15 research outputs found
A rare phytosterol, stigmast-5-en-3<i>β</i>,7<i>α</i>,22<i>α</i>-triol and other secondary metabolites from <i>Leea indica</i> showing enhanced <i>in vitro</i> cell migration and proangiogenic activity
Leea indica (Burm. f.) Merr. (Vitaceae) is used for the treatment of wounds in traditional medicine practiced in Sri Lanka. The current study is carried out to investigate its wound healing potential in terms of in vitro cell migration and proangiogenic activity. The scratch wound assay (SWA) guided fractionation of dichloromethane extract of L. indica led to the isolation of a rare phytosterol, stigmast-5-en-3β,7α,22α-triol (1), betulin (2), lupeol (3), and β-sitosterol (4) all of which showed enhanced cell migration in SWA and significant proangiogenic response in chorioallantoic membrane (CAM) assay. The identities of compounds 1–4 were established by the analysis of NMR spectroscopic data and comparison with those reported. This is the first report of the occurrence of compounds 1 and 2 in L. indica.</p
<i>In-vitro</i> cell migration enhancing and pro-angiogenic active secondary metabolites from <i>Jeffreycia zeylanica</i> (L.) H. Rob., S.C. Keeley & Skvarla (Asteraceae)
Jeffreycia zeylanica (L.) H. Rob., S. C. Keeley & Skvarla is used for the treatment of wounds in indigenous medicine practiced in Sri Lanka. The scratch wound assay (SWA) guided fractionation of hexanes extract of J. zeylanica led to the isolation of ethuliacoumarin (1), stigmasterol (2), β-amyrin (3) and lupeol (4) and a non-resolved triterpene alcohol mixture HF5D1, all of which showed enhanced cell migration. The mixture HF5D1 contained glut-5-en-3β-ol (5) and friedelin-3β-ol (6). The identities of compounds 1–6 were established by the analysis of spectroscopic data and comparison of them with those reported. The compounds 1–4 and the non-resolved triterpene alcohol mixture, HF5D1 also exhibited significant proangiogenic response in chorioallantoic membrane (CAM) assay in addition to the enhanced cell migration. This is the first report of the occurrence of the compounds 1, 2, 4 and 5 in this plant.</p
<i>In-vitro</i> cell migration enhancing constituents from <i>Decalepis hamiltonii</i>, a plant used in the preparation of ‘Pinda oil’, a medicinal oil used in Ayurveda for wound management
Decalepis hamiltonii, Wight & Arn. (Apocyanaceae) is a one of the raw materials used in the preparation of ‘Pinda oil’, a medicinal oil which is used for treatment of wounds in Ayurveda. Of the hexanes, dichloromethane, and ethyl acetate extracts derived from the plant raw materials used to prepare ‘Pinda oil’, the hexanes extract of D. hamiltonii exhibited the highest mean percentage wound closure (75.1 ± 2.9) compared to the negative controls (1% DMSO in DMEM, 4.2 ± 1.2 and 100% DMEM, 4.1 ± 0.9) in the scratch wound assay (SWA). Fractionation of the hexanes extract of stem of D. hamiltonii led to the isolation of 2-hydroxy-4-methoxybenzaldehyde (1) and a mixture of long chain esters of lupeol (2), which showed enhanced cell migration in SWA. It was observed that the esters of lupeol bind to the cell membrane and/or enter the cells during the SWA. It was found that these constituents are also present in ‘Pinda oil’ which may contribute to the enhancement of wound healing activity of ‘Pinda oil’.</p
Recommended from our members
Antimicrobial activity of some celastroloids and their derivatives
Infections are among the 10 deadliest diseases in the world. Here we screened 19 celastroloids and their derivatives 1–19 against several strains of bacteria and yeast of biomedical significance. In general, quinonemethide-type celastroloids, except isoiguesterin (8) exhibited significant antibacterial activity for Staphylococcus aureus ATCC 25923, MRSA ATCC 33592, and the clinical isolate STA6 with MICs of 0.39–12.50 µg/mL, whereas 14(15)-enequinonemethide, balaenol (12), showed antifungal activity against Candida albicans ATCC 10261 with an MIC of 3.12 µg/mL. Among the phenolic triterpenes and their derivatives, zeylasterone (14) had an MIC of 1.56 µg/mL for all 3 strains of S. aureus, and zeylasteral (15) was active against C. albicans at 3.12 µg/mL. Cytotoxicity assays revealed