Pobeguinine: a monoterpene indole alkaloid and other bioactive constituents from the stem bark of Nauclea pobeguinii

Abstract

Phytochemical investigation of dichloromethane neutral phase of stem bark ofNauclea pobeguiniiled to the isolation of a new monoterpene indole alkaloid, pobeguinine1along with 14 known compounds including (−)-naucleofficine D (2a), (+)-naucleofficine D (2b), naucleidinal (3), quafrinoic acid (4), betulinic acid (5), ursolic acid (6), quinovic acid (7), quinovic acid 3-O-α-L-rhamnopyranoside (8a), quinovic acid 3-O-β-D-fucopyranoside (8b), β-sitosterol (9), β-sitosterol 3-O-β-D-glucopyranoside (10), benzoic acid (11), lacceroic acid (12) andn-heptacosane (13). The structure of compound1was unambiguously assigned on the basis of single-crystal X-ray diffraction technique. The Hirshfeld surface analysis was further carried out to quantitatively analyze the role of various types of hydrogen bonding in crystal stability. These structures were elucidated using spectroscopic methods. The isolates were evaluated for their radical scavenging properties as well as inhibitory activities against urease and tyrosinase enzymes with IC50values ranging from 13.4 to 58.9, 46.0 to 86.7 and 39.4 to 87.1 μg/mL, respectively. Compound6exhibited maximum radical scavenging activity with IC5013.4 μg/mL, while compound4exhibited maximum tyrosinase with IC5039.4 μg/mL. All the isolates showed moderate urease inhibition.

GC-MS metabolic profiling and anti-urease activity of nonpolar fractions of Calligonum Polygonoides L. (Polygonaceae) and Crateva Adansonii DC. Prodr. (Capparaceae)

“…Fatty acids and lipids inhibit urease and the activity of H. pylori [26,27]. Alkanes such as n-heptacosane havealso shown moderate urease inhibition [28], and several terpenoids (mono-, di-, and tri-) have anti-urease activity [29]. Of particular interest is the fact that oleanolic acid, which has displayed remarkable urease inhibition, has also been identified in the n-hexane fraction of C. adansonii [30][31][32].…”

A New Ceramide (Rumexamide) and Other Chemical Constituents from <i>Rumex abyssinicus</i> Jacq (Polygonaceae): Isolation, Characterization, Antibacterial Activities and Chemophenetic Significance

“…A set of signals appearing as broad in the range of δ H 1.52 -1.20 corresponding to the methylenes (-CH 2 -) associated to the two long chains, and a downfield signal at δ H 5.14 (1H, m, H-2) assigned to the aminomethine H-2 of sphingosine were also observed [33]. All the above spectral data (Table 1) revealed that compound 1 was a phytosphingosine type sphingolipid [34]. In addition, its 1 H NMR spectrum exhibited two olefinic protons at δ H 5.57 (1H, m, H-16) and 5.51 (1H, m,…”

Synthesis, Urease Inhibition and Molecular Modelling Studies of Novel Derivatives of the Naturally Occurring β-Amyrenone

“…Trifloroacetic acid, phenylhydrazine, 2,4-dinitrophenylhydrazine, and p -methoxyphenylhydrazine, all of analytical grade and purchased from Aldrich, USA, were used for synthesis. Olean-12-en-3-one commonly called β -amyrenone ( 1 ) was isolated from of the fruits of Ficus vallis - choudae Delile, collected from the North-West region of Cameroon [ 13 ]. The following reagents, all purchased from Sigma, were used for the urease assay: Phenol, sodium nitroprusside, dipotassium hydrogen phosphate trihydrate, EDTA, lithium chloride and thiourea.…”

“…Indole alkaloids have been reported from many plant species [ 7 – 10 ]. They have also been reported to play an important role in medicinal chemistry as potential UE inhibitors [ 7 ] and antibacterial agents [ 8 ].…”

“…Indole alkaloids have been reported from many plant species [ 7 – 10 ]. They have also been reported to play an important role in medicinal chemistry as potential UE inhibitors [ 7 ] and antibacterial agents [ 8 ]. However, the treatment of HP using the current known synthetic drugs is often associated with high treatment cost, bacterial resistance and adverse side effects related to currently used drugs [ 11 , 12 ].…”