Antitubercular and Cytotoxic Chlorinated <i>seco</i>-Cyclohexenes from <i>Uvaria alba</i>

Macabeo, Allan Patrick G.; letada, arianne; Budde, Simon; Faderl, Christian; Dahse, Hans Martin; Franzblau, Scott G.; Alejandro, Grecebio Jonathan D.; Pierens, Gregory K.; Garson, Mary J.

doi:10.1021/acs.jnatprod.7b00679

Cited by 23 publications

(27 citation statements)

References 26 publications

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“…The biosynthetic pathway of polyoxygenated cyclohexene and secocyclohexene were proposed from the shikimic acid pathway (Hsu et al, 2016;Macabeo et al, 2017;Suthiphasilp et al, 2019). The primary intermediate A as shown in Figure 4, is proposed as a forerunner based on our results.…”

Section: Discussionmentioning

confidence: 65%

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Suthiphasilp

Maneerat

Duangyod

et al. 2020

Heliyon

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Phytochemical investigations from the flower and leaf extracts of D. cochinchinensis resulted in the isolation and structural elucidation of five new polyoxygenated seco -cyclohexene derivatives, desmoscochinchinenes A-E ( 1 – 5 ), together with 11 known compounds ( 6 – 16 ). The structures on the new compounds were elucidated from their spectroscopic data, including UV, IR, NMR, and HRESITOFMS. Some of the isolated compounds were evaluated for their α -glucosidase inhibitory activities. Chrysin ( 9 ), pinocembrin 7- O -benzoate ( 12 ), and (−)-(5 R )-desmoscochinoxepinone B ( 16 ) inhibited α -glucosidase better than the standard control (acarbose, IC 50 = 83.5 μM) with IC 50 values of 5.7, 33.8, 53.3 μM, respectively.

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Section: Discussionmentioning

confidence: 65%

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Suthiphasilp

Maneerat

Duangyod

et al. 2020

Heliyon

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“…Uvaria genus belongs to the Annonaceae family which is distributed throughout tropical and subtropical countries and 26 species have been found in Thailand (Auranwiwat et al 2017;Chuan-Rui et al 2006). In previous studies, various types of secondary metabolites, including flavonoids (Auranwiwat et al 2017;Hsu et al 2016;Huang et al 1998), alkaloids (Hasan et al 2001;Nahar Asha et al 2004), chalcones (Macabeo et al 2017b), polyoxygenated cyclohexenes (Chuan-Rui et al 2006;Jolad et al 1981;Yong-Hong et al 1997), polyoxygenated seco-cyclohexenes (Macabeo et al 2017a;Zhang et al 2010) and aurones (Huang et al 1998) were reported. Many of these compounds displayed interesting biological activities, including cytotoxic (Asha et al 2003;Auranwiwat et al 2017;Huang et al 1998;Macabeo et al 2004), antibacterial (Asha et al 2003;Nahar et al 2004) and antitubercular (Macabeo et al 2017a) activities.…”

Section: Introductionmentioning

confidence: 97%

Potent α-glucosidase inhibitory activity of compounds isolated from the leaf extracts of Uvaria hamiltonii

Meesakul

Pyne

Laphookhieo

2018

Natural Product Research

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The phytochemical investigation of the leaf extracts of Uvaria hamiltonii (Annonaceae) led to the isolation and identification of ten compounds including a new seco-cyclohexene (1) together with nine known compounds (2-10). Their structures were elucidated by intensive analysis by spectroscopic methods and comparisons of their spectroscopic data with those of compounds reported in the literature. Compounds 2, 8, and 9 showed potent α-glucosidase inhibitory activity with the IC50 values ranging from 2.6-7.1 µM. AbstractThe phytochemical investigation of the leaf extracts of Uvaria hamiltonii (Annonaceae) led to the isolation and identification of ten compounds including a new seco-cyclohexene(1) together with nine known compounds (2-10). Their structures were elucidated by intensive analysis by spectroscopic methods and comparisons of their spectroscopic data with those of compounds reported in the literature. Compounds 2, 8, and 9 showed potent α-glucosidase inhibitory activity with the IC50 values ranging from 2.6-7.1 µM.

