Two New Lupane-Triterpene Glycosides from Leaves of Acanthopanax koreanum.

Chang, Seung‐Yeup; Yook, Chang‐Soo; Nohara, Toshihiro

doi:10.1248/cpb.46.163

Cited by 33 publications

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“…[8][9][10][11][12] Of these compounds, many of the activities of flavonoids have been identified. Hyperin was found to exhibit strong aldose reductase inhibitory activity; 13 furthermore, hyperin, quercetin, and isoquercitrin all exhibit protective activity against glucose-mediated protein damage.…”

Section: -7mentioning

confidence: 99%

Yield Analysis of Flavonoids inAcanthopanax divaricatusandA. koreanumGrown using Different Cultivation Methods

Lee

Lee³

et al. 2016

Nat Prod Sci

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− High-performance liquid chromatography was performed in order to analyze the changes in the flavonoid content (rutin, hyperin, afzelin, quercetin, and kaempferol) of Acanthopanax divaricatus and A. koreanum, in response to different cultivation methods (pinching height, planting time, and top dressing). The total flavonoid content of A. divaricatus and A. koreanum ranged from 0.201 to 0.690 mg/g with different pinching heights, 0.143 to 1.001 mg/g for different planting times, and 0.156 to 1.074 mg/g depending on the rate of fertilizer application. In both A. divaricatus and A. koreanum, the total flavonoid content in the upper section of the plant was greater than that in the lower section. These results demonstrate which cultivation methods maximize the flavonoid content of A. divaricatus and A. koreanum, and thus help to optimize flavonoid yields to improve production for nutraceutical, pharmaceutical, and cosmeceutical applications.

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Section: -7mentioning

confidence: 99%

Yield Analysis of Flavonoids inAcanthopanax divaricatusandA. koreanumGrown using Different Cultivation Methods

Lee

Lee³

et al. 2016

Nat Prod Sci

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“…Several studies on the triterpenoid constituents of Acanthopanax koreanum NAKAI, have been reported. [1][2][3] As a results of an in-going search for the phytochemical constituents in Acanthopanax genus, [4][5][6][7][8][9] we report on the isolation of a new lupane triterpene glycoside, acankoreosideester from the leaves of Acanthopanax koreanum and describe the determination of its structure.The methanolic extract of A. koreanum leaves gave acankoreoside E (1) by the various chromatographic techniques. Acankoreoside E (1) was obtained as a white amorphous powder of molecular formula C 48 H 76 O 20 , as determined by HR-FAB-MS (molecular ion peak at m/z 995.4828 due to [MϩNa] ϩ ).…”

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“…[1][2][3] The structure of 1 was established by comparing its chemical shifts to those of acankoreoside A (3), 2) which differed from 1 due to the presence of an aldehyde group , 2) indicating that the aldehyde group was located at C-20 of the aglycone.…”

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“…53, No. 1 supposing that the absolute configurations of the sugars assumed the common forms, L-rhamnose and D-glucose, in naturally occurring glycosides from Acanthopanax species, [1][2][3][4][5][6][7][8][9] the respective sugar components and the sequence of the oligosaccharide chain were determined to be [a-L-rhamnopyranosyl- ( Enzymetic Hydrolysis of 1 A mixture of compound 1 (30 mg) and the esterase, separated and purified from the leaves of Acanthopanax divaricatus by the method described in previous paper, 5) was incubated at 37°C for 5 d. The reaction mixture was extracted with ethyl acetate, concentrated to dryness, and purified by silica gel column chromatography (CHCl 3 Acid Hydrolysis of 1 Compound 1 (3 mg) was hydrolyzed with 2 ml of 2 N HCl in H 2 O for 4 h at 80°C, which was followed by neutralization with 2 N NaOH in H 2 O and extraction with CHCl 3 . The aqueous layer was evaporated to dryness under vacuum.…”

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A New Lupane Glycoside from the Leaves of Acanthopanax koreanum

Park

Choi

Yook

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Acanthopanax genus is a shrub indigenous to Northeast Asia. Its bark, known as Acanthopanis Cortex, is used to treat sinew and bone pains in traditional oriental medicine. Several studies on the triterpenoid constituents of Acanthopanax koreanum NAKAI, have been reported. [1][2][3] As a results of an in-going search for the phytochemical constituents in Acanthopanax genus, [4][5][6][7][8][9] we report on the isolation of a new lupane triterpene glycoside, acankoreosideester from the leaves of Acanthopanax koreanum and describe the determination of its structure.The methanolic extract of A. koreanum leaves gave acankoreoside E (1) by the various chromatographic techniques. Acankoreoside E (1) was obtained as a white amorphous powder of molecular formula C 48 H 76 O 20 , as determined by HR-FAB-MS (molecular ion peak at m/z 995.4828 due to [MϩNa] ϩ ). Its 13 C-NMR and DEPT spectra revealed 48 carbons signals, 30 of which were assigned to a triterpenoid sapogenol moiety, and 18 to three monosaccharide moieties. Relevant 1 H-NMR data showed the following; four tertiary methyl groups [d 0.85, 0.96, 1.19

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Naturally Occurring Triterpenoid Saponins

Dinda

Debnath²,

Mohanta

et al. 2010

Chemistry & Biodiversity

140

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Naturally occurring new triterpenoid saponins reported from mid-1996 to March, 2007 are reviewed including their physical constants and plant sources, and are compiled in Table 1. New saponins are arranged in Table 1 on the basis of the skeletal structures of their aglycones, e.g., oleanane type, ursane type, lupane type, hopane type, taraxastane type, cycloartane type, lanostane type, tirucallane type, dammarane type, cucurbitane type, and holostane type. The known triterpenoid saponins and prosapogenins of the new saponins, the biological and pharmacological activities of which were published during 1996-2007, are also reviewed together with their plant sources listed in Table 2 according to the skeletal structures of their aglycones in the same fashion as in Table 1. The plant and animal sources of both new and known bioactive triterpenoid saponins are collected in Table 3 in alphabetical order. The biological and pharmacological activities such as antiallergic, antiatherosclerosis and antiplatelet, antibacterial, anticomplementary, antidiabetic, contraceptive, antifungal, anti-inflammatory, antileishmanial, antimalarial/antiplasmodial, anti-obesity, anti-proliferative, antipsoriatic, antispasmodic, antisweet, antiviral, cytotoxic/antitumor, detoxication, gastroprotective, haemolytic, hepatoprotective, immunomodulatory, anti-enzyme, anti-osteoporotic, insecticidal, insulin-like, membrane-porosity, molluscicidal, neuropharmacological, anti-endothelial dysfunction, snake venom antidote, and sweet activities of these saponins or derived prosapogenins are discussed briefly after Table 3.

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Two New Lupane-Triterpene Glycosides from Leaves of Acanthopanax koreanum.

Cited by 33 publications

References 0 publications

Yield Analysis of Flavonoids inAcanthopanax divaricatusandA. koreanumGrown using Different Cultivation Methods

Yield Analysis of Flavonoids inAcanthopanax divaricatusandA. koreanumGrown using Different Cultivation Methods

A New Lupane Glycoside from the Leaves of Acanthopanax koreanum

Naturally Occurring Triterpenoid Saponins

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