New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance
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. Fi...
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2006-01-01
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| Series: | Journal of the Brazilian Chemical Society |
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| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000200010 |
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| author | Gallo Margareth B. C. Silva Fernando C. da Vieira Paulo C. Fernandes João B. Silva Maria Fátima das G. F. da |
| author_facet | Gallo Margareth B. C. Silva Fernando C. da Vieira Paulo C. Fernandes João B. Silva Maria Fátima das G. F. da |
| author_sort | Gallo Margareth B. C. |
| collection | DOAJ |
| description | 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-alpha-L-2"-O- and its isomer 4-O-alpha-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-beta-D-6"-O- and 4-O-beta-D-3",6"-diacetylglucopyranoside, accompanied by ellagic acid 4-O-alpha-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, alpha- and beta-amyrin, a new pentacyclic triterpene was isolated and named as beta-D-glucopyranosyl-2alpha,3beta,6beta-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. |
| first_indexed | 2024-12-23T11:29:01Z |
| format | Article |
| id | doaj.art-c89e89719ed04179a7ad1c7f2447115d |
| institution | Directory Open Access Journal |
| issn | 0103-5053 1678-4790 |
| language | English |
| last_indexed | 2024-12-23T11:29:01Z |
| publishDate | 2006-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Journal of the Brazilian Chemical Society |
| spelling | doaj.art-c89e89719ed04179a7ad1c7f2447115d2022-12-21T17:48:52ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50531678-47902006-01-01172279288New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significanceGallo Margareth B. C.Silva Fernando C. daVieira Paulo C.Fernandes João B.Silva Maria Fátima das G. F. daSiphoneugena 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-alpha-L-2"-O- and its isomer 4-O-alpha-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-beta-D-6"-O- and 4-O-beta-D-3",6"-diacetylglucopyranoside, accompanied by ellagic acid 4-O-alpha-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, alpha- and beta-amyrin, a new pentacyclic triterpene was isolated and named as beta-D-glucopyranosyl-2alpha,3beta,6beta-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.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000200010Siphoneugena densifloraMyrtaceaechemotaxonomyhydrolysable tanninpentacyclic triterpene |
| spellingShingle | Gallo Margareth B. C. Silva Fernando C. da Vieira Paulo C. Fernandes João B. Silva Maria Fátima das G. F. da New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance Journal of the Brazilian Chemical Society Siphoneugena densiflora Myrtaceae chemotaxonomy hydrolysable tannin pentacyclic triterpene |
| title | New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance |
| title_full | New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance |
| title_fullStr | New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance |
| title_full_unstemmed | New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance |
| title_short | New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance |
| title_sort | new natural products from siphoneugena densiflora berg myrtaceae and their chemotaxonomic significance |
| topic | Siphoneugena densiflora Myrtaceae chemotaxonomy hydrolysable tannin pentacyclic triterpene |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000200010 |
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