that most quinonemethides were cytotoxic with IC50s of 0.16–0.36 µg/mL that are below their MIC values. However, 14(15)-enequinonemethide 12 and phenolic triterpenes 14 and 15 exhibited antimicrobial activity at sub-cytotoxic concentrations, suggesting that these celastroloids are potential candidates for further studies. Molecular docking studies were used to investigate the theoretical affinities for potential protein targets of 12 and 14 in S. aureus, and 15 in C. albicans. Based on their docking scores, it can be inferred that 12 and 14 inhibits GyrB in S. aureus, and 15 inhibits Bdf1 in C. albicans.12 month embargo; published: 13 July 2022This item from the UA Faculty Publications collection is made available by the University of Arizona with support from the University of Arizona Libraries. If you have questions, please contact us at [email protected]
Geopyxins A–E, <i>ent</i>-Kaurane Diterpenoids from Endolichenic Fungal Strains <i>Geopyxis</i> aff. <i>majalis</i> and <i>Geopyxis</i> sp. AZ0066: Structure–Activity Relationships of Geopyxins and Their Analogues
Four new <i>ent</i>-kaurane diterpenoids, geopyxins
A–D (<b>1</b>–<b>4</b>), were isolated from <i>Geopyxis</i> aff. <i>majalis</i>, a fungus occurring
in the lichen <i>Pseudevernia intensa</i>, whereas <i>Geopyxis</i> sp. AZ0066 inhabiting the same host afforded two
new <i>ent</i>-kaurane diterpenoids, geopyxins E and F (<b>5</b> and <b>6</b>), together with <b>1</b> and <b>3</b>. The structures of <b>1</b>–<b>6</b> were
established on the basis of their spectroscopic data, while the absolute
configurations were assigned using modified Mosher’s ester
method. Methylation of <b>1</b>–<b>3</b>, <b>5</b>, and <b>6</b> gave their corresponding methyl esters <b>7</b>–<b>11</b>. On acetylation, <b>1</b> and <b>7</b> yielded their corresponding monoacetates <b>12</b> and <b>14</b> and diacetates <b>13</b> and <b>15</b>. All compounds were evaluated for their cytotoxic and heat-shock
induction activities. Compounds <b>2</b>, <b>7</b>–<b>10</b>, <b>12</b>, <b>14</b>, and <b>15</b> showed
cytotoxic activity in the low micromolar range against all five cancer
cell lines tested, but only compounds <b>7</b>–<b>9</b>, <b>14</b>, and <b>15</b> were found to activate
the heat-shock response at similar concentrations. From a preliminary
structure–activity perspective, the electrophilic α,β-unsaturated
ketone carbonyl motif present in all compounds except <b>6</b> and <b>11</b> was found to be necessary but not sufficient
for both cytotoxicity and heat-shock activation
Oxaspirol B with p97 Inhibitory Activity and Other Oxaspirols from <i>Lecythophora</i> sp. FL1375 and FL1031, Endolichenic Fungi Inhabiting <i>Parmotrema tinctorum</i> and <i>Cladonia evansii</i>
A new metabolite, oxaspirol D (<b>4</b>), together with oxaspirols
B (<b>2</b>) and C (<b>3</b>) were isolated from <i>Lecythophora</i> sp. FL1375, an endolichenic fungus isolated
from Parmotrema tinctorum, whereas <i>Lecythophora</i> sp. FL1031 inhabiting the lichen Cladonia evansii afforded oxaspirols A (<b>1</b>), B (<b>2</b>), and C (<b>3</b>). Of these, oxaspirol
B (<b>2</b>) showed moderate p97 ATPase inhibitory activity.
A detailed characterization of all oxaspirols was undertaken because
structures proposed for known oxaspirols have involved incomplete
assignments of NMR spectroscopic data leading only to their planar
structures. Thus, the naturally occurring isomeric mixture (<b>2a</b> and <b>2b</b>) of oxaspirol B was separated as their
diacetates (<b>5a</b> and <b>5b</b>) and the structures
and absolute configurations of <b>1</b>, <b>2a</b>, <b>2b</b>, <b>3</b>, and <b>4</b> were determined by
the application of spectroscopic techniques including two-dimensional
NMR and the modified Mosher’s ester method. Oxaspirol B (<b>2</b>) and its diacetates <b>5a</b> and <b>5b</b> were
evaluated for their ATPase inhibitory activities of p97, p97 mutants,
and other ATP-utilizing enzymes, and only <b>2</b> was found
to be active, indicating the requirement of some structural features
in oxaspirols for their activity. Additional biochemical and cellular
assays suggested that <b>2</b> was a reversible, non-ATP competitive,
and specific inhibitor of p97