Studies on the Constituents of Polygala japonica HOUTT. III. Structures of Polygalasaponins XX-XXVII.

ZHANG, Dongming; Miyase, Toshio; Kuroyanagi, Masanori; Umehara, Kaoru; Ueno, Akihiko

doi:10.1248/cpb.44.173

Cited by 38 publications

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“…Ternatumosides XI (22) and XII (23) were proposed to have the molecular formulae C 48 H 56 O 27 and C 57 H 62 O 29 , based on HR-FAB-MS, and were larger than 20 and 21 by an oxygen atom, respectively. The NMR spectroscopic data for the aglycone and 3-O-linked sugar and ester moieties of 22 and 23 were consistent with those of 20 and 21.…”

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confidence: 99%

Flavonoid Glycosides from <i>Botrychium ternatum</i>

2012

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The MeOH extract from dried whole Botrychium ternatum plants yielded 33 compounds, including seventeen new flavonoid glycosides and sixteen known compounds. The structures of new compounds were established using NMR spectroscopic analysis and chemical evidence.Key words Botrychium ternatum; Ophiolossaceae; flavonoid glycoside; kaempferol; ternatumoside Recently, plants in the Ophiolossaceaus family were reported to be effective in the cosmetic field, for example, skin moisturizing and lightning actions, improvement and protection of rough skin, and proliferation of skin fibroblasts. 1,2)Botrychium ternatum is one of the Ophiolossaceaus plants and distributed to the Honshu, Shikoku, and Kyushu Islands in Japan, the Korean Peninsula, and China. In Japan, this plant is called "Fuyunohanawarabi" and used to treat dizziness, headache, cough, and fever as a folk medicine. In the course of research to find the efficient agents in the cosmetic field from the Ophiolossaceaus family, we investigated the constituents of B. ternatum and their biological activities.A MeOH extract from dried whole B. ternatum plants was suspended in water. The suspension was extracted with diethyl ether and partitioned into an ether-soluble fraction and a H 2 Osoluble fraction. The ether-soluble fraction was then separated into a n-hexane-soluble fraction and a MeOH-H 2 O (9 : 1)-soluble fraction. The residue of the water soluble-fraction and the MeOH-H 2 O (9 : 1)-soluble fraction was subjected to both silica gel column chromatography and semi-preparative HPLC to give thirty flavonoid glycosides (1-30), two flavonoids (31, 32), and a bibenzyl derivative (33 The molecular formulae of ternatumosides III (8) and IV (9) were identified as C 42 H 46 O 22 and C 51 H 52 O 24 , respectively, by HR-FAB-MS. The NMR spectroscopic data for 8 and 9 were similar to those of 7, and signals due to one and two sets of (trans)-p-coumaroyl groups were observed in 8 and 9, respectively. Additionally, both compounds yielded 7 and (trans)-p-coumaric acid by alkaline hydrolysis.

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confidence: 99%

Flavonoid Glycosides from <i>Botrychium ternatum</i>

2012

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“…This aglycone is relatively rare in this family and was only present in P. japonica (Zhang et al, 1996b). They contain one or two b-D-glucopyranosyl units at C-3 and two to four glycosidic units linked at C-28.…”

Section: Introductionmentioning

confidence: 93%

“…Most of the saponins characterized in Muraltia (Elbandy et al, 2002b(Elbandy et al, , 2004, Polygala (Sakuma andShoji, 1981a, 1981b;Miyase et al, 1995;Yoshikawa et al, 1995a, b;Zhang et al, 1996aZhang et al, , 1996bZhang et al, , 1998Desbe`ne et al, 1999;Haddad et al, 2003;Mitaine-Offer et al, 2003), Carpolobia by either E/Z-4-methoxy-, or E/Z-3,4-dimethoxy-, or E/Z-3,4,5-trimethoxycinnamoyl groups, or by one acetyl group.…”

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confidence: 99%

Triterpene Saponins from Polygalaceae

Lacaille‐Dubois

Mitaine-Offer

2005

Phytochem Rev

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The aim of this review is to give updated results on the chemistry and biological activities of Polygalaceae saponins from literature data and from authors' studies. During the last decade the improvement of isolation and structure elucidation techniques allowed the characterization of about 150 complex triterpene saponins from Polygalaceae having mainly preatroxigenin, medicagenic acid and presenegenin as aglycone. The sequence 3-O-(b-D-glucopyranosyl)-presenegenin 28-[O-a-L-rhamnopyranosyl-(1 fi 2)-b-D-fucopyranosyl] ester with additional acylations with p-methoxy-, di-or trimethoxycinnamoyl groups at the position 4 of the fucopyranosyl moiety often encountered in the genera Polygala, Muraltia, Carpolobia, and Securidaca may represent a chemotaxonomic marker for the Polygalaceae family. The biological and pharmacological properties of some Polygalaceae species such as in vitro activity on the central nervous system, the hypoglycemic, cytotoxic, immunomodulatory activities and in vivo immunoadjuvant properties are highlighted.

