A New Sesquiterpene Lactone from<i>Elephantopus mollis</i>

But, Paul Pui Hay; Hon, Po‐Ming; Cao, Hui; Che, Chun‐Tao

doi:10.1055/s-2006-957945

Cited by 17 publications

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“…Na medicina popular, as folhas são usadas como emoliente, resolutivo, sudorífi co, no combate aos cálculos urinários e para tratar bronquite, tosse e gripe, principalmente na forma de chá por infusão ou decocção (Cabrera & Klein, 1980;Corrêa, 1984;Takeda & Farago, 2001;Lorenzi & Matos, 2002;Biavatti et al, 2007). Estudos fi toquímicos indicaram a presença de fl avonóides, triterpenóides e lactonas sesquiterpênicas (Banerjee et al, 1986;But et al, 1996;Lorenzi & Matos, 2002), algumas das quais com propriedades antitumoral (Lee et al, 1975(Lee et al, , 1980 e leishmanicida (Fuchino et al, 2001). O extrato bruto revelou efeitos hepatoprotetor (Lin et al, 1991;Lin et al1995) e antiinfl amatório contra artrite aguda e crônica (Tsai & Lin, 1999).…”

Section: Introductionunclassified

Estudo anatômico de folha e caule de Elephantopus mollis Kunth (Asteraceae)

Empinotti¹,

Duarte²

2008

Rev. bras. farmacogn.

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RESUMO:Conhecida comumente como erva-de-colégio, erva-grossa e sussuaiá, Elephantopus mollis Kunth (Asteraceae) é uma espécie herbácea perene, de base sublenhosa, ramos curtos e fl ores arroxeadas. Suas folhas são empregadas como emoliente, resolutivo, sudorífi co e no tratamento de bronquite, tosse e gripe na medicina popular. O objetivo deste trabalho foi estudar caracteres anatômicos foliares e caulinares, a fi m de fornecer subsídios aplicáveis à identifi cação da planta medicinal. Folhas adultas e fragmentos de caules foram fi xados, seccionados e corados com azul de astra/fucsina básica ou com azul de toluidina. Testes microquímicos e análise ultraestrutural de superfície foram também executados. A folha possui epiderme uniestratifi cada, recoberta por cutícula estriada e, em vista frontal, tem células com contorno ondulado. Ocorrem tricomas tectores e glandulares. Os primeiros são eretos, pluricelulares e unisseriados. Os tricomas glandulares são capitados e bisseriados. O mesofi lo é dorsiventral e a nervura central é percorrida por feixes vasculares colaterais dispostos em arco aberto. O caule, em estrutura secundária inicial, possui epiderme unisseriada com cutícula estriada e tricomas semelhantes aos da folha. No córtex, observam-se colênquima anelar alternado com clorênquima e endoderme com estrias de Caspary. Calotas esclerenquimáticas apõem-se ao fl oema. Este é formado pelo câmbio vascular em direção à periferia e o xilema é gerado de modo centrípeto. A medula é parenquimática. Pequenos cristais de oxalato de cálcio estão presentes na folha e no caule.Unitermos: Elephantopus mollis, Asteraceae, cristais, endoderme, tricoma glandular, tricoma tector.ABSTRACT: "Anatomical study of the leaf and stem of Elephantopus mollis Kunth (Asteraceae)". Commonly known as erva-de-colégio in Portuguese, Elephantopus mollis Kunth (Asteraceae) is a perennial herb, with slightly lignifi ed base, short branches and purple fl owers. Its leaves are used as emollient, vulnerary and diaphoretic, and to treat bronchitis, coughs and infl uenza in folk medicine. The aim of this work was to study leaf and stem anatomical characters, in order to expand the knowledge for this medicinal plant identifi cation. Adult leaves and stem fragments were fi xed, sectioned and stained either with astra blue/basic fuchsine or toluidine blue. Microchemical essays and scanning electron analysis were also carried out. The leaf has wavy-contoured cells in surface view, forming a single layer and coated with striate cuticle. Nonglandular and glandular trichomes occur. The former is erect, multicellular and uniseriate. The glandular ones are capitate and biseriate. The mesophyll is dorsiventral and the midrib is traversed by collateral vascular bundles arranged in open arc. The stem, in initial secondary growth, has uniseriate epidermis coated with striate cuticle and trichomes similar to the leaf. In the cortex, annular collenchyma alternates with chlorenchyma and an endodermis with Casparian strips is found. Sclerenchymatic caps adjoin the ph...

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Section: Introductionunclassified

Estudo anatômico de folha e caule de Elephantopus mollis Kunth (Asteraceae)

Empinotti¹,

Duarte²

2008

Rev. bras. farmacogn.

