Non-volatile constituents from Monimiaceae, Siparunaceae and Atherospermataceae plant species and their bioactivities: An up-date covering 2000-2021.

The Monimiaceae, Siparunaceae, and Atherospermataceae, formerly included in the broad ''old'' Monimiaceae family, have long been known for their uses in traditional medicine and have proven to be rich sources of chemically diverse specialized metabolites with numerous potent biological and therapeutical properties. The progress made recently has expanded their phytochemistry and pharmacology albeit to different extents. This review focuses on the non-volatile constituents isolated from the three plant families during the last two decades and their emerging therapeutic potential. Based on the data collected from multiple databases without statistical analysis, approximately 93 components, of which 35 undescribed compounds including γ-lactones, alkaloids, terpenoids, flavonoids, and homogentisic acid derivatives, have been reported. Moreover, diverse biological activities of pure isolated compounds such as anticancer, antioxidant, antiparasitic, antiviral, and antibacterial activities have been evidenced. Besides offering new important perspectives for different diseases' management, the chemical and biological diversities among the isolated compounds, open promising avenues of research and contribute to renewed interest in these families needing further studies. This review provides an updated overview of their potential as sources of leads for drug discovery, while also highlighting ongoing challenges and future research opportunities.

Antimicrobial Benzyltetrahydroisoquinoline-Derived Alkaloids from the Leaves of Doryphora aromatica.

Four new alkaloids, (R)-nomimantharine trifluoroacetate (2), 12-demethylphaeantharine trifluoroacetate (3), nominanthranal trifluoroacetate (4), and the enolic form of 1-hydroxy-6,7-dimethoxy-2-methylisoquinoline trifluoroacetate (5), together with the known dimeric alkaloid phaeantharine trifluoroacetate (1), have been isolated from the extract of the leaves of the rainforest tree Doryphora aromatica (Monimiaceae). The structures of these compounds were elucidated by HRMS and 1D and 2D NMR data. (R)-Nomimantharine trifluoroacetate (2) contains an ether linkage connecting a benzylisoquinoline unit with a tetrahydroisoquinoline, a novel class of dimeric alkaloid. The absolute configuration of (R)-nomimantharine trifluoroacetate (2) was established via electronic circular dichroism data. The compounds isolated were subjected to in vitro antimicrobial assays against a panel of pathogenic microorganisms, including Mycobacterium smegmatis, M. tuberculosis, Escherichia coli, Staphylococcus aureus (SA), and five clinical isolates of oxacillin/methicillin-resistant S. aureus (MRSA). Phaeantharine trifluoroacetate (1) and (R)-nomimantharine trifluoroacetate (2) showed moderate inhibitory activities against Mycobacteria and MRSA strains.

Anatomy and Histochemistry of Leaf and Stem of Brazilian Endemic Species Mollinedia clavigera Tul

Abstract This study aimed to investigate the anatomy and histochemistry of Mollinedia clavigera leaves and stems through photonic microscopy and scanning electron microscopy. Noteworthy features of leaves were: presence of paracytic stomata on both surfaces; simple as well as bifurcate non-glandular trichomes; prismatic calcium oxalate crystals; flat-convex midrib with a central and two dorsal bundles; concave-convex petiole with a single vascular bundle in open archh. Stems were cylindrical and showed prismatic and styloid crystals in the pith. Histochemical analysis detected lipophilic and phenolic compounds, starch grains and lignified elements such as brachysclereids and fibers. These features may assist in future identifications and quality control of M. clavigera, avoid misidentification between other genus members, once species and genus studies are scarce.

A protecting group-free synthesis of (-)-hortonones A-C from the Inhoffen-Lythgoe diol.

A synthesis of hortonones A-C has been accomplished from vitamin D2via the Inhoffen-Lythgoe diol without the use of protective groups. Key steps in the syntheses include a TMS-diazomethane mediated regioselective homologation of the cyclohexanone ring to a cycloheptanone moiety and a sodium naphthalenide-mediated allylic alcohol transposition. It has been found that the absolute configuration of the natural hortonones is opposite that of the synthetic material prepared from vitamin D2.

Flavonoid Glycosides from Siparuna gigantotepala Leaves and Their Antioxidant Activity.

