Two New Biflavonoids from <i>Ochna obtusata</i>

Rao, Karumanchi V.; Sreeramulu, K.; Rao, C. Venkata; Gunasekar, Duvvuru; Martín, M.T.; Bodo, Bernard

doi:10.1021/np9604590

Cited by 30 publications

(34 citation statements)

References 10 publications

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“…Comparison of NMR data ( Table 2) of compound 1 with loniflavone and ochnaflavone 10 (7) (Figure 2). These findings permitted to identify 1 as being loniflavone.…”

Section: Resultsmentioning

confidence: 99%

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Bahia¹,

David²,

David³

2010

Quím. Nova

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Recebido em 17/9/09; aceito em 2/2/10; publicado na web em 18/6/10The chloroform partition of methanol extract of leaves of Caesalpinia pyramidalis was submitted to different chromatographic procedures which afforded besides agathisflavone and taxifolin, the minor biflavones loniflavone, amentoflavone, 5'-hydroxyamentoflavone and podocarpusflavone A. The structures of the compounds were established on the basis of NMR and MS data analysis. Besides, the content of biflavones of different specimens of C. pyramidalis, which are collected in different habitats of the Brazilian semi-arid region, was determinated by LC-APCI-MS analysis. These analysis demonstrated that only the specimens harvested in Bahia state showed collectively the presence of agathisflavone, amentoflavone, sequoiaflavone and podocarpusflavone A.Keywords: Caesalpinia pyramidalis; biflavones; flavonoid analysis. INTRODUCTIONCaesalpinia pyramidalis Tul. is a tree belonging to the family Leguminosae-Caesalpinoideae, which is endemic of Brazilian northeastern, especially in the caatinga. It is popularly known as "catingueira" or "pau-de-rato" and its leaves are used in the preparation of infusions and decocts, which are used by the local population as diuretic, antidispeptic, stomach aches and for fever. 1 Species of this genus are known to present different biological activities. For instance, the extract of seeds of C. bonducella showed antimicrobial activities 2 and they are also employed in the treatment of diabetes. 3 Extracts of C. volkensii and C. pluviosa presents antimalarial activity 4 and C. pulcherrima antiviral activity. 5 The extract of C. pyramidalis is responsible for antibacterial, 6 larvicidal and moluscicidal 7 activities.The presence of diterpenes and flavonoids besides other phenolics is characteristic of this genus as well as the subfamily. 8 From the previous studies regarding with C. pyramidalis were isolated phenylpropanoids, biflavonoids, lignan, flavonoids besides gallic acid. 9 In the present study it was reported the isolation and characterization of the minor biflavonoids loniflavone (1), amentoflavone (2), 5¢-hydroxyamentoflavone (3) and podocarpusflavone A (5), besides agathisflavone (4) and taxifolin (6) from the leaves of C. pyramidalis (Figure 1). It was also evaluated by LC-MS the composition of biflavonoids present in leaves of specimens of C. pyramidalis collected in different habitats of Brazilian semi-arid region. EXPERIMENTAL General proceduresThe NMR spectra were obtained in Varian Gemini 2000, Inova 500 and Bruker AMX500 spectrometers operating at 300 and 500 MHz ( 1 H) and, 75 and 125 MHz ( 13 C), employing CD 3 OD, C 5 D 5 N and (CD 3 ) 2 CO as solvents and TMS as internal standard. The MS and the LC-MS analysis were carried out in a Shimadzu chromatographer mod. Bahia et al. 1298 Quim. Nova LCMS-2310, with autosampler 5 mL loop. The detection of biflavonoids was obtained in positive and negative APCI mode. The chromatograms were obtained using a VP-ODS (RP18 -5 mm; 3.9 x 150 mm) column and as mobile pha...

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“…Comparison of NMR data ( Table 2) of compound 1 with loniflavone and ochnaflavone 10 (7) (Figure 2). These findings permitted to identify 1 as being loniflavone.…”

Section: Resultsmentioning

confidence: 99%

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Bahia¹,

David²,

David³

2010

Quím. Nova

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“…The NMR samples, 5.0 mg, were transferred to 5 mm tubes, using CDCl 3 and DMSO-d 6 (0.5 ml) as solvent. The 1 H and 13 C chemical shifts were expressed on the υ scale and were referenced to residual CHCl 3 at υ 7.24 for proton and to the solvent 13 CDCl 3 at υ 77.0 for carbon, and at υ 2.50 for proton and υ 39.5 for carbon in DMSO. The one-dimensional (1D) 1 H and 13 C NMR spectra were acquired under standard conditions (5 mm DUAL 1 H/ 13 C direct detection).…”

