Phenylethanoid and aliphatic alcohol glycosides from Acanthus ilicifolius

Wu, Jun; Zhang, Si; Xiao, Qiang; Li, Qingxin; Huang, Jianshe; Long, Lijuan; Huang, Liangmin

doi:10.1016/s0031-9422(03)00100-6

Cited by 50 publications

(25 citation statements)

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“…7 Recently we have reported the isolation and structural elucidation of two new aliphatic alcohol glycosides, two new Z -4-coumaric acid glycosides and one new and five known phenylethanoid glycosides from the aerial parts of this plant. 8,9 In this paper, we report the complete 1 H and 13 C NMR assignments of 10 phenylethanoid glycosides (1-10), including two new ones (9 and 10), from the same plant. Although the chemical shifts of the eight known compounds 1-8 are well described in the literature, 9 -14 the assignment of the sugar moieties is always confused and no completely assigned NMR data have been published.…”

Section: Introductionmentioning

confidence: 99%

Complete assignments of ¹H and ¹³C NMR data for 10 phenylethanoid glycosides

Wu¹,

Huang²,

Xiao³

et al. 2004

Magnetic Reson in Chemistry

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Section: Introductionmentioning

confidence: 99%

Complete assignments of ¹H and ¹³C NMR data for 10 phenylethanoid glycosides

Wu¹,

Huang²,

Xiao³

et al. 2004

Magnetic Reson in Chemistry

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“…7) Recently we reported the isolation and structural elucidation of a new aliphatic alcohol glycoside, a new and five known phenylethanoid glycosides from the aerial parts of this plant. 8) As part of our continuing search for bioactive natural products from tropical medicinal plants, we now describe the isolation and structural elucidation of a new aliphatic alcohol glycoside (1) and two new (Z)-4-coumaric acid glycosides (2, 3) from the same plant.…”

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confidence: 99%

New Aliphatic Alcohol and (Z)-4-Coumaric Acid Glycosides from Acanthus ilicifolius

Zhang

Huang

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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Acanthus ilicifolius L. (Acanthaceae) is a spiny herb of mangrove widely distributed in southeastern Asia. In traditional Chinese medicine, it is used as anti-inflammatory and anti-hepatitis agents. Previous pharmaceutical studies on this plant revealed that the crude alcoholic extract of its leaves showed antioxidant, hepatoprotective, antitumour and anticarcinogenic effects.1,2) The constituents of this plant had been previously investigated and shown to contain a triterpenoidal saponin,3) 2-benzoxazolinone, 4) acanthicifoline, 5) five benzoxazinoid glucosides, 6) two phenylethanoid glycosides and seven lignan glucosides. 7) Recently we reported the isolation and structural elucidation of a new aliphatic alcohol glycoside, a new and five known phenylethanoid glycosides from the aerial parts of this plant.8) As part of our continuing search for bioactive natural products from tropical medicinal plants, we now describe the isolation and structural elucidation of a new aliphatic alcohol glycoside (1) and two new (Z)-4-coumaric acid glycosides (2, 3) from the same plant.The ethanolic extract of the aerial parts of A. ilicifolius was subjected to extraction and solvent portioning as described in the Experimental. The resulting aqueous layer was applied to column chromatography using D 101 macroporous adsorbing resin, silica gel, octadecylsilyl silica gel and Sephadex LH-20 gel, followed by prep. HPLC-ODS to yield compounds 1, 2 and 3 (Fig. 1) (Table 1), which were determined to be a b-D-xylopyranose and two b-D-glucopyranose units, in addition to eight-carbon signals for the aliphatic aglycone. Acid hydrolysis of 1 afforded D-glucose and D-xylose, which were identified by TLC and comparison of the optical rotation with authentic samples.Distortionless enhancement by polarization transfer (DEPT) experiments indicated the presence of five methylenes (d 25.7, 27.2, 35.3, 38.7, 117.4), two methines (d 83.8, 140.1) and one quaternary carbon (d 178.0) in the aglycone moiety of 1, among which d C 140.1 (CH), 117.4 (CH 2 ) suggested a terminal double bond. The IR spectrum showed absorption bands due to a carboxyl group (3100, 1720 cm Ϫ1 ), which was supported by the 13 C-NMR signal at d C 178.0. The chemical shifts of the aglycone carbons were quite similar to those of ilicifolioside B 8) isolated from the same plant. However, the absence of the methylene carbon at d 62.9 together with the presence of one more carboxyl carbon at d 178.0 were observed in 1, indicating that the terminal hydroxyl was substituted by a carboxyl group. Consequently, the aglycone was established as 6-hydroxyl-7-octenoic acid, which was confirmed by the 1 H-1 H correlation spectroscopy (COSY) and heteronuclear multiple bond connectivity (HMBC) experiments (Fig. 2). The absolute configuration at C-6 was suggested to be in the R-form by comparing the optical rotation value of this aglycone ( Ϫ22.5°). Additionally, the position of glycosylation was assigned to C-6 due to the downfield shift (d C 83.8) of this carbon signal.The assignments of protons...