Two new flavonol glycosides were isolated from the leaves of Siparuna gigantotepala. Their structures were determined to be kaempferol 3-O-ß-xylopyranosyl-(1→2)-α-arabinofuranoside (1) and kaempferol 3,7-di-O-methyl-4'-O-α-rhamnopyranosyl-(1→2)-ß-glucopyranoside (2). In addition, three known flavonol glycosides, rutin (3), kaempferol 3-O-rutinoside (4), and kaempferol 3,7-di-O-methyl-4'-O-rutinoside (5), and three flavonol aglycones, quercetin (6), kaempferol 3,7-dimethyl ether (7), and kaempferol 3,7,4'-trimethyl ether (8), were also isolated and are reported here for the first time in this species. The structures of compounds 1 and 2 were established on the basis of their LC-MS and one- and two-dimensional (1D)- and (2D)-NMR spectroscopic analyses, combined with acid methanolysis and silylation of sugar moieties for GC-MS. Evaluation of the antioxidant activity, conducted in the 96-well plate format, showed that the flavonoids isolated possess strong 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity and moderate oxygen radical absorption capacity.

Frugivory and potential of birds as dispersers of Siparuna guianensis.

Siparuna guianensis is a neotropical tree species, found both on edge and interior of forest fragments, mainly on understory and regeneration areas. The fruit are zoochorous with a sweet aril. This work aims to determine the bird species that eat the fruits of S. guianensis in a semi deciduous forest fragment in Brazilian Cerrado and measure which species have the highest potential as seed dispersers. Seven individuals of S. guianensis were sampled, totaling 69 hours. A hundred and fifty four visits were registered by seven species of birds. Antilophia galeata had the biggest potential as seed dispersal agent. Antilophia galeata, Lanio penicillatus and Dacnis cayana can be important seed dispersers, since they have a high consumption and visitation rate. The consumption of S. guianensis by species of different feeding guilds can be an important strategy for dispersal of plant species in regeneration habitats, raising the chances of an effective dispersal.

Frugivory and potential of birds as dispersers of Siparuna guianensis / Frugivoria e potencial de aves como dispersores de Siparuna guianensis

Siparuna guianensis is a neotropical tree species, found both on edge and interior of forest fragments, mainly on understory and regeneration areas. The fruit are zoochorous with a sweet aril. This work aims to determine the bird species that eat the fruits of S. guianensis in a semi deciduous forest fragment in Brazilian Cerrado and measure which species have the highest potential as seed dispersers. Seven individuals of S. guianensis were sampled, totaling 69 hours. A hundred and fifty four visits were registered by seven species of birds. Antilophia galeata had the biggest potential as seed dispersal agent. Antilophia galeata, Lanio penicillatus and Dacnis cayana can be important seed dispersers, since they have a high consumption and visitation rate. The consumption of S. guianensis by species of different feeding guilds can be an important strategy for dispersal of plant species in regeneration habitats, raising the chances of an effective dispersal.

Siparuna guianensis é uma espécie arbórea neotropical do Cerrado, encontrada tanto na borda quanto no interior de fragmentos florestais, principalmente no sub-bosque de matas em regeneração. Os frutos são zoocóricos com arilos adocicados. Os objetivos desse estudo foram: determinar quais espécies de aves consomem os frutos de S. guianensis em um fragmento de floresta semidecídua do Cerrado brasileiro, e inferir quais espécies apresentaram maior potencial de dispersão. Sete indivíduos de S. guianensis foram amostrados, totalizando 69 horas-planta. Foram registradas 153 visitas, realizadas por sete espécies de aves. Antilophia galeata apresentou o maior potencial de dispersão. Entre as espécies exclusivamente florestais, A. galeata, Dacnis cayana e Lanio penicillatus podem ser importantes dispersores, devido à taxa de consumo elevada, maior número de visitação e maior potencial para dispersar as sementes em sítios viáveis de germinação. O consumo dos frutos de S. guianensis por espécies de diferentes guildas alimentares pode ser uma importante estratégia para esta espécie em ambientes em regeneração, por maximizar a possibilidade de dispersão.

A new monoterpene glycoside from Siparuna thecaphora.

Phytochemical investigation of the extracts of the leaves of Siparuna thecaphora (Poepp. et Endl.) A. DC. (Siparunaceae) allowed the isolation of one monoterpene glycoside, named trans-thujane-1α,7-diol 1-O-ß-D-glucopyranoside (1) along with rutin, quercetin 3-O-ß-D-glucopyranoside and 3,4-dihydroxybenzaldehyde. Their structural characterisation was obtained on the basis of extensive spectroscopic analyses, including 1D and 2D NMR experiments and HR-ESI-MS.

