Application of molecular mechanics in the total stereochemical elucidation of spicigerolide, a cytotoxic 6-tetraacetyloxyheptenyl-5,6-dihydro-α-pyrone from Hyptis spicigera

Pereda‐Miranda, Rogelio; Fragoso‐Serrano, Mabel; Cerda-Garcı́a-Rojas, Carlos M.

doi:10.1016/s0040-4020(00)00987-x

Cited by 85 publications

(51 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The proposed 5R configuration for lippialactone is in agreement with the configuration of this stereogenic centre in several other naturally occurring lactones [11,12]. It is therefore a diastereomer of synargentolide A [13] and closely related to d-lactones such as hyptolide [14], spicigerolide [15], synrotolide [16], passifloricin A [17,18], anamarine [19], and strictifolione [20]. The traditional medicinal uses of this plant [4,21] and several other Lippia species [22] are justified.…”

Section: Tablesupporting

confidence: 61%

Isolation and relative stereochemistry of lippialactone, a new antimalarial compound from Lippia javanica

2013

View full text Add to dashboard Cite

The aerial parts of Lippia javanica were investigated for biologically active chemical compounds present in them. Chromatographic separation of the ethyl acetate extract of the aerial parts yielded a new antimalarial α-pyrone, lippialactone (2). Lippialactone is active against the chloroquine-sensitive D10 strain of P. falciparum with an IC 50 value of 9.1 mg/mL, and is also mildly cytotoxic The relative stereochemistry of lippialactone was determined by molecular modeling based on the determination of the relative configuration by quantum mechanical GIAO 13 C chemical shift calculations.

show abstract

Section: Tablesupporting

confidence: 61%

Isolation and relative stereochemistry of lippialactone, a new antimalarial compound from Lippia javanica

2013

View full text Add to dashboard Cite

show abstract

“…[6] The Michael reaction is an important step in the chemicals ynthesis of antimicrobial [7] and antibiotic [8,9] drugs. a,b-Unsaturated lactone rings are particular cases of Michael acceptors [10] that have been shown to exhibit cytotoxic, [11][12][13][14] anticancer, [15][16][17] antifungal, [18][19][20][21] antibacterial, [22] andt rypanocidal [23,24] activities,a mong…”

Section: Introductionmentioning

confidence: 99%

Insight into the Mechanism of the Michael Reaction

et al. 2016

View full text Add to dashboard Cite

The mechanism for the nucleophilic addition step of the Michael reaction between methanethiol as a model Michael donor and several α-substituted methyl acrylates (X=F, Cl, Me, H, CN, NO2 ) as model Michael acceptors is described in detail. We suggest a novel way to condense electrophilic Fukui functions at specific atoms in terms of the contributions from the atomic orbitals to the LUMO or, more generally, to the orbital controlling the reaction. This procedure correctly associates activation energies to local electrophilic Fukui indices for the cases treated in this work. The calculated reaction barriers strongly depend on the nature of the substituent. As a general rule, activation energies are governed by structural changes, although electronic factors are significant for electron-withdrawing groups. Nucleophilic addition to Michael receptors is best described as a highly nonsynchronous process, in which the geometry of the transition state comprises a nonplanar six-membered ring. Formation of the S⋅⋅⋅C bond, which defines the interaction between the reactants, progresses ahead of all other primitive processes in the early stages of the transformation. In view of our results, we postulate that highly complex chemical reactions, as is the case for the nucleophilic addition step studied herein, that involve cleavage/formation of a total of six bonds, lower their activation energies by favoring nonsynchronicity, that is, for these types of systems, primitive changes should advance at different rates.

show abstract

“…Anti-hypertensive activity [18, 69, 129,-135, 157-159, 177, 200] Hyptis spicigera Anti-insect activity [116,209] Lagochilus hirsutissimus Hemostatic activity [229] Leonotis nepetaefolia Treating skin infections [235] Leonurus heterophyllus Immune system [69, Moldenhavera nutans Antivirus activity [145] Phlomis medicinalis, P. younghushband Against cough and fever [236] Plectranthus fruticosus L´Herit. Antimicrobial activity [103,104] Salvia candidissima [105] Salvia linariaefolia strong antibacterial activity [74] Salvia palestina antimicrobial activity [73] Sideritis hirsuta, S. nutans, S. perfoliata Against Leishmania donovani [150][151][152][153][154] Sideritis javalabrensis Anti-inflammatory activity [160,161,183,184] S. varoi subsp.…”

Section: Coleus Forskohliimentioning

confidence: 99%

“…showed significant cytotoxicity (IC50= 0.5-1.0µg/ml) spicigera (Lamiaceae) a new natural compound (spicigerolide) was isolated possessing strong cytotoxic activity on KB cell line [116]. Several diterpenoids have been isolated from the resinous wood of Excoecaria agallocha (Euphorbiaceae) and their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) in Raji cells were examined to search for potent anti-tumourpromoters from natural resources.…”

Section: Cytotoxic Activitiesmentioning

confidence: 99%

Labdanes of Natural Origin-Biological Activities (1981-2004)

Chinou

2005

CMC

View full text Add to dashboard Cite

Terpenoids is a class of natural compounds found in higher plants, mosses, liverworts, algae and lichens, as well as in insects, microbes or marine organisms. Through centuries many of these compounds have been used as ingredients of perfumes, drugs, narcotics or pigments. Labdanes, belonging to the bicyclic diterpenoids group, have been found as secondary metabolites in tissues of fungi, insects, marine organisms, and in essential oils, resins and tissues of higher plants. The diterpenes of labdane type, have been reported to have broad spectrum of biological activities. In this study, the reported bioactivities and/or uses of them, the last two decades (1981-2004), are selected as an attempt to underline their role in nature.

show abstract

Application of molecular mechanics in the total stereochemical elucidation of spicigerolide, a cytotoxic 6-tetraacetyloxyheptenyl-5,6-dihydro-α-pyrone from Hyptis spicigera

Cited by 85 publications

References 24 publications

Isolation and relative stereochemistry of lippialactone, a new antimalarial compound from Lippia javanica

Isolation and relative stereochemistry of lippialactone, a new antimalarial compound from Lippia javanica

Insight into the Mechanism of the Michael Reaction

Labdanes of Natural Origin-Biological Activities (1981-2004)

Contact Info

Product

Resources

About