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

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