Actividad insecticida del polvo de Peumus boldus Molina (Monimiaceae) contra Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae) / Insecticidal activity of Peumus boldus Molina (Monimiaceae) powder against Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae)

The insecticidal properties of foliage´s powder of Peumus boldus Molina against adults and immature S. zeamais were evaluated. The highest toxicity in contact and fumigant activity was reached by concentrations upper to 1.25 percent showing mortality over to 90 percent. The treatments with high mortality showed a lower adult insect emergence (F1) and grain weight loss too. In immature S. zeamais control lower F1 was observed in highest concentrations of powder. The storage of powder under refrigerated conditions not prevents the insecticidal properties lost. All evaluated concentrations exhibited repellent activity against S. zeamais adults. The powder of P. boldus does not affect the grain germination. We concluded that powder of P. boldus has promissory perspectives to stored products pests control.

Se evaluaron las propiedades insecticidas del polvo de follaje de Peumus boldus Molina para el control de adultos y estados inmaduros de S. zeamais. La mayor toxicidad por contacto y fumigación se obtuvo con las concentraciones iguales o mayores a 1,25 por ciento registrando una mortalidad superior a 90 por ciento. Los tratamientos con mayor mortalidad mostraron también una baja emergencia de insectos adultos (F1) y menor pérdida de peso del grano. En el control de estados inmaduros la menor F1 se observó en las concentraciones más altas de polvo. El almacenamiento del polvo en refrigeración no impidió la pérdida en el tiempo de las propiedades insecticidas. Todas las concentraciones evaluadas mostraron efecto repelente contra adultos de S. zeamais. El polvo de P. boldus no afectó significativamente la germinación de los granos. Se concluye que el polvo de P. boldus tiene perspectivas auspiciosas para el control de plagas de los productos almacenados.

Hortonones A to C, hydroazulenones from the genus Hortonia.

The new hexahydroazulenones hortonones A (1) to C (3) were isolated from the leaves of three representative species of the endemic Sri Lankan genus Hortonia that belongs to the family Monimiaceae. Hortonones A (1) and B (2) have the unprecedented rearranged hortonane sesquiterpenoid carbon skeleton, and hortonone C (3) has the unprecedented rearranged and degraded 13-norhortonane skeleton. Hortonone C (3) exhibited in vitro cytotoxicity against human breast cancer MCF-7 cells at 5 µg/mL.

Wood anatomy of Mollinedia glabra (Spreng.) Perkins (Monimiaceae) in two Restinga Vegetation Formations at Rio das Ostras, RJ, Brazil.

This paper aimed to characterize the anatomical structure of the wood of specimens of Mollinedia glabra (Spreng.) Perkins growing in two contiguous formations of restinga vegetation at Praia Virgem, in the municipality of Rio das Ostras, RJ. Both the Open Palmae (OPS) and the Sandy Strip Closed Shrub (SSCS) formations are found in coastal regions that receive between 1,100 and 1,300 mm of rainfall per year. Sapwood samples were collected in both formations. Typical anatomical features for this species include: solitary vessels, radial multiples or clusters elements, that are circular to angular in outline, 5-15 barred scalariform perforation plates, wood parenchyma scanty, septate fiber-tracheids, and wide multiseriate rays with prismatic crystals. Statistical analyses indicated a significant increase in the frequency of vessel elements and an increase in fiber-tracheid diameters in OPS individuals. These characteristics are considered structural adaptations to increased water needs caused by a greater exposure to sunlight. Continuous pruning may be responsible for the tyloses observed in OPS plants. The greater lengths and higher frequencies of the rays in SSCS trees may be due to the greater diameters of their branches. Our results suggest that M. glabra develops structural adaptations to the restinga micro-environmental variations during its development.

Wood anatomy of Mollinedia glabra (Spreng.) Perkins (Monimiaceae) in two Restinga Vegetation Formations at Rio das Ostras, RJ, Brazil

This paper aimed to characterize the anatomical structure of the wood of specimens of Mollinedia glabra (Spreng.) Perkins growing in two contiguous formations of restinga vegetation at Praia Virgem, in the municipality of Rio das Ostras, RJ. Both the Open Palmae (OPS) and the Sandy Strip Closed Shrub (SSCS) formations are found in coastal regions that receive between 1,100 and 1,300 mm of rainfall per year. Sapwood samples were collected in both formations. Typical anatomical features for this species include: solitary vessels, radial multiples or clusters elements, that are circular to angular in outline, 5-15 barred scalarifor perforation plates, ood parenchya scanty, septate fiber-tracheids, and wide multiseriate rays with prismatic crystals. Statistical analyses indicated a significant increase in the frequency of vessel elements and an increase in fiber-tracheid diameters in OPS individuals. These characteristics are considered structural adaptations to increased water needs caused by a greater exposure to sunlight. Continuous pruning may be responsible for the tyloses observed in OPS plants. The greater lengths and higher frequencies of the rays in SSCS trees ay be due to the greater diaeters of their branches. ur results suggest that . glabra develops structural adaptations to the restinga micro-environmental variations during its development.

