Ahmed Kareem Obaid Aldulaimi et al., Int. J. Res. Pharm. Sci., 2020, 11(3), 4353-4358 ORIGINAL ARTICLE INTERNATIONAL JOURNAL OF RESEARCH IN PHARMACEUTICAL SCIENCES Published by JK Welfare & Pharmascope Foundation Journal Home Page: www.pharmascope.org/ijrps Secondary Metabolites from Leaves of Polyalthia lateri lora and Their Antimicrobial Activity Saripah Salbiah Syed Abdul Azziz1 , Ahmed Kareem Obaid Aldulaimi*2 , Saadon Abdulla Aowda3 , Yuhanis Mhd Bakri1 , Ali Arkan Majhool4 , Rawdha Mohammed Ibraheem5 , Tamara Kareem Obaid Aldulaimi6 , Hamidah Idris4 , Chee Fah Wong4 , Khalijah Awang7 , Marc Litaudon8 , Fauziah Abdullah9 Department of Chemistry, Faculty of Science and Mathematics, Sultan Idris Education University, 35900 Tanjong Malim, Perak, Malaysia 2 Department of Pharmacy, Al-Zahrawi University college, Karbala, Iraq 3 Department of Chemistry, Faculty of Science, University of Babylon, Babylon, Iraq 4 Department of Biology, Faculty of Science and Mathematics, Sultan Idris Education University, 35900 Tanjong Malim, Perak, Malaysia 5 Medical City, Surgical Hospital, Baghdad, Iraq 6 Faculty of Pharmacy, University of Babylon, Babylon, Iraq 7 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia 8 Centre de Recherche de Gif, Institute de Chimie des Substances Naturelles, CNRS, 1, Avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France 9 Forest Research Institute Malaysia, 52109 Kepong, Selangor, Malaysia 1 Article History: Received on: 20 Mar 2020 Revised on: 25 May 2020 Accepted on: 29 May 2020 Keywords: Alkaloid, Triterpene, Antimicrobial, Bacterial, Yeast * ABSTRACT The study aimed to isolate and identify the phytochemical components of Polyalthia lateri lora leaves and evaluate the antimicrobial activity. Six well-known compounds, including three triterpene lupeol (1) betulinic acid (2), β -Sitosterol-β -D-glucoside (3) and three oxoaporphine alkaloids Omethylmoschotaline (4), liriodenine (5) and atherosperminine (6). Structural elucidation of compounds were established through spectroscopic techniques such as 1D and 2D NMR (1 H and 13 C, DEPT, COSY, NOESY, HMBC, HMQC), IR and LC-MS. The isolated compounds and crude extracted were tested for their antibacterial potential against several microorganisms including P. aeruginosa, E. coli, s, S. aureus, B. subtilis and Saccharomyces cerevisiae and its showed signi icant inhibition toward the organisms species with different concentration range. Corresponding Author Name: Ahmed Kareem Obaid Aldulaimi Phone: Email: Ahmedaldulaimi1@gmail.com ISSN: 0975-7538 DOI: https://doi.org/10.26452/ijrps.v11i3.2652 Production and Hosted by Pharmascope.org © 2020 | All rights reserved. INTRODUCTION Annonaceae family is part of the Angiosperma lowering plants that was described to be one of the largest in the family. They comprise of approximate 128 genera and around 3,000 species (Lopes et al., 2018). Annonaceae family has long been used as traditional medicines to treat diarrhea,dysentery, fever and rheumatism (Bele et al., 