Lignans from of the Seeds of Brochoneura Acuminate
Total Page：16
File Type：pdf, Size：1020Kb
Journal of Pharmacognosy and Phytochemistry 2021; 10(2): 104-109 E-ISSN: 2278-4136 P-ISSN: 2349-8234 www.phytojournal.com Lignans from of the seeds of Brochoneura JPP 2021; 10(2): 104-109 Received: 07-01-2021 acuminate (Myristicaceae) and the antioxidant Accepted: 21-02-2021 and wound healing properties of the methanol Marie Claire Raharisoa extract a) Laboratoire de Chimie et de Valorisation des Produits Naturels. Faculté des Sciences. Université d’Antananarivo, Marie Claire Raharisoa, Claudine Aimée Rasolohery, Nantenaina France Tombozara, David Ramanitrahasimbola, Solofoniaina Andriantiaray b) Institut Malgache de Recherches Appliquées. Razafimahefa, Bernard Bodo and Marcelle Rakotovao Antananarivo, France Abstract Claudine Aimée Rasolohery The seeds of Brochoneura acuminata (Lam.) Warb. (MYRISTICACEAE), endemic to Madagascar, are a) Laboratoire de chimie – used in Malagasy traditional medicine for their wound healing virtue in the South-Eastern part of the Faculté des Sciences - Université island. Two lignans named Otobanone (1) and 1-hydroxyotobain (2) were isolated for the first time from de Fianarantsoa, France the methanol extract. Their chemical structures were established using MS and NMR technics. The free b) Laboratoire Plante Santé, Fanambinantsoa – Fianarantsoa, radical DPPH scavenging assay was used to determine the antioxidant capacity of the methanol extract. France The wound healing effect of the methanol extract was assessed on the rat dorsal created experimental wound. The methanol extract showed a potent scavenging capacity with an IC50 value of 105.31 ± 0.24 Nantenaina Tombozara μg / mL. Topical application of both 2% (w/w) methanol extract of the seeds of B. acuminata and OFM® Institut Malgache de Recherches ointments in excision wound model significantly increased (p < 0.001) wound contraction rate at the 3rd, Appliquées. Antananarivo, the 6th and the 9th day and shortened the epithelization time compared with control treatment. These France results contribute to the chemotaxonomy of the Myristicaceae family and support the traditional uses of B. acuminata. David Ramanitrahasimbola Institut Malgache de Recherches Keywords: Brochoneura acuminata, Myristicaceae, antioxidant, healing activity, lignans, otobain Appliquées. Antananarivo, France 1. Introduction Solofoniaina Andriantiaray Plants remain the first source of new drugs and discovery of new molecules. The development Razafimahefa of new drugs is taking place in various scientific and medical research settings (Chominot, Institut Malgache de Recherches 2000) [1]. Since years, plants have been used in traditional medicine to treat a large range of Appliquées. Antananarivo, human diseases (Sofowora et al., 2013; Dawid- Pać, 2013) [2, 3]. Leaves and barks are generally France prepared in infusion for internal use and oil and/or extract from the fruits or seeds is rather [4] Bernard Bodo used topically (Dzoyem et al., 2014) . Madagascan flora biodiversity is well- known by its Laboratoire de Chimie des high rate of endemicity estimated at 85% from 12,000 to 14,000 species (Rasoanaivo et al., Substances Naturelles (CNRS 1992) [5]. The majority of Malagasy people still rely on traditional medicine to take care of ESA 8041), Muséum National their health due to the unaffordable price of conventional drugs. d'Histoire Naturelle, 63 rue Buffon, Paris, France The Myristicaceae family includes at about 300 species. Among the 16 genera of this family, the genus Brochoneura is endemic to the littoral rainforests along the eastern coast of Marcelle Rakotovao Madagascar consisting on three species including Brochoneura acuminata (Lam.) Warb., B. 1Laboratoire de Chimie et de vouri (Baill.) Warb. and B. madagascariensis Warb. (Schatz, 2001; Cadotte at al., 2002; Valorisation des Produits Figueiredo et Smith, 2020) [6, 7, 8]. B. acuminata is a tree (10 – 15 m tall) with elliptical and Naturels. Faculté des Sciences. Université d’Antananarivo, obovate evergreen leaves. The inflorescence is entirely strewn with a very short and France ferruginous purulence where the flowers are grouped. The fruits are overglobulous, irregularly 4Laboratoire Plante Santé, obovate- compressed, 5 cm long and wide, apiculate. The seed is enveloped in a ceraceous and Fanambinantsoa – Fianarantsoa, crustacean aril with a very sweet smell (De la Bâthie, 1952; Sauquet, 2004) [9, 10]. B. France accuminata is known as Madagascar nutmeg and by other local names such as ‘Rara’, ‘Hafotra’, ‘Vory’or ‘Rarahoraka’. The seeds of this specie are used by the local population as the principal ingredient in the preparation of the local cosmetics and for the treatment of Corresponding Author: wound and sore (De la Bâthie, 1952; Doyle et al.; 2004; Edmond. et al., 2005) [9, 11, 12]. The Claudine Aimée Rasolohery leaves are used to treat injury, scabies and abcess (Razafindraibe et al., 2013) [13]. The latex a) Laboratoire de chimie – from the bark of B. acuminata is used to treat fungal infection and stomachaches (Sattle r and Faculté des Sciences - Université [14] de Fianarantsoa, France Razafindravao, 2017) . According to our best knowledges, neither pharmacological nor b) Laboratoire Plante Santé, chemical studies have been undertaken on this specie. Moreover, several Madagascan and Fanambinantsoa – Fianarantsoa, other Myristicaceae species were reported for their uses in the treatment of infectious diseases, France scabies and scarring (Gottlieb, 1979; Walker and Walker, 1981; Sauquet, 2003 and 2004; ~ 104 ~ Journal of Pharmacognosy and Phytochemistry http://www.phytojournal.com Sauquet et al, 2003) [10, 15, 16, 17, 18], but chemical and mode and NMR spectrometer (Bruker 500, Germany) for the pharmacological studies remain insufficiently exploited. 