Genus Mikania Research Articles

Structural, histochemical, and phytochemical characterization of Mikania cordifolia (L. f.) Willd. (Asteraceae) in a coastal dune environment

Coastal dune is a habitat that presents determining and often limiting factors for plant development. Species of Asteraceae, such as Mikania cordifolia, are commonly found in this environment, including occupying frontal dunes, where winds, salinity, and soil represent severe environmental conditions. Asteraceae is recognized for its different secretory structures and for containing species with potential for bioprospecting. Mikania cordifolia is a species with a voluble habit, wide geographic distribution, and records of medicinal use. However, no studies in the literature cover the anatomical, histochemical, and chemical investigation of all vegetative organs of the mentioned species. In this sense, this study evaluated the anatomical organization of the vegetative organs of M. cordifolia, including secretory structures, as well as the chemical composition of the extract of each organ. For this, diaphanization, microtomy, histochemistry, and phytochemistry techniques were used. Our results showed that the vegetative organs have several adaptations to the coastal dunes environmental conditions, among them the presence of four types of secretory structures – secretory canals and cavities, trichomes and hydathodes. Histochemical analyzes indicated sesquiterpene lactones, pectic and phenolic compounds, lipophilic substances, flavonoids, coumarins, starch and tannins. Nuclear magnetic resonance analyzes showed kaurane diterpenes, steroids, fatty acids, phenolic derivatives, and methoxylated substances. Our results contribute to the understanding of the structure and phytochemistry of the genus Mikania, the adaptations of the species to the coastal dune environment, and the occurrence and distribution of secretory structures in the genus, promoting knowledge and justifying the conservation of the coastal dunes flora.

Technological prospection: the genus Mikania in therapeutic use

The genus Mikania (Asteraceae) comprises about 450 species of these, 203 are found in Brazil and present several chemical and biological activities. Considering the variety of species and their therapeutic properties, the present study aimed to perform technological prospecting of this genus, since this approach aims to contribute to technological, scientific and innovation research. For this purpose, the patent documents were analyzed, regarding the applicant countries, year of filing and the international classification of patents of the genus Mikania. The search was conducted in the databases World Intellectual Property Organization (WIPO), European Patent Office (EPO) and the National Institute of Industrial Property (INPI) in October 2020, using the descriptor “Mikania”; present in the title and/or abstract in addition, documents that included medicinal approaches were selected. Thus, taking into consideration the filing countries, Japan, Brazil and the United States led the patent deposits, with the first document filed in 1991 and the largest number of applications in the years 2000 and 2010. The data concerning the international patent classification are concentrated in subclass A61K, which deals with preparations for medical, dental or hygienic purposes. These results demonstrated the therapeutic and technological potential of the Mikania species and thus which can be evidenced the potential of this study.

Distribution of flavonoids and other phenolics in Mikania species (Compositae) of Brazil

The genus Mikania (Compositae, tribe Eupatorieae) encompasses about 430 species mainly distributed in Neotropical region. More than 200 species of this genus occur in Brazil, highlighting the species widely used in folk medicine M. glomerata and M. laevigata. Nevertheless, the chemical composition of several Mikania species found in Brazil has not been studied yet. Thus, we performed the HPLC-ESI-MS/MS analysis of 19 Mikania species with voluble and erect habits and which were obtained from natural habitats in different regions of Brazilian biodiversity. Furthermore, this is the first chemical investigation of 12 Mikania species and the first description of flavonoids and other phenolics in 16 species. Quercetin O-heterosides, 5-O-caffeoylquinic acid and dicaffeoylquinic acids were the most distributed compounds in the analyzed species. The occurrence of octulopyranosonic acid derivatives was observed for the first time in Mikania. Unsupervised statistical analysis (PCA) suggested the tendency of metabolite speciation in some plants of the group, but it did not show clustering patterns related to habits and vegetations from the habitats of species. Some flavonoids and dicaffeaoylquinic acids annotated in many species may be associated to anti-inflammatory effects of Mikania extracts. Therefore, the present study provides novelties regarding the polar compounds in Mikania and reinforces the pharmacological potential of unevaluated species of this genus.

