67667-64-5

Upstream product

• 74299-48-2 dehydrocostus lactone 
• 38236-17-8 isocostus lactone 
• 477-43-0 dehydrocostuslactone 

Downstream Products

• 38142-65-3 tetrahydrodehydrozaluzanin C 

Relevant academic research and scientific papers

Synthesis and Cytotoxic Activity of the Products of Addition of Thiophenol to Sesquiterpene Lactones

Abstract—: Derivatives of sesquiterpene lactones modified at the lactone ring with a thiophenol residue have been synthesized. The resulting conjugates with thiophenol have capacity for the oxidation–elimination reaction by the action of ROS of a tumor cell with the release of initial cytotoxic lactones. It has been proposed to use the resulting sulfur-containing conjugates as ROS-activated prodrugs of sesquiterpene lactones. The antiproliferative properties of the conjugates have been examined on tumor and pseudonormal cell lines. The cytotoxicity of the conjugates is lower than that of parent lactones; however, in some cases, as with the conjugates of alantolactone with artemisiten, it remains moderate in all tumor cell lines tested.

Sesquiterpenoids

The invention provides novel compounds and compositions for inhibiting IKKα/β, including treating disorders associated with IKKα/β activity, including cancer, autoimmune and inflammatory disorders, with a compound of structure shown above.

Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents

Several novel series of sesquiterpene mustards (SMs) bearing nitrogen mustard and glutathione (GSH)-reactive α-methylene-γ-butyrolactone groups were successfully prepared for the first time and showed excellent antiproliferative activities in vitro. Among them, compounds 2e and 2g displayed the highest antiproliferative properties with IC50 values ranging from 2.5 to 8.7 μM. The selectivity of these two compounds was evaluated by SRB method against human cancer and normal hepatic cells (HepG2 and L02). The induction of apoptosis and effects on the cell cycle distribution with compounds 2e and 2g were investigated by Hoechst 33,258 staining and flow cytometry, which exhibited that they could induce selective cell apoptosis and cell cycle arrest in HepG2 and L02 cells. In addition, further investigation showed that compounds 2e and 2g could obviously inhibit the proliferation of HepG2 cells by inducing significant DNA cross-linking and depleting GSH in cell media. The good cytotoxicity and selectivity of compounds 2e and 2g pointed them as promising leads for anticancer drug design.

Sesquiterpene lactones with potential use as natural herbicide models. 2. Guaianolides

A structure-activity study to evaluate the effect of 17 guaianolide sesquiterpene lactones (in a range of 100-0.001 μM) on the growth and germination of several mono- and dicotyledon target species is accomplished. Results are compared with those obtained in the same bioassay with an internal standard, the commercial herbicide Logran, to validate the results with a known active formulation and to compare the results with a commercial product to test their potential use as natural herbicide models. Specific conditions for the selective mono- or polyhydroxylation of guaianolides using the SeO2/tert-butyl hydroperoxide system are presented and discussed. The high regio- and stereo-selectivities of the reaction are explained through the specific structural requirements of the bulky first adduct formed during the ene reaction. These compounds appear to have deeper effects on the growth of either monocots or dicots than the previously tested germacranolides. Otherwise, the lactone group seems to be necessary for the activity, though it does not necessarily need to be unsaturated. However, the presence of a second and easily accessible unsaturated carbonyl system greatly enhances the inhibitory activity. Lipophilicity and the stereochemistry of the possible anchoring sites are also crucial factors for the activity. Finally, the levels of growth inhibition obtained with some compounds on dicots or monocots are totally comparable to those of Logran and allow proposing them as lead compounds.

Dehydrozaluzanin C: A potent plant growth regulator with potential use as a natural herbicide template

The natural product dehydrozaluzanin C (former DHZ) is a sesquiterpene lactone obtained from different weeds of the Compositae family. Its potential as a plant growth regulator has been evaluated by using a phytotoxic allelopathic bioassay, where the commercial herbicide Logran is used as internal reference. The evaluation is made based on their effects on germination and growth over several dicotyledon and monocotyledon species. The activity was tested in the range of 1000-0.001 μM. In almost all cases, DHZ was more active than the internal reference at 1000 μM, and its activity fell below the level of the internal reference at 100 μM. These results confirm DHZ as a potent plant growth regulator and good candidate for the development of new herbicide models. (C) 2000 Elsevier Science Ltd.