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“…Further chromatographic separation of the active fractions by using Sephadex LH-20 yielded 9 phenolics active against rhAR. Comparing the data from the reference literature, 12,18,19) we identified them as verbascoside (1), isoverbascoside (2), isocampneoside II (3), cistanoside F (4), luteolin (5), apigenin (6), kaempferol (7), naringenin (8), and caffeic acid (9). The chemical structures of compounds 1-9 isolated from P. coreana seeds are shown in Fig.…”

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confidence: 97%

Inhibition of Aldose Reductase by Phenylethanoid Glycoside Isolated from the Seeds of Paulownia coreana

Kim

Lee

Kim

et al. 2011

Biological & Pharmaceutical Bulletin

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Aldose reductase (AR) inhibitors have considerable therapeutic potential against diabetic complications and do not increase the risk of hypoglycemia. Through bioassay-guided fractionation of the 70% acetone extract obtained from Paulownia coreana seeds, phenylpropanoid glycosides (compounds 1-4) and 5 phenolic coumpounds were isolated (compounds 5-9). Their structures were determined on the basis of spectroscopic analysis and comparison with reported data. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against recombinant human aldose reductase (rhAR) and sorbitol formation in human erythrocytes. Phenylethanoid glycosides showed more effective than the phenolic compounds in inhibiting rhAR. Among the compounds, isocampneoside II (3) was found to significantly inhibit rhAR with an IC 50 value of 9.72 m mM. In kinetic analyses performed using Lineweaver-Burk plots of 1/velocity and 1/concentration of substrate, isocampneoside II (3) showed uncompetitive inhibition against rhAR. Furthermore, it inhibited sorbitol formation in a rat lens incubated with a high concentration of glucose; this finding indicated that isocampneoside II (3) may effectively prevent osmotic stress in hyperglycemia. Thus, the P. coreana-derived phenylethanoid glycoside isocampneoside II (3) may have a potential therapeutics against diabetic complications.

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Phenylethanoid and aliphatic alcohol glycosides from Acanthus ilicifolius

Cited by 50 publications

References 12 publications

Complete assignments of ¹H and ¹³C NMR data for 10 phenylethanoid glycosides

Complete assignments of ¹H and ¹³C NMR data for 10 phenylethanoid glycosides

New Aliphatic Alcohol and (Z)-4-Coumaric Acid Glycosides from Acanthus ilicifolius

Inhibition of Aldose Reductase by Phenylethanoid Glycoside Isolated from the Seeds of Paulownia coreana

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Phenylethanoid and aliphatic alcohol glycosides from Acanthus ilicifolius

Cited by 50 publications

References 12 publications

Complete assignments of 1H and 13C NMR data for 10 phenylethanoid glycosides

Complete assignments of 1H and 13C NMR data for 10 phenylethanoid glycosides

New Aliphatic Alcohol and (Z)-4-Coumaric Acid Glycosides from Acanthus ilicifolius

Inhibition of Aldose Reductase by Phenylethanoid Glycoside Isolated from the Seeds of Paulownia coreana

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Complete assignments of ¹H and ¹³C NMR data for 10 phenylethanoid glycosides

Complete assignments of ¹H and ¹³C NMR data for 10 phenylethanoid glycosides