Flavonoids of the flowers of Onobrychis kachetica

Moniava, I. I.; Кемертелидзе, Э. П.

doi:10.1007/bf00564761

Chem Nat Compd

1971

DOI: 10.1007/bf00564761

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Flavonoids of the flowers of Onobrychis kachetica

I. I. Moniava¹,

Э. П. Кемертелидзе²

Abstract: In the flowers of the plant Onobrychis kachetica Boiss, which is endemic to Georgia, we have found ten flavonoids, four of them in considerable amount. The combined flavonoids of the flowers were purified and separated on Sephadex G-75. This gave five individual flavonoids in the form of yellow acicular crystals-flavonoids A, B, C, D, and E. On the basis of' their IR spectra and mixed melting points, the first four substances were identified as kaempferol [1], isoastragalin [2], astragalin [3], and kaempferol … Show more

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2005

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“…Mass spectrum (EI, 70 eV, m/z): 478, C 22 H 22 O 12 [7]. Mass spectrum (EI, 70 eV, m/z): 618, C 36 H 58 O 8 [9].…”

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Biologically Active Substances from Camphorosma monspeliacum

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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″),...

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“…Mass spectrum (EI, 70 eV, m/z): 478, C 22 H 22 O 12 [7]. Mass spectrum (EI, 70 eV, m/z): 618, C 36 H 58 O 8 [9].…”

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confidence: 99%

Biologically Active Substances from Camphorosma monspeliacum

et al. 2005

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Flavonoids of the flowers of Onobrychis kachetica

Cited by 1 publication

References 2 publications

Biologically Active Substances from Camphorosma monspeliacum

Biologically Active Substances from Camphorosma monspeliacum

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