A New Prenylisoflavone from the Antifungal Extract of Leaves of Vatairea guianensis Aubl.

Souza, Ronilson Freitas de; Silva, Geilson A. da; Arruda, Alberto C.; Silva, Milton; Santos, Alberdan S.; Grisólia, Daniella P. A.; Silva, Moises B.; Salgado, Cláudio Guedes; Arruda, Mara Silvia Pinheiro

doi:10.21577/0103-5053.20160250

Cited by 4 publications

(7 citation statements)

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“…Eleven compounds could be identified by comparison with the data described in the literature. Compounds referring to peaks 4 , 7 , 11 , 12 , 13 , 14 and 15 have already been identified in the same species [ 43 , 44 ], while compounds 1 , 2 , 3 and 10 were identified based on the exact masses compared to those described in the literature [ 57 , 58 , 59 , 60 ] for compounds already reported in the Fabaceae family. Compounds 5 , 6 , 8, and 9 could not been identified.…”

Section: Resultsmentioning

confidence: 99%

Secure and Sustainable Sourcing of Plant Tissues for the Exhaustive Exploration of Their Chemodiversity

et al. 2020

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The main challenge of plant chemical diversity exploration is how to develop tools to study exhaustively plant tissues. Their sustainable sourcing is a limitation as bioguided strategies and dereplication need quite large amounts of plant material. We examine if alternative solutions could overcome these difficulties by obtaining a secure, sustainable, and scalable source of tissues able to biosynthesize an array of metabolites. As this approach would be as independent of the botanical origin as possible, we chose eight plant species from different families. We applied a four steps culture establishment procedure, monitoring targeted compounds through mass spectrometry-based analytical methods. We also characterized the capacities of leaf explants in culture to produce diverse secondary metabolites. In vitro cultures were successfully established for six species with leaf explants still producing a diversity of compounds after the culture establishment procedure. Furthermore, explants from leaves of axenic plantlets were also analyzed. The detection of marker compounds was confirmed after six days in culture for all tested species. Our results show that the first stage of this approach aiming at easing exploration of plant chemodiversity was completed, and leaf tissues could offer an interesting alternative providing a constant source of natural compounds.

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Section: Resultsmentioning

confidence: 99%

Secure and Sustainable Sourcing of Plant Tissues for the Exhaustive Exploration of Their Chemodiversity

et al. 2020

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“…Berdasarkan hasil identifikasi gugus fungsi penanda senyawa antioksidan mengindikasikan senyawa-senyawa metoksi flavonoid dan flavonoid terprenilasi berikut memiliki aktivitas antioksidan antara lain eupatorin, sinensitin, 5-hidroksi-6,7,3',4'-tetrame-toksflavon, salvegenin, 6-hidroksi-5,7,3'-trimetok-siflavon, dan 5,6,7,3'-tetrametoksi-4'-hidroksi-8-C-prenilflavon (Hossain dan Rahman 2015). Eupatorin dan 3'-hidroksi-5,6,7,4'-tetrametoksiflavon (TMF) diketahui memiliki aktivitas antioksidan yang relatif sama dengan butylated hydroxylanisole (BHA) sedangkan aktivitas antioksidan sinensitin lebih rendah dari BHA pada konsentrasi yang sama (0,05 mg/mL) (Akowuah et al, 2005 Aktivitas antioksidan oleh flavonoid dan senyawa fenol lainnya sebagian besar disebabkan oleh gugus hidroksil aromatik sehingga radikal fenolik menjadi lebih stabil langsung setelah radikal terbentuk ketika satu hidrogen radikal didonorkan ke DPPH (de Souza et al, 2013). Semakin banyak gugus hidroksi pada struktur kimia semakin tinggi aktivitas antioksidan oleh senyawa tersebut (Liu et al, 2010).…”