Composição química, atividade biológica e segurança de uso de plantas do gênero Mikania

Mikania, guaco é utilizado popularmente há muitos anos, devido às propriedades medicinais atribuídas às folhas, incluindo a ação tônica, depurativa, antipirética e broncodilatora, além de estimulante do apetite e antigripal. Também é empregado no tratamento de doenças respiratórias como asma e bronquite, na forma de xaropes para tosse. Várias dessas ações benéficas à saúde foram comprovadas cientificamente. Estudos foram publicados sobre a ação direta do guaco causando broncodilatação e relaxamento da musculatura lisa respiratória, o que pode estar relacionado ao bloqueio dos canais de cálcio, acompanhado de ações anti-inflamatória e antialérgica, sendo estas benéficas ao tratamento da asma, problema caracterizado por obstrução e inflamação das vias aéreas. Conforme indicações da ANVISA recomenda-se o uso do guaco sob as formas de tintura e extrato, sendo a cumarina o marcador de escolha no controle de qualidade da matéria prima e de produtos fitoterápicos contendo essa droga vegetal. Nesse trabalho, apresenta-se uma revisão sobre plantas do gênero Mikania, incluindo a farmacobotânica, a composição química, atividades biológicas e farmacológicas, interações medicamentosas, toxicidade e controle de qualidade.

New cadinane sesquiterpenoids from Mikania micrantha

Chemical investigation of the aerial parts of Mikania micrantha led to the isolation of eight sesquiterpenoids and ten diterpenoids, including five cadinane sesquiterpenoids (1−5), three bisabolene sesquiterpenoids (6 − 8), nine ent-kaurane diterpenoids (9–17), and an abietane diterpenoid (18). Among them, 1 − 3 are new and feature a rare lactone or furan ring derived from C-6 isopropyl group side chain. Compound 18 was isolated from genus Mikania for the first time, and was also the first example of abietane-type diterpenoids from this plant. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HRESIMS, and ECD). All compounds were examined for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophage cells, and compound 18 exhibited pronounced inhibition on NO production (IC50 = 11.04 µM), being comparable to the positive control, quercetin (IC50 = 11.15 µM).

Comparative chloroplast genomics between the invasive weed Mikania micrantha and its indigenous congener Mikania cordata: Structure variation, identification of highly divergent regions, divergence time estimation, and phylogenetic analysis

Mikania micrantha and Mikania cordata are the only two species in genus Mikania (Asteraceae) in China. They share very similar morphological and life-history characteristics but occupy quite different habitats. Most importantly, they generate totally different ecological consequences. While M. micrantha has become an exotic invasive weed, M. cordata exists as an indigenous species with no harmful effects on native plants or habitats. As a continuous study of our previously reported M. micrantha chloroplast (cp) genome, in this study we have further sequenced the M. cordata cp genome to (1) conduct a comparative genome analysis to gain insights into the mechanism of invasiveness; (2) develop cp markers to examine the population genetic adaptation of M. micrantha; and (3) screen variable genome regions of phylogenetic utility. The M. cordata chloroplast genome is 151,984 bp in length and displays a typical quadripartite structure. The number and distribution of protein coding genes, tRNA genes, and rRNA genes of M. cordata are identical to those of M. micrantha. The main difference lays in that the pseudogenization of ndhF and a 118-bp palindromic repeat only arises in M. cordata. Fourteen highly divergent regions, 235 base substitutions, and 58 indels were identified between the two cp genomes. Phylogenetic inferences revealed a sister relationship between M. micrantha and M. cordata whose divergence was estimated to occur around 1.78 million years ago (MYA). Twelve cpSSR loci were detected to be polymorphic and adopted to survey the genetic adaptation of M. micrantha populations. No cpSSR loci were found to undergo selection. Our results build a foundation to examine the invasive mechanism of Mikania weed.

