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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.

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Siparuna glycycarpa occurs in the Amazon region, and some species of this genus are used in Brazilian folk medicine. A recent study showed the inhibitory effect of this species against influenza A(H1N1)pdm09 virus, and in order to acquire active fractions, a polar solvent system n-butanol-methanol-water (9:1:10, v/v) was selected and used for bioassay-guided fractionation of n-butanol extract by centrifugal partition chromatography (CPC). The upper phase was used as stationary phase and the lower phase as mobile (descending mode). Among the collected fractions, the ones coded SGA, SGC, SGD, and SGO showed the highest antiviral inhibition levels (above 74%) at 100 µg·mL-1 after 24 h of infection. The bioactive fractions chemical profiles were investigated by LC-HRMS/MS data in positive and negative ionization modes exploring the Global Natural Products Social Molecular Networking (GNPS) platform to build a molecular network. Benzylisoquinoline alkaloids were annotated in the fractions coded SGA, SGC, and SGD collected during elution step. Aporphine alkaloids, O-glycosylated flavonoids, and dihydrochalcones in SGO were acquired with the change of mobile phase from lower aqueous to upper organic. Benzylisoquinolinic and aporphine alkaloids as well as glycosylated flavonoids were annotated in the most bioactive fractions suggesting this group of compounds as responsible for antiviral activity.

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The novel coronavirus SARS-CoV-2 has been affecting the world, causing severe pneumonia and acute respiratory syndrome, leading people to death. Therefore, the search for anti-SARS-CoV-2 compounds is pivotal for public health. Natural products may present sources of bioactive compounds; among them, flavonoids are known in literature for their antiviral activity. Siparuna species are used in Brazilian folk medicine for the treatment of colds and flu. This work describes the isolation of 3,3',4'-tri-O-methyl-quercetin, 3,7,3',4'-tetra-O-methyl-quercetin (retusin), and 3,7-di-O-methyl-kaempferol (kumatakenin) from the dichloromethane extract of leaves of Siparuna cristata (Poepp. & Endl.) A.DC., Siparunaceae, using high-speed countercurrent chromatography in addition to the investigation of their inhibitory effect against SARS-CoV-2 viral replication. Retusin and kumatakenin inhibited SARS-CoV-2 replication in Vero E6 and Calu-3 cells, with a selective index greater than lopinavir/ritonavir and chloroquine, used as control. Flavonoids and their derivatives may stand for target compounds to be tested in future clinical trials to enrich the drug arsenal against coronavirus infections. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s43450-021-00162-5.

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This paper describes the isolation of flavonoids and other aromatic compounds from an ethyl acetate extract of leaves of Siparuna glycycarpa using stepwise elution counter-current chromatography (CCC). The elution profile yielded the following compounds: diglycosylated flavonoids, quercetin 3-O-rutinoside and quercetin 7-O-rutinoside, followed by monoglycosylated flavonoids, kaempferol-3-O-ß-glucopyranoside, kaempferol-3-O-ß-rhamnopiranoside, kaempferol-3-O-ß-6''(p-coumaroyl) glucopyranoside, and quercetin-3-O-ß-glucopyranoside, and then free phenolics, protocatechuic acid, and 2',6'-dihydroxy-4, 4'-dimethoxydihydrochalcone, which shows that this type of elution covers a broader range of polarity than the traditional isocratic mode. This makes it more suitable to perform separations of mixtures containing large differences in hydrophobicity. A GC analysis of a blank CCC run was performed to determine if changes in the mobile phase composition affect the chromatographic process. Results showed a gradual variation of the composition of the mobile phase emerging after the step gradient, favoring the selectivity of the solvent system.

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Introducción: Siparuna sessiliflora Kunth A. DC. es una especie vegetal comúnmente conocida en Colombia como limoncillo, utilizada por parte de varias comunidades indígenas para tratar diferentes problemas de salud. A pesar de contar con diversos registros de usos etnobotánicos, esta especie ha sido poco estudiada desde el punto de vista fitoquímico o de su actividad biológica. Objetivos: evaluar la actividad antibacteriana de los extractos y las fracciones obtenidos a partir de las hojas de Siparuna sessiliflora sobre Bacillus subtilis, Staphylococcus aureus, Escherichia coli y Pseudomonas aeruginosa. Métodos: el material vegetal fue extraído por maceración en frío con éter de petróleo y etanol 96 por ciento; estos extractos se fraccionaron por métodos cromatográficos y partición líquido/líquido; su actividad antibacteriana se evaluó por el método de difusión en gel por perforación en placa. Posteriormente, se identificaron los principales compuestos responsables de la bioactividad por medio de cromatografía de gases acolada a espectrometría de masas. Resultados: se encontró que las fracciones de alcaloides Alk 1 y Alk 2 presentaron actividad frente a B. subtilis, S. aureus y E. coli. Adicionalmente, la subfracción Alk 2A fue la más activa frente a B. subtilis. Se identificaron sobre todo alcaloides isoquinolínicos y un derivado del ácido cinámico como posibles compuestos responsables de la bioactividad. Conclusiones: se reportó la actividad antibacteriana de S. sessiliflora frente a bacterias grampositivas y gramnegativas, y se generó nuevo conocimiento sobre su fitoquímica que corrobora su uso tradicional en la cura de cuadros infecciosos.

Introduction: Siparuna sessiliflora Kunth A. DC. is a plant species popularly known in Colombia as «limoncillo¼ and used by several indigenous communities for treating different health disorders. Despite the many records of its ethnobotanical uses, this species has been poorly studied from a phytochemical or biological standpoint. Objectives: to evaluate the antibacterial activity of the extracts and fractions obtained from Siparuna sessiliflora´s leaves against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Methods: the plant material was extracted by cold maceration with petroleum ether and 96 percent ethanol. Those extracts were fractionated by chromatographic methods and liquid-liquid partitioning; additionally, its antibacterial activity was assessed by gel diffusion. Subsequently, there were identified the main bioactive compounds by gas chromatography-mass spectrometry. Results: it was found that the alkaloidal fractions Alk 1 and Alk 2 were active against B. subtilis, S. aureus and E. coli. Additionally, the subfraction Alk 2A was the most active against B. subtilis. Isoquinoline alkaloids and a cinnamic acid derivative were identified as possible compounds responsible for bioactivity. Conclusions: the antibacterial activity of S. sessiliflora against Gram positive and Gram negative bacteria was reported, so the new knowledge about its phytochemistry endorses its traditional use in the treatment of infections.

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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.

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