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“…E. mollis and E. scaber are the most popular species of the genus [ 2 , 3 ]. They have been screened for their pharmacological and phytochemical profiles [ 1 , 4 , 5 ]. Elephantopus species are sources of a class of sesquiterpenoid lactones named elephantopus-type lactones with a furane ring (C-2/C-5) in germacranolides [ 1 , 2 , 3 , 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

“…They have been screened for their pharmacological and phytochemical profiles [ 1 , 4 , 5 ]. Elephantopus species are sources of a class of sesquiterpenoid lactones named elephantopus-type lactones with a furane ring (C-2/C-5) in germacranolides [ 1 , 2 , 3 , 4 , 5 , 6 ]. They also produce glaucoside- and guaianolide-type lactones even in less amount alongside phenolic compounds and other terpenes [ 1 , 4 , 5 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

“…Elephantopus species are sources of a class of sesquiterpenoid lactones named elephantopus-type lactones with a furane ring (C-2/C-5) in germacranolides [ 1 , 2 , 3 , 4 , 5 , 6 ]. They also produce glaucoside- and guaianolide-type lactones even in less amount alongside phenolic compounds and other terpenes [ 1 , 4 , 5 , 7 ]. Sesquiterpene lactones have been proven to be the active principle of the plant against various diseases [ 1 , 4 , 5 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

“…They also produce glaucoside- and guaianolide-type lactones even in less amount alongside phenolic compounds and other terpenes [ 1 , 4 , 5 , 7 ]. Sesquiterpene lactones have been proven to be the active principle of the plant against various diseases [ 1 , 4 , 5 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

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LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents

et al. 2021

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A total of nine sesquiterpenoid lactones together with phenolic compounds and other terpenes were identified from the crude methanol extract of Elephantopus mollis Kunth. Compounds were isolated using different chromatographic techniques and their structures were determined by NMR and IR spectroscopy as well as mass spectrometry. The structures of some detected compounds were assigned based on LC-ToF-ESI-MS screening of main fractions/subfractions from flash chromatography and comparison with isolated analogues as standards. The findings revealed not only the in-source loss of water as the base peak in hirsutinolides but also the in-source loss of corresponding alcohol when the oxygen at position 1 is alkylated. The present study also draws up a complement of data with respect to hirsutinolide-like sesquiterpene lactones whose LC-MS characteristics are not available in the literature. The chemophenetic significance is also discussed. Some of the isolated compounds were reported for the first time to be found in the species, the genus as well as the plant family. The medium-polar fractions of the crude extract, also containing the larger amount of sesquiterpenoid lactones, exhibited activity both against a cancer cell line and bacterial strains. Isolated lactones were also active against the cancer cell line, while the chlorogenic derivatives also valuable in Elephantopus genus showed potent radical scavenging activity. This is the first report of cytotoxic and antibacterial activities of our samples against the tested strains and cell line. The present study follows the ongoing research project dealing with the characterization of taxa with antibacterial and antiparasitic activities from Cameroonian pharmacopeia.

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Collective Synthesis of Highly Oxygenated (Furano)germacranolides Derived from Elephantopus mollis and Elephantopus tomentosus

Patouret,

Cham,

Chiba

2024

Angewandte Chemie

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Germacranolides, secondary metabolites produced by plants, have garnered academic and industrial interest due to their diverse and complex topology as well as a wide array of pharmacological activities. Molephantin, a highly oxygenated germacranolide isolated from medicinal plants, Elephantopus mollis and Elephantopus tomentosus, has exhibited anti‐tumor, inflammatory, and leishmanicidal activities. Its chemical structure is based on a highly strained ten‐membered macrocyclic backbone with an (E,Z)‐dienone moiety, which is fused with an α‐methylene‐γ‐butyrolactone and adorned with four successive stereogenic centers. Herein, we report the first synthesis of molephantin via 12 steps starting from readily available building blocks. The synthesis features the highly diastereoselective intermolecular Barbier allylation of the β,γ‐unsaturated aldehyde with optically active 3‐bromomethyl‐5H‐furan‐2‐one intermediate and ensuing Nozaki‐Hiyama‐Kishi (NHK) macrocyclization for the construction of the highly oxygenated ten‐membered macrocyclic framework. This synthetic route enabled access to another germacranolide congener, tomenphantopin F. Furthermore, cycloisomerization of molephantin into 2‐deethoxy‐2β‐hydroxyphantomolin could be facilitated by irradiation with ultraviolet A light (λmax = 370 nm), which opened a versatile and concise access to the related furanogermacranolides such as EM‐2, phantomolin, 2‐O‐demethyltomephantopin C, and tomenphantopin C.

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A New Sesquiterpene Lactone fromElephantopus mollis

Abstract: A methanolic extract of the whole plant of Elephantopus mollis was found to contain lupeol, lupeol acetate, epifriedelinol, molephantin, and 2-de-ethoxy-2-methoxyphantomolin, as well as a new sesquiterpene lactone determined to be 2-de-ethoxy-2-hydroxyphantomolin.

Cited by 17 publications

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Estudo anatômico de folha e caule de Elephantopus mollis Kunth (Asteraceae)

Estudo anatômico de folha e caule de Elephantopus mollis Kunth (Asteraceae)

LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents

Collective Synthesis of Highly Oxygenated (Furano)germacranolides Derived from Elephantopus mollis and Elephantopus tomentosus

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