Pharmacology of Mikania genus: A systematic review

Genus Mikania, in which “guaco” species are included, encloses many species of pharmaceutical interest that are well distributed throughout South America. This work aims to make a systematic review of the clinical and nonclinical data already published about some Mikania species and their existing products, available in the pharmaceutical market. As usual, some species are more studied than others and the most studied species to date are Mikania glomerata, Mikania laevigata, Mikania scandens, and Mikania micrantha. The first two are widely used in Brazil to treat respiratory disorders and are available in different preparations marketed in retail pharmaceutical stores. Among the reported activities, anti-inflammatory, analgesic, antibacterial, and central nervous system activities were the most tested since they are directly related to the popular use of some species of this genus. In addition, a noteworthy amount of toxicological studies in animals are published in the literature. Thus, this systematic review aims to gather knowledge about Mikania genus and consequently to contribute for a safer use of derivatives of its species.

Cytotoxicity effect of ethanolic extract of Mikania glomerata against A549 human lung cancer cell line

The genus Mikania is the largest of its kind in the family Eupatorieae (Asteraceae), with more than 430 species concentrated mainly in the tropical regions, among which, Mikania glomerata is a most common herb generally employed in the treatment of respiratory disorders. The Milania glomerata plant leaf extracts were used for anticancer study against A549 human lung cancer cell line. The solid liquid extraction method has been employed to prepare the ethanol extract of Mikania glomerata through soxhelt apparatus method. To check the anti-proliferative effect of this extract, the extract chosen was tested for cell viability on the lung cancer cells A549 in different concentrations. Cell viability was evaluated by MTT assay for 24 hour and 48 hours. The LD50 value was calculated for the level of cell death and its effectiveness. The dose-dependent manner plays an important role in the treatment of lung cancer cell lines. The present study suggests that Mikania glomerata may be used as an alternative anticancer agent and further research is needed to improve the effectiveness.

Scarlet-bodied wasp moth, Cosmosoma myrodora (Dyar) (Insecta: Lepidoptera: Arctiidae)

The scarlet-bodied wasp moth, Cosmosoma myrodora (Dyar), is a beautiful native insect. Because of its striking adult coloration, including a bright red thorax and abdomen, and transparent wings patterned with black, this moth immediately stands out in Florida landscapes. Larval feeding is restricted to two native plants in the genus Mikania, family Asteraceae. This 5-page fact sheet was written by Diego Moscoso, Rodrigo Diaz, and William A. Overholt, and published by the UF Department of Entomology and Nematology, May 2013.
 http://edis.ifas.ufl.edu/in996

Phenolic Constituents from the Roots of Mikania micrantha and Their Allelopathic Effects

Four new thymol derivatives, 8,10-dihydroxy-9-benzoyloxythymol (1), 9-isobutyryloxy-10-hydroxythymol (2), 7,8,9,10-tetrahydroxythymol (3), and 7,8,10-trihydroxy-9-E-feruloyloxythymol (4), were isolated from the fresh roots of Mikania micrantha , along with 8,9,10-trihydroxythymol (5), 8,10-dihydroxy-9-acetoxythymol (6), 8,10-dihydroxy-9-isobutyryloxythymol (7), 8,10-dihydroxy-9-(2-methylbutyryloxy)thymol (8), 8,9-dehydro-10-hydroxythymol (9), 8-methoxy-9-hydroxythymol (10), ethyl caffeate (11), ethyl ferulate (12), 3,5-di-O-caffeoylquinic acid (13), and mikanin (14). Their structures were determined by spectroscopic methods. The known thymol derivatives (5-10) were obtained from the genus Mikania for the first time. Allelopathic effects of these compounds on Arabidopsis thaliana seeds were evaluated by a filter paper assay. After the treatment at 0.1 mM for 4 days, the seed germination rate with compound 8 was 48% and the inhibitory rates of shoot growth with compounds 1, 2, 7-10, and 12 were over 40%. The IC50 values of compounds 1 and 8 on shoot growth were 342.5 and 625 μM, respectively.

