Isolation of Tryptanthrin and Reassessment of Evidence for Its Isobaric Isostere Wrightiadione in Plants of the <i>Wrightia</i> Genus

Garcellano, Rhea C; Moinuddin, Syed G. A.; Young, Robert P.; Zhou, Mowei; Bowden, Mark E.; Renslow, Ryan; Yesiltepe, Yasemin; Thomas, Dennis; Colby, Sean; Chouinard, Christopher D.; Nagy, Gabe; Attah, Isaac K.; Ibrahim, Yehia; Ma, Rui; Franzblau, Scott G.; Lewis, Norman G.; Aguinaldo, Alicia M.; Cort, John

doi:10.1021/acs.jnatprod.8b00567

Cited by 17 publications

(9 citation statements)

References 71 publications

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“…Wrightiadione and β-sitosterol showed interaction with Mu-opioid receptor (−9.1 kcal/mol and −9.7 kcal/mol, respectively) than the standard drug morphine (−8.0 kcal/mol). The active binding sites of Mu-opioid receptor during docking with β-sitosterol (compound 4) were HIS 54, SER 55 6 and 7 during interaction with the isolated phytoconstituents from the plant extract.…”

Section: Inhibition Of Mu-opioid Receptor and Cox-2 Proteins: Analges...mentioning

confidence: 99%

Chemical and Pharmacological Profiling of Wrightia coccinea (Roxb. Ex Hornem.) Sims Focusing Antioxidant, Cytotoxic, Antidiarrheal, Hypoglycemic, and Analgesic Properties

et al. 2022

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The aim of the study was to conduct phytochemical and pharmacological investigations of Wrightia coccinea (Roxb. ex Hornem.) Sims via several in vitro, in vivo, and in silico models. A total of four compounds were identified and isolated from the methanol extract of the bark and the methanol extract of the seed pulp of W. coccinea through successive chromatographic techniques and were characterized as 3β-acetyloxy-olean-12-en-28-ol (1), wrightiadione (2), 22β-hydroxylupeol (3), and β-sitosterol (4) by spectroscopic analysis. The aqueous fraction of the bark and chloroform fraction of the fruits provided the most potent antioxidant capacity (IC50 = 7.22 and 4.5 µg/mL, respectively) in DPPH free radical scavenging assay compared with the standard ascorbic acid (IC50 = 17.45 µg/mL). The methanol bark extract and the methanol fruit coat extract exerted anti-diarrheal activity by inhibiting 74.55 ± 0.67% and 77.78 ± 1.5% (mean ± SEM) of the diarrheal episode in mice, respectively, after four hours of loading the samples. In the hypoglycemic test, the methanol bark extract and the methanol fruit coat extract (400 mg/kg) produced a significant (p < 0.05) reduction in the blood glucose level in mice. Both doses of the plant extracts (200 mg/kg and 400 mg/kg) used in the study induced a significant (p < 0.05) increase in pain reaction time. The in vitro and in vivo findings were supported by the computational studies. The isolated compounds exhibited higher binding affinity compared with the standard drugs towards the active binding sites of glutathione reductase, epidermal growth factor receptor (EGFR), kappa opioid receptor, glucose transporter 3 (GLUT 3), Mu opioid receptor, and cyclooxygenase 2 (COX-2) proteins due to their potent antioxidant, cytotoxic, anti-diarrheal, hypoglycemic, and central and peripheral analgesic properties, respectively. The current findings concluded that W. coccinea might be a potential natural source for managing oxidative stress, diarrhea, hyperglycemia, and pain. Further studies are warranted for extensively phytochemical screening and establishing exact mechanisms of action.

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Section: Inhibition Of Mu-opioid Receptor and Cox-2 Proteins: Analges...mentioning

confidence: 99%

Chemical and Pharmacological Profiling of Wrightia coccinea (Roxb. Ex Hornem.) Sims Focusing Antioxidant, Cytotoxic, Antidiarrheal, Hypoglycemic, and Analgesic Properties

et al. 2022

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“…A triptantrina tem sido isolada de diversas fontes naturais, incluindo plantas, fungos, bactérias e, curiosamente, também em mamíferos (nomeadamente da urina do elefante asiático, Elephas maximus, e do líquido do saco da asa do morcego Saccopteryx bilineata) [4]. De entre as plantas tradicionalmente usadas para produzir corantes, destacam-se as espécies Isatis tinctoria, Polygonum tinctorium, Strobilanthes cusia (índigo Assam), Strobilanthes formosanus (índigo naturalis) e Wrightia tinctoria [4][5][6][7]. Considerando estas fontes naturais, torna-se evidente a existência de uma relação entre a triptantrina e o índigo, um corante icónico usado desde tempos ancestrais até aos nossos dias, por exemplo no processo de tingimento da ganga [8,9].…”

Section: Estrutura E Fontes Naturais Da Triptantrinaunclassified

Triptantrina: da Natureza ao Laboratório

Melo¹,

Piñeiro²,

Brandão³

et al. 2021

BSPQuimica

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“…It was identified in several botanical individuals including Phaius mishmensis [6]; Couroupita guianensis [7], Polygonum tinctorium Lour. [8], and [9] Wrightia spp. This indoloquinazoline alkaloid is described as a pharmacologically active agent against various illnesses [10].…”

Section: Introductionmentioning

confidence: 99%

The Natural Alkaloid Tryptanthrin Induces Apoptosis-like Death in Leishmania spp.

et al. 2022

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Leishmaniasis is a vector-borne disease against which there are no approved vaccines, and the treatment is based on highly toxic drugs. The alkaloids consist of a chemical class of natural nitrogen-containing substances with a long history of antileishmanial activity. The present study aimed at determining the antileishmanial activity and in silico pharmacokinetic and toxicological potentials of tryptanthrin alkaloid. The anti-Leishmania amazonensis and anti-L. infantum assays were performed against both promastigotes and intracellular amastigotes. Cellular viability was determined by parasites’ ability to grow (promastigotes) or differentiate (amastigotes) after incubation with tryptanthrin. The mechanisms of action were explored by mitochondrion dysfunction and apoptosis-like death evaluation. For the computational pharmacokinetics and toxicological analysis (ADMET), tryptanthrin was submitted to the PreADMET webserver. The alkaloid displayed anti-promastigote activity against L. amazonensis and L. infantum (IC50 = 11 and 8.0 μM, respectively). Tryptanthrin was active against intracellular amastigotes with IC50 values of 75 and 115 μM, respectively. Mitochondrial membrane depolarization was observed in tryptanthrin-treated promastigotes. In addition, parasites undergoing apoptosis-like death were detected after 18 h of exposure. In silico ADMET predictions revealed that tryptanthrin has pharmacokinetic and toxicological properties similar to miltefosine. The results presented herein demonstrate that tryptanthrin is an interesting drug candidate against leishmaniasis.

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Isolation of Tryptanthrin and Reassessment of Evidence for Its Isobaric Isostere Wrightiadione in Plants of the Wrightia Genus

Cited by 17 publications

References 71 publications

Chemical and Pharmacological Profiling of Wrightia coccinea (Roxb. Ex Hornem.) Sims Focusing Antioxidant, Cytotoxic, Antidiarrheal, Hypoglycemic, and Analgesic Properties

Chemical and Pharmacological Profiling of Wrightia coccinea (Roxb. Ex Hornem.) Sims Focusing Antioxidant, Cytotoxic, Antidiarrheal, Hypoglycemic, and Analgesic Properties

Triptantrina: da Natureza ao Laboratório

The Natural Alkaloid Tryptanthrin Induces Apoptosis-like Death in Leishmania spp.

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