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Pdf 280.83 K Trends Phytochem. Res. 5(2) 2021 105-109 Trends in Phytochemical Research (TPR) Journal Homepage: http://tpr.iau-shahrood.ac.ir Original Research Article Chemical composition of Leplaea mayombensis (Pellegrin) Staner CHARLIE KENMOE DJEUKEU1, HERMINE LAURE DJOMKAM MAZA1 * , ARIANE KOUAM KENMOGNE2, NORBERT SEWALD2, JEAN DUPLEX WANSI1 AND JULIETTE CATHERINE VARDAMIDES1 * 1Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon 2Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany ABSTRACT ARTICLE HISTORY One new coumarinolignan, cleomiscosin F (1) along with ten known compounds namely Received: 05 February 2021 3,4-secotirucalla-4(28),7,24-trien-21-hydroxy-21,23-epoxy-3-oic acid (2), 3,4-secotirucalla- Revised: 10 May 2021 4(28),7,24-trien-3,21-dioic acid (3), ceramid A (4), ceramid B (5), mayombensin (6), aridanin Accepted: 20 May 2021 (7), stigmasterol and β-sitosterol and their glucosides were isolated from the seeds and roots ePublished: 16 June 2021 of Leplaea mayombensis (Meliaceae). The structures of the compounds were elucidated based on the interpretation of their spectroscopic data. Some of the isolated compounds (3, 4 and 5) were tested in vitro against bacteria strains Escherichia coli, Bacillus subtilis, Pseudomonas KEYWORDS agarici, and Micrococcus luteus. Compound 3 displayed good activity against Bacillus subtilis, Micrococcus luteus, and Pseudomonas agarici with MIC values of 1.7, 2.3 and 9.8 µM, Antibacterial activity Micrococcus luteus respectively; while compound 4 showed significant activity against with MIC Coumarinolignan value of 11.9 µM. Leplaea mayombensis Minimum inhibitory concentration © 2021 Islamic Azad University, Shahrood Branch Press, All rights reserved. 1. Introduction et al., 1992; Furlan et al., 1996; Garcez et al., 1998; Pereira et al., 2012). As part of our continuous studies on this eplaea mayombensis (Pellegrin) Staner, is a plant genus (Djeukeu et al., 2017), the composition of the species described for the first time by Pellegrin in methanol extracts of seeds and roots of L. mayombensis Lthe region of Mayombe Bayaka near Tchibanga in were examined. This paper describes the isolation and the south of Gabon (Koenen et al., 2012). It is a big tree identification of one new compound cleomiscosin F (1) up to 15-30 m high, belonging to the Meliaceae family along with 3,4-secotirucalla-4(28),7(8),24(25)-trien-21- and commonly distributed in tropical Africa (Shultes hydroxy-21,23-epoxy-3-oic acid (2) (Hernandez et al., and Raffaud, 1990). Leplaea species are well known 2018), 3,4-secotirucalla-4(28),7,24-trien-3,21-dioic acid in traditional medicine in Africa for the treatment of (3) (Akinniyi et al., 1980), ceramid A (4), ceramid B (5), several illnesses such as malaria, rheumatism, syphilis, mayombensin (6) (Djeukeu et al., 2017), aridanin (7) leprosy and other microbial infections (Mulholland et (Feumo et al., 2016), stigmasterol, β-sitosterol and their al., 2000; Fonge et al., 2012). Their previous chemical glucosides (Chaturvedula and Prakash, 2012; Khatun et investigations led to the report of a wide variety of al., 2012) as well as the evaluation of antibacterial activity secondary metabolites including sesqui-, di- and of compounds (3), (4) and (5) against Escherichia coli, triterpenes, limonoids, steroids, flavonoids, and Bacillus subtilis, Pseudomonas agarici, and coumarins (Akinniyi et al., 1980; John et al., 1980; Moutoo Micrococcus luteus by microdilution method. Corresponding author: Juliette Catherine Vardamides and Hermine Laure Djomkam Maza Tel: +237 677 91 96 03; Fax: +237 677 91 96 03 E-mail address: [email protected] ; [email protected], doi: 10.30495/tpr.2021.1922669.1197 106 Djeukeu et al. / Trends in Phytochemical Research 5(2) 2021 105-109 2. Experimental 21,23-epoxy-3-oic acid (2) (17.4 mg). Fraction B (27.0 g) was also studied using the same method, 382 fractions 2.1. Apparatus of 100 mL each were collected. Ceramid A (4) (23.2 mg) was obtained in the combined fractions 105-122, EI-MS was performed on a Finnigan MAT95 eluted with n-hexane-ethyl acetate (1:1), ceramid B (5) spectrometer with perfluorkerosene as reference (15.6 mg) in the combined fractions 135-147, eluted substance. ESI-HR-MS were measured on a Bruker FTICR with n-hexane-ethyl acetate (2:3). This same fraction 4.7 T mass spectrometer. The 1H and 13C NMR spectra B afforded glucosides of stigmasterol and β-sitosterol were recorded at 500 MHz and 125 