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A New Iridolactone from Bremeria Erectiloba Wernham (Rubiaceae)

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A New Iridolactone from Bremeria Erectiloba Wernham (Rubiaceae) International Journal of Chemical Studies 2018; 6(5): 78-80 P-ISSN: 2349–8528 E-ISSN: 2321–4902 IJCS 2018; 6(5): 78-80 A new iridolactone from Bremeria erectiloba © 2018 IJCS Received: 25-07-2018 Wernham (Rubiaceae) Accepted: 27-08-2018 Daniel Sendranirina Safidindray Daniel Sendranirina Safidindray, Anne Wadouachi, Amélie Raharisololalao a) Mention Chimie Médicinale, and Léa Herilala Rasoanaivo Faculté de Sciences, Université de Fianarantsoa Madagascar, East Africa Abstract b) Laboratoire de Chimie des From the leaves of a Madagascar endemic Bremeria erectiloba Wernham, a new iridoid 2 4β- Substances Naturelles et Chimie carbomethoxy-6α, 8α-dihydroxy-8β-methyliridolactone and a known triterpene 1 ursolic acid were Organique Biologique isolated and its structure was established by NMR spectroscopic methods. These compounds are (LCSN/COB), Faculté de Sciences, Université d’ Antananarivo, BP described for the first time for this plant. Ankatso, Antananarivo, Madagascar, East Africa Keywords: Rubiaceae, Bremeria erectiloba, triterpene, iridolactone, NMR Anne Wadouachi Laboratoire de Glycochimie des 1. Introduction Antimicrobiens et des Rubiaceae family contains about 13,143 species and 660 genera in which Mussaenda, Agroressources CNRS UMR Bremeria. Evidence from molecular phylogenies suggests that Rubiaceae family can be Institut de Chimie de Picardie subdivided into three subfamilies (Cinchonoideae, Ixoroideae, and Rubioideae) [1, 2, 3, 4, 5]. CNRS FRE. Université de Picardie [6, 7] Jules Verne, France, Europe About 28 species from Mussaenda were transferred to Bremeria with 18 species endemic of Madagascar whose distinctive characters are given. Bremeria populary known as “fatora” or Amélie Raharisololalao “nofotrakoho”. This species are found in humid to sub-humid evergreen forests [8, 9]. Bremeria Laboratoire de Chimie des genus is met more exclusively in Madagascar and Mascarenes. The juicy of leaves of Substances Naturelles et Chimie Organique Biologique Bremeria erectiloba Wernham is used in traditional medicine Malagasy to treat the (LCSN/COB), Faculté de Sciences, splenomegalie. Not much has been reported on the chemical constituents or biological Université d’ Antananarivo, BP properties of this plant. Bremeria erectiloba Wernham syn. Mussaenda erectiloba belongs to Ankatso, Antananarivo, Madagascar, East Africa the Ixoroideae subfamily in Rubiaceae family. This subfamily is rich of iridoids compounds, 10, 11] which are presented as chemotaxonomic markers [ . The present study has led to the Léa Herilala Rasoanaivo isolation of a new iridoid 4β-carbomethoxy-6α, 8α-dihydroxy-8β-methyliridolactone named Laboratoire de Chimie des bremerine and a known triterpene ursolic acid (Figure 1). Substances Naturelles et Chimie Organique Biologique (LCSN/COB), Faculté de Sciences, Université d’ Antananarivo, BP Ankatso, Antananarivo, Madagascar, East Africa Ursolic acid bremerine Correspondence Daniel Sendranirina Safidindray Fig 1: Compounds isolated from leaves of Bremeria erectiloba Wernham a) Mention Chimie Médicinale, Faculté de Sciences, Université de Fianarantsoa Madagascar, East 2. Materials and methods Africa 2.1. Plant Material b) Laboratoire de Chimie des The leaves of Bremeria erectiloba Wernham were collected from Ambodiamontana commune Substances Naturelles et Chimie Organique Biologique of Ranomafana district of Ikongo, Region Vatovavy-Fitovinany. The plant was identified to (LCSN/COB), Faculté de Sciences, the herbarium references at Botanical and Zoological Park Tsimbazaza (PBZT, Antananarivo Université d’ Antananarivo, BP Madagascar) and a voucher specimen has been deposited in the “Laboratoire de Chimie des Ankatso, Antananarivo, Substances Naturelles Chimie Organique et Biologique” (LCSN/COB). Madagascar, East Africa ~ 78 ~ International Journal of Chemical Studies 2.2. General experimental procedures MHz): δ (ppm), DEPT Q (CD3OD, 125.78 MHz) of 2 are 1H and 13C NMR spectra were recorded on a Bruker Varian given in table 1. 