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Nevadensin: Isolation, Chemistry and Bioactivity Nevadensin: Isolation, chemistry and bioactivity TICLE Goutam Brahmachari Department of Chemistry, Natural Products Laboratory, Visva-Bharati University, Santiniketan, West Bengal, India R A Nevadensin (5,7-dihydroxy-6,8,4'-trimethoxyflavone) has already established itself as a promising natural bioactive substance that bears the potential to become a novel “natural lead” in drug discovery programmes. The bioflavonoid exhibited a wide range of significant biological activities including hypotensive, anti-tubercular, antimicrobial, anti-inflammatory, anti-tumour and anti-cancer activities. This review deals with natural sources, isolation, chemistry and biological activities of the flavonoid in detail. The present resume is aimed to boost the ongoing researches on pharmaceutically potential natural “lead molecules” in drug discovery programmes. EVIEW Key words: Bioactivity, chemistry, isolation, natural sources, nevadensin R INTRODUCTION distributed in several medicinal plants as listed below: Acanthopanax trifoliatus (Linn.) Merr. (syn. Acanthopanax [10] At the present scenario of scientific medicinal research, aculeatum Seem.) (family: Araliaceae) bioflavonoids are being considered much effective Baccharis species (family: Asteraceae): Baccharis nitida [11] [12] and useful due to their multidirectional therapeutic Pers. and Baccharis grisebachii [13] efficacies, and have already established as a class Biebersteinia orphanidis (family: Geraniaceae) [14] of therapeutically promising natural drugs and/or Esenbeckia almawillia Kaastra (family: Rutaceae) effective “lead molecules” in drug development and Helianthus species (family: Compositae): Helianthus [15,16] [17] discovery processes.[1-3] Flavonoids comprise a large annuus Linn., Helianthus pumilus [18] group of secondary plant metabolites, which are Hyptis albida H.B.K. (family: Labiatae/Lamiaceae) [9] widely distributed throughout the plant kingdom, Iva species (family: Asteraceae) : Iva nevadensis M.E. and are of importance and interest to a wide variety Jones, Iva acerosa (Nutt.) Jackson of physical and biological scientists. These naturally Limnophila species (family: Scrophulariaceae): Limnophila [19,20] [21] occurring polyphenolics exhibit a wide range of aromatica, Limnophila geoffrayi Bon., Limnophila [22] biological properties including antioxidant, anti- rugosa (syn. Limnophila roxburghii), Limnophila [23] tumour, cytotoxic, enzyme inhibitory, antimicrobial, heterophylla (Linn.) Druce [24-27] insecticidal and oestrogenic activities;[4,5] they are also Lysionotus pauciflorus (family: Gesneriaceae) [28-32] used in the treatment of diabetes and cancer.[6-8] Ocimum species (family: Labiatae/Lamiaceae) : Ocimum americanum Linn. (syn. Ocimum canum Sims.), Nevadensin is a natural bioactive flavonoid, isolated for Ocimum x citriodorum Vis., Ocimum basilicum Linn., the first time fromIva species by Farkas et al.;[9] other natural Ocimum minimum Linn. [33-35] new sources for the compound have also been reported Ononis species (family: Fabaceae/Leguminosae) : following this.[10-37] Nevadensin [systematic name: Ononis natrix ssp. hispanica, Ononis natrix ssp. ramosissima [36,37] 2-(4-methoxyphenyl)-5,7-dihydroxy-6,8-dimethoxy-4H- Viguiera species (family: Asteraceae) : Viguiera mollis, 1-benzopyran-4-one] is a pentaoxygenated flavone, i.e. Viguiera procumbens, Viguiera bicolor. 5,7-dihydroxy-6,8,4'-trimethoxyflavone [Figure 1]. This flavonoid molecule has been already shown to have EXTRACTION AND ISOLATION a lot of pharmacological efficacies, and hence bears a promising potential of being a “natural lead” in the Typical procedures as reported for the extraction and ongoing researches directed towards drug development isolation of nevadensin from few of its natural sources and discovery. In this review, isolation, chemistry and are described herein. biological activities of this important natural agent have been considered for discussion. From I. nevadensis Ground whole plants of I. nevadensis (740 g) were NATURAL SOURCES extracted with chloroform for 2 days; the crude gummy mass (22 g), obtained on removal of the solvent under Exhaustive literature survey revealed that nevadensin is reduced pressure was then chromatographed over www.greenpharmacy.info Address for correspondence: Dr. Goutam Brahmachari, Department of Chemistry, Natural Products Laboratory, Visva-Bharati University, Santiniketan - 731 235, West Bengal, India. E-mail: [email protected] Received: 02-12-2009; Accepted: 03-07-2010; DOI: 10.4103/0973-8258.74128 213 International Journal of Green Pharmacy | October-December 2010 | Brahmachari: Nevadensin - A pharmaceutically potent bio-flavonoid 3' OMe PHYSICAL AND SPECTRAL PROPERTIES OF OMe 2' NEVADENSIN 1 4' HO 8 7 O Nevadensin (molecular formula: C H O ) was obtained as 1' 5' 18 16 7 2 6' golden yellow needles (from ethanol); Rf value measured 6 as: 0.70 (CHCl :EtOAc = 1:5). UV, IR, 