Antimycobacterial Friedelane-terpenoid from the Root Bark of Terminalia avicennioides

Mann, Abdullahi; Ibrahim, K.; Oyewale, A. O.; Amupitan, J. O.; Fatope, Majekodunmi O.; Okogun, Joseph I.

doi:10.5923/j.chemistry.20110102.11

Cited by 47 publications

(44 citation statements)

References 21 publications

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“…All soluble extracts were concentrated and dried in vacuo gave extractive values as indicated in the earlier report [11]. The n-hexane extract (3 g, oily) subjected to successively elution with gradient system gave nine fractions namingly: TaF1 (F1-9), TaF10 (F10-16), TaF17 (F17-19), TaF20 (F20-30), TaF31 (F31-46), TaF47 (F47-77), TaF79 (F79-96), TaF97 (F97-110) and TaF111 (F111-126).…”

Section: Extraction and Fractionationmentioning

confidence: 99%

“…The antimycobacterial activity test was conducted on the isolated triterpenoidal compounds as earlier described [11].…”

Section: Determination Of Antimycobacterial Activitymentioning

confidence: 99%

“…The air-dried solvent extracts obtained were packed in well labelled vials, wrapped with aluminium foil and kept in the fridge until required. Phytochemical screenings were performed as described in previous works [11] (Mann et al, 2008c;2009). n-Hex and EtOAc soluble extracts were subjected to column chromatography with glass column (Φ2.0 x 40 cm) packed with slurry of silica gel (70 -230 mesh, 40g) (Merck, Darmstadt, Germany) and then eluted successively with gradient system of n-Hex-EtOAc (100:0→95:5→90:10→80:20→40:60→ 50:50→40:60→20:80→10:90→5:95→0:100).…”

Section: Extraction Fractionation and Isolationmentioning

confidence: 99%

“…Some compounds earlier isolated from T. avicennioides are hydrolysable tannins that indicated antitrypanosomal activity [12]. However, extensive array of triterpenes has been reported to exhibit diverse biological activities such as anti-HIV-1 activity [13], antimycobacterial activity [11], antifungal and antimicrobial [14,15]; antiulcerogenic, anti-inflammatory, fibrocystic, antipyretic, analgesic, larvicidal, and antiedematous activities [16,17]. Moreover, information on triterpenoidal compounds of T. avicennioides is lacking.…”

Section: Introductionmentioning

confidence: 99%

“…Since this plant is very common in Nigeria, further study and investigation of its active constituents may prove its potential biological activities and medicinal values. Compounds with antimycobacterial activities have been isolated from plants [11]. Some compounds earlier isolated from T. avicennioides are hydrolysable tannins that indicated antitrypanosomal activity [12].…”

Section: Introductionmentioning

confidence: 99%

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Isolation and Elucidation of Three Triterpenoids and Its Antimycobacterial Activty of Terminalia Avicennioides

Mann¹,

Ibrahim²,

Oyewale³

et al. 2012

AJOC

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Terminalia avicennioides Guill. & Perr. (Combretaceae) has been traditionally used as traditional medicine for centuries in Nupeland, North Central Nigeria for the treatment of respiratory diseases such as tuberculosis and cough. This study evaluates the in vitro antimycobacterial activities of the isolated compounds in order to support the therapeutic use of T. avicennioides for treating these infectious diseases. Chemical investigation by bioassay-guided fractionation led to the isolation of three triterpenoids namely, arjunolic acid (1), α-amyrin (2) and 2, 3, 23-trihydroxylolean-12-ene (3). Among them, arjunolic acid manifested the most potent antimycobacterial activity against a strain of Mycobacterium bovis (BCG). Structure elucidation of the isolated compounds were based primarily on the analysis of 1-D and 2-D NMR spectral data including HMQC, HMBC, COSY and NOESY correlations, as well as comparison with reported authentic data of arjunolic acid, α-amyrin and 2, 3, 23-trihydroxylolean-12-ene. To the best of our knowledge, this is the first time these compounds (1-3) are reported from this plant. The present result further confirms the value of ethnopharmacological investigations into traditional herbs for leads for potential drug development.

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Section: Extraction and Fractionationmentioning

confidence: 99%

“…The antimycobacterial activity test was conducted on the isolated triterpenoidal compounds as earlier described [11].…”

Section: Determination Of Antimycobacterial Activitymentioning

confidence: 99%

Section: Extraction Fractionation and Isolationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Isolation and Elucidation of Three Triterpenoids and Its Antimycobacterial Activty of Terminalia Avicennioides

Mann¹,

Ibrahim²,

Oyewale³

et al. 2012

AJOC

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Therapeutic Potentials of Phytochemicals AgainstMycobacterium tuberculosis, the Causative Agent of Tuberculosis

Ogodo¹,

Tatah²,

Ebuara³

et al. 2021

Neglected Tropical Diseases and Phytochemicals in Drug Discovery

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Functional characterization of an oxidosqualene cyclase (PdFRS) encoding a monofunctional friedelin synthase in Populus davidiana

Han

Ahn

Adhikari

et al. 2018

Planta

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An oxidosqualene cyclase (PdFRS) from Populus davidiana was characterized as a monofunctional friedelin synthase by its heterologous expression in yeast and overexpression in plants. Triterpenes are one of the largest classes of plant chemical compounds composed of three terpene units, which form the basic skeleton of all sterols and saponins. Friedelin (friedelan-3-one), a pentacyclic triterpene, occurs in many plant families and is particularly present in rich amounts in cork tissues from trees. The biosynthesis of friedelin occurs through the oxidosqualene cyclase (OSC) enzyme that generates friedelin from 2,3-oxidosqualene after the maximum rearrangement of a triterpene skeleton. Populus davidiana is called Korean aspen and grows in northern East Asia. From 57,322 unique sequences generated from the P. davidiana transcriptome database, one complete coding sequence (PdFRS) was obtained from a contig, which showed 74% identity to Betula platyphylla β-amyrin synthase and 73% identity with friedelin synthase from Maytenus ilicifolia. The open reading frame (ORF) region of the PdFRS sequence was 2280 bp long and composed a 759 amino acid protein with a predicted molecular mass of 87.81 kDa. qPCR analysis revealed that methyl jasmonate treatments strongly upregulated PdFRS gene expression and resulted in enhanced friedelin accumulation in leaves. Heterologous expression of the PdFRS gene in yeast resulted in the production of friedelin triterpene as a single product, which was confirmed by comparison with the mass fragmentation pattern from an authentic friedelin standard by GC/MS analysis. Transgenic P. davidiana overexpressing the PdFRS gene was constructed via Agrobacterium-mediated transformation. Overexpression of PdFRS in transgenic P. davidiana lines resulted in enhanced friedelin production.

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Antimycobacterial Friedelane-terpenoid from the Root Bark of Terminalia avicennioides

Cited by 47 publications

References 21 publications

Isolation and Elucidation of Three Triterpenoids and Its<b> Antimycobacterial </b><b>Activty </b>of Terminalia Avicennioides

Isolation and Elucidation of Three Triterpenoids and Its<b> Antimycobacterial </b><b>Activty </b>of Terminalia Avicennioides

Therapeutic Potentials of Phytochemicals AgainstMycobacterium tuberculosis, the Causative Agent of Tuberculosis

Functional characterization of an oxidosqualene cyclase (PdFRS) encoding a monofunctional friedelin synthase in Populus davidiana

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