Terpenoids and a coumarin from aerial parts of Psychotria vellosiana Benth. (Rubiaceae)

Moreno, Beatriz Pereira; Fiorucci, Letycia Lopes Ricardo; Carmo, Marta Regina Barrotto do; Sarragiotto, María Helena; Baldoqui, Débora Cristina

doi:10.1016/j.bse.2014.04.013

“… 54 Phytochemically, studies on the isolation of a range of small molecules including squalene, stigmasterol, sitosterol, lupeol, scopoletin, coumarin, and monoterpene indole alkaloids have been reported. 56 , 57 …”

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confidence: 99%

“…54 Phytochemically, studies on the isolation of a range of small molecules including squalene, stigmasterol, sitosterol, lupeol, scopoletin, coumarin, and monoterpene indole alkaloids have been reported. 56,57 The current study aimed to characterize new cyclotides isolated from P. sessilis (Rubiaceae), because plant species from the Rubiaceae tribe Palicoureeae have been previously examined to contain cyclotides. 53 This included the taxonomically related species Palicourea coriacea and Palicourea rigida, and more distant species from the tribe Psychotrieae such as Psychotria longipes.…”

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confidence: 99%

Cyclotides from Brazilian Palicourea sessilis and Their Effects on Human Lymphocytes

Pinto

¹

,

Chan

²

,

Koehbach

³

et al. 2021

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Cyclotides are plant-derived peptides found within five families of flowering plants (Violaceae, Rubiaceae, Fabaceae, Solanaceae, and Poaceae) that have a cyclic backbone and six conserved cysteine residues linked by disulfide bonds. Their presence within the Violaceae species seems ubiquitous, yet not all members of other families produce these macrocyclic peptides. The genus Palicourea Aubl. (Rubiaceae) contains hundreds of neotropical species of shrubs and small trees; however, only a few cyclotides have been discovered hitherto. Herein, five previously uncharacterized Möbius cyclotides within Palicourea sessilis and their pharmacological activities are described. Cyclotides were isolated from leaves and stems of this plant and identified as pase A–E, as well as the known peptide kalata S. Cyclotides were de novo sequenced by MALDI-TOF/TOF mass spectrometry, and their structures were solved by NMR spectroscopy. Because some cyclotides have been reported to modulate immune cells, pase A–D were assayed for cell proliferation of human primary activated T lymphocytes, and the results showed a dose-dependent antiproliferative function. The toxicity on other nonimmune cells was also assessed. This study reveals that pase cyclotides have potential for applications as immunosuppressants and in immune-related disorders.

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“…Although all these compounds are isolated from P. succulenta for the first time, some of them have already been obtained from other Psychotria species. It is the case of barbinervic acid ( 5 ) previously found in P. stachyoides [ 25 ], oleanolic acid ( 7 ) and β -sitosterol-3- O - β -D-glucopyranoside ( 8 ) isolated from P. viridis [ 26 ], and scopoletin ( 9 ) obtained from P. vellosiana and P. stachyoides [ 25 , 27 ]. The results obtained are in agreement with the chemotaxonomy of plants of the genus Psychotria since according to Calixto et al (2016), they are characterized as an abundant source of indole, monoterpene indole, quinoline, and isoquinoline alkaloids as well as flavonoids.…”

Section: Discussionmentioning

confidence: 99%

Chemotaxonomy and Antibacterial Activity of the Extracts and Chemical Constituents of Psychotria succulenta Hiern. (Rubiaceae)

