New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance

Abstract

Siphoneugena Berg (Myrtaceae) é um pequeno gênero eugenióide segregado de Eugenia por Berg. A investigação fitoquímica de Siphoneugena densiflora foi realizada com o objetivo de se descobrir metabólitos secundários que possam ser considerados marcadores quimiotaxonômicos e auxiliar na distinção entre os dois gêneros. Cinco taninos hidrolisáveis inéditos foram isolados do extrato metanólico da casca da raiz e caracterizados como 4-O-α-L-2"-O-e seu isômero 4-O-α-L-3"-O-acetilramnopiranosídeo do ácido elágico, siphoneugenina, constituído por uma nova aglicona de estrutura dibenzo-1,4-dioxínica, 4-O-β-D-6"-e 4-O-β-D-3",6"-di-O-acetilglucopiranosídeo do ácido 3,4'-di-O-metilelágico, juntamente com o 4-O-α-L-4"-O-acetilramnopiranosídeo do ácido elágico, eschweilenol C, sitosterol, daucosterol, ramnose, casuarinina, castalagina e ácidos elágico, gálico e siríngico. Do extrato metanólico das folhas, além dos compostos conhecidos como a quercetina, quercitrina, guiajaverina, reinoutrina, chebulosídeo II, ácidos terminólico, madecássico e asiático, lupeol, α-e β-amirina, foi isolado um novo triterpeno pentacíclico nomeado como 2α,3β,6β-triidroxiolean-12-en-28-ato de β-D-glucopiranosila. Todas as substâncias foram identificadas através da análise dos dados espectrais e químicos obtidos, além da comparação com dados relatados na literatura.Siphoneugena Berg (Myrtaceae) is a small eugenioid genus segregated from Eugenia by Berg. The phytochemical survey of Siphoneugena densiflora was carried out in order to find secondary metabolites which may be considered as chemotaxonomic characters and help to distinguish between the two genera. Five novel hydrolysable tannins were isolated from the methanolic extract of root bark and were characterized as ellagic acid 4-O-α-L-2"-O-and its isomer 4-O-α-L-3"-O-acetylrhamnopyranoside, siphoneugenin, that supports a new aglycone with a dibenzo-1,4-dioxin structure, 3,4'-di-O-methylellagic acid 4-O-β-D-6"-O-and 4-O-β-D-3",6"-diacetylglucopyranoside, accompanied by ellagic acid 4-O-α-L-4"-O-acetylrhamnopyranoside, eschweilenol C, sitosterol, daucosterol, rhamnose, casuarinin, castalagin, ellagic, gallic and syringic acids. From methanolic extract of leaves, in addition to the well known compounds quercetin, quercitrin, guiajaverin, reynoutrin, chebuloside II, terminolic, madecassic and asiatic acids, lupeol, α-and β-amyrin, a new pentacyclic triterpene was isolated and named as β-D-glucopyranosyl-2α,3β,6β-trihydroxyolean-12-en-28-ate. Structures were established on the basis of spectroscopic and chemical evidence, along with the comparison of the data reported in the literature. Keywords:Siphoneugena densiflora, Myrtaceae, chemotaxonomy, hydrolysable tannin, pentacyclic triterpene IntroductionThe genus Siphoneugena comprises only eight species and belongs to Myrtaceae family. It is one of the specialized genera segregated from Eugenia by Berg. 1 Siphoneugena densiflora Berg, commonly known as Uvatinga, occurs in montane grasslands ("campos rupestres"), deciduous forests ("cerradões") and gall...

Bioactivity of extracts and isolated compounds from Vitex polygama (Verbenaceae) and Siphoneugena densiflora (Myrtaceae) against Spodoptera frugiperda (Lepidoptera: Noctuidae)

“…Casuarinin ( 14 ; C 41 H 28 O 26 ): amorphous brown powder; ESI/MS m / z 935 [M − H] − ; 1 H NMR (400 MHz, acetone‐d 6 /deuterium oxide): δ 7.13 (galloyl group; s); 6.88, 6.58 and 6.53 (HHDP groups; s); glucose moiety: 5.53 (anomeric proton; d; J 5.0 Hz); 4.58 (H‐2; dd; J 2.0 and 5.0 Hz); 5.39 (H‐3 and 4; m); 5.26 (H‐5; dd; J 8.7 and 2.6 Hz); 4.80 (H‐6a; dd; J 13.7 and 3.8 Hz); 4.02 (H‐6b; d; J 13.7 Hz); IR, UV and 13 C NMR data were similar to those reported in the literature 28. Castalagin ( 15 ; C 41 H 26 O 26 ): amorphous brown powder; ESI/MS m / z 933 [M − H] − ; 1 H NMR (400 MHz, acetone‐d 6 /deuterium oxide): δ 6.70, 6.69 and 6.55 (HHDP groups; s); glucose moiety: 5.60 (anomeric proton; d; J 4.6 Hz); 4.94 (H‐2, 3 and 6a; m); 5.12 (H‐4; t; J 7.1 Hz); 5.49 (H‐5; brd; J 6.5 Hz); 3.95 (H‐6b; d; J 12.6 Hz); 13 C NMR data were similar to those reported in the literature 28. Syringic acid ( 16 ; C 9 H 10 O 5 ): amorphous white powder; ESI/MS m / z 197 [M − H] − ; 1 H NMR (200 MHz, acetone‐d 6 ): δ 7.25 (H‐2 and 6; s); 3.61 (OCH3‐3 and 5; s); 13 C NMR and UV data were similar to those reported in the literature 28.…”