Developing new herbicide models from allelochemicals

Plants contain allelochemicals which are their own defence systems and can act as herbicides. Selected examples of guaianolides and heliannuols, which are sesquiterpenes, are discussed in the context of their potential use as natural herbicide templates.

Stereoselective epoxidation studies of isozaluzanin-C with vanadium(V)/t-butyl hydroperoxide

Isozaluzanin-C (2) (sesquiterpene lactone), an allylic alcohol having α-methylene-γ-lactone butyro moiety has been reacted with perbenzoic acid to yield two hydroxy epoxides (3 and 4).To confirm stereochemistry of epoxides, isozaluzanin-C on treatment with TBHP/VO(acac)2 yields only one compound having oxirane ring, which resembles one of the products as obtained from perbenzoic acid reaction.The stereochemistry of these epoxides has also been cofirmed by spectroscopic techniques.

POTENTIAL ALLELOPATHIC ACTIVITY OF SEVERAL SESQUITERPENE LACTONE MODELS

A collection of 12 natural and synthetic sesquiterpene lactones with eudesmanolide, melampolide, cis,cis-germacranolide, and guaianolide skeletons have been prepared and tested as allelochemicals.The effect of a series of aqueous solutions at 10-4-10-9 M of this collection is evaluated.The specific structural requirements related to their activity is discussed.The natural sesquiterpene lactones soulangianolide A, melampomagnolide A and B, zaluzanin C and isozaluzanin C have been synthesized from costunolide, parthenolide and dehydrocostuslactone using SeO2 and tert-butylhydroperoxide.The structures of the synthetic compounds were established by NMR spectroscopy. Key Word Index - Sesquiterpene lactones; melampolides; cis,cis-germacranolides; guaianolides; eudesmanolides; allelopathy; Lactuca sativa.

Studies on the Syntheses of Sesquiterpene Lactones. 11. The Syntheses of 3-Epizaluzanin C, Zaluzanin C, Zaluzanin D, and Related Compounds 3&α-Hydroxyguaia-1(10),4(15),11(13)-trieno-12,6&α-lactone and 3&α-Hydroxyguaia-4(15),9,11(13)-trieno-12,6&α-lactone

3-Epizaluzanin C (10), 3α-hydroxyguaia-1(10),4(15),11(13)-trieno-12,6α-lactone (36), and 3α-hydroxyguaia-4(15),9,11(13)-trieno-12,6α-lactone (37) have been synthesized in 4.0percent, 3.0percent, and 1.7percent overall yields, respectively, from α-santonine (13) in 14 steps.Zaluzanin C (11) and zaluzanin D (12) have also been synthesized in 2.4percent and 2.5percent overall yields from α-santonin (13) in 16 steps and 15 steps, respectively.The key step involves the solvolytic rearrangement of (11S)-3α,4α-epoxy-1β-(mesyloxy)eudesmano-13,6α-lactone (27).The stereochemistry of3-epizaluzanin C (10), zaluzanin C (11), and zaluzanin D (12) have been established by these stereospecific syntheses.

DEHYDROCOSTUSLACTONE AND PLANT GROWTH ACTIVITY OF DERIVED GUAIANOLIDES

Key Word Index-Saussurea lappa; Compositae; root promoters; sesquiterpene lactone; guaianolide; dehydrocostuslactone; estafiatin; isozaluzanin C; isodehydrocostuslactone.The stereostructures of two new guaianolides, isodehydrocostuslactone and isozaluzanin C, isolated previously from Saussurea lappa, have been confirmed by their correlation with dehydrocostuslactone.Twenty new derivatives have been synthesized from these guaianolides and these have been tested as plant growth regulators.The conjugated lactones which have an exocyclic methylene group at C-4, conjugated with a C-3 ketone, show distinct enhancement in their root-forming potential, as compared with their 3-deoxy derivatives.Of further significance is the fact that these ketones display maximum activity only at lower concentrations.Other compounds show the expected structure-biological activity relationships displayed in general by guaianolides.However, the presence of an epoxide at the C-3, C-4 position does not affect the biological activity, which is indeed the case when the epoxide group occupies the C-4, C-14 position in guaianolides.The major biological parameter studied was rooting in-stem cuttings of Phaseolus aureus.