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The dewaxed dichloromethane extract of Urolepis hecatantha and the compounds isolated from it were tested for their in vitro activity on Trypanosoma cruzi epimastigotes and Leishmania infantum promastigotes. The extract of U. hecatantha showed activity against both parasites with IC50 values of 7 µg/mL and 31 µg/mL, respectively. Fractionation of the dichloromethane extract led to the isolation of euparin, jaceidin, santhemoidin C, and eucannabinolide. The sesquiterpene lactones eucannabinolide and santhemoidin C were active on T. cruzi with IC50 values of 10 ± 2 µM (4.2 µg/mL) and 18 ± 3 µM (7.6 µg/mL), respectively. Euparin and santhemoidin C were the most active on L. infantum with IC50 values of 18 ± 4 µM (3.9 µg/mL) and 19 ± 4 µM (8.0 µg/mL), respectively. Eucannabinolide has also shown drug-like pharmacokinetic and toxicity properties. Fil: Elso, Orlando G. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Cátedra de Farmacognosia; Argentina. CONICET–Universidad de Buenos Aires. Instituto de Química y Metabolismo del Fármaco (IQUIMEFA); Argentina Fil: Clavin, Maria. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Cátedra de Farmacognosia; Argentina. CONICET–Universidad de Buenos Aires. Instituto de Química y Metabolismo del Fármaco (IQUIMEFA); Argentina Fil: Hernández, Natalia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Cátedra de Farmacognosia; Argentina. Fil: Sgarlata, Tomas. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Cátedra de Farmacognosia; Argentina. Fil: Bach, Hernán Gerónimo. Instituto Nacional de Tecnología Agropecuaria (INTA). Instituto de Recursos Biológicos; Argentina Fil: Catalán, César A. N. Universidad Nacional de Tucumán. Facultad de Bioquímica Química y Farmacia. Instituto de Química Orgánica; Argentina Fil: Aguilera, Elena. Universidad de la República. Facultad de Ciencias. Grupo de Química Medicinal. Laboratorio de Química Orgánica; Uruguay Fil: Álvarez, Guzmán. Universidad de la República. CENUR Litoral Norte. Laboratorio de Moléculas Bioactivas; Uruguay Fil: Sulsen, Valeria P. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Cátedra de Farmacognosia; Argentina. CONICET–Universidad de Buenos Aires. Instituto de Química y Metabolismo del Fármaco (IQUIMEFA); Argentina

The phytochemical investigation on Tanacetum sinaicum (Fresen.) Delile ex Bremer & Humphries led to the isolation of eight flavonoid aglycones (apigenin 1 , acacetin 2 , luteolin 3 , chrysoeriol 4 , cirsilineol 5 , jaceidin 6 , chrysosplenetin 7 and vitexicarpin; casticin 8 ), four flavonoid glycosides (apigenin 7- O -β-glucopyranoside 9 , apigenin 7- O -β-glucuronide 10 , luteolin 7- O -β-glucopyranoside 11 and luteolin 7- O -β-glucuronide 12 ) and three phenolics (4-hydroxy-3-methoxy benzoic acid 13 , 3,4-dimethoxy benzoic acid 14 and 4-hydroxy acetophenone 15 ). Their structures were determined by chemical and spectroscopic analysis. Among them, compounds 1–3, 9, 11, 13 and 14 were reported for the first time from T. sinaicum . The chemotaxonomic significance of the isolated flavonoids was also summarized.

Stemodinol, a new natural compound, together with known compounds including jaceidin, stemodin, stemodinoside B, isocrenatoside, verbascoside, crenatoside, and isoverbascoside, were isolated from Stemodia maritima Linn. The antioxidant (DPPH method) and antimicrobial activities of stemodin, stemodinoside B, and crenatoside were investigated. Among the components tested, only crenatoside isolated from the roots showed a high antioxidant power. Stemodin and stemodinoside B exhibited antibacterial activities.

