Abstract
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.
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Claims 7
Claim · model-written summary
Five cycloartane triterpenoids were isolated from Krameria pauciflora roots.
- Taxon
- K. pauciflora
Krameria pauciflorae0 - Organ / stage
- roote0
- Outcome
- five cycloartane-type triterpenoids were isolatede0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
t0“Krameria pauciflora”
e0“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)”
Claim · model-written summary
The lignan 6'-methoxyrataniaphenol was isolated.
- Taxon
- Krameria paucifloraKrameria pauciflorat0
- Outcome
- 6'-methoxyrataniaphenol was isolatede0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
t0“Krameria pauciflora”
e0“the lignane 6'-methoxyrataniaphenol was isolated”
Claim · model-written summary
Compounds 1–3 were reported as new natural products.
- Taxon
- Krameria paucifloraKrameria pauciflorat0
- Outcome
- new natural productse0
- Qualifier
- compounds 1-3e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
t0“Krameria pauciflora”
e0“compounds 1-3 are new natural products”
Claim · model-written summary
Compounds 4 and 5 were isolated for the first time in Krameria and Krameriaceae.
KrameriaOrganisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
t0“Krameria pauciflora”
e0“compounds 4 and 5 are isolated for the first time in the Krameria genus and the Krameriaceae family”
Claim · model-written summary
Cyclomargenyl-3-O-β-caffeoyl ester inhibited phospholipase A₂, cyclooxygenase-1 and cyclooxygenase-2 in vitro.
- Taxon
- Krameria paucifloraKrameria pauciflorat0
- Outcome
- inhibition of phospholipase A₂, cyclooxygenase-1, and cyclooxygenase-2e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
t0“Krameria pauciflora”
e0“Cyclomargenyl-3-O-β-caffeoyl ester (1) showed inhibition of phospholipase A₂, cyclooxygenase-1, and cyclooxygenase-2”
Claim · model-written summary
Cyclomargenol inhibited both cyclooxygenases.
- Taxon
- Krameria paucifloraKrameria pauciflorat0
- Outcome
- Both cyclooxygenases were inhibitede0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
t0“Krameria pauciflora”
e0“Both cyclooxygenases were inhibited by cyclomargenol (4)”
Claim · model-written summary
Cyclomargenyl-3-O-β-feruloyl ester inhibited cyclooxygenase-1 only.
- Taxon
- Krameria paucifloraKrameria pauciflorat0
- Outcome
- inhibition only on cyclooxygenase-1e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
t0“Krameria pauciflora”
e0“cyclomargenyl-3-O-β-feruloyl ester (2) showed inhibition only on cyclooxygenase-1”