Genus Mikania: chemical composition and phytotherapeutical activity

The genus Mikania ranks high in the list of best-selling natural products in the world. Its main distribution is in South America, but some species are found in Asia, North America and Africa. It is used for treating fever, rheumatism, colds and respiratory diseases, as well as snake bites and scorpion stings, due to its broad spectrum of action. There are approximately 430 species of this genus and only 12% have been studied, highlighting their chemical and pharmacological diversity. The main chemical groups are: coumarins and derivatives, sesquiterpenes, sesquiterpenes lactones, diterpenes, phytosterols/terpenoids and flavonoids. This review aims to supply useful references for scientists interested in natural products and the search for new compounds, from over the 300 already described for the genus.

Contribuição ao estudo farmacognóstico de Mikania laevigata Sch. Bip. ex Baker (guaco), visando o controle de qualidade da matéria-prima

O gênero Mikania, pertencente à família Asteraceae e à tribo Eupatoriae, tem cerca de 430 espécies distribuída principalmente na América do Sul. No Brasil, o gênero está representado por aproximadamente 171 espécies. Várias espécies do gênero Mikania de hábito trepador recebem a denominação vulgar de "guaco". Mikania laevigata Sch. Bip. ex Baker, conhecida como "guaco", "guaco-de-casa" e "guaco-do-mato", é uma espécie nativa do sul do Brasil. Suas folhas são empregadas na medicina tradicional como expectorante e como anti-reumáticas. É muito semelhante morfologicamente com M. glomerata, que é a espécie oficializada pela Farmacopéia Brasileira I. Alguns estudos de M. laevigata comprovaram atividades farmacológicas como, antiinflamatória, antimutagênica, antimicrobiana e antiulcerogênica. Objetivou-se estudar a morfologia externa e a anatomia do caule e da folha de M. laevigata, com a finalidade de fornecer dados farmacognósticos referentes à identificação e à diferenciação dessa espécie das demais Mikania, visando o controle de qualidade da matéria-prima. O material botânico foi submetido às microtécnicas fotônicas e eletrônicas de varredura usuais. As características morfoanatômicas descritas para a folha e o caule de M. laevigata auxiliam na identificação da espécie.

Biology and host range of the rust fungus Puccinia spegazzinii: A new classical biological control agent for the invasive, alien weed Mikania micrantha in Asia

The neotropical rust fungus, Puccinia spegazzinii, was released in India in 2005 for the classical biological control of the invasive alien weed, Mikania micrantha. This paper contains data from the pest risk assessment that was undertaken prior to release. It includes studies on the life-cycle, pathotype variation, infection parameters and host-specificity testing. Inoculation studies confirmed the rust to be microcyclic and autoecious. Seven pathotypes of the rust from six countries were assessed for variation in macroscopic morphology, phenology, and disease development on M. micrantha. The results conclude that two ecotypes can be identified, and that this could be linked to potential efficacy under different climatic conditions. A pathotype of P. spegazzinii from Trinidad (IMI 3930670) was selected for detailed assessment prior to release in the Western Ghats of Kerala State, south-west India. The rust was able to infect M. micrantha at temperatures ranging from 15 to 25°C (optimum near to 18°C) and also after less than 10h of exposure to free-water on the plant surface (optimum near to 15h). More than 60 non-target plants were challenged with the rust, including 11 other Mikania species. The rust was found to be highly specific within the genus Mikania; only three species from Africa and one from Asia became infected with the rust to varying degrees. Three other species, closely-related to M. micrantha, developed chlorotic spots in response to the rust; however, the symptoms progressed no further. The anticipated field efficacy of the rust in the invasive range of the plant is discussed.

