Structure elucidation of an acetylated saponin of Blighia welwitschii by NMR spectroscopy

Penders, André; Delaude, Clément

doi:10.1016/0008-6215(94)00160-x

Cited by 11 publications

(4 citation statements)

References 16 publications

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“…The anomeric configuration of rhamnose could not be deduced from the 3 J H1-H2 value. However, the Faculty of Pharmaceutical Sciences, Sojo University; Japan: b Faculty of Engineering, Kyushu Kyoritsu University;[1][2][3][4][5][6][7][8] Japan: c Faculty of Pharmaceutical Sciences, Fukuoka University; 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan: and d Faculty of Medical and Pharmaceutical Sciences, Kumamoto University; 5-1 Oe-honmachi, Kumamoto 862-0973, Japan. Received November 15, 2006; accepted December 22, 2006; …”

Section: Resultsmentioning

confidence: 99%

“…In the HMBC experiments, the anomeric proton signals at In regard to the chemical constituents of N. damascena, alkaloid, 1) sesquiterpenes, 2) and phenolic compounds 3) have been characterized from the seeds, but no report on the aerial parts (leaves and stems) has been published to date. To our knowledge, these triterpene glycosides (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) are first isolated from N. damascena. Meanwhile, a sugar sequence of 3- 13) and Scabiosa tschiliensis (Dipsacaceae), 11) respectively.…”

Section: And Hederagenin 3-o-a-lrhamnopyranosyl-(1→2)-a-l-arabinopyramentioning

confidence: 99%

“…These spectral data indicated that 3 was the 3,28-bisdesmoside of hederagenin, 7) possessing four monosaccharide units. The configuration of the hydroxyl group at C-3 bearing a saccharide moiety was determined to be b from the coupling constants of the proton (dd, Jϭ4.5, 11.5 Hz, H-3).…”

Section: And Hederagenin 3-o-a-lrhamnopyranosyl-(1→2)-a-l-arabinopyramentioning

confidence: 99%

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Four New Triterpene Glycosides from Nigella damascena

Yoshimitsu

Nishida

Okawa

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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The genus Nigella with some 20 species belongs to Ranunculaceae. These are distributed from the southern area of Europa to the northern Africa, the southwestern Asia, and the Central Asia. Nigella damascena L. (Japanese name, kurotanesou) is cultivated as a garden plant. From its seeds, alkaloid, 1) sesquiterpenes, 2) and phenolic compounds 3) were isolated. A survey of the literature showed no chemical work being done on the aerial parts of N. damascena. As part of our continuing investigation on the chemical constituents in the Ranunculaceous plants, [4][5][6] this paper deals with structural elucidation of four new triterpene glycosides, named nigellosides A (1), B (2), C (3), and D (4). Results and DiscussionThe methanolic extract of the air-dried aerial parts of N. damascena was partitioned into a chloroform-water solvent system. The water-soluble portion was separated by MCI gel CHP20P, octadecyl silica gel (ODS), and silica gel column chromatographies, and finally HPLC to give nigellosides A (1), B (2), C (3), and D (4) together with eight triterpene gly-14)The molecular formula of nigelloside A (1) 7, 101.4, 102.0, and 105.3. A detailed analysis of these spectral data indicated that 1 was the 3,28-bisdesmoside of gypsogenin, 15) having four monosaccharide units. The configuration of the hydroxyl group at C-3, bearing a saccharide moiety, was determined to be b from the coupling constants of the proton (dd, Jϭ4.6, 11.5 Hz, H-3). Hydrolysis of 1 afforded L-arabinose, D-glucose, and L-rhamnose, the structure of which was confirmed by the 1 H-NMR coupling pattern and optical rotation using chiral detection in the HPLC analysis, together with gypsogenin. The NMR data could be assigned with the aid of 1 H-1 H correlation spectroscopy (COSY), 1 H-detected heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connection (HMBC) experiments. The anomeric centers of the arabinose and glucose moieties were determined to be a-and b-configurations, respectively, from each 3 J H1-H2 value. The anomeric configuration of rhamnose could not be deduced from the 3 J H1-H2 value. However, the Faculty of Pharmaceutical Sciences, Sojo University; Japan: b Faculty of Engineering, Kyushu Kyoritsu University;[1][2][3][4][5][6][7][8] Japan: c Faculty of Pharmaceutical Sciences, Fukuoka University; 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan: and d Faculty of Medical and Pharmaceutical Sciences, Kumamoto University; 5-1 Oe-honmachi, Kumamoto 862-0973, Japan. Received November 15, 2006; accepted December 22, 2006;

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Section: Resultsmentioning

confidence: 99%

Section: And Hederagenin 3-o-a-lrhamnopyranosyl-(1→2)-a-l-arabinopyramentioning

confidence: 99%

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Four New Triterpene Glycosides from Nigella damascena

Yoshimitsu

Nishida

Okawa

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The latter isolated saponins are not chemotaxonomic markers of the Nigella genus because they have been isolated from various species such as Blighia welwitschii (Hiern) Radlk. [35], Dipsacus azureus Schrenk [36], Schefflera rotundifolia [37], Patrinia scabiosaefolia Link, a Chinese drug whose extract has shown hepatotoxic activities [38], as well as anti-tumor and anti-inflammatory effects [39], Lonicera japonica Thunb. [40], and Anemone anhuiensis roots [41].…”

Section: Discussionmentioning

confidence: 99%

Phytochemical Characterization, Antioxidant, and Anti-Proliferative Activities of Wild and Cultivated Nigella damascena Species Collected in Sicily (Italy)

Scognamiglio,

Maresca,

Basile

et al. 2024

Antioxidants

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The use of Nigella damascena seeds in the culinary field or as aerial parts infusions in the pharmaceutical and cosmetic fields is widely reported. The biological activity of this plant, as demonstrated over the years, is closely related to its phytochemical content. This investigation focused on the comparative study of the same plants of N. damascena, one totally wild (WND), while the other two, one with white flowers (CWND) and the other with blue flowers (CBND), were subject to cultivation, irrigation, and manual weeding. Using the potential of 1D and 2D-NMR spectroscopy, coupled with MS/MS spectrometric studies, the three methanolic extracts of N. damascena were investigated. Chemical studies have highlighted the presence of triterpene saponin compounds and various glycosylated flavonoids. Finally, the in vitro antiproliferative and antioxidant activities of the three individual extracts were evaluated. The antiproliferative activity performed on U-937, HL-60, and MCF-7 tumor cell lines highlighted a greater anticancer effect of the CBND and CWND extracts compared to the data obtained using WND. The antioxidant activity, however, performed to quantify ROS generation is comparable among the extracts used.

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