Chemical constituents of Salacia elliptica (Celastraceae) (original) (raw)
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Salacianone and salacianol, two triterpenes from Salacia beddomei
Phytochemistry, 1995
Two new lupane triterpenes, salacianone (lup-20(29)-en-3,21-dione) and salacianol (21fl-hydroxylup-20(29)-en-3-one), have been isolated from the hexane extract of the stem bark of Salacia beddomei together with the known compounds lup-20(29)-en-3-one, friedelan-3-one, 15~-hydroxyfriedelan-3-one, 15~-hydroxyfriedelane-l,3dione, pristimerin and sitosterol. Their structures have been elucidated with the aid of IR, NMR and mass spectroscopic techniques.
Biogenetically important quinonemethides and other triterpenoid constituents of Salacia reticulata
Phytochemistry, 1996
Phytochemical investigation of the outer root bark of Salacia reticulata var. fl-diandra (Celastraceae) has resulted in the isolation of two novel quinonemethide triterpenoids (celastroloids), isoiguesterinol and 30-hydroxypristimerin, along with salacenonal, several known celastroloids and friedo-oleanane triterpenoids. Details of the structural elucidation and 1H and ~3C NMR spectral assignments of these compounds are presented and their biogenetic significance is discussed.
Química Nova, 2020
Recebido em 29/10/2019; aceito em 12/02/2020; publicado na web em 14/04/2020 Salacia crassifolia traditionally known as "Bacupari-do-Cerrado" is used to treat kidney problems, and as a healing agent for coughs and malaria. The phytochemical study of the S. crassifolia roots led to the isolation of thirteen compounds: abruslactone-A (1), urs-12-ene-3β,25,30-triol (2), carioprystimerin (3), β-sitosterol (4), pristimerin (5), dispermoquinone (6), netzahualcoyonol (7), 20-hydroxy-20-epi-tingenone (8), 6-oxo-pristimerol (9), 9β,10β-epoxi-3β-hydroxy-1βH,4βH,5βH,7βH,11αH-guaian-12,8β-olide (10), 3-O-β-D-glucosyl-β-sitosterol (11), 4`-O-methylepigalocatechin (12) and cerebroside (13). The chemical structures of 1-13 were determined by IR, 1D/2D NMR together with X-ray diffractometry. Compounds 2 and 10 are herein described for the first time. Extracts of S. crassifolia and compounds 3, 5, 8 and 9 were evaluated on acetylcholinesterase inhibition, in vitro cytotoxic activity and in vivo toxicity tests using Caenorhabditis elegans model. All tested compounds inhibited acetylcholinesterase, and compounds 3, 8 and 9 demonstrated a greater potential when compared to the standard eserine. The tested compounds showed low cytotoxicity against the THP-1, K562 and MDA-MB-231 cancer cell lines. None of the tested compounds and extracts were toxic against C. elegans since the larvae survival rate in L1 stage was higher than 90%.
Journal of Natural Products, 2003
Three new friedelane-type triterpenes named salasones A (1), B (2), and C (3), a new norfriedelane-type triterpene, salaquinone A (4), and a new acylated eudesmane-type sesquiterpene, salasol A (5), were isolated from the 80% aqueous methanolic extract of the stems of Salacia chinensis collected in Thailand. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. In addition, six constituents, 3 ,22-dihydroxyolean-12-en-29-oic acid, tingenone, tingenine B, regeol A, triptocalline A, and mangiferin, were found to show an inhibitory effect on rat lens aldose reductase.
Salacia crassifolia(Celastraceae): CHEMICAL CONSTITUENTS AND ANTIMICROBIAL ACTIVITY
Química Nova, 2015
The phytochemical study of hexane extract from leaves of Salacia crassifolia resulted in the isolation of 3β-palmitoxy-urs-12-ene, 3-oxofriedelane, 3β-hydroxyfriedelane, 3-oxo-28-hydroxyfriedelane, 3-oxo-29-hydroxyfriedelane, 28,29-dihydroxyfriedelan-3-one, 3,4-seco-friedelan-3-oic acid, 3β-hydroxy-olean-9(11):12-diene and the mixture of α-amirin and β-amirin. β-sitosterol, the polymer gutta-percha, squalene and eicosanoic acid were also isolated. The chemical structures of these constituents were established by IR, 1 H and 13 C NMR spectral data. Crude extracts and the triterpenes were tested against Entamoeba histolytica, Giardia lamblia and Trichomonas vaginalis and no activity was observed under the in vitro assay conditions. The hexane, chloroform, ethyl acetate and ethanol crude extracts, and the constituent 3,4-seco-friedelan-3-oic acid and 28,29-dihydroxyfriedelan-3-one showed in vitro antimicrobial activity against Salmonella typhimurium, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes, Streptococcus sanguinis and Candida albicans.
Journal of the Brazilian Chemical Society, 2019
Two new compounds, caryopristimerin and 2α,3α,22β-trihydroxy-21-oxo-29-nor-friedelan-24-oic acid, were isolated from the hexane/ethyl ether extract of Salacia crassifolia roots. Caryopristimerin represents the first example of a homo Diels-Alder adduct of a sesquiterpene and a triterpene, and the new 29-nor-friedelane displays a highly oxygenated A ring with a carboxylic group at the unusual C-5 position. The new compounds were elucidated by infrared (IR), highresolution-atmospheric pressure chemical ionization-mass spectrometry (HR-APCI-MS), 1D/2D nuclear magnetic resonance (NMR) and single crystal X-ray diffraction analysis. Additionally, the known compounds 3-oxo-29-hydroxyfriedelane, pristimerin, tingenone and netzahualcoyonol are herein reported for the first time as constituents of S. crassifolia. Their structures were established by spectroscopic analysis.
Diterpenoids Including a Novel Dimeric Conjugate from Salvia leriaefolia
Planta Medica, 2012
Salvialeriafone (1), a novel diterpene-norditerpene conjugate, was isolated from Salvia leriaefolia. Additionally, two new abietane-type diterpenoids, salvialerial (2) and salvialerione (3), as well as four known compounds, sugiol (4), salvicanaric acid (5), dehydroroyleanone (6), and cariocal , were isolated and identified. Their structures were determined by spectroscopic data analyses. Known compounds were isolated from this plant for the first time. Compounds 1, 5, 6, and 7 exhibited in vitro antiproliferative activity against the human cervical cancer cell line (Hela), while 6 showed cytotoxicity against the human prostate cancer cell line (PC3).