A new benzofuranic acid from the leaves of<b><i>Rhus alata</i></b>

Parveena, M.; Basudan, Omer A.; Mushfiq, M.; Ghalib, Raza Murad

doi:10.1080/14786410601133558

Cited by 6 publications

(5 citation statements)

References 8 publications

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“…The family Anacardiaceae, which consists of 73 genera and approximately 600 species [ 1 , 2 ], is comprised mainly of trees, shrubs, and/or woody vines. The majority of these belong to the genus Rhus [ 3 , 4 ], including over 250 species that bear the common name sumac [ 5 ].…”

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confidence: 99%

Proanthocyanidins from the stem bark of Rhus tripartita ameliorate methylgloxal-induced endothelial cell apoptosis

Alqahtani

Abdel‐Mageed

Shahat

et al. 2019

Journal of Food and Drug Analysis

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In traditional Arabian medicine, the Rhus tripartita plant (family Anacardiaceae) has been used to treat inflammatory conditions. Although Rhus extracts have been reported for their cardioprotective effects, information regarding their active principle compounds remains insufficient. The present investigation was aimed at determining the antioxidant chemical constituents of the methanolic extract of R. tripartita stem bark and evaluating their ability to ameliorate methylglyoxal-induced endothelial cell apoptosis. Ten flavonoid compounds ( 1 – 10 ) were isolated and identified using DPPH radical scavenging bioassay-guided chromatographic separation. A new proanthocyanidin (rhuspartin) ( 1 ) was isolated and identified as 3,5,13,14-flavantetrol-(4β→8)-catechin, using extensive spectroscopic data and high resolution-mass spectrometry. Among the compounds ( 1 , 5 , 7 – 10) tested for toxicity toward cultured endothelial cells (HUVECs), the non-cytotoxic compounds 1 and 7 evinced cytoprotective potential that reversed the methylglyoxal-induced apoptosis (by 62% and 64%, respectively) through downregulation of caspase 3/7.

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Section: Introductionmentioning

confidence: 99%

Proanthocyanidins from the stem bark of Rhus tripartita ameliorate methylgloxal-induced endothelial cell apoptosis

Alqahtani

Abdel‐Mageed

Shahat

et al. 2019

Journal of Food and Drug Analysis

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“…(Jalali et al, 2011), the plant Carpobrotus edulis, (Martins et al, 2011), the leaves of Clerodendrum inerme (L.) (22.5 mg/kg) (Parveen et al, 2010), the chloroform and ethyl acetate fractions of the methanolic extract of Carpobrutus edulis (Martins et al, 2010), chloroform extract of aerial parts of the plants or calli of Euphorbia tirucalli L. (Uchida et al, 2010), seed oil of Capparis spinosa (Tlili et al, 2011), chloroform extract of the leaves of Ficus benjamina (var. camosa) (Moraceae) (Simo et al, 2009), leaves (2 mg/kg) of Pyrenacantha staudii, (Falodun et al, 2009), ethanol extract of leaves of Olea europea L. (Wang et al, 2009), ethyl acetate extract of apple peels of the Red Delicious variety (Malus domestica Borkh) (He et al, 2008), air-dried leaves of Tectona philippinensis, an endemic and endangered Philippine medicinal plant (Ragasa et al, 2008), a mixed benzene and chloroform extract of leaves of Rhus alata (Parveena et al, 2008), and an extract of stem bark of Piptadenia Africana, a western Cameroonian plant (Mbouangouere et al, 2008).…”

Section: Sources Of - -Amyrinsmentioning

confidence: 99%

The Pentacyclic Triterpenes , -amyrins: A Review of Sources and Biological Activities

Vázquez¹,

Palazón²,

Navarro‐Ocaña³

2012

Phytochemicals - A Global Perspective of Their Role in Nutrition and Health

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Fig. 1. Estructure of amyrins NMR methods have indisputably become the single most important spectroscopic techniques for the identification and structure elucidation of amyrins. Several ID and 2D NMR methods are now commonly used for the characterization of pentaclyclic triterpenes. These methods incluye 1 H and 13 C-NMR, APT, DEPT, COSY, HMQC, HMBC and TOCSY. The 1 H and 13 C-NMR assignments of --amyrin are presented in Table 1, (Dias et al., 2011). 2.1.2 Detection Amyrins are found in various plants and plant materials such as leaves, bark, wood, and resins. This material has to be pre-treated prior to isolation of the target compounds. First, the plant material is usually dried, then ground into a power and sieved. Second, extractions are carried out with dichloromethane, chloroformo, n-hexane, and methanol. The samples can be subjected to alkaline hydrolysis, derivatization and separation by thin layer chromatography, and the resulting material can be directly subjected to analysis. Gas chromatography (CG) and high performance thin layer chromatography (HPTLC) techniques are the most commonly employed methods to quantitate -, -amyrin in plants. TLC provided an easy and rapid way to study plant extract profiles and partially identify compounds. The first step for the identification of -amyrin, -amyrin and 3-epi-lupeol was to compare R F values of reference standards with those of sample extracts. TLC on silica gel revealed that -amyrin on tracks 6 and 15, -amyrin on track 14 and the -, -amyrin mixture on track 16, as well as two standards, all had the same R F (Fig. 2). The -amyrin band was observed as brown, while the -amyrin band appeared violet, as did the band for the -, -amyrin mixture. TLC analysis revealed the presence of -amyrin, -amyrin and 3epi-lupeol by a comparison of the position and color of the triterpene spots with those of authentic compounds (Fig. 2). The bands of and -amyrin or their mixture were observed in all commercial resin tracks 1-5 and medicinal plant tracks 8-13, while 3-epi-lupeol track 7 was detected only in the commercial Mexican Copal resins tracks 1-4. Attempts were made to separate the -, -amyrin mixture, which had appeared homogenous on TLC, but without success. These results showed that TLC can be used as a simple method for a preliminary analysis of these triterpenes in extracts of commercial resins and plants, but cannot be employed for the analysis of the -, -amyrin mixture.