2011; Moghadamtousi et al., 2015). Polyalthia lateri lora (Bl.) King belongs to the genus Polyalthia lowering plant, of Annonaceae family are often dispersed in the tropics and subtropics regions and known to have large © International Journal of Research in Pharmaceutical Sciences 4353 Ahmed Kareem Obaid Aldulaimi et al., Int. J. Res. Pharm. Sci., 2020, 11(3), 4353-4358 genus of shrubs and trees. They have approximately around 120 species and is predominantly dispersed in the Old World tropics with major species in Malaysia and south-east Asia (Taylor et al., 2001). Polyalthia genus has been investigated as source of many potential compounds and was reported to have biological applications such as anticancer activity (Nahata, 2017), antibacterial activity (Barman et al., 2016; Negi and Sharma, 2010), anti fungal activity (Barman et al., 2016) and antioxidant activity (Adaramola et al., 2017). (3.3mg). The sub-fractions 21-40 were puri ied by CC on SiO2 using (95:5 to 50:50 v/v) ratio of hexane/EA as mobile phase and afforded 22 sub-fractions. Subfraction number 5-14 were further placed on CC on SiO2 eluted with (90:10 v/v) of hexane/DCM and produced 36 fractions; fraction number 12-16 were identi ied as compound 2 (5.2mg). The fraction 1325 from irst column were grouped and sequentially submitted to puri ication through CC on SiO2 using DCM/MeOH as eluted solvent (100:00 to 90:10 v/v) to yield compound 4 (4mg), compound 5 (2.3mg) and compound 6 (3.6mg). The fractions 26-35 from irst column were chromatographed over CC on SiO2 with DCM/MeOH (100:00 to 80:20 v/v) as mobile phase to produce compound 3 (4.8mg) The chemical investigation studies of Polyalthia species showed various types of secondary metabolites, such as alkaloids (Shono et al., 2016), terpenes (Yu et al., 2016), lavones (Ghani et al., 2011) and chalcone (Ahmat et al., 2012). According to the literature, this study is the irst report on phyto- Antimicrobial Screening chemical components of P. lateri lora leaves. According to Nascimento et al. (2000), the microorganisms were grown in the BHI at 37◦ C temperature. Experimental Each microorganism was inoculated on agar plates Instruments surface (MH) with concentration of 106 cells/mL 1 13 The NMR ( H, C, DEPT, COSY, NOESY, HMQC, after 6 hours of growth. As a result, the ilter discs HMBC) were studied using 500 MHz JEOL ECX sys- with 6mm diameter had saturated with the crude tem at (UPSI) instrument. An Agilent LC–MS analy- extracts and isolated compounds (50 µL) placed on sis was performed using the AccelaT M UHPLC Sys- the surface of the inoculated plates. Each sample tem (Thermo Scienti ic, San Jose, USA) equipped was implanted concurrently in a hole of plates. Incuwith quarternary pump, A Phemomenex Kinetex bated the plates for 24 hours at the temperature of RP C18 column (3 µm, 2.2 mm I.D. x 150 mm), 37◦ C. The plates were left incubated for 24 hours at was recorded at FRIM, Malaysia. FTIR Model 6700 the temperature of 37◦ C. As time ended, observation