600 NMR instrument with a 600.19/125.78 MHz operating 1 frequency using CD3OD solutions with Tetramethylsilane Compound 1: white powder; δ(ppm) H NMR (600.19 MHz, (TMS) as internal standard. Chemical shifts are reported in CD3OD): 5.49 (1H,br.s, H-12), 3.45 (1H,dd, J=5.7, 9.9 Hz, H- ppm and δ scale with the coupling constants given in Hz. 3), 2.63 (1H,d, J=11.2 Hz, H-18), 1.24 (3H,s, H-23), 1.23 Column chromatography was carried out using silica gel 60 (3H,s, H-27), 1.05 (3H,s, H-25), 1.03 (3H,s, H-26), 1.00 (Merck 70 to 230 Mesh ASTM 0.063-0.200 mm). Thin Layer (3H,br.s, H-29), 0.96 (3H,s, H-30), 0.90 (3H,s, H-24). Chromatography (TLC) was carried out on silicagel 60 F254 δ(ppm) DEPT Q (125.78 MHz, CD3OD) : 180.0 (C-28), 139.3 (Merck). (C-13), 125.7 (C-12), 78.2 (C-3), 55.9 (C-5), 53.6 (C-18), 48.1 (C-9), 48.1 (C-17), 42.6 (C-14), 40.0 (C-19), 39.5 (C- 2.3. Extraction and isolation 20), 39.5 (C-8), 39.2 (C-1), 37.7 (C-4), 37.5 (C-22), 37.3 (C- The dried powder (500 g) was kept for maceration with 80% 10), 33.6 (C-7), 33.1 (C-21), 28.8(C-23), 28.2 (C-2), 25.0 (C- aqueous ethanol (2000 mL) at room temperature for 6 days. 16), 24.0 (C-27), 23.7 (C-11), 21.4 (C-30), 18.8 (C-6), After concentration under reduced pressure. The percentage 17.5(C-29), 17.5 (C-26), 16.6 (C-24), 15.7 (C-25). yield of extract was found to be 6.83%. The hydro-alcoholic extract (32.43 g) was suspended in water at 40°C and then 3. Results and discussion partitioned sequentially using hexane and ethyl acetate, The phytochemical screening subjected to detect the presence furnishing hexanic (0.53 g), ethyl acetate (8.56 g) and of some secondary metabolites following standard procedure aqueous (23.12 g) extracts respectively. showed presence of terpenic compounds (triterpenes and The ethyl acetate extract was first subjected to fractionation iridoids), phenolic compounds (leucoanthocyanins, using silica gel column. Elution with hexane, then gradually coumarins) polyphenols, catechictanins, the polysaccharides increasing polarity with ethyl acetate (100:0 → 0:100) and and saponins in ethanolic extract from the leaves of a ethyl acetate-methanol (100:0 → 0:100). 488 fractions were Bremeria erectiloba. collected and combined as usual using TLC monitoring. Compound 1 was obtained as white amorphous from ethyl Combined fractions were purified. Compound 1 (6 mg, RF= acetate extract. The 1H and 13C NMR spectroscopic data of 1 0.75, Dichloromethane/MeOH 3/7) was obtained as white was in agreement with those reported for ursolic acid (3β- amorphous from fractions 142-145 eluted by hexane/AcOEt hydroxyurs-12-en-28-oic acid) [12] previously isolated from 80/20 and compound 2 (10.34 mg, RF= 0.30, AcOEt/MeOH Mussaenda pubscens, Mussaenda hainanensis, Mussaenda 9/1) was isolated as white powder from fractions 278-284 frontosa [13,14] 1 eluted by AcOEt. Data spectral of NMR H (CD3OD, 600.19 1 Table 1: H, DEPT Q and HMBC NMR data of compound 2 Position 휹1H (ppm) 휹13C (ppm) HMBC 1 -- 175.7 -- 3 3.84 (12.60, 6.00) 3.97 (12.00, 6.00) 63.9 C-1, C-4, C-5, C-11 4 2.84 50.9 C-3, C-5, C-6, C-11 5 2.69 50.2 C-1, C-3, C-4, C-6, C-7, C-9, C-11 6 4.39 76.5 C-5, C-7, C-8 7 1.70 (12.00, 6.00) 2.40 (12.00, 6.00) 49.5 C-6, C-8, C-9 C-5, C-6, C-7, C-10 8 -- 79.6 -- 9 2.76 (6.00, 1.80) 61.9 C-1, C-4, C-5, C-6, C-7, C-8 10 1.28 25.3 C-7, C-8, C-9 11 -- 175.9 -- OMe 3.67 51.9 C-11 Coupling constant in Hz are given in parentheses Compound 2 was isolated from the ethyl acetate extract. The The 13C NMR data along with HMBC clearly corroborated 1 H NMR spectrum in CD3OD showed signals for one tertiary the proposed structure. The correlations from protons H-3 (훿 methyl at 훿 1.28 (3H, s), one carbomethoxy at 훿 3.67 (3H, s), 3.84 and 3.97) with C-1 (훿 175.7), C-4 (훿 50.9), C-5 (훿 50.2) four methine protons at 훿4.39 (1H, m, H-6), 2.84 (1H, m, H- and C-11 (훿 175.9) and of OCH3 (훿 3.67) with C-11 4), 2.76 (1H, dd, J = 6.00 and 1.80 Hz, H-9) and 2.69 (1H, m, demonstrated that the carboxyl is methoxylated. In addition, H-5), two methylene groups at 훿2.40 (1H, dd, J = 12.00 and the correlations between H-7 (훿 1.70 and 2.40) with C-5 (훿 6.00 Hz, Hβ-7), 1.70 (1H, dd, J = 12.00 and 6.00 Hz, Hα-7), 50.2), C-6 (훿 76.5), C-7 (훿 49.5), C-8 (79.6), C-9 (훿 61.9) and 3.97 (1H, dd, J = 12.60 and 6.00 Hz, He-3), 3.84 (1H, dd, C-10 (훿 25.3) corroborated the partial structure of 2 as similar [15, 16] 12.00 and 6.00 Hz, Ha-3). to those of iridolactone . The COSY and HSQC correlations indicate that proton in β These findings were also supported by 13C chemical shift position at 2.40/49.5 is correlated to proton at 4.39/76.5 itself values analyzed for 2 in comparison with those observed for correlates to proton at 2.69/50.2 that itself correlates to proton shanzilactone and shanzilactone acetate model compounds at 2.76/61.9.
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