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“…The precipitate was removed with centrifugation, and the supernatant next subjected to GC analysis. 20,21) GC conditions: column; GL capillary column TC-1 (GL Science, Inc.) 0.25 mmϫ30 m, carrier gas N 2 , column temperature 230°C; t R D-glucose 21.3 min, L-glucose 20.4 min. D-Glucose was detected from compounds 7-11.…”

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confidence: 99%

Studies on the Constituents from the Aerial Part of Baccharis dracunculifolia DC. II.

2002

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In the course of our research on the constituents of Brazilian plants, we started investigation of the glycosides from Baccharis dracunculifolia DC. (Compositae); we previously reported the structures of dracunculifosides A-J from the aerial part of this plant.1) Recently, ten new glycosides were isolated along with five known compounds identified by their NMR spectral data [1: 3,4-O-dicaffeoylquinic acid methyl ester, 2) 2:]. This paper also describes the isolation and structural elucidation of these new compounds.The extraction of the constituents from B. dracunculifolia DC. was described in a previous paper.1) The adsorbed material on the Mitsubishi Diaion HP-20 column was eluted with 50% MeOH in water, 70% MeOH in water and MeOH, continuously. The residues of the 50% and 70% MeOH eluates gave compounds 1-15.Compound 4 was suggested to have the molecular formula, C 35 (d 149.7, 147.0, 127.8, 123.0, 116.7, 115.3) and six carbon signals due to the sugar moiety (d 102.6, 77.9, 75.6, 74.9, 72.2, 64.7) along with the signal due to the aglycone moiety. Thus, compound 4 was believed to consist of an aglycone, one monosaccharide and an (E)-caffeoyl group.Concerning the aglycone moiety, the 13 C-NMR spectrum showed twenty carbon signals including twelve aromatic carbon signals and the methoxyl carbon signals, and in the 1 H-NMR spectrum, the AMX type- [d 7.05 (1H, d, Jϭ8. Mild alkaline hydrolysis of compound 4 afforded 4a which was identified as pinoresinol O-b-D-glucopyranoside (2) 3,6) by the HPLC analysis and The molecular formulae of dracunculifosides K (5) and L (6) were expected to be C 25 H 28 O 11 and C 28 H 30 O 13 by the HR-FAB-MS. The 1 H-and 13 C-NMR spectra of 5 and 6 displayed the signals due to glucopyranose and an (E)-caffeoyl group in addition to the signal due to each aglycone. The similarity of the 13 C-NMR spectral data of 5 to those of myzodendrone 7) and dracunculifoside I 1) let us to guess that the aglycone of 5 was 4-(3,4-dihydroxyphenyl)-butan-2-one. Similarly, comparison of the 1 H-and 13 C-NMR spectral data of 6 with those of dracunculifoside J 1) indicated the presence of dracunculifoside J and the (E)-caffeoyl group in 6. Production of myzodendrone and (E)-caffeic acid from 5, and dracunculifoside J and (E)-caffeic acid from 6 by mild alkaline hydrolysis confirmed the above presumption. Consistency of the 1 H-and 13 C-NMR spectral data of the sugar and ester moieties in 5 and 6 with those in 4 suggested that the (E)-caffeoyl group was attached to the C-6 position of b-D-glucopyranose. Accordingly, the structures of dracunculifosides K (5) and L (6) were determined as shown in Chart 1.Dracunculifoside M (7) had the molecular formula, . The 1 H-and 13 C-NMR spectra of 7 also showed the signals due to glucopyranose and an (E)-caffeoyl group. The J value of the anomeric proton signal of glucopyranose (Jϭ8.0 Hz) and GC analysis after acid hydrolysis indicated that this glucopyranose had a b-D-configuration. With regard to the aglycone moiety, fifteen carbon signals were observed in the 1...

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Studies on the Constituents of Polygala japonica HOUTT. III. Structures of Polygalasaponins XX-XXVII.

Cited by 38 publications

References 0 publications

Flavonoid Glycosides from <i>Botrychium ternatum</i>

Flavonoid Glycosides from <i>Botrychium ternatum</i>

Triterpene Saponins from Polygalaceae

Studies on the Constituents from the Aerial Part of Baccharis dracunculifolia DC. II.

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