spectrophotometer was used for IR study (FRIM). of the inhibition zone took place that was measured Thermo Scienti ic BIOMATE 3S UV-Visible Spec- using a ruler. The testing materials were dissolved trophotometer (UPSI). in MeOH. The solvents were controlled for tested microorganism in the study, there had been no sign Plant sample of inhibition. The methanol solvents were used as Leaves of P. lateri lora (KL 5255) were collected and positive control. Meanwhile, samples that appeared identi ied by University of Malaya group, Depart- bioactivity were applied to estimate the MIC for each ment of Chemistry, Kuala Lumpur, Malaysia, from microorganism. Perak, Chemor, Bukit Kinta, Hutan Simpan. In nutrient broth for 6 hours, ive bacterial samples Extraction and isolation known as P. aeruginosa , S. aureus, Saccharomyces Through the cold extraction procedure, the dried cerevisiae, and E. aerogenes were grown. Later, difleaves of P.lateri lora that weigh 2.0kg were ferent concentration ranging from 25-250 µL to the extracted by three different solvent systems; hex- extracts and isolated compounds were inoculated broth. After 24 hours at the temperane, dichloromethane (DCM) and methanol (MeOH) with nutrient ◦ ature of 37 C, by measuring the optical density the to produce crude extracts. Rotary evaporator was MIC from each sample was determined using the used to concentrate the extracts in order to prospectrophotometer (620 nm). All tests were carried duce 37g of MeOH, 25g of DCM and 35g of hexout in duplicates. ane. The DCM crude extract (25g) was fractionized using open CC silica gel, eluted with different ratio of DCM/MeOH and yielding 90 fractions. Fractions 1– 3 were poured in CC on SiO2 eluted with (100:00 to 80:20 v/v) hexane/EA to produced 40 sub-fractions. Sub-fractions 6-20 were further puri ied by CC over SiO2 using (95:5 v/v) hexane/EA to produced 30 fractions; fractions 18-26 identi ied as compound 1 4354 RESULTS AND DISCUSSION Results and discussion The known compounds (Figure 1) were investigated by spectroscopic NMR and LC-MS techniques and comparison with literature; these compounds © International Journal of Research in Pharmaceutical Sciences Ahmed Kareem Obaid Aldulaimi et al., Int. J. Res. Pharm. Sci., 2020, 11(3), 4353-4358 include; lupeol (1) (Obaid et al., 2018), betulinic acid (2) (Haque et al., 2013), β -Sitosterol-β -D-glucoside (3) (Peshin and Kar, 2017) and three oxoaporphine alkaloids O-methylmoschotaline (Aldulaimi et al., 2019) (4), liriodenine (5) (Kareem et al., 2018) and atherosperminine (6) (Obaid et al., 2018). Lupeol (1) White steroid, Chemical Formula: C30 H50 O, HRESIMS: 409.3894 [M+H-18]+ ; IR vmax cm−1 : 3361 (OH), 2939 and 2864 (C-H), 1456 and 1042 (CH2 ). UV (DCM) lmax 320 nm. 1 H-NMR (CDCl3 , 500 MHz) ppm (δ ): 1.68 (3H, s, H-30), 4.64 (1H, s, H-29), 4.52 (1H, s, H-29), 0.76 (3H, m, H-28), 0.90 (3H, m, H-27), 1.04 (3H, m, H-26), 0.82 (1H, m, H-25), 0.72 (1H, m, H-24), 0.96 (3H, s, H-23), 1.16 (1H, m, H-22), 1.31 (1H, m, H-21), 2.37 (1H, m, H-19), 1.32 (1H, t, H-18), 1.39 (1H, m, H-16), 1.06 (1H, m, H-15), 1.65 (1H, m, H-13), 1.09 (1H, m, H-12), 1.23, 1.38 (1H each, m, H11), 1.29 (1H, d, J = 3.50 Hz, H-9), 1.42 (1H, m, H- 7), 1.31, 1.50 (1H each, m, H-6), 0.64 (1H, d, J = 10.0 Hz, H-5), 3.15 (1H, m, H-3), 1.57 (1H, m, H-2) and 0.85 (1H, m, H-1). 