Lignan glucosides from Acanthus ilicifolius

Kanchanapoom, Tripetch; Kamel, Mohamed S.; Kasai, Ryoji; Yamasaki, Kazuo; Picheansoonthon, Chayan; Hiraga, Yoshikazu

doi:10.1016/s0031-9422(00)00362-9

Cited by 67 publications

(51 citation statements)

References 10 publications

(10 reference statements)

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“…A phenylethanoid glycoside (ilicifolioside A) and an aliphatic alcohol glycoside (ilicifolioside B) have been isolated from the aerial parts [3]. Two lignan glucosides, (+)-lyoniresinol 3a-[2-(3,5-dimethoxy-4-hydroxy)-benzoyl]-O-betaglucopyranoside, and dihydroxymethyl-bis (3, 5-dimethoxy-4-hydroxyphenyl) tetrahydrofuran-9(or 9')-O-beta-glucopyranoside have been isolated from the aerial parts [4]. [7].…”

Section: Phytochemistrymentioning

confidence: 99%

Acanthus ilicifolius Linn.-Lesser Known Medicinal Plants with Significant Pharmacological Activities.

Singh¹,

Duggal²,

Suttee³

2009

Int. J. Phytomed

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Abstract:Acanthus ilicifolius Linn. (Acanthaceae) is relatively lesser-known, yet important medicinal plant of Herbal Materia Medica. The plant is used in traditional systems of medicine, including Traditional Indian Medicine (TIM) or Ayurveda and Traditional Chinese Medicine (TCM). The plant is reported to contain phytochemicals including alkaloid and wide range of glucosides (lignan and phenylethanoid). In traditional medicine, the plant is used in the treatment of diseases ranging from snake bite to skin diseases. Laboratory investigations on extracts of the plant have demonstrated significant pharmacological activities like antioxidant, anticarcinogenic, anti-osteporotic and hepatoprotective. The review analyses traditional medicinal usage, and phyto-pharmacological investigations done on the medicinal plant.

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Section: Phytochemistrymentioning

confidence: 99%

Acanthus ilicifolius Linn.-Lesser Known Medicinal Plants with Significant Pharmacological Activities.

Singh¹,

Duggal²,

Suttee³

2009

Int. J. Phytomed

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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.…”

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confidence: 99%

“…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.…”

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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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“…From these functionalities, the aglycone suggested a 2,5-diaryltetrahydrofuranoid-type lignan. 29,30) In addition, HMBC correlations from the protons of one methoxyl group (d H 3.83, 3H, s) to C-3 (d C 148.4) showed that the methoxyl group was located at C-3, which was further confirmed by the ROESY correlation of the methoxyl group protons with H-2. HMBC correlations of protons of one methylenedioxy group with C-3Ј and C-4Ј determined the methylenedioxy group was located between C-3Ј and C-4Ј.…”

Section: Resultsmentioning

confidence: 77%