MHz, respectively, (14.8 mg) in the combined fractions 172-186, eluted on Bruker DRX 500 NMR spectrometer with TMS as with n-hexane-ethyl acetate (2:3), mayombensin (6) internal standard. The chemical shifts (δ) are given (9.6 mg) in the combined fractions 118-240, eluted with in ppm and coupling constant (J) in Hertz. Melting n-hexane-ethyl acetate (3:7), and aridanin (7) (27.3 mg) points were measured on a Mettler FP61 melting point in the combined fractions 328-345, eluted with ethyl L. mayombensis apparatus. Compounds were dissolved in C5D5N, CDCl3. acetate-MeOH (39:1). Root powder of Flash chromatography was performed using silica gel was extracted by maceration with 12 L of MeOH at room (Macherey Nagel & Co; Düren, Germany; 230-400 temperature. After evaporation, 132.0 g of extract were mesh). Column chromatography and vacuum liquid obtained. The crude extract was subjected to column chromatography were carried out on silica gel (70-230 chromatography over silica gel 60 (70-230 mesh, mesh, ASTM, Merck). Thin-layer chromatography was ASTM, Merck), with a gradient system of n-hexane- performed using Merck precoated silica gel 60 F254 ethyl acetate, ethyl acetate-methanol. A total of 289 and spots were visualized with UV light (254 and 365 fractions of ca. 200 ml each were collected. The pure nm) or using ceric sulfate spray reagent before heating. compounds were obtained by direct crystallization. Gentamycin was purchased from Jinling Pharmaceutic Fractions 50-67, eluted with n-hexane-ethyl acetate (Group) Corp. All reagents used were of analytical grade. (4:1) gave 3,4-dimethyl-secotirucalla-4(28),7,24-trien- 3,21-dioic acid (3) (13.1 mg). The combined fractions 2.2. Plant material 98-106, eluted with n-hexane-ethyl acetate (1:1) gave cleomiscosin F (1) (9.6 mg). Fractions 148-161 eluted Seeds and roots of L. mayombensis were collected with n-hexane-ethyl acetate (2:3) precipitated at room in December 2014 from Mount Kala located at 3º52’ temperature to give glucosides of stigmasterol and of latitude North and 11º31’ longitude East, 800 m β-sitosterol (28.2 mg). altitude, near Yaounde, Cameroon. Their authentication was carried out by M. Victor Nana at the National 2.4. Spectroscopic data of compounds 1-7 Herbarium of Cameroon where a voucher specimen has been deposited (accession number: 46220HNC). Cleomiscosin F (1) Yellow amorphous powder, Rf = 0.42 silica gel 60 F254 n-hexane-ethyl acetate (1:1); 2.3. Extraction and isolation m/z + 1 13 EI-MS 386.1 [M] (C20H18O8); H and C NMR data (Table 1). The air-dried powders of L. mayombensis roots and 3,4-secotirucalla-4(28),7,24-trien-21-hydroxy- seeds gave 4.6 and 4.3 kg, respectively. The seed powder 21,23-epoxy-3-oic acid (2) White amorphous powder, was extracted by maceration with 10 L of methanol at n Rf = 0.53 silica gel 60 F254 -hexane- ethyl acetate room temperature for 48 h. After evaporation under m/z + 1 (3:2); HR-ESI-MS [M+Na] 493,3309 (C30H46O4). H reduced pressure, 142.6 g of crude extract were NMR (500 MHz, C5D5N) 5.71 (d, 2.35, H-21); 5.50 (d, obtained. Crude extract was then fractionated by 8.15, H-24); 5.26 (d, H-7); 5.09 (m, H-23); 4.92, 4.90 (brs, vacuum liquid chromatography (VLC) using the silica H-28); 2.45 (m, H-20); 2.25 (m, H-22); 1.78 (s, H-29); 1.69 gel (70-230 mesh, Merck) with gradient of n-hexane- (s, H-26); 1.59 (s, H-27); 1.00 (s, H-30); 0.91 (s, H-18); ethyl acetate (v:v) (9:1); (8:2); (3:2); (1:1); (2:3) and ethyl 0.86 (s, H-19); 13C NMR (125 MHz, C5D5N) 176.0 (C- acetate. The sub-fractions were combined in two main 2); 149.4 (C-4); 145.9 (C-8); 131.9 (C-25); 126.4 (C-24); fractions A-B, based on their TLC analysis. Fraction A 118.0 (C-7); 113.8 (C-28); 102.0 (C-21); 74.3 (C-23); 49.3 (78.6 g) was subjected to column chromatography (C-5); 51.3 (C-14); 51.2 (C-17); 49.7 (C-20); 43.7 (C-13); over silica gel 60 (70-230 mesh, ASTM, Merck) with 40.8 (C-9); 39.4 (C-22); 36.9 (C-10); 34.0 (C-15); 32.6 (C- a gradient of n-hexane-ethyl acetate; ethyl acetate- 1); 32.0 (C-6); 28.8 (C-16); 27.6 (C-2); 27.2 (C-30); 25.5 methanol. A total of 374 fractions of around 100 mL (C-26); 22.8 (C-18); 22.5 (C-29); 18.2 (C-27); 18.0 (C-11); each were collected. The pure compounds were 15.8 (C-19). obtained by direct crystallization. Fractions 40-69 3,4-secotirucalla-4(28),7,24-trien-3,21-dioic acid eluted with n-hexane-ethyl acetate (19:1) gave a - (3) White crystals; (-)-ESI-MS 469.4 [M-H] (C30H46O4) mixture of stigmasterol and β-sitosterol (48 mg).
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