Section: Penanda Senyawa Antioksidanunclassified

SENYAWA INHIBITOR Α-Glukosidase DAN ANTIOKSIDAN DARI KUMIS KUCING DENGAN PENDEKATAN METABOLOMIK BERBASIS FTIR

Juliani

Yuliana

Budijanto

et al. 2016

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Plant is well known as an excellent source for b ioactive compounds. Metab olomics was reported as a potential tool to accelerate plant acitive compounds identification. In this research, FTIR-b ased metab olomics method was used to identify active compounds with α-glucosidase inhib itory and antioxidant activity in aerial parts of Orthosiphon stamineus (OS OPLS). Based on the VIP (variab le influence on projection), the coefficient value of the respective OPLS models, and IR datab ase of compounds previously identified in OS, it was suggested that methoxy flavonoid (sinensitin and 5,6,7,3'-tetramethoxy-4'-hydroxy-8-C-preny-lflavone), diterpenes (orthosiphols, orthoarisins, neoorthosiphols, staminols, and stam inolactones) and triterpenes (ursolic acid, oleanolic acid, b etulinic acid, hydroxyb etulinic acid, maslinic acid, α-amyrin and β-amyrin) were identified as responsib le compounds for the α-glucosidase inhibitory activity. Meanwhile phenolic (rosmarinic acid ), methoxy flavonoid (eupatorin, sinensetin, 5-hydroxy-6,7,3',4'-tetramethoxyflavone, salvigenin, 6-hydroxy-5,7,3'-trimethoxyflavone and 5,6,7,3'-tetramethoxy-4'-hydroxy-8-C-prenylflavone), diterpenes (orthosiphols, orthoarisins, neoorthosiphols, staminols, and staminolactones) and triterpenes (ursolic acid, oleanolic acid, b etulinic acid, hydroxyb etulinic acid, maslinic acid, α-amyrin and β-amyrin) were identified as responsib le compounds for the antioxidant activity. Keywords: α-glucosidase inhib itors, antioxidants, metab olomics, Orthosiphon stamineus ABSTRAK1Tumbuhan merupakan salah satu sumber senyawa aktif yang potensial. Pendekatan metabolomik dilaporkan sebagai salah satu metode alternatif yang dapat mempercepat proses identifikasi komponen aktif dari tumbuhan. Pada penelitian ini, metode metabolomik berbasis FTIR digunakan untuk meng-identifikasi senyawa aktif dengan aktivitas penghambatan terhadap enzim α-glukosidase dan antioksidan pada ekstrak dan fraksi tanaman kumis kucing (OS). Profil kimia ekstrak metanolik dan fraksi heksana, kloroform, butanol, dan air OS diukur dengan FTIR. Ekstrak dan fraksi OS menunjukkan aktivitas penghambatan terhadap enzim α-glukosidase dengan nilai IC50 berkisar 154,07±30,60-465,83±85,34 µg/mL dan aktivitas antioksidan dengan nilai IC50 berkisar 7,41±0,02-19,35±0,09 µg/mL. Fraksi butanol adalah fraksi dengan aktivitas penghambatan α-glukosidase tertinggi dan aktivitas antioksidan menengah dengan nilai IC 50 berturut-turut turut 154,07±30,60 µg/mL dan 10,84±0,54 µg/mL. Korelasi antara data aktivitas biologis dan komposisi kimia dianalisis dengan orthogonal projections to latent structures (OPLS). Berdasarkan nilai VIP (variab le influence on projection), nilai koefisien dari model OPLS, dan pangkalan data IR senyawa yang telah teridentifikasi pada OS. Metoksi flavonoid (sinensitin dan 5,6,7,3'-tetrametoksi-4'-hidroksi-8-C-prenilflavon), diterpena (ortosifol, ortoarisin, neoortosifol, staminol, dan staminolakton), triterpena (asam ursolat, asam oleanolat, asam betulinat, asam hidroksibetulinat, ...

