of (d Hphenol6.93 ( dδHJ 6.93= 2.4d J = Hz; 2.4 Hz; 6.85 6.85 d Jd =J = 2.4 2.4 Hz), two two methoxy methoxy groups groups (δH ( 3.85/3.42),dH 3.85/3.42), and oneand 2 one‐oxo 2-oxo-propyl‐propyl group group (δH 1.34 (d dH J 1.34= 6.0 dHz;J =4.34 6.0 m; Hz; 2.67 4.34 dd J m; = 18.0, 2.67 4.0 dd Hz;J = 2.58 18.0, dd 4.0 J = 18.0, Hz; 2.584.0 Hz). dd TheJ = 18.0, remaining 4.0 Hz). Thetwo remaining degrees twoof degreesunsaturation of unsaturation supported supported a tricyclic a tricyclic carbon carbon framework framework of dihydropyrano[4,3of dihydropyrano[4,3-b]chromen-10(1H)-one‐b]chromen‐10(1H)‐one in 1 in, which1, which was was confirmed confirmed by the by the correlations correlations between between H‐ 13H-13 and and C‐ C-2/C-112/C‐11 in inheteronuclear heteronuclear multiple multiple-bond‐bond correlation correlation (HMBC) (HMBC) spectroscopy. spectroscopy. In In the the HMBC spectrum (Figure 22),), richrich correlationcorrelation datadata allowedallowed usus toto unambiguouslyunambiguously establishestablish thethe locationslocations ofof substituents on the carbon skeleton. The HMBC correlation between H H-8‐8 and C C-14‐14 revealed that the carbonyl group was located at the C-9C‐9 position; the correlation between H3‐-11 and C C-3‐3 demonstrated that the CH33‐-11 was locatedlocated atat thethe C-2 C‐2 position; position; and and the the correlations correlations between between H 3H-153‐15 and and C-14 C‐14 as as well well as asbetween between H 3H-163‐16 and and C-13 C‐13 indicated indicated that that the the two two methoxy methoxy groups groups were were located located atat thethe C-14C‐14 and C C-13‐13 positions, respectively.respectively. One One hydroxyl hydroxyl group group was was identified identified at theat the C-7 C position‐7 position based based on the on lower the lower field fieldchemical chemical shift (shiftdc 162.6, (δc 162.6, C-7). C‐7). Mar. Drugs 2016, 14, 215 3 of 11 Table 1. 1H-NMR and 13C-NMR data of compounds 1–4 (400/100 MHz, J in Hz). 1 (in C3D6O) 2 (in CDCl3) 3 (in CDCl3) 4 (in CD3OD) dC dH dC dH dC dH dC dH 1 21.0 q 1.34 d 6.0 21.0 q 1.39 d 6.4 21.3 q 1.38 d 6.0 23.8 q 1.31 d 6.0 2 62.8 d 4.34 m 62.1 d 4.41 m 70.0 d 3.83 m 66.7 t 4.23 m 3 34.6 t 2.67 dd 18.0, 4.0 34.4 t 2.63 m 34.6 t 2.64 m 42.1 t 2.94 m 2.58 dd 18.0,10.8 4 164.1 s 163.6 s 160.7 s 167.7 s 5 158.4 s 144.4 s 144.8 s 159.3 s 6 104.3 d 6.93 d 2.4 134.7 s 134.9 s 104.4 d 6.87 d 2.4 7 162.6 s 149.2 s 149.0 s 164.2 s 8 113.8 d 6.85 d 2.4 108.0 d 6.89 s 107.9 d 6.93 s 114.8 d 6.77 d 2.4 9 114.6 s 124.5 s 124.0 s 113.7 s 10 136.4 s 116.0 s 115.6 s 136.2 s 11 173.2 s 173.5 s 174.1 s 177.2 s 12 117.4 s 116.6 s 116.5 s 122.1 s 13 95.2 d 5.40 s 94.5 d 5.57 s 62.5 t 4.82 d 15.2 55.0 t 4.55 s 4.48 d 15.2 14 169.5 s 169.8 s 170.0 s 171.6 s 15 52.8 q 3.85 s 53.2 q 3.95 s 53.2 q 3.96 s 53.3 q 3.91 s 16 55.6 q 3.42 s 55.9 q 3.55 s Mar. Drugs17 2016, 14, 215 56.8 q 3.98 s 56.9 q 3.99 s 3 of 11 Figure 2. The key 1HH-‐11HH COSY COSY and and HMBC HMBC correlations correlations of of compounds compounds 11––44.. Table 1. 1H‐NMR and 13C‐NMR data of compounds 1–4 (400/100 MHz, J in Hz). The relative stereochemistry of 1 was established by its nuclear Overhauser effect spectroscopy (NOESY). The NOE1 (in correlation C3D6O) between2 H-2(in CDCl and H3) -16 indicated3 (in CDCl the relative3) stereochemistry4 (in CD3OD) of 1 as 3 shown in FigureδC 3.
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