Lupane Triterpenes with a δ-Lactone at Ring E, from <i>Lippia mexicana</i>

Maldonado, Emma; Díaz-Arumir, Humberto; Toscano, Rubén A.; Martínez, Mahinda

doi:10.1021/np100571v

Cited by 12 publications

(10 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This lignane was previously found in the K. ramosissima extract [28]. Triterpene compounds, including cycloartane-type triterpenes, reportedly have anti-inflammatory and/or quimiopreventive activities [8,9,[29][30][31][32][33]. Cycloartane triterpenoids from K. pauciflora exhibited in vitro inhibitory effects of the NSAIDs target enzymes PLA 2 , COX-1, and COX-2 (l " Figs.…”

Section: Resultsmentioning

confidence: 61%

“…five cycloartane-type triterpenes, which are compounds that have previously been determined to have anti-inflammatory [8], cancer chemopreventive [9], and other activities. Therefore, the in vitro inhibitory activity on prostaglandin synthesis from compounds 1, 2, 4, and 5 was evaluated by investigating the ability of these compounds to inhibit enzymes involved in inflammation, such as PLA 2 , COX-1, and COX-2.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Cycloartanes from Krameria pauciflora and Their In Vitro PLA2, COX-1, and COX-2 Enzyme Inhibitory Activities

et al. 2012

View full text Add to dashboard Cite

Krameria pauciflora is a species belonging to the Krameriaceae family. It has been used to treat inflammatory disorders in folkloric Mexican medicine; however, chemistry and pharmacological studies have not been carried out on this species. In this work, from the dichloromethane root extract of K. pauciflora, five cycloartane-type triterpenoids were isolated: cyclomargenyl-3-O-β-caffeoyl ester (1), cyclomargenyl-3-O-β-feruloyl ester (2), cyclomargenyl-3-O-β-coumaroyl ester (3), cyclomargenol (4, polysthicol), and cyclomargenone (5). Additionally, the lignane 6'-methoxyrataniaphenol was isolated. To the best of our knowledge, compounds 1-3 are new natural products, whereas compounds 4 and 5 are isolated for the first time in the Krameria genus and the Krameriaceae family. The structures of all of these compounds were established by 1D and 2D NMR spectroscopy including ¹H, ¹³C, DEPT, COSY, HSQC, and HMBC experiments, as well as by EI mass spectrometry. There is an incomplete previous report about the spectroscopic data of compounds 4 and 5. However, in this work, a complete and unambiguous assignation has been realized. Due to the traditional use of this plant and other species from this genus, such as K. lappacea, cycloartanes isolated herein were evaluated by their inhibition of phospholipase A₂, cyclooxygenase-1, and cyclooxygenase-2 enzymes. Cyclomargenyl-3-O-β-caffeoyl ester (1) showed inhibition of phospholipase A₂, cyclooxygenase-1, and cyclooxygenase-2 target enzymes for nonsteroidal anti-inflammatory drugs. Both cyclooxygenases were inhibited by cyclomargenol (4); however, cyclomargenyl-3-O-β-feruloyl ester (2) showed inhibition only on cyclooxygenase-1.

show abstract

Section: Resultsmentioning

confidence: 61%

mentioning

confidence: 99%

Cycloartanes from Krameria pauciflora and Their In Vitro PLA2, COX-1, and COX-2 Enzyme Inhibitory Activities

et al. 2012

View full text Add to dashboard Cite

show abstract

“…This anti-inflammatory effect could be attributed to the cyclomargenol ( 1 ) and β-sitosterol ( 2 ) in the extracts (see Section 2.4 ). Some sterols and cycloartane-type triterpenes have been reported as anti-inflammatory compounds [ 16 , 17 ] and cancer chemopreventive compounds by Kikuchi et al . [ 18 ].…”

Section: Resultsmentioning

confidence: 99%

Phytochemical Study and Anti-inflammatory, Antidiabetic and Free Radical Scavenger Evaluations of Krameria pauciflora Methanol Extract

et al. 2012

View full text Add to dashboard Cite

The plant Krameria pauciflora MOC et. Sessé ex DC. is used as an anti-inflammatory and antidiabetic in traditional medicine. The aim of this study was to evaluate the in vivo anti-inflammatory and antidiabetic effects of a methanol extract from the roots of K. pauciflora. Dichloromethane and ethyl acetate extracts obtained by partitioning the methanol extract were also evaluated. Complete methanol and dichloromethane extracts showed anti-inflammatory effects at 3 mg/kg. An anti-inflammatory effect similar to indomethacin (10 mg/kg) was observed when the methanol and dichloromethane extracts, which contain a cycloartane-type triterpene and an sterol, were administered orally at several doses (3, 10, 30 and 100 mg/kg), whereas no anti-inflammatory effect was observed at any dose for the ethyl acetate extract, which contains catechin-type flavonoids. The antidiabetic effect of each extract was also determined. An antihyperglycaemic effect was observed in diabetic rats, but no effect in normoglycaemic animals was observed when the methanol extract was administrated at 30 mg/kg. All of the extracts exhibited radical scavenger activity. Additionally, constituents from all of the extracts were identified by NMR. This article supports the use of K. pauciflora as an anti-inflammatory because it exhibits a similar effect to indomethacin. However, its antidiabetic effect is not completely clear, although it could be useful for preventing diabetic complications.

show abstract

“…Lippiolide, containing a δ-lactone at ring E, showed significant edema reduction (74.9%); however, the IC 50 value (0.73 µM) was three times higher than the value recorded for the standard indomethacin (IC 50 0.24 µM) (Figure 2). The edema reduction induced by lippiolic acid was significant (74.9%), but the IC 50 value could not be determined due to its low solubility at concentrations over 1 µM [16].…”

Section: Haavikko Et Al Synthesized and Tested Againstmentioning

confidence: 94%

Ring-Modified Triterpene Derivatives as Potential Pharmacological Active Compounds

Ulici¹,

Milan²,

Mioc³

et al. 2021

Timisoara Med

View full text Add to dashboard Cite

Pentacyclic triterpenes represent an important class of intensively studied substances in the past two decades due to their wide spectrum of pharmacological effects. Even though this class is being thoroughly researched for the development of new drugs, to date, no representative has qualified to become a suitable candidate for various therapies. Although a large part of past and ongoing studies focuses on triterpene chemical derivatization or formulation to increase its bioavailability, other researchers are focused on obtaining semisynthetic derivatives not necessarily with increased hydrophilicity but with a superior biological effect compared to their parent compound. The current review aims to report the biological assessment of several ring-modified pentacyclic triterpene derivative series.

show abstract

Lupane Triterpenes with a δ-Lactone at Ring E, from Lippia mexicana

Cited by 12 publications

References 15 publications

Cycloartanes from Krameria pauciflora and Their In Vitro PLA2, COX-1, and COX-2 Enzyme Inhibitory Activities

Cycloartanes from Krameria pauciflora and Their In Vitro PLA2, COX-1, and COX-2 Enzyme Inhibitory Activities

Phytochemical Study and Anti-inflammatory, Antidiabetic and Free Radical Scavenger Evaluations of Krameria pauciflora Methanol Extract

Ring-Modified Triterpene Derivatives as Potential Pharmacological Active Compounds

Contact Info

Product

Resources

About