“…Castalagin ( 15 ; C 41 H 26 O 26 ): amorphous brown powder; ESI/MS m / z 933 [M − H] − ; 1 H NMR (400 MHz, acetone‐d 6 /deuterium oxide): δ 6.70, 6.69 and 6.55 (HHDP groups; s); glucose moiety: 5.60 (anomeric proton; d; J 4.6 Hz); 4.94 (H‐2, 3 and 6a; m); 5.12 (H‐4; t; J 7.1 Hz); 5.49 (H‐5; brd; J 6.5 Hz); 3.95 (H‐6b; d; J 12.6 Hz); 13 C NMR data were similar to those reported in the literature 28. Syringic acid ( 16 ; C 9 H 10 O 5 ): amorphous white powder; ESI/MS m / z 197 [M − H] − ; 1 H NMR (200 MHz, acetone‐d 6 ): δ 7.25 (H‐2 and 6; s); 3.61 (OCH3‐3 and 5; s); 13 C NMR and UV data were similar to those reported in the literature 28. Ellagic acid 4‐ O ‐α‐ L ‐rhamnopyranoside ( 17 ; C 20 H 16 O 12 ): pale yellow powder; ESI/MS m / z 447 [M − H] − ; 1 H NMR (400 MHz, CD 3 OD): δ 7.84 (H‐5; s); 7.49 (H‐5′; s); 5.52 (H‐1″; d; J 1.6 Hz); 4.20 (H‐2″; dd; J 1.6 and 3.4 Hz); 4.02 (H‐3″; dd; J 9.5 and 3.4 Hz); 3.48 (H‐4″; t; J 9.5 Hz); 3.77 (H‐5″; dd; J 9.5 and 6.2 Hz); 1.27 (H‐6″; d; J 6.2 Hz); IR, UV and 13 C NMR data were similar to those reported in the literature 28.…”

“…Syringic acid ( 16 ; C 9 H 10 O 5 ): amorphous white powder; ESI/MS m / z 197 [M − H] − ; 1 H NMR (200 MHz, acetone‐d 6 ): δ 7.25 (H‐2 and 6; s); 3.61 (OCH3‐3 and 5; s); 13 C NMR and UV data were similar to those reported in the literature 28. Ellagic acid 4‐ O ‐α‐ L ‐rhamnopyranoside ( 17 ; C 20 H 16 O 12 ): pale yellow powder; ESI/MS m / z 447 [M − H] − ; 1 H NMR (400 MHz, CD 3 OD): δ 7.84 (H‐5; s); 7.49 (H‐5′; s); 5.52 (H‐1″; d; J 1.6 Hz); 4.20 (H‐2″; dd; J 1.6 and 3.4 Hz); 4.02 (H‐3″; dd; J 9.5 and 3.4 Hz); 3.48 (H‐4″; t; J 9.5 Hz); 3.77 (H‐5″; dd; J 9.5 and 6.2 Hz); 1.27 (H‐6″; d; J 6.2 Hz); IR, UV and 13 C NMR data were similar to those reported in the literature 28. Ellagic acid ( 18 ; C 14 H 6 O 8 ): amorphous pale yellow solid; ESI/MS m / z 301 [M − H] − ; 1 H NMR (200 MHz, CD 3 OD): δ 7.47 (H‐5 and 5′; s); 13 C NMR and IR data were similar to those reported in the literature 28.…”

Lipoxygenase inhibitory activity of crude bark extracts and isolated compounds from Commiphora berryi

“…The structures of compounds (1-8) were determined using 1 H, 13 C NMR, and MS spectral data which were in complete agreement with reported ones [3␤-hydroxyglutin-5-ene (1) (Lee et al, 2005), friedelin (2) (Manoharan et al, 2005), cycloeucaneol (3) (Khuong et al, 1975), nimbiol (4) (Aladesanmi and Odediran, 2000), sugiol (5) (Chao et al, 2008), surianol (6) (Suhag et al, 2000;), daucosterol (7) (Gallo et al, 2006) and ursolic acid (8) (Seebacher et al, 2003)] (Supplemental Fig. 3).…”

Chemical and Antidiarrheal Studies ofPlinia cauliflora

“…Figure 1A shows the chromatographic profile of leaf extract, exhibiting peaks belonging to three main groups of phenolic compounds. The peaks eluted at retention times (R t ) in the range 10.2-25.2 minutes have the UV maximum around 275 and 285 nm, typical of hydrolyzable tannins, 27 while in the region of R t 25.2-34.2 minutes, there were intense UV bands at 252 and 363 nm, indicative of ellagic acid derivatives, 28 and for the last group, in the region of R t 34.2-40.5 minutes, the UV spectrum displays maximum absorption at 259 and 348 nm, typical for flavonoids. 29 Figure 1B exhibits the chromatographic profile of fruit extract, which exhibited the same peaks corresponding to hydrolyzable tannins and ellagic acid derivatives as those found in leaf extract, whereas flavonoids were not detected.…”