13 C-NMR (CDCl3 , 125 MHz) δ (ppm): 20.0 (C-30), 110.2(C-29), 18. 9 (C-28), 16.4 (C-27), 16.0 (C-26), 17.2 (C-25), 15.9 (C-24), 29.0 (C-23), 40. 8 (C-22), 29.7 (C-21), 151.0 (C-20), 47.0 (C-19), 48.2 (C-18), 43.5 (C-17), 35.4 (C-16), 26.5 (C-15), 42.9 (C-14), 38.0 (C-13), 25.2 (C-12), 20.3 (C-11), 37.2 (C-10), 50.6 (C-9), 40.4 (C-8), 34.2 (C-7), 18.9 (C-6), 55.8 (C-5), 38.0 (C-4), 78.8 (C-3), 27.1 (C-2) and 38.5 (C-1). m, H-17), 1.28 (1H, m, H-16), 1.08 (1H, m, H-15), 0.97 (1H, m, H-14), 1.51 (1H, m, H-12), 1.43 (1H, m, H-11), 0.89 (1H, m, H-9), 1.27 (1H, m, H-8), 1.75 (1H, m, H- 7), 5.28 (1H, d, J = 4.55 Hz, H-6), 2.32 (1H, m, H4), 2.96 (1H, m, H-3), 1.60 (1H, m, H-2), 0.98 (1H, m, H-1), 5.02 (1H, m, H-‘6), 3.07 (1H, t, H-‘5), 3.00 (1H, t, H-‘4), 3.24 (1H, t, H-‘3), 2.87 (1H, t, H- ‘2), 4.24 (1H, d, J = 8.00 Hz, H-‘1), 3.45 (OH, t, H-‘5), 3.45 (OH, t, H-‘4), 3.65 (OH, d, J = 4.50 Hz, H-;3) and 3.65 (OH, d, J = 4.50 Hz, H-‘2). 13 C-NMR (CDCl3 , 125 MHz) ppm (δ ): 12.3 (C-29), 23.4 (C-28), 19.6 (C-27), 20.2 (C26), 28.2 (C-25), 45.9 (C-24), 26.7 (C-23), 32.1 (C22), 19.3 (C-21), 34.1 (C-20), 19.2 (C-19), 12.2 (C18), 56.3 (C-17), 28.2 (C-16), 24.4 (C-15), 56.8 (C14), 42.5 (C-13), 40.3 (C-12), 20.1 (C-11), 39.9 (C10), 50. 9 (C-9), 31.9 (C-8), 32.1 (C-7), 121.5 (C-6), 141.2 (C-5), 39.8 (C-4), 74.2 (C-3), 29.7 (C-2), 37.4 (C-1), 61.9 (C-‘6), 77.8 (C-‘5), 71.31 (C-‘4), 77.2 (C‘3), 74.1 (C-‘2) and 101.6 (C-‘1). O -methylmoschatoline (4) Orange amorphous. HRESIMS 322.1092 m/z [M+H]+ ; IR vmax cm−1 : 1660 (C=0). UV (DCM) lmax 433 and 272 nm. 1 H-NMR (CDCl3 , 500 MHz) ppm (δ ): 8.20 (1H,d,J=5.5 Hz, H-4), 8.96 (1H,d,J=5.5 Hz,H-5), 8.53 (1H,d,J=8.0 Hz,H-8), 7.51 (1H, t, H-9), 7.70 (1H, t, H-10), 9.09 (1H,d,J=8.0 Hz,H-11), 4.04 (3H, s, OCH3 -1), 4.09 (3H, s, OCH3 -2) and 4.15 (3H, s, OCH3 -3); 13 C-NMR (CDCl3 , 125 MHz) ppm (δ ): 127.7 (C-11), 134.6 (C-11a), 134.4 (C-10), 128.2 (C-9), 128.9 (C-8), 182.2 (C-7), 131.5 (C-7a), 145.5 (C-6a), 144.6 (C-5), 119.2 (C-4), 122.9 (C-3b), 131.1 Betulinic acid (2) (C-3a), 148.5 (C-3), 147.4 (C-2), 115.7 (C-1a), 156.5 Needle crystalls, HRESIMS: [M+H]+ 457.3637. 1 H- (C-1), 61.9 (OCH3 -3), 61.6 (OCH3 -2), 61.1 (OCH3 -1). NMR (CDCI3 , 500 MHz) ppm (δ ): 0.82, 0.76 (each 3H, Liriodenine (5) s, H-25, 24), 0.92, 0.98, 0.90 (each 3H, s, H-26, 27, 23), 1.67 (3H, s, H-30), 2.94 (1H, d, J = 11.0, H-19), Yellow amorphous, HRESIMS m/z 276.0674 3.17 (1H, d, J = 5.0, Hz, H-3) and 4.69, 4.57 (each 1H, [M+H]+ ; IR vmax cm−1 : 1661 (C=0), 1447, 1310 s, H-29); 13 C-NMR (CDCI3 , 125 MHz) ppm (δ ): 19.0 and 1260 OCH2 O. UV (DCM) lmax at 261, 316 and (C-30), 109.2 (C-29), 177.0 (C-28), 13.5 (C-27), 16.6 410 nm. 1 H-NMR (CDCl3 , 500 MHz) δ (ppm): 8.63 (C-26), 15.4 (C-25), 15.8 (C-24), 29.2 (C-23), 29.9 (1H,d,J=8.0 Hz,H-11), 7.74 (1H, t, H10), 7.55 (1H, (C-22), 37.9 (C-21), 151.8 (C-20), 44.1 (C-19), 46.7 t, H-9). 