Lupane Pentacyclic Triterpenes Isolated from Stems and Branches of <i>Maytenus imbricata</i> (Celastraceae)

Silva, Silvia Ribeiro de Souza e; Silva, Grácia Divina de Fátima; Barbosa, Luiz Cláudio de Almeida; Duarte, Lucienir Pains; Filho, Sidney Augusto Vieira

doi:10.1002/hlca.200590081

Cited by 24 publications

(11 citation statements)

References 19 publications

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“…Spectra characteristics The analysis of 1 H NMR spectral data [12] indicated the presence of two hydroxyl groups and double bond in the .00 related to olefinic hydrogen. The 13 C NMR and DEPT-135 spectra show 29 signals establishing the presence of five methyl, 12 methylene and six methane groups and also six quaternary carbons.…”

Section: Resultsmentioning

confidence: 99%

“…This paper reports the crystal structure of a PCTT (1) that was isolated during the phytochemical investigation of Maytenus imbricata (Celastraceae). Its molecular structure and its relative stereochemistry have been previous established by us with one-dimensional (1D) and two-dimensional (2D) NMR techniques (DEPT, HSQC, HMBC and NOESY) [12]. The goal of the present work is to determine unambiguously the molecular configuration of (1) and to (1) describe its intra and inter-molecular geometry by X-ray crystallography.…”

Section: Introductionmentioning

confidence: 96%

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A pentacyclic triterpene from Maytenus imbricata: structure elucidation by X-ray crystallography

Pimenta

Silva

et al. 2006

Struct Chem

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A pentacyclic triterpene, 3β,30-dihydroxy-lup-20(29)-ene, was isolated from the powder extract of Maytenus imbricata. The structure and stereochemistry of the compound were established by spectroscopic techniques and unambiguously determined by single crystal X-ray crystallography. The crystal structure shows one molecule in the asymmetric unit. The crystal packing is stabilized by O-H···O intermolecular hydrogen bonds, which give rise to infinite helical chains along the c unit cell axis. The intramolecular geometry was analyzed using MOGUL, a knowledge base of molecular geometry derived from the Cambridge Structural Database (CSD).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

A pentacyclic triterpene from Maytenus imbricata: structure elucidation by X-ray crystallography

Pimenta

Silva

et al. 2006

Struct Chem

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“…The isolation and structural elucidation of these triterpenes are reported herein. Because of the limited amounts of samples, compounds 4-10 and known compounds, such as 13β,28-epoxy-3β-hydroxyurs-11-ene (14) [7,8], 28,30-dihydroxylup-20(29)-en-3-one (15) [9], 30-hydroxybetulin (16) [9], and 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17), which were previously isolated from the stems of M. fokienensis [4,6], were selected and evaluated for anti-inflammatory activity based on their inhibition of superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB.…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory Triterpenoids from the Stems of Microtropis Fokienensis

Chen

Du²,

Hwang

et al. 2014

Molecules

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Three new ursane-and four new oleanane-type triterpenoids 1-7 were isolated, along with six known compounds 8-13, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates 4-10 and known compounds 14-17 that were previously isolated from this material were evaluated for anti-inflammatory activity based on effects against superoxide anion generation and elastase release by neutrophils in response to fMLP/CB. 11α,30-Dihydroxy-2,3-seco-olean-12-en-2,3-dioic anhydride (7) was the first triterpene anhydride from the genus of Microtropis to have the ring A expanded to a seven-membered ring; it showed significant anti-inflammatory activity against superoxide anion generation and elastase release. Unexpectedly, 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17) showed the best effect against superoxide anion generation and elastase release with IC 50 values of 0.06 ± 0.01 and 1.03 ± 0.35 µg/mL, respectively. Compound 17 had a dioic acid function, and compound 7 had an anhydride function modification in ring A; both showed promising activity in the target assays.

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“…Previous chemical investigations of this genus have resulted in the isolation of several secondary metabolites including glycosides, flavonoids, alkaloidic and non alkaloidic sesquiterpenes, friedelanes, oleananes, lupanes, quinonoid triterpenes and other pentacyclic triterpenes (PCTTs) [1]. In general, PCTTs compose a class of chemical compounds commonly obtained from plants that belong to the Celastraceae family [2]. These terpenes and their derivatives have shown many interesting biological properties, such as anti-inflammatory [3], anti-HIV [4], anti-cancer [5], nematostatic effects [6].…”

Section: Introductionmentioning

confidence: 99%

Influence of hydrogen bonds on the molecular structure and conformations of two (C30H48O2) pentacyclic triterpene isomers

et al. 2012

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The structural study of two (C 30 H 48 O 2 ) pentacyclic triterpene (PCTT) isomers is presented. These terpenes, known as 30-hydroxy-lup-20(29)-en-3-one (1) and (11α)-11-hydroxy-lup-20(29)-en-3-one (2), were isolated from Maytenus imbricata Mart. Ex Reissek (Celastraceae). The molecular structure of 1 and 2 differs in the position of the hydroxyl group. Both compounds crystallize in non-centrosymmetric space groups with two molecules in the asymmetric unit. The crystal structure of 1 shows a triclinic P1 space group (a = 9.5518 (1) Å, b = 9.7083(1) Å, c = 14.4696(2) Å, α = 93.832(1)°, β = 102.833(1)°, and γ = 103.307(1)°), while compound 2 crystallizes in a monoclinic P2 1 one (a = 13.4439(16) Å, b = 14.4463(14) Å, c = 13.5224(9) Å and β = 99.703(8)°). The two molecules independent by symmetry of 1 differ slightly due to the presence of static disorder in oxygen atoms. In addition, the intermolecular geometries of 1 and 2 were analysed, and in each isomer the crystal packing is stabilized by O-H⋯O intermolecular hydrogen bonds and van der Waals forces.

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Lupane Pentacyclic Triterpenes Isolated from Stems and Branches of Maytenus imbricata (Celastraceae)

Abstract: numbering of compounds 1 and 4 is identical to that of 2 and 3; for systematic names, see Exper. Part.

Cited by 24 publications

References 19 publications

A pentacyclic triterpene from Maytenus imbricata: structure elucidation by X-ray crystallography

A pentacyclic triterpene from Maytenus imbricata: structure elucidation by X-ray crystallography

Anti-Inflammatory Triterpenoids from the Stems of Microtropis Fokienensis

Influence of hydrogen bonds on the molecular structure and conformations of two (C30H48O2) pentacyclic triterpene isomers

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