Ixorine, a New Cyclopeptide Alkaloid from the Branches of<i>Ixora brevifolia</i>

Medina, Rebeca Previate; Schuquel, Ivânia T.A.; Pomini, Armando M.; Silva, Cleuza C.; Oliveira, Cecília Maria Alves de; Kato, Lucília; Nakamura, Celso Vataru; Santin, Silvana M. O.

doi:10.5935/0103-5053.20150326

Cited by 5 publications

(6 citation statements)

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“…Subfraction MC5 was further divided into six subfractions (MC5a−MC5f) by passage over Sephadex LH-20, eluted with a mixture of CH 2 Cl 2 −CH 3 OH (3:1). The CH 3 OH-insoluble precipitate of subfraction MC5d was collected and purified by washing with CH 3 OH, and was identified as frangulanine (28.3 mg) by comparison of its spectroscopic data (NMR, HRESIMS) to the data reported in the literature [ 13 ].…”

Section: Methodsmentioning

confidence: 99%

Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

et al. 2017

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Cyclopeptide alkaloids are polyamidic, macrocyclic compounds, containing a 13-, 14-, or 15-membered ring. The ring system consists of a hydroxystyrylamine moiety, an amino acid, and a β-hydroxy amino acid; attached to the ring is a side chain, comprised of one or two more amino acid moieties. In vitro antiplasmodial activity was shown before for several compounds belonging to this class, and in this paper the antiplasmodial and cytotoxic activities of ten more cyclopeptide alkaloids are reported. Combining these results and the IC50 values that were reported by our group previously, a library consisting of 19 cyclopeptide alkaloids was created. A qualitative SAR (structure-activity relationship) study indicated that a 13-membered macrocyclic ring is preferable over a 14-membered one. Furthermore, the presence of a β-hydroxy proline moiety could correlate with higher antiplasmodial activity, and methoxylation (or, to a lesser extent, hydroxylation) of the styrylamine moiety could be important for displaying antiplasmodial activity. In addition, QSAR (quantitative structure-activity relationship) models were developed, using PLS (partial least squares regression) and MLR (multiple linear regression). On the one hand, these models allow for the indication of the most important descriptors (molecular properties) responsible for the antiplasmodial activity. Additionally, predictions made for interesting structures did not contradict the expectations raised in the qualitative SAR study.

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Section: Methodsmentioning

confidence: 99%

Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

et al. 2017

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“…With this purpose, compounds 1 -6 were hydrolyzed and their amino acids analyzed through the chiral HPLC. In , Kang et al 2015, Maldaner et al 2011, Medina et al 2016, Suksamrarn et al 2005, Tuenter et al 2017.…”

Section: Resultsmentioning

confidence: 99%

“…C 81.5, whereas for the D-erythro configuration it appears at ca. C 87.0 (Abu-Zarga et al 1995, Caro et al 2012, Dongo et al 1989, Gournelis et al 1997, Medina et al 2016, Mostardeiro et al 2013, Tuenter et al 2016.…”

Section: Resultsmentioning

confidence: 99%

Isolation and structure elucidation of cyclopeptide alkaloids from the leaves of Heisteria parvifolia

et al. 2019

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“…Finally, previous phytochemical work described the isolation of some bioactive compounds: lignan syringaresinol and cyclopeptide alkaloids ixorine and frangulanine from CF; and daucosterol from HF and HF (Medina et al 2016) ( Figure S11). The cyclopeptide alkaloids ixorine and frangulanine have never been described as antiproliferative or anti-inflammatory agents.…”

Section: Resultsmentioning

confidence: 99%

“…One of our previous studies, carried out with the branches of this species, described the isolation and identification of a new cyclopeptide alkaloid, named ixorine, along with five known compounds, frangulanine, cinnamtannin B-1, syringaresinol, daucosterol and mannitol. The study also reported the activity of two cyclopeptide alkaloids mixture against Leishmania amazonensis (Medina et al 2016).…”

Section: Introductionmentioning

confidence: 97%

Anti-inflammatory and antiproliferative activities of Ixora brevifolia Benth. (Rubiaceae)

Medina

Moura

Silva

et al. 2017

Natural Product Research

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The crude extract and fractions from the branches of Ixora brevifolia, a tree found in the Brazilian Cerrado, were tested for anti-inflammatory and in vitro antiproliferative effects. The crude extract and n-hexane fraction exhibited significant inhibition of ear oedema in mice, while n-hexane-precipitated and chloroform fractions strongly inhibited the myeloperoxidase activity in ear tissue. The n-hexane and n-hexane-precipitated fractions showed strong growth inhibition for glioma cell line and the hydromethanolic fraction inhibited the growth of leukaemia cell line.

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Ixorine, a New Cyclopeptide Alkaloid from the Branches ofIxora brevifolia

Cited by 5 publications

References 0 publications

Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

Isolation and structure elucidation of cyclopeptide alkaloids from the leaves of Heisteria parvifolia

Anti-inflammatory and antiproliferative activities of Ixora brevifolia Benth. (Rubiaceae)

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