Sesquiterpenes from southern Magnolia virginiana

Song, Qi; Gomez-Barrios, Marco L.; Fronczek, Frank R.; Vargas, David; Thien, Leonard B.; Fischer, Nikolaus H.

doi:10.1016/s0031-9422(97)00412-3

Cited by 16 publications

(9 citation statements)

References 20 publications

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“…Parthenolide has previously been isolated and characterized from different species of Ambrosia (19,48), Magnolia (13,18,39), and other species of the genus Tanacetum (3,21). In the study reported here, this compound had an IC 50 of 0.37 g/ml and inhibited parasite growth in macrophages.…”

Section: Discussionmentioning

confidence: 60%

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Antileishmanial Activity of Parthenolide, a Sesquiterpene Lactone Isolated from Tanacetum parthenium

Tiuman

Ueda-Nakamura

Cortez³

et al. 2005

Antimicrob Agents Chemother

183

116

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The in vitro activity of parthenolide against Leishmania amazonensis was investigated. Parthenolide is a sesquiterpene lactone purified from the hydroalcoholic extract of aerial parts of Tanacetum parthenium. This isolated compound was identified through spectral analyses by UV, infrared, 1 H and 13 C nuclear magnetic resonance imaging, DEPT (distortionless enhancement by polarization transfer), COSY (correlated spectroscopy), HMQC (heteronuclear multiple-quantum coherence), and electron spray ionization-mass spectrometry. Parthenolide showed significant activity against the promastigote form of L. amazonensis, with 50% inhibition of cell growth at a concentration of 0.37 g/ml. For the intracellular amastigote form, parthenolide reduced by 50% the survival index of parasites in macrophages when it was used at 0.81 g/ml. The purified compound showed no cytotoxic effects against J774G8 macrophages in culture and did not cause lysis in sheep blood when it was used at higher concentrations that inhibited promastigote forms. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis with gelatin as the substrate showed that the enzymatic activity of the enzyme cysteine protease increased following treatment of the promastigotes with the isolated compound. This finding was correlated with marked morphological changes induced by parthenolide, such as the appearance of structures similar to large lysosomes and intense exocytic activity in the region of the flagellar pocket, as seen by electron microscopy. These results provide new perspectives on the development of novel drugs with leishmanicidal activities obtained from natural products.

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Section: Discussionmentioning

confidence: 60%

“…Parthenolide was isolated and purified as described previously (19,21,39), with slight modifications. The aerial parts of T. parthenium were kindly furnished by the Herbarium Laboratório Botānico Ltda (lot 166871; Colombo, Paraná, Brazil).…”

Section: Methodsmentioning

confidence: 99%

Antileishmanial Activity of Parthenolide, a Sesquiterpene Lactone Isolated from Tanacetum parthenium

Tiuman

Ueda-Nakamura

Cortez³

et al. 2005

Antimicrob Agents Chemother

183

116

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“…The annual variation pattern in the occurrence of parthenolide, costunolide, and costunolactol in the southern variety of M. virginiana has been studied. Parthenolide and costunolactol show an inverse relationship with a parthenolide maximum occurring in July/August (Song et al, 1998). It is significant to point out that the southern and the northern varieties of M. virginiana show distinctly different chemical profiles.…”

Section: Sesquiterpene Lactonesmentioning

confidence: 89%

“…The melampolides-type melampomagnolide A (7) and B (8) are found in the southern magnolia in lower concentrations than parthenolide and costunolide (Macias et al, 1992). They may play a role in allelopathy (Song et al, 1998), but their cytotoxic properties are still unknown. The annual variation pattern in the occurrence of parthenolide, costunolide, and costunolactol in the southern variety of M. virginiana has been studied.…”

Section: Sesquiterpene Lactonesmentioning

confidence: 99%

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The Ethnomedicinal Uses of Magnoliaceae from the Southeastern United States as Leads in Drug Discovery

Schühly

Khan

Fischer

2001

Pharmaceutical Biology

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In Asia and North America, members of the family Magnoliaceae have been and are presently used extensively in indigenous herbal medicine. Many taxa of the genus Magnolia produce lignans and sesquiterpene lactones, some with considerable in vitro bioactivities. This review focuses on selected natural products of the genus Magnolia from the southeastern United States with demonstrated biological and pharmacological properties. Ethnomedicinal data obtained from the Native Americans of the southeastern United States correlate well with the results of pharmacological investigations.

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Dimeric Sesquiterpenoids

Liao¹,

Yue²

2016

Progress in the Chemistry of Organic Natural Products 101

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It is widely accepted that a large number of proteins that are responsible for cellular function exist as dimers or need to be activated by dimerization before mediating certain signaling pathways. Simultaneously targeting both monomeric moieties of the dimeric proteins has shown potential in the development of various therapeutic agents. As dimeric molecules might be able to act on both moieties of a dimeric protein, dimeric sesquiterpenoids (DSs), which are generated biogenetically from coupling of two sesquiterpenoid molecules, are in essence potential biologically active molecules, and have attracted in recent years great attention for their peculiar structures and biological activities. In fact, a number of DSs are more potent than their monomeric precursors for some activities such as anti-inflammatory, anti-tumor, immunosuppressive, potassium channel blocking, antimalarial, anti-virus, and neurotrophic activities.The complex and diversified structures of DSs also attracted attention of chemists in their isolation, structural elucidation, and synthetic construction.In the contribution, a general view of the classification and distribution of DSs will be provided. Strategies for the structural elucidation of DSs and their analogues is presented. Chemical strategies for the convergence of the two sesquiterpenoid units is reviewed. Biological activities are discussed under each type of activity.

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Sesquiterpenes from southern Magnolia virginiana

Cited by 16 publications

References 20 publications

Antileishmanial Activity of Parthenolide, a Sesquiterpene Lactone Isolated from Tanacetum parthenium

Antileishmanial Activity of Parthenolide, a Sesquiterpene Lactone Isolated from Tanacetum parthenium

The Ethnomedicinal Uses of Magnoliaceae from the Southeastern United States as Leads in Drug Discovery

Dimeric Sesquiterpenoids

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