C-15-Functionalized Eudesmanolides from Mikania campanulata

The aerial parts of Mikania campanulata Gardner afforded the nine new eudesmanolides (1S,4S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide (1), (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide (2), (1R,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide (3), (1R,4S,5S,6S,7S,10R)-1-hydroxy-4,15-diacetoxyeudesm-11(13)-en-6,12-olide (4), (1S,4R,5S,6S,7S,10R)-1,15-diacetoxy-4-hydroxyeudesm-11(13)-en-6,12-olide (5), (1S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesma-4(15),11(13)-dien-6,12-olide (6), (1S,5S,6S,7S,10R)-1,15-dihydroxyeudesma-3,11(13)-dien-6,12-olide (7a), (1S,2R,5S,6S,7S,10R)-1,2,15-trihydroxyeudesma-3,11(13)-dien-6,12-olide (8a), and (1R,6S,7S,10R)-1,15-dihydroxyeudesma-4,11(13)-dien-6,12-olide (9a), among which the last three were characterized as their corresponding peracetates (7b-9b). The structures of 1-6 and 7b-9b were elucidated using 1D and 2D NMR measurements, while that of major constituent 1 was confirmed by single-crystal X-ray diffraction analysis, and its absolute configuration evidenced from vibrational circular dichroism measurements, which were compared to results obtained from density functional theory calculations. The chemistry of the large genus Mikania is briefly analyzed.

An ent-kaurane diterpene from Mikania laevigata (Asteraceae)

The genus Mikania contains more than 450 species and around 150 of them are found in Brazil [1]. This genus is divided in two groups of species, one of them produces preferently sesquiterpene lactones and the other, diterpenic acids. The late compounds seem to play an important role in defense system of plants [2]. Mikania laevigata Schultz Bip. ex Baker („guaco“) is the most abundant Mikania species in Southern Brazil [3]. The leaves are used mainly to treat respiratory diseases, but antiseptic, antiasthmatic and antirheumatic properties have been described. The characteristic smell of Mikania species is due to coumarins and some of their properties are also attributed to these compounds [4]. The plant material was cultivated at Federal University of Santa Catarina. The dried and powdered leaves (281g) were macerated with ethanol during 7 days. The crude extract was treated with MeOH:H2O (9:1), and extracted with petrol (PE), CH2Cl2, ethyl acetate and n-butanol. PE fraction was fractionated by flash chromatography (gradient of PE:CH2Cl2) followed by silica gel column chromatography (PE:ethyl acetate gradient) and Sephadex LH-20 (MeOH), yielding 21mg of compound 1. The NMR-H1, NMR-C13, IR and UV data suggested compound 1 to be ent-15β-benzoyloxy-kaur-16(17)-en-19-oic acid. This compound has been isolated also from other Mikania species [5,6], but it has never been found in M. laevigata, therefore being a new compound of this species.

Diterpene acids from Mikania sp. nov (Asteraceae)

1. Subject and sourceIn continuation with our studies on Mikania species (Nun˜ez and Roque, 1999;Nun˜ez et al., 2002), leaves of Mikania sp. nov. (Asteraceae) were collected in “Morrodo Pai Ina´cio”, Chapada Diamantina, Bahia, Brazil (S 12°27 341 and W41°28 502 ), in July, 1997. The collection was identified by Prof. Nicholas Hind(Kew Gardens, UK) (Hind, personal communication); a voucher specimen (Nun˜ez003) is deposited in the Herbarium of the Instituto de Biocieˆncias at Universidadede Sa˜o Paulo (SPF), Sa˜o Paulo, SP, Brazil.2. Previous workThe genus Mikania has more than 450 species, 150 of which occur in Brazil (Hind,1993). Almost 40 species of Mikania have been investigated previously, sesquiter-pene lactones and diterpene acids being the main metabolites (Herz, 1998).