1H and 13C NMR registration in CDCl3 and confirmed by Recently, there is a growing interest in natural antioxidants the literature reviews. due to their ability to delay the oxidation of other molecules and inhibit the initiation or propagation of oxidizing chain 2.4 Antioxidant activity reactions by free radicals, protecting the human body and 2.4.1 Autobiography assay reducing oxidative damages that may significantly cause the The autobiography assay is based on the protocol described development of many chronic diseases, as diabetes, cancer by Dieng et al. (2015) slightly modified. The methanol extract and cardiovascular diseases (Donno et al., 2018, Shiekh et al., or gallic acid (reference antioxidant) were dissolved in 2020) [19, 20]. They are also used in the enhancement of wound methanol and placed on a plate of silica gel. Silica plate was healing by accelerating the tissue remodeling (Xian et al., eluted a mixture of dichloromethane, ethyl and methanol 2020) [21]. (2/5/3, v/v/v) acidified with 2 drops of acetic acid. At the end In this work, we reported the isolation of two lignans, the of the development, DPPH methanolic solution (2mg/mL) major compounds, from the seeds of B. accuminata as well as was sprayed on the dried plate. The presence of antioxidant the antioxidant capacity of the seed methanol extract compounds was revealed by light yellow areas on a purple compared to gallic acid and the wound healing effect of the background after an optimal time of 30 minutes. seed methanol extract compared to the reference product OFM® (Madécassol). 2.4.2 DPPH free radical scavenging assay The methanol extract free radical removal capacity was 2. Methods evaluated using the radical DPPH assay, described by 2.1 Plant materials Tombozara et al. (2020) slightly modified. Briefly, 25 µL of The seeds of B. acuminata were harvested in December 2016, the methanol extract with a concentration ranging from 5 to from the dense humid forest of the Ranomafana National 125 µg/mL was added to 175 µL methanol DPPH solution Park, located at 450 Km in the south-east of Antananarivo (0.25 mmol/L) in a 96-well microplate and incubated at room during the fruiting period. A voucher specimen was identified temperature for 30 min. Methanol was used as blank and a by Dr Hanta Vololona RAZAFINDRAIBE and deposited at methanol solution of DPPH was used as negative control. fauna and flora department of the Tsimbazaza Zoological Gallic acid with a concentration ranging from 1.25 to 40 Park (RHKV-025/2016), Antananarivo, Madagascar. µg/mL was used as antioxidant reference compound. Results were expressed as means of inhibiting concentration (IC), 2.2 Extraction and phytochemical screening calculated using the following equation: IC (%) = 100 x (A0 – Plant materials were dried in a cool and airy place, away of A1) / A0 where A0 and A1 are the values for the absorbance sunlight, before to be ground into fine powder. 100 g of raw of the negative control and sample at 517 nm. The IC50 materials was extracted by the soxhlet for 4 hours with (inhibition concentration at 50%) values of extract and gallic methanol. The resulting solution was then evaporated under acid were calculated by linear regression (concentration of reduced pressure, at 40 °C using a rotary evaporator (Buchi tested sample or gallic acid vs average percent of scavenging R114). The phytochemical screening was carried out capacity by three replicates). according to the protocols described by Tombozara et al. (2017) [22]. 2.5 Wound healing effect of the methanol extract The in vivo wound healing effect of the methanol of the seeds 2.3 Isolation and structure elucidation of B. acuminate consist on the creation of an experimental Vacuum liquid chromatography was carried out for the wound on previously anesthetized rat and the treatment of this fractionation of the methanolic extract. 1 g of the methanol wound with the ointment preparations to be tested according extract was deposited on a column of 60 Merck silica gel with to the protocol described by Sagliyan et al. (2010) [24]. a particle size of 40-60 Å and eluted with a mixture of dichloromethane and methanol with an increasing polarity 2.5.1 Animals starting 100 – 0 to 0 – 100 (v/v) giving 178 fractions which Wistar adult male rats (weighing 200 ± 20 g and aged were pooled on the basis of their TLC profile affording six between 2 and 3 months), kept under controlled conditions fractions (F1 - F6).