Jouogo

¹

,

Tamokou

²

,

Teponno

³

et al. 2022

BioMed Research International

1

0

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The use of natural products for medicinal purposes is becoming more and more common nowadays, as evidenced by the presence in plants of secondary metabolites with different potentials such as antioxidant and antibacterial properties. We evaluated in this work the antimicrobial activities of the extracts and some isolated compounds from the seeds of Psychotria succulenta Hiern. (Rubiaceae), a Cameroonian medicinal plant traditionally used to cure microbial infections. The ethanol extract was prepared by maceration and extracted with ethyl acetate and n-butanol. The EtOAc ( m = 168 g ) and n-BuOH ( m = 20 g ) extracts were further fractionated by silica gel column chromatography to isolation of compounds. Their structures were elucidated by spectroscopic analysis and by comparison with published data. The antibacterial activity of extracts and compounds was assessed by evaluating the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against pathogenic bacteria. Thirteen compounds including four alkaloids (veprisine (1), naucleofficine III (2), vepridimerine B (3), and vepridimerine C (4)), three triterpenes (barbinervic acid (5), 3-O-α-L-rhamnopyranosyl quinovic acid (6), and oleanolic acid (7)), one steroid (β-sitosterol-3-O-β-D-glucopyranoside (8)), four phenolic compounds (scopoletin (9), gallic acid (10), quercetin-3-O-β-D-glucopyranoside (11), and kaempferol 3-O-α-L-rhamnopyranoside-7-O-α-L-rhamnopyranoside (12)), and one iridoid (borreriagenin (13)) were isolated from the EtOAc and n-BuOH extracts. These compounds were identified by 1D and 2D NMR combined analysis as well as by melting point comparison. The EtOH, EtOAc, and n-BuOH extracts exhibited significant antibacterial activities ( MIC = 32 ‐ 128 μ g / mL ; MBC = 64 ‐ 256 μ g / mL ) against Staphylococcus aureus (Gram-positive bacterium), Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumonia (Gram-negative bacteria). Among the isolated compounds, scopoletin (9) showed a moderate activity against Klebsiella pneumoniae with MIC and MBC values of 16 μg/mL and 32 μg/mL, respectively. It appears that, chemotaxonomically, some of the isolated compounds have already been obtained from the genus Psychotria but to the best of our knowledge, this is the first report on the phytochemical investigation of P. succulenta. Although many other studies need to be achieved, our results support the use of P. succulenta in traditional medicine to cure infectious diseases particularly those caused by the tested bacteria.

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“…2 13 C{ 1 H} NMR data acquired in NMR 300 MHz (CDCl 3 ) in according to Elufioye et al (2017). The β-Sitosterol compound has already been identified in P. adenophylla, P. hainanensis, P. malayana (Calixto et al, 2016), P. vellosiana (Moreno et al, 2014), P. carthagenensis (Lopes et al, 2000), and P. nilgiriensis (Lopes et al, 2000). The campesterol steroid has been identified in P. nilgiriensis (Lalitha et al, 2015).…”

Section: Phytochemical Studymentioning

confidence: 99%

Phytochemical and morpho-anatomical study of the vegetative organs of Psychotria fractistipula L.B.Sm., R.M. Klein & Delprete (Rubiaceae)

Oliveira

¹

,

Oliveira

²

,

Bobek

³

et al. 2020

Braz. J. Pharm. Sci.

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Psychotria fractistipula L.B.Sm, R.M. Klein & Delprete (Rubiaceae) is found in the existing Atlantic Forest in the South of Brazil, in the Paraná and Santa Catarina States. The members of Rubiaceae are characterized chemically by the presence of alkaloids, some pharmacological properties of which include antifungal, antibacterial, analgesic, antioxidant, antimutagenic, and antiviral activities. In this study, we report the results of anatomical, morphological, and histochemical analyses of the leaves and stems of the Rubiaceae family member, P. fractistipula. The anatomical analysis involved of light microscopy and scanning electron microscopy. Morpho-anatomical and histochemical characterization were made using standard methodology. The isolated compounds were identified by Nuclear Magnetic Resonance spectroscopic analysis. The following structures are highlighted as the distinctive features of the species: presence of petiolate leaves and a petiole base, leaf blade with smooth cuticle on both surfaces, paracytic stomata, and, dorsiventral mesophyll and presence of trichomes on the leaves and stems. Phytosteroids, identified as β-sitosterol and campesterol, were observed in the hexane fraction of the stem. Future studies should focus on the isolation of other fractions of interest and their characterization through specific biological and cytotoxicity assays.

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Terpenoids and a coumarin from aerial parts of Psychotria vellosiana Benth. (Rubiaceae)

Cited by 13 publications

References 37 publications

Cyclotides from Brazilian Palicourea sessilis and Their Effects on Human Lymphocytes

Cyclotides from Brazilian Palicourea sessilis and Their Effects on Human Lymphocytes

Chemotaxonomy and Antibacterial Activity of the Extracts and Chemical Constituents of Psychotria succulenta Hiern. (Rubiaceae)

Phytochemical and morpho-anatomical study of the vegetative organs of Psychotria fractistipula L.B.Sm., R.M. Klein & Delprete (Rubiaceae)

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