Este trabalho objetiva caracterizar a estrutura anatômica do lenho de Mollinedia glabra, ocorrente em duas formações vegetais contíguas na restinga da Praia Virgem, município de Rio das Ostras, RJ. Essas formações Arbustiva Aberta de Pal-mae (AAP) e Arbustiva Fechada do Cordão Arenoso (AFCA) estão sobre cordão arenoso e recebem precipitações anuais de 1.100-1.300 mm. Foram obtidas amostras do lenho das duas forações. São características anatôicas gerais da espécie: elementos de vasos solitários, em arranjos radiais ou cachos, de seção de circular a angular; placa de perfuração es-calariforme, com 5-15 barras; parênquima axial escasso; fibro-traqueídes septadas e raios multisseriados largos, com cristais prismáticos. A análise estatística evidenciou aumento significativo na frequência dos elementos de vasos e aumento no diâmetro das fibrotraqueídes nos indivíduos de AAP. Essas características são consideradas adaptações estruturais ao aumento da necessidade de água causada por maior exposição à luz solar. A realização de podas frequentes pode ter relação com a formação de tilos nesses indivíduos. O aumento significativo no comprimento e frequência de raios podem representar uma resposta ao maior diâmetro dos indivíduos em AFCA. Os resultados obtidos sugerem que M. glabra desenvolve adaptações estruturais às variações micro-ambientais da restinga durante seu desenvolvimento.

Bioactivity and chemistry of the genus Hortonia.

The dichloromethane extracts of the leaves, stem bark, bark and the roots of the three species of the primitive endemic genus Hortonia, H. angustifolia, H. floribunda and H. ovalifolia, collected from nine geographical locations ranging from lower elevations (84-420 m) to higher (2000 m) showed comparable HPLC profiles and mosquito larvicidal and antifungal activities; protein analysis of the leaves of the three species of Hortonia showed identical peaks and bands. The two major metabolites (4S)-4-methyl-2-(11-dodecynyl)-2-butenolide (2) and (4S)-4-methyl-2-(11-dodecenyl)-2-butenolide (3), which were previously reported from all three plants, showed potent larvicidal activities. Compound 2 was excessively high in the extracts of the stem bark and the roots of all three species amounting to approximately 38 and 60%, respectively. A minor new butenolide (4), (4S)-4-methyl-2-((2R)-hydroxy-11-dodecenyl)-2-butenolide, with much reduced larvicidal activity and ishwarane (1), which showed antifungal activity, were also isolated from all three plants. Treatment of compound 2 with H(2)/Pd-C afforded the completely reduced compound 5, which showed no larvicidal activity, indicating that unsaturation in both 2 and 3 is necessary for their bioactivity. The foregoing evidence showed that there are major similarities between the three species of Hortonia.

Estudos florísticos no município de Presidente Figueiredo, Amazonas, Brasil - II: famílias Myristicaceae, Siparunaceae e Monimiaceae / Floristic studies in township of Presidente Figueiredo, Amazonas, Brazil - II: families Myristicaceae, Siparunaceae and Monimiaceae / Floristic studies in township of Presidente Figueiredo, Amazonas, Brazil ­ II: families Myristicaceae, Siparunaceae and MonimiaceaeFloristic studies in township of Presidente Figueiredo, Amazonas, Brazil ­ II: families Myristicaceae, Siparunaceae and Monimiaceae

O Município de Presidente Figueiredo, do Estado do Amazonas, Brasil, foi visitado durante três anos consecutivos (1996 a 1999), com o objetivo de obter-se amostras botânicas da área para estudos do Subprojeto "Elaboração de Revisões e Monografias Taxonômicas", com a finalidade de elaborar-se a Flórula para o Município. As coleções feitas nesse período encontram-se depositadas no acervo do Herbário do INPA e as informações gerais sobre os taxa aqui estudados foram complementadas com as obtidas das coleções feitas anteriormente por outros pesquisadores. Para a família Myristicaceae Br. R. foram identificadas 23 espécies e duas variedades, distribuídas em quatro gêneros. Destes, Iryanthera Warb. e Virola Aubl. destacaram-se pela diversidade em espécies, sendo Iryanthera ulei Warb. e Virola calophylla (Spruce) Warb. var. calophylla as espécies mais coletadas. A família Monimiaceae Juss. está representada apenas pelo gênero Mollinedia Ruiz & Pavón, pela espécie M. ovata Ruiz & Pavón; já a família Siparunaceae (A. DC.) Schodde encontra-se representada pelo gênero Siparuna Aubl. com oito espécies, sendo S. cristata (Poepp. & Endl.) A. DC. a espécie mais coletada.

