Diterpenes of Podocarpus ferrugineus bark

Wenkert, Ernest; Campello, Jayr de Paiva; McChesney, James D.; Watts, Daniel J.

doi:10.1016/s0031-9422(00)86934-4

Cited by 28 publications

(8 citation statements)

References 25 publications

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“…From the methanol extract of S. staminea, we isolated the new triterpenoid, 3b,11a,21a-trihydroxyurs-12-ene (1), together with three flavones apigenin (2), luteolin (3), apigenin 7-O-glucoside (4), and sitosterol 3b-D-glucoside (5). The acetone extract yielded the two sesquiterpenes spathulenol (6) [4], and caryophyllene oxide (7) [5], the two steroids b-sitosterol (8) and stigmast-4-en-3-one (9) [6], the triterpenoid oleanolic acid 3b-acetate (10) [7], and the six diterpenes, ferruginol (11), taxodione (12) [8], microstegiol (13) [9], manoyloxide (14) [10],1-oxo-salvibretol (15) [9], cryptojaponol (16) [11] and the flavone apigenin 7,4¢-methyl ether (17).…”

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confidence: 99%

Studies on Di- and Triterpenoids fromSalvia stamineawith Cytotoxic Activity

Topcu¹,

Altiner²,

Gozcu³

et al. 2003

Planta med

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A new ursane-type triterpenoid, 3 beta,11 alpha,21 alpha-trihydroxyurs-12-ene, named salvistamineol (1), has been isolated from the methanol extract of Salvia staminea. In addition to 1, the methanol extract yielded four known compounds and the acetone extract yielded twelve known compounds consisting of two sesquiterpenes, six diterpenoids, a triterpenoid, two steroids and one flavone. DNA damaging properties of the extracts and some isolated diterpenes were investigated against three yeasts and only taxodione gave a positive response and also showed the highest cytotoxic activity against a panel of cell lines among the investigated compounds in this study.

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confidence: 99%

Studies on Di- and Triterpenoids fromSalvia stamineawith Cytotoxic Activity

Topcu¹,

Altiner²,

Gozcu³

et al. 2003

Planta med

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“… The reduction of ketone 25 and subsequent dehydration of the resulting alcohol gave alkene 26 , , which was transformed into the tetrahydrofluorene derivative 27 , utilizing a new patented procedure developed in our laboratory . The reductive ozonolysis of the latter gave the new O -methyltaxodal ( 28 ), which was readily transformed into the target compound 8 . , The treatment of methyl ether 28 with NaClO 2 gave a 1:2.5 mixture of 12- O -methylcupressol 29 and its 5-epimer 30 , which were subsequently being converted into the corresponding phenolic derivatives cupressol ( 9 ) and its epimer 31 , respectively.…”

Section: Resultsmentioning

confidence: 99%

“…47 The observed and reported spectroscopic data of aldehyde 24 are identical. 48 Finally, taxodal (8) and cupressol (9) were synthesized starting from 12-O-methylsugiol (25), a natural terpenoid, 49 also available from other natural abietane diterpenoids (Scheme 4). 50 The reduction of ketone 25 and subsequent dehydration of the resulting alcohol gave alkene 26, 51,52 which was transformed into the tetrahydrofluorene derivative 27, utilizing a new patented procedure developed in our laboratory.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

In Vivo Biological Evaluation of a Synthetic Royleanone Derivative as a Promising Fast-Acting Trypanocidal Agent by Inducing Mitochondrial-Dependent Necrosis

et al. 2020

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The life-long and life-threatening Chagas disease is one of the most neglected tropical diseases caused by the protozoan parasite Trypanosoma cruzi. It is a major public health problem in Latin America, as six to seven million people are infected, being the principal cause of mortality in many endemic regions. Moreover, Chagas disease has become widespread due to migrant populations. Additionally, there are no vaccines nor effective treatments to fight the disease because of its long-term nature and complex pathology. Therefore, these facts emphasize how crucial the international effort for the development of new treatments against Chagas disease is. Here, we present the in vitro and in vivo trypanocidal activity of some oxygenated abietane diterpenoids and related compounds. The 1,4-benzoquinone 15, not yet reported, was identified as a fast-acting trypanocidal drug with efficacy against different strains in vitro and higher activity and lower toxicity than benznidazole in both phases of murine Chagas disease. The mode of action was also evaluated, suggesting that quinone 15 kills T. cruzi by inducing mitochondrion-dependent necrosis through a bioenergetics collapse caused by a mitochondrial membrane depolarization and iron-containing superoxide dismutase inhibition. Therefore, the abietane 1,4-benzoquinone 15 can be considered as a new candidate molecule for the development of an appropriate and commercially accessible anti-Chagas drug.

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“…The acetone extract of the roots of S. yunnanensis was subjected to silica gel column chromatography eluting with petroleum ether-EtOAc to obtain seven fractions (I-VII), which were further purified by silica gel, Sephadex LH-20, and HPLC to afford two new diterpenoids (salyunnanins I and J, 1 and 2 ) and ten known analogues: normiltioane ( 3 ) [ 11 ]; 5,6,7,8-tetrahydro-2,8,8-trimethyl-3-phenanthrenol ( 4 ) [ 12 ]; 6 α -hydroxysugiol ( 5 ) [ 13 ]; sugiol ( 6 ) [ 14 ] 6- oxo -ferruginol ( 7 ) [ 15 ]; danshenxinkun B ( 8 ) [ 16 ]; tanshinone I ( 9 ) [ 17 ]; methyltanshinonate ( 10 ) [ 18 ]; tanshinone IIA ( 11 ) [ 19 ] and crypotanshinone ( 12 ) [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

Diterpenoids from the Roots of Salvia yunnanensis

Xia

Yang

et al. 2015

Nat. Prod. Bioprospect.

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Two new diterpenoids, salyunnanins I and J (1 and 2), together with ten analogues, were isolated from the roots of Salvia yunnanensis. The structures of the new isolates, possessing different neo-clerodane and seco-abietane diterpenoid skeletons respectively, were elucidated on the basis of comprehensive spectroscopic data. All of the compounds were tested for the inhibitory activities against six human tumor lines in vitro, and several ones showed moderate cytotoxic activities.Graphical AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s13659-015-0080-4) contains supplementary material, which is available to authorized users.

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Diterpenes of Podocarpus ferrugineus bark

Cited by 28 publications

References 25 publications

Studies on Di- and Triterpenoids fromSalvia stamineawith Cytotoxic Activity

Studies on Di- and Triterpenoids fromSalvia stamineawith Cytotoxic Activity

In Vivo Biological Evaluation of a Synthetic Royleanone Derivative as a Promising Fast-Acting Trypanocidal Agent by Inducing Mitochondrial-Dependent Necrosis

Diterpenoids from the Roots of Salvia yunnanensis

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