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“…The extracts and compounds of P. ophthalmicus exhibit photosensitizing effects useful in photodynamic therapies [13]. As part of our growing interest to validate the ethnomedicinal use of Philippine Annonaceae plants [14][15][16][17][18][19], we herein report the inhibitory activity of P. ophthalmicus extracts and tetrahydrobisbenzylisoquinoline alkaloids tetrandrine (1) and limacusine (2) ( Figure 1) against drug resistant bacterial strains in addition to their cyclooxygenase (COX-1 and -2) inhibitory activities. To probe on the (selective) binding affinity and to depict binding mechanism of antimicrobial and COX-2 inhibitory activity, molecular docking studies and all-atom molecular dynamics simulation experiments were performed against bacterial enzymes and ovine COX isoenzymes.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial and COX-2 Inhibitory Tetrahydrobisbenzylisoquinoline Alkaloids from the Philippine Medicinal Plant Phaeanthus ophthalmicus

Magpantay

Malaluan

Manzano

et al. 2021

Plants

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Phaeanthus ophthalmicus (Roxb. ex G.Don) J.Sinclair (previously known as P. ebracteolatus (Presl) Merr) is a Philippine medicinal plant occurring as evergreen shrub in the lowland forests of Luzon islands. It is used traditionally by Filipinos to treat bacterial conjunctivitis, ulcer and wound infections. Based on previous investigations where cyclooxygenase-2 (COX-2) functions as immune-linked factor in infectious sensitivities to bacterial pathogens by triggering pro-inflammatory immune-associated reactions, we investigated the antimicrobial and COX inhibitory activities of the extracts and tetrahydrobisbenzylisoquinoline alkaloids of P. ophthalmicus in vitro and in silico to validate its ethnomedicinal uses. Thus, the dichloromethane–methanol (DCM–MeOH) crude extract and alkaloid extracts exhibiting antibacterial activities against drug-resistant bacterial strains such as methicillin-resistance Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus (VRE), Klebsiella pneumoniae + CRE and Pseudomonas aeruginosa + MBL afforded (+)-tetrandrine (1) and (+)-limacusine (2) as the major biologically active tetrahydrobisbenzylisoquinoline alkaloidal constituents after purification. Both tetrahydrobisbenzylisoquinoline alkaloids 1 and 2 showed broad spectrum antibacterial activity with strongest inhibition against the Gram-negative bacteria MβL-Pseudomonas aeruginosa Klebsiella pneumoniae + CRE. Interestingly, the alkaloid limacusine (2) showed selective inhibition against ovine COX-2 in vitro. These results were ascertained by molecular docking and molecular dynamics simulation experiments where alkaloid 2 showed strong affinity in the catalytic sites of Gram-negative bacterial enzymes P. aeruginosa elastase and K. pneumoniae KPC-2 carbapenemase (enzymes involved in infectivity mechanisms), and of ovine COX-2. Overall, our study provides credence on the ethnomedicinal use of the Philippine medicinal plant P. ophthalmicus as traditional plant-based adjuvant to treat bacterial conjunctivitis and other related infections. The antibacterial activities and selective COX-2 inhibition observed for limacusine (2) point to its role as the biologically active constituent of P. ophthalmicus. A limited number of drugs with COX-2 inhibitory properties like celecoxib also confer antibacterial activity. Thus, tetrahydrobisbenzyl alkaloids, especially 2, are promising pharmaceutical inspirations for developing treatments of bacterial/inflammation-related infections.

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Antitubercular and Cytotoxic Chlorinated seco-Cyclohexenes from Uvaria alba

Cited by 23 publications

References 26 publications

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Potent α-glucosidase inhibitory activity of compounds isolated from the leaf extracts of Uvaria hamiltonii

Antibacterial and COX-2 Inhibitory Tetrahydrobisbenzylisoquinoline Alkaloids from the Philippine Medicinal Plant Phaeanthus ophthalmicus

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