One new tetracyclic triterpene ester (1) has been isolated from the chloroform-soluble portion of the whole plant of Nepeta suavis along with two known compounds, namely artemetin (2) and jaceidin (3). The structures of the isolated compounds were assigned on the basis of their (1)H and (13)C NMR spectra including two-dimensional NMR techniques such as COSY, HMQC, and HMBC experiments and comparison with the literature data.

A new acylated flavonoid glucoside named algerianin 1 and a new as natural product, 4′-methyl gossypetin 2, together with 10 known compounds, isovanillic acid ethyl ester, β-sitosterol, β-sitosterol 3-O-glucoside, a mixture of α and β-amyrin, 3′-hydroxyflindulatin, chrysoeriol, jaceidin, corniculatusin and centaurein were isolated from the ethanolic extract of the flowering and aerial parts of Centaurea africana Lamk var. africana (Bonnet) M., an endemic species to Algeria and Tunisia collected from El-Kala in the eastern Algeria. The structures were established by chemical and spectral analysis, mainly HREIMS, ESIMS, UV and NMR experiments (GOESY, COSY, ROESY, HSQC and HMBC). Algerianin showed cytotoxicity against the human myeloid leukaemia cell line HL-60.

New infraspecific chemotypes based on methoxylated flavonoids were determined in Chamomilla recutita (L.) Rauschert (Compositae), the jaceidin (quercetagetin-3,6,3′-trimethyl ether) chemotype and the chrysosplenetin (quercetagetin-3,6,7,3′-tetramethyl ether) chemotype. These substances are distributed on the surface of tubular florets of anthodia but were not detected on ligulate florets and involucral bracts. The chemotypes were identified in both, diploid and tetraploid cultivars. The amount of flavonoids accumulated in tetraploid plants was approximately twice as high as in diploids. The chrysosplenetin chemotype plants in populations of both, diploid and tetraploid cultivars predominate, while the amount of the jaceidin type plants in populations is approximately 20%. The variation of the flavonoid content during the anthodium ontogeny is also discussed.

From spinach leaves (cv Viroflay), five new naturally occurring flavonoids have been isolated and identified by 13 C NMR, 1 H NMR, FAB-MS, UV and hydrolytic and enzymatic procedures. The new compounds were identified as spinacetin 3- O -β- d -glucopyranosyl(1 → 6)-[β- d -apiofuranosyl(1 → 2)]-β- d -glucopyranoside, patuletin 3- O -β- d -(2″feruloylglucopyranosyl)(1 → 6)-[β- d -apiofuranosyl(1 → 2)]-β- d -glucopyranoside, spinacetin 3- O -β- d -(2″- p -coumaroylglucopyranosyl)(1 → 6)-[β- d -apiofuranosyl(1 → 2)]-β- d -glucopyranoside, spinacetin 3- O -β- d -(2″feruloylglucopyranosyl)(1 → 6)-[β- d -apiofuranosyl(1 → 2)]-β- d -glucopyranoside and spinacetin 3- O -β- d -(2″feruloylglucopyranosyl)(1 → 6)-β- d -glucopyranoside. The known compounds jaceidin 4′-glucuronide, 5,3′,4′-trihydroxy-3-methoxy-6:7-methylenedioxyflavone 4′-glucuronide, 5,4′-dihydroxy-3,3′-dimethoxy-6:7-methylenedioxyflavone 4′-glucuronide, patuletin 3-glucosyl(1 → 6)-[apiosyl(1 → 2)] glucoside and patuletin and spinacetin 3-gentiobiosides, were also detected. © 1997 Elsevier Science Ltd. All rights reserved

Aqueous and alcoholic extracts, volatile oil and four flavonoids, xanthomicrol ( 1 ), kumatokenin ( 2 ), jaceidin ( 3 ) and 3, 3′-di- O -methylquercetin ( 4 ), isolated from Varthemia iphionoides were investigated for their in vitro anti-platelet activity. Aqueous extract and compounds ( 1 ), ( 2 ) and ( 4 ) showed anti-platelet activity. Volatile oil and the alcoholic extract did not exhibit any anti-platelet activity. Structures of the isolated compounds ( 1 )–( 4 ) were determined by spectroscopic methods (UV, IR, MS, 1 H-NMR).