8.55 (1H,d,J=8.0 Hz,H-8), 8.92 (1H,d,J=5.0 (C-18), 56.1 (C-17), 33.4 (C-16), 30.0 (C-15), 41.8 Hz, H-5), 7.75 (1H,d,J=5.0 Hz,H-4), 7.22 (1H, s, H-3), (C-14), 38.2 (C-13), 25.4 (C-12), 21.4 (C-11), 37.4 6.37 (2H, s, O-CH2 -O), 13 C-NMR (CDC13 , 125 MHz) (C-10), 50.2 (C-9), 40.9 (C-8), 36.5 (C-7), 19.1 (C-6), ppm (δ ): 127.4 (C-11), 132.9 (C-11a), 134.0 (C-10), 55.3 (C-5), 38.9 (C-4), 77.3 (C-3), 26.6 (C-2) and 38.2 128.9 (C-9), 128.7 (C-8), 182.5 (C-7), 131.27 (C-7a), (C-1) 145.2 (C-6a), 144.8 (C-5), 124.4 (C-4), 103.3 (C-3), 123.3 (C-3a), 108.1 (C-3b), 151.9 (C-2), 148.1 (C-l), β -Sitosterol-β -D-glucoside (3) 135.9 (C-la) and 102.6 (1-O-CH2 O-2). White steroid, HRESIMS: 575.4266 [M+H]+ ; 1 HAtherospermidine (6) NMR (CDCl3 , 500 MHz) ppm (δ ): 1.03 (3H, s, H-29), 1.35 (3H, m, H-28), 0.97 (3H, d, J = 7.00 Hz, H-27), Orange amorphous powder, HRESIMS m/z 0.88 (3H, d, J = 7.00 Hz, H-26), 1.65 (3H, m, H-25), 306.0652 [M+H]+ ; IR vmax cm−1 : 1715 (C=0), 0.97 (3H, m, H-24), 1.28 (3H, m, H-23), 1.22 (1H, m, 1040 and 940 (OCH2 O). UV (DCM) lmax 428 and H-22), 0.91 (3H, d, J = 6.50 Hz, H-21), 1.45 (1H, m, H- 280 nm. 1 H-NMR (CDCl3 , 500 MHz) ppm (δ ): 8.48 20), 0.94 (3H, s, H-19), 0.65 (3H, s, H-18), 1.22 (1H, (1H,d,J=8.0 Hz,H-11), 7.66 (1H, t, H-10), 7.48 (1H, © International Journal of Research in Pharmaceutical Sciences 4355 Ahmed Kareem Obaid Aldulaimi et al., Int. J. Res. Pharm. Sci., 2020, 11(3), 4353-4358 Figure 1: The structures of 1-6 isolated compounds 4356 © International Journal of Research in Pharmaceutical Sciences Ahmed Kareem Obaid Aldulaimi et al., Int. J. Res. Pharm. Sci., 2020, 11(3), 4353-4358 Table 1: Antimicrobial activity of extracts and isolated compounds Compound Gram positive Gram negative S. aureus B. subtilis E. coli P. aeruginosa 1 2 3 4 5 6 Methanol crude DCM crude Hexane crude IZ MIC IZ MIC IZ MIC IZ MIC IZ MIC IZ MIC IZ MIC IZ MIC IZ MIC 11.1 100 8.1 150 8.7 200 9.3 100 12.5 150 7.7 100 14.2 100 12.2 150 11.2 100 7.2 150 10.2 250 9.8 200 10.8 100 11.8 100 9.2 150 12.5 100 13.1 200 11.6 100 9.5 250 11.5 150 7.3 50 12.5 250 13.5 250 21.0 100 12.2 150 13.5 100 8.2 250 7.3 100 12.2 100 10.5 100 12.6 200 12.6 100 8.5 250 15.2 50 7.2 100 7.1 200 Yeast Saccharomyces cerevisiae 8.5 250 7.4 50 15.3 150 15.3 150 12.9 100 9.3 100 7.4 100 7.5 50 12.5 100 IZ = Inhibition Zone (mm) ± SE (0.5-1.8), MIC = Minimum Inhibition Concentration (µg/mL) t, H-9), 8.43 (1H,d,J=8.0 Hz,H-8), 8.89 (1H,d,J=5.5 Hz,H-5), 8.12 (1H,d,J=5.5 Hz,H-4), 6.31 (2H, s, 1-OCH2 O-2) and 4.29 (3H, s, OCH3 -3). 13 C-NMR (CDC13 , 125 MHz) ppm (δ ): 60.2 (OCH3 -3), 102.4 (1-OCH2 O-2), 126.7 (C-11), 133.2 (C-11a), 134.0 (C-10), 127.7 (C-9), 128.7 (C-8), 182.6 (C-7), 130.6 (C-7a), 145.0 (C-6a), 144.3 (C-5), 119.4 (C-4), 136.5 (C-3), 130.7 (C-3a), 122.9 (C-3b), 136.3 (C-2), 149.7 (C-l) and 102.6 (C-la). 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