1H-NMR, 13C-NMR, 4 3 3 MeO 5 EIMS and 2D-NMR spectral properties of the compound are given below: OH O 1. UV (ethanol): λmax 280, 335 nm; (+AlCl3): 280, 310 (sh), Figure 1: Nevadensin (5,7-dihydroxy-6,8,4'-trimethoxyflavone) 355 nm 2. IR (KBr) ν cm−1: 3407, 3100, 2936, 2840, 1663, 1591, 1508, 250 g of silicic acid. The column was eluted successively with 1060, 1025 1 benzene-chloroform (3:1) and benzene-chloroform (5:2). The 3. H NMR (CDCl3, 300 MHz; TMS): δ 12.78 (1H, s, C5-OH), fractions obtained on elution with benzene-chloroform (5:2) 7.89 (2H, dd, J = 2.7 Hz, 11.7 Hz, H-2′ and H-6′), 7.045 solidified on trituration with ether and were recrystallised (2H, dd, J = 3 Hz, 11.7 Hz, H-3′ and H-5′), 6.585 (1H, s, repeatedly from benzene. This furnished nevadensin (0.2 g) C3-H), 4.04 (3H, s, C6-OCH3), 4.02 (3H, s, C8-OCH3) and which exhibited a double melting point of 186–188°C and 3.90 (3H, s, C4′-OCH3) [9] 13 193–195°C (block). 4. C NMR (CDCl3, 75 MHz): δ 164.2 (C-2), 104.2 (C-3), 183.4 (C-4), 148.8 (C-5), 131.5 (C-6), 149.2 (C-7), 128.5 From I. acerosa (C-8), 146.2 (C-9), 105.0 (C-10), 124.0 (C-1′), 127.8 (C-2′, Ground whole plants of I. acerosa (950 g) were extracted C-6′), 115.0 (C-3′, C-5′), 163.1 (C-4′), 61.4 (8-OCH3), 62.3 with chloroform for 2 days; the crude gummy mass (30.5 (6-OCH3), 56.0 (4′-OCH3) g) obtained on removal of the solvent under reduced 5. EIMS (70 ev): m/z 344 ([M]+), 329 (base peak), 316 [M– pressure was then chromatographed over 225 g of silicic CO]+, 315 [M–CO–H]+, 314 [M–2Me]+, 312 [M–2Me– acid. The column was eluted with benzene. The fractions 2H]+, 301 [M–CO–Me]+, 212 and 132 (retro-Diels-Alder 22–26 (400 ml of benzene each) were solidified on fragmented ion peaks), 197 and 132 (retro-Diels-Alder trituration with ether and were recrystallised repeatedly cleavage of mass fragment 329), 169 [197-CO]+, 168 from benzene. This furnished nevadensin (0.15 g) which [169-H]+, 153[168-Me]+, 141 [169-CO]+, 135 (fragmented exhibited a double melting point of 186–188°C and ion peak), 126 [141-Me]+, 113 [141-CO]+, 107 [135-CO]+, 193–195°C (block).[9] 101 [132-OMe]+ 6. 2D-NMR: Heteronuclear multiple-quantum coherence From L. geoffrayi (HMQC) spectrum of nevadensin shows the expected The pulverised, dried aerial plant materials (615 g) were one-bond heteronuclear (1H–13C) correlations; these are extracted successively with n-hexane, chloroform and shown in Table 1. methanol in a Soxhlet apparatus. The chloroform extract (crude mass of 7.79 g) was chromatographed over silica gel CHARACTERISATION (0.063–0.200 mm, 200 g), eluted with n-hexane-chloroform, chloroform and chloroform-methanol, with gradually The present characterisation of nevadensin is based on the increasing quantity of the more polar solvent. Fraction 11 work of Brahmachari et al.[12] The dihydroxytrimethoxy + was concentrated (4.99 g) and then chromatographed over flavone, 18C H16O7 ([M] at m/z 344), responded positively silica gel (0.063–0.200 mm, 50 g) using chloroform and towards flavonoid colour reactions and ferric chloride chloroform-methanol as eluents, with increasing percentage solution, and exhibited characteristic UV absorptions. The of the more polar solvent, to afford 13 subfractions; the infrared absorption bands of the compound are also of the 10th subfraction (110 mg) was further chromatographed expected outcome, i.e. the flavonoid showed IR absorption to furnish nevadensin (15 mg).[21] bands for the presence of bonded hydroxyl function (3407 cm−1), chelated α, β-unsaturated carbonyl attached with From L. heterophylla aromatic nucleus (1663, 1591, 1508 cm−1) and methoxy group Air-dried defatted powered whole plants (1.5 kg) of L. (s) (1060 cm−1). The high resolution 1H NMR spectrum of the heterophylla were extracted with petrol (60–80°C) in a Soxhlet flavone displayed signals at (i) δ12.78 (1H,s) due to strongly apparatus for 56 hours. The extract was concentrated bonded phenolic hydroxyl function, (ii) 7.89 (2H, dd, J = 2.7 under reduced pressure and then subjected to column Hz, 11.7 Hz, H-2′ and H-6′), (iii) 7.045 (2H, dd, J = 3 Hz, 11.7 chromatography on silica gel (60–120 mesh, 200 g); the Hz, H-3′ and H-5′), (iv) δ 6.585 (1H,s) attributed to C3-H, (v) petrol:benzene (1:2) eluent afforded nevadensin as golden δ 4.04 (3H,s), 4.02 (3H,s) and 3.90 (3H,s) for three methoxyl yellow needles (ethanol; 0.80 g).[23,38] functions. | October-December 2010 | International Journal of Green Pharmacy 214 Brahmachari: Nevadensin - A pharmaceutically potent bio-flavonoid The mass spectral fragmented ion peaks of the compound the methoxyl carbons at δ56.0 (C4′-OCH3), 61.4 (C8′-OCH3) clearly suggest that two methoxyl and two hydroxyl and 62.3 (C6′-OCH3). functions are attached to the ring A, while the remaining methoxyl group is linked with the ring B, and unambiguously The proposed structure of nevadensin was also confirmed by it must be placed at C-4′ as evidenced from the 1H-NMR its conversion experiment [Figure 2].
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