ABSTRACT
The genus Poiretia belongs to the Fabaceae (Leguminosae) family and it encompasses twelve species of flowering plants. The chemistry of this genus is scarcely investigated, although some studies have demonstrated the potential of Poiretia species to produce important bioactive compounds. Herein, we describe the phytochemical investigation of P. bahiana C. Mueller leaves. A new isoflavone glucoside named as 2',4',5'-trimethoxyisoflavone-7-O-ß-D-glucopyranoside (1), along with six known isoflavones (2-7), two rotenones (8-9), cyclitol 3-O-methyl-chiro-inositol (10), the amino acid proline (11), a mixture of sitosterol (12) and stigmasterol (13), and a mixture of the triterpenes lupeol (14) and ß-amirine (15) were obtained from P. bahiana leaves. The structures were established by extensive analysis of their spectroscopic data, which included 1H NMR, 13C NMR, DEPT, and 2D-NMR (13C1H HETCOR and 13C1H COLOC). Two isoflavones (3 and 5) and two rotenones (8-9) exhibited antifungal activity against the plant pathogenic fungus Cladosporium sphaerospermum. Furthermore, the biogenetic implications of the oxygenation pattern of the B-ring of the isoflavones, and the chemophenetics and fragmentation pattern of the isoflavones and rotenones are discussed.
Subject(s)
Fabaceae/chemistry , Fungicides, Industrial/pharmacology , Glucosides/pharmacology , Isoflavones/pharmacology , Brazil , Cladosporium/drug effects , Fungicides, Industrial/isolation & purification , Glucosides/isolation & purification , Isoflavones/isolation & purification , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Leaves/chemistryABSTRACT
Three new polyprenylated benzophenone derivatives (1-3) were identified in the hexane extract of Clusia burle-marxii trunks, through the isolation and structural elucidation of their methyl derivatives, along with two known polyprenylated benzophenone derivatives sampsonine N (4) and obdeltifolione C (5). Burlemarxiones A (1) and B (2) show an unprecedent tetracyclo[8.3.1.03,11.05,10]tetradecane core skeleton. These compounds are a pair of ß-diketones in tautomeric equilibrium, whereas isonemorosonol (3) is the respective ß-diketone pair in tautomeric equilibrium with nemorosonol. Burlemarxione A methyl derivative (1a) and sampsonine N exhibited strong in vitro cytotoxic activity against GL-15 glioblastoma-derived human cell line.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Benzophenones/pharmacology , Clusia/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Benzophenones/isolation & purification , Brazil , Cell Line, Tumor , Glioblastoma/drug therapy , Humans , Phytochemicals/isolation & purification , Phytochemicals/pharmacologyABSTRACT
One new chromone 3,3-dimethylallylspatheliachromene methyl ether (1), as well as five known chromones, 6-(3-methylbut-2-enyl) allopteroxylin methyl ether (2), 6-(3-methylbut-2-enyl) allopteroxylin (3), 3,3-dimethylallylspatheliachromene (4), 5-O-methylcneorumchromone K (5) and spatheliabischromene (6), two alkaloids, 8-methoxy-N-methylflindersine (7) and 8-methoxyflindersine (8), and two limonoids, limonin diosphenol (9) and rutaevin (10), were isolated from Dictyoloma vandellianum A. Juss (Rutaceae). Cytotoxic activities towards tumor cell lines B16-F10, HepG2, K562 and HL60 and non-tumor cells PBMC were evaluated for compounds 1 - 6. Compound 1 was the most active showing IC50 values ranging from 6.26 to 14.82 µg/ml in B16-F10 and K562 cell lines, respectively, and presented IC50 value of 11.65 µg/ml in PBMC cell line.
Subject(s)
Chromones/chemistry , Rutaceae/chemistry , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/toxicity , Animals , Cell Line, Tumor , Cell Survival/drug effects , Chromones/isolation & purification , Chromones/toxicity , HL-60 Cells , Hep G2 Cells , Humans , K562 Cells , Leukocytes, Mononuclear/cytology , Leukocytes, Mononuclear/drug effects , Leukocytes, Mononuclear/metabolism , Limonins/chemistry , Limonins/isolation & purification , Limonins/toxicity , Magnetic Resonance Spectroscopy , Mice , Plant Leaves/chemistry , Plant Leaves/metabolism , Rutaceae/metabolismABSTRACT
Phytochemical investigation of the aerial parts of Eriope blanchetii and E. latifolia (Lamiaceae) yielded podophyllotoxin, as well as the aryltetralin lignans α- and ß-peltatin and yatein. Oleanolic, ursolic and epikatonic acids were also isolated. This is the first occurrence of podophyllotoxin in the family.
Subject(s)
Lamiaceae/chemistry , Lignans/isolation & purification , Podophyllotoxin/pharmacology , Tetrahydronaphthalenes/isolation & purification , Chromatography, Thin Layer , Magnetic Resonance Spectroscopy , Spectrometry, Mass, Electrospray IonizationABSTRACT
Himatanthus lancifolius (Müll. Arg.) Woodson é um arbusto nativo do Brasil, latescente, popularmente conhecido como agoniada e utilizado principalmente para distúrbios menstruais. O presente trabalho teve como objetivo caracterizar morfoanatomicamente a folha, o caule e a casca caulinar dessa planta medicinal, a fim de contribuir para o controle de qualidade e a autenticidade dessa espécie. O material vegetal foi fixado e submetido às microtécnicas usuais. A folha é simples, glabra e obovado-lanceolada. A epiderme é uniestratificada, revestida por cutícula estriada e possui estômatos anisocíticos na face abaxial. O mesofilo é dorsiventral. A nervura central é biconvexa e o pecíolo é circular, ambos apresentando feixes vasculares bicolaterais. Laticíferos, amiloplastos e idioblastos fenólicos estão presentes no parênquima fundamental da nervura central e do pecíolo. O sistema vascular do caule é tipicamente bicolateral. Laticíferos e idioblastos fenólicos ocorrem no córtex, no floema e na medula. Esses caracteres morfoanatômicos, em conjunto, podem ser utilizados como parâmetros para o controle de qualidade dessa espécie.
Himatanthus lancifolius (Müll. Arg.) Woodson is a Brazilian native shrub, laticiferous, popularly known as "agoniada" and it is mainly used for uterine disorders. The present work aimed to study the leaf, stem and stem bark morpho-anatomy of this medicinal plant, in order to contribute to its quality control and identification. The plant material was fixed and submitted to standard microtechniques. The leaf is simple, glabrous and obovate-lanceolate. The epidermis is uniseriate, coated with striated cuticle and it has anysocitic stomata on the abaxial surface. The mesophyll is dorsiventral. The midrib is biconvex and the petiole is circular, both presenting bicollateral vascular bundles. Laticiferous ducts, amyloplasts and phenolic idioblasts are found in ground parenchyma of the midrib and petiole. The vascular system of the stem is tipically bicollateral. Laticiferous ducts and phenolic idioblasts are present in the cortex, phloem and pith. These morpho-anatomical characters, all together, can be used as quality control parameters of this species.
