New diterpenoids from leaves of Guarea macrophylla (Meliaceae) (original) (raw)

Terpenoid constituents from leaves of Guarea kunthiana

Journal of the Brazilian Chemical Society, 2004

Das folhas de Guarea kunthiana foram obtidos um novo diterpeno com esqueleto do tipo caurano (ent-caur-16-eno-2-ona), além de oito diterpenos (ent-caur-16-eno, ent-3α-e 3β-hidroxicaur-16-eno, kolavelool, kolavenol, kolavenal, ent-13-epi-óxido de manoíla e (-)-neftenol), quatro sesquiterpenos (alismol, alismóxido, espatulenol e 4β,10α-aromadendranodiol), poliprenol-12 e αe δ-tocoferóis. Kolavenal está sendo relatado pela primeira vez como produto natural, assim como a ocorrência de diterpenos do tipo cembrano e ent-caurano na família Meliaceae. From leaves of Guarea kunthiana one new kaurene diterpene (ent-kaur-16-en-2-one) was isolated along with eight known diterpenes (ent-kaur-16-ene, ent-3α-and 3β-hydroxykaur-16-ene, kolavelool, kolavenol, kolavenal, ent-13-epi-manoyloxide and (-)-nephthenol), four sesquiterpenes (alismol, alismoxide, spathulenol and 4β,10α-aromadendranediol), polyprenol-12 and αand δtocopherols. Kolavenal is reported for the first time as a natural product, as well as the occurrence of cembrane-and ent-kaurane-type diterpenes in the Meliaceae.

Phytochemistry and Biological Activities of Guarea Genus (Meliaceae)

Molecules

Guarea is one of the largest genera of the American Meliaceae family, consisting of over 69 species which are widely distributed in Mexico, Argentina, and Africa and are used in traditional medicine for several diseases. Previous studies reported that the Guarea species produce secondary metabolites such as sesquiterpenoid, diterpenoid, triterpenoid, limonoid, steroid, and aromatic compounds. The preliminary chemical investigation commenced by isolating the limonoid compound, dihydrogedunin, in 1962; then, 240 compounds were obtained from the isolation and hydrodistillation process. Meanwhile, sesquiterpenoid is a significant compound with 52% of Guarea species. The extract and compounds were evaluated for their anti-inflammation, antimalarial, antiparasitic, antiprotozoal, antiviral, antimicrobial, insecticidal, antioxidant, phosphorylation inhibitor, and cytotoxic biological activities. The Guarea genus has also been reported as one of the sources of active compounds for medicinal...

Dammarane-Type Triterpenoids from The Stembark of Aglaia argentea (Meliaceae)

Jurnal Kimia VALENSI, 2018

Two dammarane-type triterpenoids, 20S,24S-epoxy-3α,25-dihydroxydammarane (1) and 3α-acetyl-20S,24S-epoxy-3α,25-dihydroxydammarane (2), have been isolated from the stembark of Aglaia argentea. The chemical structure of compounds (1 and 2) were identified by spectroscopic evidences including UV, IR, 1D-NMR, 2D-NMR and MS as well as by comparing with previously reported spectral data. Those compounds were isolated from this plant for first time. Compounds (1 and 2) showed cytotoxic activity against P-388 murine leukemia cells with IC50 values of 23.96 and 8.14 mM, respectively.DOI:http://dx.doi.org/10.15408/jkv.v4i1.7065

Tetranortriterpenoids and related compounds. Part 25. Two 3,4-secotirucallane derivatives and 2′-hydroxyrohitukin from the bark of Guarea cedrata (Meliaceae)

Canadian Journal of Chemistry, 1980

Three new compounds, 3,4-secotirucalla-4(28),7,24-trien-3,21-dioic acid 1, the corresponding 3-monomethyl ester 12, and 2′-hydroxyrohitukin 13, have been isolated from the bark of Guareacedrata (Meliaceae). The structures of 1 and 12 were confirmed by correlation with methyl 3-oxotirucalla-8,24-dien-21-oate (methyl isoelemonate) 6. The 1H and 13C nmr data are reported.

Abietane diterpenes from Sagittaria montevidensis ssp montevidensis Charm. & Schltdl

Journal of the Brazilian Chemical Society, 2007

Dois novos diterpenos do tipo abietano 3β-hidroxi-9α, 13α-epidioxiabiet-8(14)-eno (1) e 3-oxo-9α,13α-epidioxiabiet-8(14)-eno (2) foram isolados do extrato bruto metanólico dos pecíolos de Sagittaria montevidensis ssp montevidensis (Alismataceae). As estruturas de 1 e 2 foram determinadas com base em análises espectrométricas do tipo EM-AR, IV, bem como, RMN de 1 H e 13 C uni e bi dimensionais. Two new abietane-type diterpenes, 3β-hydroxy-9α, 13α-epidioxyabiet-8(14)-ene (1) and 3-oxo-9α,13α-epidioxyabiet-8(14)-ene (2), were isolated from the methanolic crude extract of the petioles of Sagittaria montevidensis ssp montevidensis (Alismataceae). The structures of 1 and 2 were determined on the basis of spectrometric analyses including HREIMS, IR as well as 1 H and 13 C 1 and 2D NMR.

Bioactive polar triterpenoids from Melilotus messanensis

Phytochemistry, 1998

In addition to the known 3-oxoplatanic acid, melilotigenin and soyasapogenol E, two new lupane (messagenic acids F, G), two nor-lupane triterpenic acids (messagenic acids H, I), and three new oleanane triterpenes (melilotigenins B-D) were isolated and characterized from the polar bioactive fractions of Melilotus messanensis. The synthesis of messagenic acids D, F, G, betulonic acid and 3,29-dioxolup-20(30)-en-28-oic acid has been carried out from betulinic acid. These compounds exhibited clear selectivity (parameters and species) over germination and growth of monocotyledon species with average of inhibition of -50% on the germination of Hordeum vulgare, and average of stimulation of 30% on the germination of Allium cepa.

ent-Isopimarane-type diterpenoids from the New Zealand liverwort Trichocolea mollissima

Phytochemistry, 2003

Two ent-isopimarane-type diterpenoids were isolated from the New Zealand liverwort Trichocolea mollissima (Hook. f. and Tayl.) Gott., together with a known 1alpha-hydroxy-ent-sandaracopimara-8(14),15-diene. Their absolute structures have been established by modified Mosher's method, X-ray crystallography and by analyses of their CD spectra.