Biologically Active Substances from Camphorosma monspeliacum

Abstract

Over 700 species of plants belonging to one group or another of halophytes are indigenous to saline soils of the arid zone of Central Asia. Representatives of the Chenopodiaceae and Tamaricaceae families are euhalophytes and are among the most numerous species in the flora of saline soils [1].Camphorosma monspeliacum L. (Chenopodiaceae) is known to be a source of essential oil [2] and an alkaloid [3]. However, other groups of natural compounds have been insufficiently studied.The plant is used in folk medicine to treat lung diseases and as a stimulant, diuretic, and sudorific [4].We have initiated an investigation of the MeOH extract of the aerial part of C. monspeliacum collected in Almaty District during flowering. Chromatography (PC, TLC) using specific developers detected flavonoids; coumarins; alkaloids; amino, phenolic, and fatty acids; carbohydrates; and triterpenoids. The MeOH extract was worked up successively with CHCl 3 , EtOAc, and n-BuOH. Adsorption-distribution chromatography of the EtOAc fraction over silica gel (CHCl 3 :MeOH) and polyamide (MeOH:H 2 O) isolated compounds 1-5.The structures of the isolated compounds were established by chemical (acid hydrolysis, alkaline destruction, anthocyanidine test) and spectral methods (UV, mass, PMR, 13 C NMR, and 2D NMR spectroscopies) and by comparison with the literature.The attachment sites of the carbohydrate units were determined by 2D heteronuclear correlation spectroscopy HMBC and UV spectroscopy with ionizing and complexing reagents. Compounds 1-5 were isolated for the first time from a plant of the Camphorosma genus. Isorhamnetin (3,5,7,4′-tetrahydroxy-3′-methoxyflavone) (1), mp 304-305°C (MeOH). PMR spectrum (300 MHz, CD 3 OD, δ, ppm, J/Hz): 3.94 (3H, s, OCH 3 ), 6.18 (1H, d, J = 2.0, H-6), 6.38 (1H, d, J = 2.0, H-8), 6.75 (1H, d, J = 8.0, H-5′), 7.65 (1H, dd, J = 2.0, 8.0, H-6′), 7.73 (1H, d, J = 2.0, H-2′). Mass spectrum (EI, 70 eV, m/z): 316, C 16 H 12 O 7 [5]. Isorhamnetin-3-O-β-D-glucopyranoside (2), mp 198-200°C (70% CH 3 OH). UV spectrum (MeOH, λ max , nm): 346, 256; +CH 3 COONa: 355, 268; +CH 3 COONa + H 3 BO 3 : 355, 261; +AlCl 3 : 433, 275; +AlCl 3 + HCl: 396, 270; +NaOMe: 400, 275. PMR spectrum (400 MHz, CD 3 OD, δ, ppm, J/Hz): 3.90 (3H, s, OCH 3 ), 6.20 (1H, d, J = 2.0, H-6), 6.30 (1H, d, J = 2.0, H-8), 6.80 (1H, d, J = 8.0, H-5′), 7.52 (1H, dd, J = 2.0, 8.0, H-6′), 7.80 (1H, d, J = 2.0, H-2′), 4.90 (1H, d, J = 7.0, H-1′′), 3.50-3.30 (6H, m, H-2″, H-3″, H-4″, H-5″, H-6″). Mass spectrum (EI, 70 eV, m/z): 478; C 22 H 22 O 12 [6]. Isorhamnetin-3-O-β-D-galactopyranoside (3), mp 210-211°C (70% CH 3 OH). UV spectrum (MeOH, λ max , nm): 334, 252; +CH 3 COONa: 331, 270; +CH 3 COONa + H 3 BO 3 : 334, 252; +AlCl 3 : 403, 275; +AlCl 3 + HCl: 400, 276; +NaOMe: 400, 275. PMR spectrum (600 MHz, CD 3 OD, δ, ppm, J/Hz): 3.94 (3H, s, OCH 3 ), 6.14 (1H, d, J = 2.0, H-6), 6.39 (1H, d, J = 2.0, H-8), 6.68 (1H, d, J = 8.0, H-5′), 7.31 (1H, dd, J = 2.0, 8.0, H-6′), 7.33 (1H, d, J = 2.0, H-2′), 5.28 (1H, d, J = 7.7, H-1″), 3.88 (1H, dd, J = 10.0, 7.0, H-2″),...

Isoflavones from Camphorosma lessingii Inhibit the Organic Anion Transporters OAT1 and OAT3

“…They are also used topically in Central Asia to treat fungal skin diseases and internally as a diuretic, diaphoretic, stimulant, and aphrodisiac [10]. In previous studies, C. monspeliaca has been reported to be a source of essential oils and alkaloids [11]. Essential oils have been previously reported from C. lessingii [8], as have amino acids and monoterpenes.…”

“…Phytochemical investigation of Camphorosma lessingii has resulted in the isolation of four previously unreported isoflavones (1)(2)(3)(4) and eight known compounds (5)(6)(7)(8)(9)(10)(11)(12). Nine of these compounds (1)(2)(3)(4)(5)(6)(8)(9)(10) are reported for the first time from members of the family Amaranthaceae.…”