Bio-guided fractionation of an extract from Tanacetum parthenium showing activity as mitotic blocker allowed the isolation and identification of santin 3, jaceidin 2 and centaureidin 1. The latter two closely related flavonols, which, to the best of our knowledge, are isolated here together for the first time, form a mixture difficult to resolve and which is probably the reason for the confusion in the literature regarding their occurrence. Centaureidin 1 had an IC50 of 1 microM while jaceidin 2 and santin 3 were 200 times less active.

The rare dihydroquercetin 3-O-β- d -xyloside, caryatin 7-O-β- d -glucoside and the previously unknown 6-methoxylated flavonoid glycoside jaceidin 5-O-β- d -glucoside were isolated from twigs of Eucryphia glutinosa where they co-occur with the widespread reynoutrin.

Roots, green parts and flower heads of Centaurea nervosa and C. phrygia were examined separately. Eight flavones, nine polyacetylenes and four tetraenic aldehydes of known structures, together with aplotaxene and the lignan (−)-aretigenin were isolated and characterized. The flavones apigenin, kaempferol 3-methyl ether, kaempferol 3,6-dimethyl ether, centaureidin, jaceidin and hispidulin were found in appreciable amounts in both plants.

The isolation of three highly oxygenated guaianolides, desacetyl-1α-4α- dihydroxybishopsolicepolide [1], its 4β-hydroxy epimer 2 (a new compound), and 1β,2β:3β,4β-diepoxy-8α,10α-dihydroxyguai-12(13)-en-12,6α-olide [3], from the aerial parts of Achillea crithmifolia is reported. Because lactone 3 was shown to be identical with rupin A, the initially proposed 1α,2α:3α,4α-diepoxy stereochemistry of rupin A should be revised.

Droplet counter-current chromatographic separation and subsequent TLC demonstrated the existence of at least 14 phenolics in the leaves of Spinacia oleracea . Three have now been isolated and identified, respectively, as the 4′-glucuronides of 5,7,4'-trihydroxy-3,6,3′-trimethoxyflavone (jaceidin), 5,3′,4′-trihydroxy-3-methoxy-6:7-methylene-dioxyflavone and 5,4′-dihydroxy-3,3′-dimethoxy-6:7-methylenedioxyflavone.

The Hoesch reaction of iretol with methoxyacetonitrile yielded 2,4,6-trihydroxy-3,ω-dimethoxyacetophenone. According to the Allan-Robinson flavone synthesis with O-benzylvanillic anhydride, the acetophenone afforded 4′-benzyloxy-5,7-dihydroxy-3,3′,6-trimethoxyflavone. The catalytic debenzylation of the flavone gave jaceidin, 4′,5,7-trihydroxy-3,3′,6-trimethoxyflavone, which had previously been isolated from Centaurea species. Its triethyl ether was prepared from 3,5-diethoxy-4-methoxyphenol via the corresponding acetophenone, followed by the abovementioned flavone synthesis with O-ethylvanillic anhydride. The ultraviolet spectra of these flavones will also be reported.

The isolation of eucannabinolide, jaceidin and the new glycoside absinthifolide from Bahia absinthifolia var. absinthifolia is reported. The structure and stereochemistry of the new compound was established by chemical and spectroscopic means.

Durch Kondensation nachAllan-Robinson wurde aus 2,4,6-Trihydroxy-3, ω-dimethoxy-acetophenon das 4′-Benzyloxy-5,7-dihydroxy-3,6,3′-trimethoxyflavon dargestellt. Entbenzylierung in C-4′-Stellung fuhrte zum 5,7,4′-Trihydroxy-3,6,3′-trimethoxyflavon. Die Eigenschaften dieser Verbindung und ihre Derivate sind identisch mit dem ausCentaurea jacea L. isolierten Jaceidin bzw. seinen Derivaten.

The three species comprising Balsamorhiza section Artorhiza were examined for their external leaf flavonoids. Eight methylated flavonoids were isolated: patuletin, jaceidin, betuletol, axillarin, spinacetin, 6-methoxykaempferol, hispidulin and santin. The chemotaxonomy of the group and morphological correlations are discussed.