2013•Shenyang Yaoke Daxue xuebaoRequires access

Isolation and identification of triterpenes of fruit of Rosa laevigata Michx.

Liu Xue-gu

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Abstract

Objective To investigate the chemical constituents of Rosa laevigata Michx. Methods Various techniques including column chromatography over silica gel,and HPLC w ere employed for isolation and purification of ethanol extract of R. laevigata Michx. The structures w ere identified by spectroscopic analyses including1H-NMR,13C-NMR and ESI-MS. Results Tw elve triterpenoids w ere isolated and their structure w ere identified as 1α,2α,3β,19α-tetrahydroxyurs-12-en-28-oic acid (1),2α,3α,19α,23-tetrahydroxyurs-12-en-28-oic acid (2),2α,3α,19α-trihydroxyurs-12-en-28-oic acid (3),2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid (4),19α-hydroxyasiatic acid-28-O-β-D-glucopyrannoside (5),betulinic acid (6),2α,3β-dihydroxylup-20-en-28-oic acid (7),2α,3β-dihydroxylup-20-en-28-acid methyl ester (8),3-O-trans-p-coumaroyl alphitolic acid (9),3-O-cis-p-coumaroyl alphitolic acid (10),3-O-trans-p-coumaroyl maslinic acid( 11),3-O-cis-p-coumaroyl maslinic acid (12). Conclusions Compounds 8 and 9 are isolated from the Rosaceae for the first time,compounds 10-12 are isolated from the plant for the first time.

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What this paper is about

Objective To investigate the chemical constituents of Rosa laevigata Michx. Methods Various techniques including column chromatography over silica gel,and HPLC w ere employed for isolation and purification of ethanol extract of R. laevigata Michx. The structures w ere identified by spectroscopic analyses including1H-NMR,13C-NMR and ESI-MS. Results Tw elve triterpenoids w ere isolated and their structure w ere identified as 1α,2α,3β,19α-tetrahydroxyurs-12-en-28-oic acid (1),2α,3α,19α,23-tetrahydroxyurs-12-en-28-oic acid (2),2α,3α,19α-trihydroxyurs-12-en-28-oic acid (3),2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid (4),19α-hydroxyasiatic acid-28-O-β-D-glucopyrannoside (5),betulinic acid (6),2α,3β-dihydroxylup-20-en-28-oic acid (7),2α,3β-dihydroxylup-20-en-28-acid methyl ester (8),3-O-trans-p-coumaroyl alphitolic acid (9),3-O-cis-p-coumaroyl alphitolic acid (10),3-O-trans-p-coumaroyl maslinic acid( 11),3-O-cis-p-coumaroyl maslinic acid (12). Conclusions Compounds 8 and 9 are isolated from the Rosaceae for the first time,compounds 10-12 are isolated from the plant for the first time.

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Available abstract

Objective To investigate the chemical constituents of Rosa laevigata Michx. Methods Various techniques including column chromatography over silica gel,and HPLC w ere employed for isolation and purification of ethanol extract of R. laevigata Michx. The structures w ere identified by spectroscopic analyses including1H-NMR,13C-NMR and ESI-MS. Results Tw elve triterpenoids w ere isolated and their structure w ere identified as 1α,2α,3β,19α-tetrahydroxyurs-12-en-28-oic acid (1),2α,3α,19α,23-tetrahydroxyurs-12-en-28-oic acid (2),2α,3α,19α-trihydroxyurs-12-en-28-oic acid (3),2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid (4),19α-hydroxyasiatic acid-28-O-β-D-glucopyrannoside (5),betulinic acid (6),2α,3β-dihydroxylup-20-en-28-oic acid (7),2α,3β-dihydroxylup-20-en-28-acid methyl ester (8),3-O-trans-p-coumaroyl alphitolic acid (9),3-O-cis-p-coumaroyl alphitolic acid (10),3-O-trans-p-coumaroyl maslinic acid( 11),3-O-cis-p-coumaroyl maslinic acid (12). Conclusions Compounds 8 and 9 are isolated from the Rosaceae for the first time,compounds 10-12 are isolated from the plant for the first time.

Key concepts: Betulinic acid, Chemistry, Terpene, Silica gel, Chromatography, Column chromatography, Stereochemistry, Biology

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