Section: Nmr Spectroscopymentioning

confidence: 99%

“…G. Barbosa, M. A. S. Lima and E. R. Silveira crowded methoxyl groups at υ 3.76 OCH 3 -6 and 3.75 (OCH 3 -6 00 ) and both chelated hydroxyl at υ 13.09 (OH-5) and 13.08 (OH-5 00 ) with the two superimposable carbons at υ 132.2 (C-6 and C-6 00 ) established the location of the methoxyl groups at C-6 and C-6 00 , respectively. The significant correlation of the methoxyl group at υ 3.90 OCH 3 -3 000 and the hydrogen at υ 7.56 H-2 000 with the carbon at υ 148.9 C-3 000 , whereas only the latter showed a correlation with the other oxygenated carbon at υ 151.6 C-4 000 , suggested the location of the hydroxyl groups at C-4 0 and C-4 000 ( Table 2).…”

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confidence: 99%

Total NMR assignments of new [C₇OC_7″]‐biflavones from leaves of the limonene–carvone chemotype of Lippia alba (Mill) N. E. Brown

Barbosa¹,

Lima²,

Silveira³

2005

Magnetic Reson in Chemistry

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Phytochemical analysis of leaves of the limonene-carvone chemotype of Lippia alba led to the isolation of two biflavonoids with a new structural pattern with an ether linkage: 5,5''-dihydroxy-6,4',6'',3''',4'''-pentamethoxy-[C(7)--O--C(7'')]-biflavone (1) and 4',4,5,5''-tetrahydroxy-6,6'',3'''-trimethoxy-[C(7)--O--C(7'')]-biflavone (2). Structural elucidation of the new compounds was established on the basis of spectral data, through the use of 1D NMR and several 2D shift correlated NMR pulse sequences (COSY, HMQC, HMBC and NOESY).

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“…This genus is known to be rich in biavonoids, anthranoids and oavonoids (Mohammad et al 1982, Kamil et al 1983, 1987Messanga et al 1992Messanga et al , 1994Messanga et al , 2000Rao et al 1997;Sibanda et al 1990Sibanda et al , 1993Kittisak et al 2001;Williams and Grayer 2004). Ochna integerrima (Loureiro) Merrill is a small tree.…”

Section: Introductionmentioning

confidence: 99%

Shoot organogenesis and somatic embryogenesis from leaf and shoot explants of Ochna integerrima (Lour)

Lü

Silva

et al. 2010

Plant Cell Tiss Organ Cult

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Ochna integerrima is a medicinal and ornamental plant in Southeastern Asia. It has been listed as a rare and endangered species in China. Here we studied the effects of plant growth regulators and their concentrations on the induction of somatic embryogenesis and shoot organogenesis from leaf and shoot explants of O. integerrima for the first time. Cytokinins played a crucial role in somatic embryogenesis and shoot organogenesis. Among them, a higher concentration of thidiazuron (10.0-15.0 lM TDZ) could induce both somatic embryogenesis and adventitious shoot formation whereas low concentrations of TDZ (5.0 lM) could only induce adventitious shoots. However, 6-benzyladenine (BA at 5-15 lM) could only induce adventitious shoots. Shoot explants induced more adventitious shoots and somatic embryos than leaf explants when cultured on medium with the same concentration (5-15 lM) of TDZ or 15 lM BA. Medium containing 0.5 lM a-naphthaleneacetic acid and 8 lM indole-3-butyric acid and 0.1% activated charcoal could induce adventitious roots within 1 month. An efficient mass propagation and regeneration system has been established.

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Two New Biflavonoids from Ochna obtusata

Cited by 30 publications

References 10 publications

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Total NMR assignments of new [C₇OC_7″]‐biflavones from leaves of the limonene–carvone chemotype of Lippia alba (Mill) N. E. Brown

Shoot organogenesis and somatic embryogenesis from leaf and shoot explants of Ochna integerrima (Lour)

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Two New Biflavonoids from Ochna obtusata

Cited by 30 publications

References 10 publications

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Total NMR assignments of new [C7OC7″]‐biflavones from leaves of the limonene–carvone chemotype of Lippia alba (Mill) N. E. Brown

Shoot organogenesis and somatic embryogenesis from leaf and shoot explants of Ochna integerrima (Lour)

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Total NMR assignments of new [C₇OC_7″]‐biflavones from leaves of the limonene–carvone chemotype of Lippia alba (Mill) N. E. Brown