Chromosome studies in the genus Mikania (Asteraceae)

Mikania is the largest genus of the tribe Eupatorieaewith about 430 species distributed in the pantropics, tem-perate America, and Southern Africa, but with its two majordiversity centers in the highlands of southeastern Brazil andthe eastern foothills of the Andes from Bolivia to Colom-bia (King and Robinson, 1987; Holmes, 1995). The genusis widely distributed in Brazil with about 200 described spe-cies (Barroso, 1958, 1986), many of which are endemic tosouthern Brazil, but with a greater number of species beingfound in Amazon region.The species are characterized by their capitula whichis composed of four florets and an involucre composed offour phyllaries that is subtended by a subinvolucral bract.There is no variation from this basic organization, and spe-cific differences mostly involve the type of capitulescence,size of habit, shape of organs, and plant texture (Holmes,1995).Until 1987 chromosome studies of the genus havebeen limited to chromosome counts, but such counts areavailable for only about 10% of the species (Gaiser, 1954;Mangenot and Mangenot, 1958; Turner, 1962; Turner et al. ,1967; Baquar, 1967-1968; Mitra and Datta, 1967; Sharmaand Sakar, 1967-1968; Coleman, 1968; Nevlin, 1969;Powell and King, 1969; King et al., 1976; Turner et al.,1979; Nauman, 1981; Mathew and Mathew, 1983; Strother,1983; Waisman et al. , 1984).The first karyotype studies in Mikania were made byRuas and Ruas (1987) on six species from which they sug-gested that there was an evolutionary trend in the genus to-wards the formation of aneuploid and polyploid series. In astudy of ten species of Mikania Ruas (1989) and Ruas andAguiar-Perecin (1997) proposed a correlation betweenmorphological and chromosomal evolution, while an analy-sis of 12 cytotypes of Mikania micrantha by Maffei (1996)showed that the same evolutionary mechanisms that occuramong species also occur at intraspecific level, results alsoseen in a study of two populations of M. cordifolia by Maffeiet al. (1999a).In this review, the chromosomal evolution of the ge-nus Mikania is discussed based on currently available data.

Chromosome evolution in the genus Mikania (Compositae)

Karyotypic analysis of ten species of the genus Mikania was carried out using Feulgen staining. Species belonging to the following sections were analyzed: Section Thyrsigerae containing M. additicia (2n = 34), M. hemisphaerica, M. lanuginosa, and M. punctata (2n = 36), and Mikania sericea (2n = 42), which adds a new basic chromosome number (x = 21) to the genus and to the tribe Eupatorieae; Section Corymbosae with M. hastato-cordata (2n = 34) and M. involucrata and M. microptera with 2n = 36 chromosomes; Section Spicato-Racemosae with M. sessilifolia, with 2n = 108 chromosomes. One unidentified species with 2n = 34 chromosomes was also analyzed. All the species studied show one large pair of chromosomes with a secondary constriction in the middle region of the long arm. The morphology of this chromosome suggests that it can be considered as a cytological marker for the genus. Because of the distinctive inflorescence types found in the genus Mikania and the high frequency of species with x = 18, a correlation between morphological and chromosomal evolution is discussed. The present study suggests that the basic original chromosome number for the genus is x = 18, from which the others (x = 17, 19, 20, 21) have been derived by aneuploidy to form the observed aneuploid series.

Karyotypes and chromosome morphology in the genus Mikania (Compositae). I.

Karyotypes from six species of genus Mikania were studied utilizing root tip metaphase mitoses. Two species were diploid with 2n=36, M. cordifolia was diploid with 2n=34, M. laevigata, was diploid with 2n=38, M. micrantha and M. viminea were tetraploid with 2n=72 and 2n=68, respectively. Five out of the six species analysed had one pair of a comparatively long chromosome with a secondary constriction in the long arms, and one species (M. micrantha) had two pairs of such long chromosomes. The basic chromosome number of this genus is 18, and we suggest that there is an evolutionary trend towards formation of aneuploid series and polyploidy.

Synopsis of the Mexican and Central American species of the genus Mikania

Synopsis of the Mexican and Central American species of the genus Mikania