A bioactive cycloartane triterpene from Garcinia hombroniana

Abstract

The dichloromethane bark extract of Garcinia hombroniana yielded one new cycloartane triterpene; (22Z,24E)-3β-hydroxycycloart-14,22,24-trien-26-oic acid (1) together with five known compounds: garcihombronane G (2), garcihombronane J (3), 3β acetoxy-9α-hydroxy-17,14-friedolanostan-14,24-dien-26-oic acid (4), (22Z, 24E)-3β, 9α-dihydroxy-17,14-friedolanostan-14,22,24-trien-26-oic acid (5) and 3β, 23α-dihydroxy-17,14-friedolanostan-8,14,24-trien-26-oic acid (6). Their structures were established by the spectral techniques of NMR and ESI-MS. These compounds together with some previously isolated compounds; garcihombronane B (7), garcihombronane D (8) 2,3',4,5'-tetrahydroxy-6-methoxybenzophenone (9), volkensiflavone (10), 4''-O-methyll-volkensiflavone (11), volkensiflavone-7-O-glucopyranoside (12), volkensiflavone-7-O-rhamnopyranoside (13), Morelloflavone (14), 3''-O-methyl-morelloflavone (15) and morelloflavone-7-O-glucopyranoside (16) were evaluated for cholinesterase enzymes inhibitory activities using acetylcholinesterase and butyrylcholinesterase. In these activities, compounds 1-9 showed good dual inhibition on both the enzymes while compounds 10-16 did not reasonably contribute to both the cholinesterases inhibitory effects.

Validation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties

“…krugianus revealed potent protective effects against oxidative stress [22]. Furthermore, one new cycloartane triterpene, namely (22Z,24E)-3β-hydroxycycloart-14,22,24-trien-26-oic acid isolated from Garcinia hombroniana bark, displayed potent cholinesterase inhibitory potential versus both acetylcholinesterase and butyrylcholinesterase [23]. New cycloartane-type triterpenoids isolated from the Amberboa ramosa entire plant revealed considerable tyrosinase inhibitory potential, together with those isolated from Astragalus, and thus could serve as skin-whitening agents in pharmaceuticals or cosmeceuticals [24,25].…”

Phytochemical profile and diverse pharmacology of Garcinia celebica L

“…2 ) from various parts of G. celebica ( Table 2 ). Compounds 10 – 14 were isolated from dichloromethane bark and methanol leaf extracts [ 33 , 32 ], while compounds 15 and 16 were found in ethyl acetate twig and bark extracts [ 30 , 34 ]. The number of compounds recorded from this class was the highest among other classes in this review.…”

A new xanthone and a new benzophenone from the roots of Garcinia hombroniana

“…Besides, the ethanolic extracts of this species have been shown to exhibit cytotoxicity, antitrypanosomal, antioxidation and antiplatelet aggregation activities (Saputri and Jantan, 2012;Dyary et al, 2015;Jamila et al, 2017). Although phytochemical analyses were performed on the pericarp, leaves, and twigs of G. hombroniana yielding compounds such as lanostanes, friedolanostanes, xanthones, biflavonoids and triterpenes (Klaiklay et al, 2013;Jamila et al, 2014aJamila et al, , 2014bJamila et al, , 2016, no phytochemical investigation has ever been performed on the roots of the G. hombroniana. Thus, as a continuation of the phytochemical studies on this species (On et al, 2017;Salleh et al, 2017), we now report on the isolation and identification of novel derivatives of xanthone and benzophenone, known as garcihomxanthone (1) and garcihombrianone (2), (Figure 1), respectively, from the roots of G. hombroniana.…”