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“…This is a new steroidal glycoside isolated from a natural or synthetic source for the first time. The known compounds have been identified as stigmast-5en-3E-ol (E-sitosterol) [15,16], lup-20(29)-en-3E-ol(lupeol) [16,17], and stigmast-5en-3E-ol-E-D-glucopyranoside (E-sitosterol glucoside) [16,18].…”

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New steroidal glycosides from the stem bark of Mimusops elengi

2010

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Two new steroidal glycosides (1 and 2) have been isolated from the ethanolic extract of the stem bark of Mimusops elengi L. and characterized as Keywords: Mimusops elengi L., Sapotaceae, stem bark, steroidal glycosides.Mimusops elengi L. (Sapotaceae) is an ornamental small tree with sweet scented flowers growing wild throughout the greater part of India [1]. All parts of the plant are prescribed in the indigenous system of medicine as a febrifuge, astringent, purgative, and stimulant [2]. The decoction of the bark is used as a gargle [3]. It exhibited antimicrobial, antiulcer, hypotensive, anti-HIV, and spasmolytic activities [4][5][6][7][8]. Ursolic acid, betulinic acid, the fatty acid ester of D-spinasterol [9], 3E,6E,19D,23-tetrahydroxyurs-12-ene, 1E-hydroxy-3E-hexanoyllup-20(29)-ene-23,28-dioic acid, and bassic acid have been isolated from the bark [10,11]. This paper deals with the isolation and structural elucidation of two new steroidal glycosides from the stem bark of Mimusops elengi L.Compound 1, designated as stigmasterol-E-D-glycopyranoside, was obtained as a colorless amorphous powder from chloroform-methanol (19:1) eluants. It gave a positive test for sterol glycosides. Its IR spectrum exhibited absorption bands for hydroxyl groups (3450, 3380, 3260 cm -1 ), ester group (1738 cm -1 ), and unsaturation (1614 cm -1 ). On the basis of mass and 13 C NMR spectra, its molecular weight was established at m/z 750, consistent with the molecular formula of a sterol diglucoside, C 41 H 66 O 12 , and confirmed by HR-MS 751.9713 [M + H] + . Its mass spectrum showed important ion fragments appearing at m/z 411 [M -C 12 H 19 O 11 , diglycoside] + , 271 [411 -C 10 H 19 , side chain] + , 255 [271 -Me] + , and 239 [255 -Me] + .These fragments suggested that it was a C 29 sterol possessing one double bond in the carbocyclic ring system and one double bond in the side chain. The mass spectrum indicated the presence of an ethyl group in the side chain, which was placed at C-24 on the basis of biosynthesis analogy as well as similarities in chemical shifts of protons and carbons of the side chain with the related compounds. The ion fragments at m/z 339 [M -411] + and 179 [C 6 H 11 O 6 ] + suggested the glucuronosyl glucoside nature of the carbohydrate moiety. The 1 H NMR spectrum of 1 exhibited two one-proton multiplets at G 5.07 and 5.28 assigned to vinylic H-22 and H-23. A one-proton broad signal at G 5.30 was ascribed to vinylic H-6. A one-proton broad multiplet at G 3.85 with half-width 16.5 Hz was attributed to D-oriented C-3 carbinol proton. Two one-proton doublets at G 4.95 (J = 7.2 Hz) and 4.88 (J = 7.0 Hz) were attributed to H-1c and H-1cc anomeric protons, respectively. A two-proton broad signal at G 3.33 was associated with oxygenated C-6cc methylene protons. The remaining hydroxymethine protons of the glycosidic linkage appeared between G 4.50-3.35. Two three-proton broad signals at G 0.66 and 1.19 were assigned to C-18 and C-19 tertiary methyl protons. Four doublets at G 0.96 (J = 6.1 Hz), 0.86 (J = 8.4 Hz), ...

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A new benzofuranic acid from the leaves ofRhus alata

Cited by 6 publications

References 8 publications

Proanthocyanidins from the stem bark of Rhus tripartita ameliorate methylgloxal-induced endothelial cell apoptosis

Proanthocyanidins from the stem bark of Rhus tripartita ameliorate methylgloxal-induced endothelial cell apoptosis

The Pentacyclic Triterpenes , -amyrins: A Review of Sources and Biological Activities

New steroidal glycosides from the stem bark of Mimusops elengi

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