(+)-(5S)-δ-Lactone of 5-hydroxy-7-phenylhepta-2,6-dienoic acid, a natural product from Cryptocarya caloneura (Scheff.) Kostermans

Hlubucek, J.; Robertson, AV

doi:10.1071/ch9672199

Cited by 79 publications

(29 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It has been well reported that compounds that contain an α,β-unsaturated δ-lactone unit, often present in plants and marine organisms, show different structural complexities and a broad range of biological activities (Abe, 1937;Amemiya et al, 1994;Hlubucek and Robertson, 1967;Tunac et al, 1983). For example, (+)-Goniothalamin (isolated from Goniothalamus species) induced apoptosis in tumor cell lines (de Fatima et al, 2006) and was reported to be toxic to A. aegypti larvae (Goh et al, 1995).…”

Section: Introductionmentioning

confidence: 96%

Effects of α,β-unsaturated lactones on larval survival and gut trypsin as well as oviposition response of Aedes aegypti

Barros

Freitas

Santos

et al. 2015

Experimental Parasitology

View full text Add to dashboard Cite

Lactones are organic cyclic esters that have been described as larvicides against Aedes aegypti and as components of oviposition pheromone of Culex quinquefasciatus. This work describes the effect of six α,β-unsaturated lactones (5a-5f) on survival of A. aegypti fourth instar larvae (L4). It is also reported the effects of the lactones on L4 gut trypsin activity and oviposition behavior of A. aegypti females. Five lactones were able to kill L4 being the lactones 5a (LC50 of 39.05 ppm), 5e (LC50 of 36.30 ppm) and 5f (LC50 of 40.46 ppm) the most promising larvicides. Only the lactone 5a inhibited L4 gut trypsin activity, with an IC50 of 115.15 µg/mL. Lactones 5a, 5c, 5d and 5e did not exert deterrent or stimulatory effects on oviposition, whereas lactone 5b exhibited a strong deterrent oviposition activity. In conclusion, this work introduces new α,β-unsaturated lactones as promising alternatives to control A. aegypti dissemination. The larvicidal mechanism of the lactone 5a can involve the disruption of proteolysis at larval gut.

show abstract

Section: Introductionmentioning

confidence: 96%

Effects of α,β-unsaturated lactones on larval survival and gut trypsin as well as oviposition response of Aedes aegypti

Barros

Freitas

Santos

et al. 2015

Experimental Parasitology

View full text Add to dashboard Cite

show abstract

“…where a (+)-(5S)-δ-lactone previously identified in C. caloneura (Scheff.) Kosterm., was found to be one of the main constituents [10].…”

Section: Introductionmentioning

confidence: 99%

Comparative Chemical Analysis of the Essential Oil Constituents in the Bark, Heartwood and Fruits of Cryptocarya massoy (Oken) Kosterm. (Lauraceae) from Papua New Guinea

2007

View full text Add to dashboard Cite

Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils to be the C-10 (5,6-dihydro-6-pentyl-2H-pyran-2-one) and C-12 (5,6-dihydro-6-heptyl-2H-pyran-2-one) massoia lactones, while the major fruit oil constituent was benzyl benzoate (68.3 %). The heartwood also contained trace amounts of the C-14 (5,6-dihydro-6-nonyl-2H-pyran-2-one) massoia lactone (1.4 %) and the saturated C-10 derivative δ-decalactone (2.5 %).

show abstract

“…Goniothalamin (1), a naturally occurring styryl lactone, can be considered as a good lead compound for this purpose. Goniothalamin was first isolated from Cryptocarya caloneura in 1967, 1 and later from the other natural sources (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties

Kasaplar

Yılmazer

Çağır

2009

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

a b s t r a c t (R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines.

show abstract

(+)-(5S)-δ-Lactone of 5-hydroxy-7-phenylhepta-2,6-dienoic acid, a natural product from Cryptocarya caloneura (Scheff.) Kostermans

Cited by 79 publications

References 0 publications

Effects of α,β-unsaturated lactones on larval survival and gut trypsin as well as oviposition response of Aedes aegypti

Effects of α,β-unsaturated lactones on larval survival and gut trypsin as well as oviposition response of Aedes aegypti

Comparative Chemical Analysis of the Essential Oil Constituents in the Bark, Heartwood and Fruits of Cryptocarya massoy (Oken) Kosterm. (Lauraceae) from Papua New Guinea

6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties

Contact Info

Product

Resources

About