Phytochemistry of Trattinnickia burserifolia, T. rhoifolia, and Dacryodes hopkinsii: chemosystematic implications

Abstract

dammarenediol-II e 3α,20(S)-diidroxidamar-24-eno. Além desses foram ainda isolados o monoterpeno novo 2(S*)-fenilacetoxi-4(R*)-p-menta-1(7),5-dieno, e os triterpenos novos 3βfenilacetoxiurs-12-eno, 3β-fenilacetoxiolean-12-eno e 3β,16β,11α-triidroxiurs-12-eno. Os triterpenos de T. burserifolia, T. rhoifolia e Dacryodes foram analisados em mistura. Os espectros de RMN 13 C mostraram que os principais triterpenos eram α-amirina e estigmasterol em D. hopkinsii. A quimiossistemática da tribo Protieae é discutida.Trattinnickia burserifolia has yielded the known ursanes, α-amyrenone, α-amyrin, 3-epi-αamyrin, 3α,16β-dihydroxyurs-12-ene, the oleananes β-amyrenone, β-amyrin, 3-epi-β-amyrin, 3α,16β-dihydroxyolean-12-ene, the tirucallane acids 3α-hydroxytirucall-8,24-dien-21-oic, 3αhydroxytirucall-7,24-dien-21-oic and 3-oxotirucall-8,24-dien-21-oic, the dammaranes dammarenediol-II and 3α,20(S)-dihydroxydammar-24-ene. Besides it was isolated the new monoterpene 2(S*)-phenylacetoxy-4(R*)-p-mentha-1(7),5-diene and, the new triterpenes 3βphenylacetoxyurs-12-ene, 3β-phenylacetoxyolean-12-ene and 3β,16β,11α-trihydroxyurs-12-ene. The triterpenes from T. burserifolia, T. rhoifolia and Dacryodes were analyzed in mixture. Their 13 C NMR spectra showed that the major triterpenes were in T. burserifolia α-amyrin and β-amyrin; in T. rhoifolia α-amyrin, β-amyrin, 3-epi-α-amyrin, 3-epi-β-amyrin, and lupenone; in T. rhoifolia αamyrin, β-amyrin, 3-epi-α-amyrin, 3-epi-β-amyrin, 3α-hydroxytirucall-8,24-dien-21-oic acid and 3α-hydroxytirucall-7,24-dien-21-oic acid; in D. hopkinsii α-amyrin, β-amyrin, lupeol, tirucallol, sitosterol and stigmasterol. Aspects of chemosystematic of the tribe Protieae are discussed.

Tirucallane triterpenes from the roots of Ozoroa insignis

“…The structure of 1 was confirmed as a tirucallane triterpenoid, from the comparison of its optical rotation with that reported for related 3a-OH tirucallanes, euphanes, and lanostanes, which is positive in euphane and lanostane series, and negative in tirucallanes (Keller et al, 1996;Lin et al, 1997;Rö secke and König, 1999;Mishra et al, 2000). Compound 1 showed a ½a 25 D À 10:7 , identical to the one reported for the synthetic methyl ester derivative of a-elemolic acid (3a-hydroxy-tirucalla-8,24-dien-21-oic acid), previously isolated from several Burseraceae (Cotterrell et al, 1970;Billet et al, 1971;Pardhy and Bhattacharya, 1978;Tessier et al, 1982;Sawadogo et al, 1985;Lima et al, 2004;Usubillaga et al, 2004). Based on this evidence, the structure of 1 was confirmed as methyl 3a-hydroxy-tirucalla-8,24-dien-21-oate, whose spectroscopic data is here reported for the first time.…”

Biological potential of Stillingia oppositifolia

“…The spectral properties, including 1 H NMR and 13 C NMR data, were identical to those previously reported in the literature (Martin et al, 1984;Mahato & Kundu, 1994;De-Eknamkul & Potduang, 2003;Lima et al, 2004). Compounds 1 and 2 are oleanane triterpenes and compound 3 is friedooleanane triterpene.…”

Chemical Composition of South American Burseraceae Non‐volatile Oleoresins and Preliminary Solubility Assessment of their Commercial Blend

“…Lupeol isomers and lupenone have been reported as components of frankincense and other Asiatic and zAfrican oleoreins (Khalid, ; Rüdiger et al , 2007; Mathe et al , ). Their minor presence in Protium and Trattinickia species is usually characterised by NMR (Lima et al , ). They are not evident from the GC analyses, given that lupane‐derivatives and ursane homologues frequently co‐elute through non‐polar chromatographic columns (Guimarães, 1996; Stacey et al , ).…”