The Township of Presidente Figueiredo, in the State of Amazonas, Brazil, was visited for three consecutive years, from 1996 to 1999, with the aim of acquiring botanical samples from the area, in order to carry out studies on the "Taxonomic Monographies and Revisions Preparation" Subproject for the purpose of preparing a survey of the flora. Collections pertaining to the present work are deposited at INPA's herbarium and, general information on the taxa studied here were complemented with those obtained from earlier collections conducted by other researchers. Twenty three (23) species and two varieties, distributed in four genera were identified for family Myristicaceae Br. R. Of these Iryanthera Warb. and Virola Aubl. stood out on account of their species diversity, being Iryanthera ulei Warb. and Virola calophylla (Spruce) Warb. var. calophylla the most collected ones. Family Monimiaceae Juss. is only represented by genus Mollinedia Ruiz & Pavón through species M. ovata Ruiz & Pavón, yet family Siparunaceae (A. DC.) Schodde is represented by genus Siparuna Aubl. with eight species, being S. cristata (Poepp. & Endl.) A. DC. the most collected one.

Tambouranolide, a new cytotoxic hydroxybutanolide from a Tambourissa sp. (Monimiaceae).

A new cytotoxic hydroxybutanolide, tambouranolide, has been isolated by solid phase extraction from an ethanol extract of the dried roots of a species of Tambourissa (Monimiaceae) from the Madagascar rainforest. The structure was elucidated through the interpretation of spectral data and its comparison to data reported in the literature for related molecules. The compound showed moderate in vitro cytotoxicity with an IC50 of 8 micro g mL(-1) in the A2780 human ovarian cancer cell line assay.

Sipaucins A-C, sesquiterpenoids from Siparuna pauciflora.

The phytochemical investigation of the leaves of Siparuna pauciflora yielded three novel sesquiterpenoids: the germacrane sipaucin A, the elemane sipaucin B and sipaucin C, comprising a new type of carbon skeleton. In addition, four known aporphine alkaloids-nor-boldine, boldine, laurotetanine, and N-methyl-laurotetanine-were obtained. The evaluation of the antiplasmodial activity of the isolated compounds against two strains of Plasmodium falciparum (PoW, Dd2) showed a moderate activity of nor-boldine.

Design of Peumus boldus tablets by direct compression using a novel dry plant extract.

A solid pharmaceutical dosage formulation using a novel dry plant extract of Peumus boldus MOL. (Monimiaceae) (Pb) is proposed. The botanical evaluation of plant material, through morphological and anatomical diagnosis, is presented. This evaluation permits to identify the herb to be used correctly. The analysis of the most extractive solvent mixture and the attainment of plant extract (fluid and dry) are reported. Several formulations (tablets) containing a novel dry plant extract of Pb and common excipients for direct compression are evaluated. The following formulation: dry plant extract of Pb (170 mg), Avicel PH101 (112 mg), Lactose CD (112) and magnesium stearate (6 mg), compressed at 1000 mPa, showed the best pharmaceutical performance.

Volatile constituents of the leaves of Siparuna thecaphora (Siparunaceae) from Turrialba, Costa Rica.

The composition of the essential oil from leaves of Siparuna thecaphora (Poepp. et Endl.) A. DC. collected in Turrialba, Costa Rica, was determined by capillary GC/MS. Seventy-six compounds were identified corresponding to ca. 95% of the oil. The major components were germacrene D (32.7%), alpha-pinene (16.3%), beta-pinene (13.8%) and beta-caryophyllene (4.1%). Thirty-one minor compounds were identified for the first time in this genus of plants.

Quantitative determination of liriodenine and moupinamide in five species of Mollinedia by high performance liquid chromatography.

A simple method for the resolution and subsequent quantitative determination of liriodenine and moupinamide in Mollinedia species was developed using reversed-phase HPLC based on an octadecyl silane-packed column eluted with gradients of methanol and water.

A benzylisoquinoline alkaloid from Doryphora sassafras.

Chemical investigation of the Australian rainforest plant Doryphora sassafras has resulted in the isolation of a new natural product, 2-methyl-1-(p-methoxybenzyl)-6,7-methylenedioxyisoquinolinium chloride (1). The iodide salt of compound 1 has previously been synthesized but only partially characterized. This paper reports the full spectroscopic characterization of 1 by MS, IR, UV, and NMR data.