The structure of cacalone

Casares, Antonio; Maldonado, Luis A.

doi:10.1016/s0040-4039(00)78125-1

Cited by 10 publications

(5 citation statements)

References 8 publications

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“…19 The unambiguous structure for 3 was established by several syntheses, 20 and the absolute stereochemistry was reported to be 5S. 21 The structure of 2a was estab-lished by the conversion of 3 to 2a, 22,23 and the structure and 5S stereochemistry were verified by X-ray crystallography. 24 A 1:1 mixture of 2a and 2b was reported from C. delphiniifolia 25 and C. adenostyloides.…”

Section: Resultsmentioning

confidence: 99%

Antihyperglycemic Sesquiterpenes fromPsacaliumdecompositum

et al. 1999

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Psacalium decompositum was investigated for antihyperglycemic compounds using diabetic ob/ob mice as a model for type 2 diabetes. In vivo bioassay-guided fractionation of an aqueous extract from the roots of P. decompositum led to the isolation of two new eremophilanolides, 3-hydroxycacalolide (1a) and epi-3-hydroxycacalolide (1b). A 1:1 mixture of 1a/1b exhibited antihyperglycemic activity when tested at 1.09 mmol/kg in ob/ob mice. The known furanoeremophilanes, cacalone (2a) and epicacalone (2b), were also isolated from the aqueous extract and were inactive. The known furanoeremophilane, cacalol (3), was isolated from a CH2Cl2 extract of P. decompositum roots and possessed antihyperglycemic activity. The relative stereochemistry in 1a and 1b was assigned 3R,5S and 3S,5S, respectively, based on ROESY data, 3J H-H values, and molecular mechanics calculations. Complete 13C and 1H NMR chemical shifts were assigned for 1a, 1b, 2a, 2b, and 3, and several revisions in 13C NMR assignments for 2a and 3 were made. Results from the conformational analysis of 1a, 1b, 2a, and 2b indicate that each compound exists in one major conformation in solution with H3-12 in a pseudoaxial position.

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Section: Resultsmentioning

confidence: 99%

Antihyperglycemic Sesquiterpenes fromPsacaliumdecompositum

et al. 1999

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“…Previous studies on P. decompositum have led to the isolation and structural studies of several eremophilanes and rearranged eremophilanes . The structures of cacalol ( 1 ), cacalone ( 2 ), and related compounds , were the subject of several structural revisions, and the final structures were confirmed by chemical synthesis − and crystallographic analysis . A root decoction of P. decompositum , P. peltatum, and A. thurberi has been shown to lower the glucose levels in mice .…”

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confidence: 99%

New Modified Eremophilanes from the Roots of Psacalium radulifolium

Garduño-Ramı́rez¹,

Trejo²,

Navarro³

et al. 2001

J. Nat. Prod.

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The investigation of the chemical constituents from the roots of Psacalium radulifolium, a member of the matarique complex of medicinal plants, which includes several members of the Asteraceae, resulted in the isolation of four new modified eremophilanes: radulifolin A (4), epi-radulifolin A (5), radulifolin B (6), and radulifolin C (7), together with the known natural substances cacalol, cacalone, epi-cacalone, O-methyl-1,2-dehydrocacalol, adenostin A, decompostin, and neoadenostylone. Antimicrobial evaluation of the extracts and the isolated compounds indicated that cacalol was the major active compound.

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“…The analysis of the roots of P. decompositum led to the isolation of the sesquiterpenes cacalol and cacalone whose structures were proposed as 79 and 80, respectively. Later, these structures were revised to 81 [42] and 82 [43].…”

Section: Genus Psacaliummentioning

confidence: 99%

Secondary Metabolites from Mexican Species of the Tribe Senecioneae (Asteraceae)

et al. 2020

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Abstract. A revision of the Mexican species belonging to the tribe Senecioneae chemically studied so far, shows that the genera Senecio and Packera (subtribe Senecioninae), and the genera Barkleyanthus, Pittocaulon, Psacalium, and Telanthophora (subtribe Tussilagininae) contain pyrrolizidine alkaloids (PAs) and eremophilane derivatives as their main secondary metabolites. However, from Roldana and Robinsonecio (subtribe Tussilagininae) no PAs have been isolated. A special case is the genus Pseudogynoxys in which neither PAs nor eremophilanes are reported. Resumen. Una revisión de las especies mexicanas de la tribu Senecioneae estudiadas químicamente hasta el momento, muestra que los géneros Senecio y Packera (subtribu Senecioninae), y los géneros Barkleyanthus, Pittocaulon, Psacalium y Telanthophora (subtribu Tussilagininae) contienen alcaloides pirrolizidínicos (APs) y derivados de eremofilano como sus metabolitos secundarios principales. Sin embargo, de Roldana y Robinsonecio (subtribu Tussilagininae) no se han aislado APs. Un caso especial es el género Pseudogynoxys para el cual no se han reportado ni APs ni eremofilanos.

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The structure of cacalone

Cited by 10 publications

References 8 publications

Antihyperglycemic Sesquiterpenes fromPsacaliumdecompositum

Antihyperglycemic Sesquiterpenes fromPsacaliumdecompositum

New Modified Eremophilanes from the Roots of Psacalium radulifolium

Secondary Metabolites from Mexican Species of the Tribe Senecioneae (Asteraceae)

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