A Review of the Phytochemistry and Pharmacology of the Medicinal Plant: Khaya Senegalensis (Desr.) A. Juss

Tyoapine, Daniel Aondongu; Victory, Promise Chinecherem; Yusuf, Alhassan; Badamasi, Aisha Muhammad

doi:10.55248/gengpi.2022.3.8.41

Cited by 1 publication

(5 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The protolimonoid compound (1abc) was found to be a mixture of a new limonoid 21βhydroxybourjotinolone A (1a) together with an epimeric mixture of 21α-melianodiol (1b) and 21β-melianodiol (1c). However, degraded triterpenoid-type limonoids (compounds 4-6), lupanes (3), oleanane (7) and steroids (11)(12)(13)(14), two flavonoids (8)(9) and one ceramide (10) were also identified here. Most of these compounds (2, 3-9 and 11-14) have been previously reported from K. senegalensis [8,11].…”

Section: Discussionmentioning

confidence: 70%

“…A mass of 275.0 g of the MeOH extract of K. senegalensis was partitioned into n-hexane (15.6 g) and EtOAc (160.8 g) fractions. Repeated column chromatography with Sephadex as well as silica gel as the stationary phase of the EtOAc (160.0 g) and n-hexane (15.0 g) extracts led to the isolation of 16 secondary metabolites, including nine triterpenoids (1abc-7), four steroids (11)(12)(13)(14), two flavonoids (8)(9) and one ceramide (10) (Figure 1). led to the isolation of 16 secondary metabolites (1abc-14).…”

Section: Resultsmentioning

confidence: 99%

“…The criteria for antiplasmodial activity were focused on the established limits [40], where IC 50 < 1 µg/mL indicates that the compound has excellent activity; IC 50 of 1-20 µg/mL indicates good activity; IC 50 of 20-100 µg/mL indicates moderate activity; IC 50 of 100-200 µg/mL indicates low activity; and IC 50 > 200 µg/mL indicates inactivity. Overall, compounds 1abc-14 showed antiplasmodial activity with IC 50 values ranging from 56.98 µg/mL (khayanolide E) (6) to 165.19 µg/mL (methylangolensate) (4) on Pf 3D7 and 2.95 µg/mL (catechin) (9) to 50.97 µg/mL (belamcanidin) (8) on Pf Dd2 with catechin (9), khayanolide E (6), gyrunamide IV (10), rhohituka-3 (5) and methylangolensate (4) displaying the highest activity against Pf Dd2 (IC 50 < 20 µg/mL) with IC 50 values of 2.95, 14.03, 14.13, 15.92, and 20.51 µg/mL, respectively. Alphitolic acid (3) and the mixture of β-sitosterol (11) and stigmasterol (13) were inactive against the multidrug-resistant Pf Dd2 strain (IC 50 > 200 µg/mL).…”

Section: Antileishmanial Antiplasmodial and Cytotoxic Activitiesmentioning

confidence: 99%

“…Almost all naturally reported limonoids contain either a furan or a pyran ring linked to the D-ring at C-17, and the preferable oxygenated carbons are C23, C21, C-17, C-16, C-7, C-4, C-3, and C1 [2,[5][6][7][8]. Limonoids exhibit a panel of biological activities, such as insect antifeedant, and insecticidal, antimalarial, antimicrobial, antiviral, and anticancer activities [2,3,9].…”

Section: Introductionmentioning

confidence: 99%

“…K. senegalensis is a tree of approximately 25 m in height whose leaves, fruit, and stems are largely used by many African tribes in Cameroon and Nigeria for the treatment of malaria, headache, and yellow fever [9][10][11][12]. Previous chemical and biological studies of different parts of K. senegalensis have revealed the occurrence of flavonoids, alkaloids, triterpenoids, steroids, and limonoids with cytotoxic, antimicrobial, hepatoprotective, antiviral, and antioxidant activities [2,9,[11][12][13]. Limonoids are reported to be the most abundant and chemophenetic taxon of K. senegalensis as well as the Khaya genus [3,13].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Antiplasmodial and Antileishmanial Activities of a New Limonoid and Other Constituents from the Stem Bark of Khaya senegalensis

Amang à Ngnoung,

Nganso Ditchou,

Leutcha

et al. 2023

Molecules

View full text Add to dashboard Cite

Plasmodium falciparum and Leishmania sp. resistance to antiparasitic drugs has become a major concern in malaria and leishmaniasis control. These diseases are public health problems with significant socioeconomic impacts, and mostly affect disadvantaged populations living in remote tropical areas. This challenge emphasizes the need to search for new chemical scaffolds that preferably possess novel modes of action to contribute to antimalarial and antileishmanial research programs. This study aimed to investigate the antimalarial and antileishmanial properties of a methanol extract (KS-MeOH) of the stem bark of the Cameroonian medicinal plant Khaya senegalensis and its isolated compounds. The purification of KS-MeOH led to the isolation of a new ordered limonoid derivative, 21β-hydroxybourjotinolone A (1a), together with 15 known compounds (1bc–14) using a repeated column chromatography. Compound 1a was obtained in an epimeric mixture of 21α-melianodiol (1b) and 21β-melianodiol (1c). Structural characterization of the isolated compounds was achieved with HRMS, and 1D- and 2D-NMR analyses. The extracts and compounds were screened using pre-established in vitro methods against synchronized ring stage cultures of the multidrug-resistant Dd2 and chloroquine-sensitive/sulfadoxine-resistant 3D7 strains of Plasmodium falciparum and the promastigote form of Leishmania donovani (1S(MHOM/SD/62/1S). In addition, the samples were tested for cytotoxicity against RAW 264.7 macrophages. Positive controls consisted of artemisinin and chloroquine for P. falciparum, amphotericin B for L. donovani, and podophyllotoxin for cytotoxicity against RAW 264.7 cells. The extract and fractions exhibited moderate to potent antileishmanial activity with 50% inhibitory concentrations (IC50) ranging from 5.99 ± 0.77 to 2.68 ± 0.42 μg/mL, while compounds displayed IC50 values ranging from 81.73 ± 0.12 to 6.43 ± 0.06 μg/mL. They were weakly active against the chloroquine-sensitive/sulfadoxine-resistant Pf3D7 strain but highly potent toward the multidrug-resistant PfDd2 (extracts, IC50 2.50 ± 0.12 to 4.78 ± 0.36 μg/mL; compounds IC50 2.93 ± 0.02 to 50.97 ± 0.37 μg/mL) with selectivity indices greater than 10 (SIDd2 > 10) for the extract and fractions and most of the derived compounds. Of note, the limonoid mixture [21β-hydroxylbourjotinolone A (1a) + 21α-melianodiol (1b) + 21β-melianodiol (1c)] exhibited moderate activity against P. falciparum and L. donovani. This novel antiplasmodial and antileishmanial chemical scaffold qualifies as a promising starting point for further medicinal chemistry-driven development of a dually active agent against two major infectious diseases affecting humans in Africa.

show abstract