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“…Compounds 1 – 4 and 8 were identified as lupiwighteone ( 1 ), 5,7,4′-trihydroxy-3′-methoxy-8-prenylisoflavone ( 2 ), 5,7,3′-trihydroxy-4′-methoxy-8-prenylisoflavone ( 3 ), lupiwighteone hydrate ( 4 ), and erypoegin K ( 8 ) by comparison of their MS and NMR spectra with literature data (Tables S1–S3). ,− Optical rotation measurements combined with chiral phase HPLC analysis suggested that the latter compound was obtained as a scalemic mixture with an enantiomeric excess of 64% of the ( R )-isomer (Figure S105). However, in the case of compound 3 , initial structural assignment by comparison with literature data afforded a rather unusual 3′,5′-substitution of the B-ring, a fact that we clarified by spectra simulations and that will be explained later on.…”

Section: Resultsmentioning

confidence: 99%

“…8−10 A study by de Souza et al revealed moderate antioxidant activity for three isolated isoflavones, 8 whereas another study confirmed the antifungal activity against Candida dublinienis and C. parapsilosis of lupiwighteone (1) and 5,7,3′-trihydroxy-4′methoxy-8-prenylisoflavone (2). 9 Da Silva et al reported a cytotoxic effect of 1 against MCF-7 breast cancer cells, with an IC 50 of 4.7 μM. 10 Phytochemical investigations of the sapwood did not yield prenylated isoflavonoids, but the well-known isoflavone formononetin and the isoflavanol bolusanthol D. 2 In addition, the triterpenoids lupeol, αand β-amyrin, germanicol, and betulinic acid were detected in the leaves of V. guianensis.…”

mentioning

confidence: 99%

“…Previous phytochemical investigations on the leaves of V. guianensis afforded prenylated isoflavones of the derrone and lupiwighteone type, such as vatairenones A and B. − A study by de Souza et al revealed moderate antioxidant activity for three isolated isoflavones, whereas another study confirmed the antifungal activity against Candida dublinienis and C. parapsilosis of lupiwighteone ( 1 ) and 5,7,3′-trihydroxy-4′-methoxy-8-prenylisoflavone ( 2 ) . Da Silva et al reported a cytotoxic effect of 1 against MCF-7 breast cancer cells, with an IC 50 of 4.7 μM .…”

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confidence: 99%

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Antimicrobial Prenylated Isoflavones from the Leaves of the Amazonian Medicinal Plant Vatairea guianensis Aubl.

et al. 2022

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Vatairea guianenis Aubl. (Fabaceae) is an Amazonian medicinal plant species traditionally used for treating skin diseases. In an initial screening, a V. guianensis leaf extract and its subextracts showed antibacterial and antifungal activities. The EtOAc subextract was selected for chemical workup and afforded five known (1−4 and 8) and six undescribed isoflavones, vatairenones C−H (5−7 and 9−11). All isoflavones are prenylated in position C-8, displaying either chain-prenylated (1−7) or ring-closed forms (8−11). The most bioactive compound (3) exhibited in vitro activity against clinically relevant bacteria and fungi with IC 50 values ranging from 6.8 to 26.9 μM. Due to its broad antimicrobial activity and low general toxicity, compound 3 is a potential lead compound for structural modifications. The results of the present study support the ethnomedicinal use of V. guianensis in the treatment of dermatological disorders. 1 H NMR spectra of some of the isolated compounds showed intricate signal patterns, which might explain repeated errors in assigning the correct structure of the isoflavonoid B-ring in the literature and which we resolved by higher order spectra simulations.

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A New Prenylisoflavone from the Antifungal Extract of Leaves of Vatairea guianensis Aubl.

Cited by 4 publications

References 17 publications

Secure and Sustainable Sourcing of Plant Tissues for the Exhaustive Exploration of Their Chemodiversity

Secure and Sustainable Sourcing of Plant Tissues for the Exhaustive Exploration of Their Chemodiversity

SENYAWA INHIBITOR Α-Glukosidase DAN ANTIOKSIDAN DARI KUMIS KUCING DENGAN PENDEKATAN METABOLOMIK BERBASIS FTIR

Antimicrobial Prenylated Isoflavones from the Leaves of the Amazonian Medicinal Plant Vatairea guianensis Aubl.

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