Goniothalamin oxide: An embryotoxic compound from (annonaceae)

Sam, T. W.; Sew-Yeu, Chew; Matsjeh, Sabirin; Gan, E. K.; Razak, Dzulkifli Abdul; Mohamed, Abdul L

doi:10.1016/s0040-4039(00)95462-5

Cited by 82 publications

(27 citation statements)

References 8 publications

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“…(Note: Color caused by Grubbs catalyst) R f = 0.9 (8:2 (v/v) hexanes:EtOAc). Spectral data gave a satisfactory match to previous reports xvii. [α] 25 D + 100 ( c 0.4, CHCl 3 ); IR (neat, cm −1 ) 1724, 1247, 1041, 815; 1 H NMR (CDCl 3 , 600 MHz) 7.34 (m, 5H), 6.94 (ddd, J = 9.7, 4.9, 3.7 Hz, 1H), 6.08 (ddd, J = 9.6, 3.7, 1.7, 1H), 4.45 (ddd, J = 9.1, 5.8, 5.8 Hz, 1H), 3.89 (d, J = 1.9 Hz, 1H), 3.27 (dd, J = 5.6, 1.9 Hz, 1H), 2.59 (m, 2H); 13 C NMR (CDCl 3 , 600 MHz) δ 163.7, 144.2, 135.7, 128.7, 128.6, 125.7, 121.6, 77.1, 61.5, 57.3, 25.9; HRMS (CI) calcd for [C 13 H 13 O 3 + Na] + : 239.0684 Found: 239.0686.…”

Section: Methodssupporting

confidence: 87%

De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations

Harsh

O’Doherty

2009

Tetrahedron

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Section: Methodssupporting

confidence: 87%

De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations

Harsh

O’Doherty

2009

Tetrahedron

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“…Different authors have evaluated alternative therapies for cancer treatment, including drugs with anti‐inflammatory properties and cytotoxicity activity such as Goniothalamin (GTN). GTN is a styryl lactone originated from plants of the Goniothalamus genus, which has presented toxicity against different lineages of cancer cells (Sam et al, ; Vendramini‐Costa et al, ; Al‐Qubaisi et al, ). In the prostate, GTN effects were able to decrease the inflammatory process and improve glandular morphology during senescence (Kido et al, ).…”

Section: Introductionmentioning

confidence: 99%

Steroidal hormone and morphological responses in the prostate anterior lobe in different cancer grades after Celecoxib and Goniothalamin treatments in TRAMP mice

Silva

Kido

Montico

et al. 2018

Cell Biology International

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Prostate cancer is the second most diagnosed cancer in the world, and alternative methods to prevent and treat different lesion grades need to be evaluated. The objective was to evaluate the morphological, hormonal, and inflammatory responses in the prostate anterior lobe in transgenic adenocarcinoma of the mouse prostate (TRAMP), following Celecoxib and Goniothalamin (GTN) treatments. All animals were treated for 4 weeks, from 8 weeks of age and euthanized either immediately after treatment (12-week-old mice: immediate response) or later (22-week-old mice: late response). The results showed a significant increase of high-grade prostatic intraepithelial neoplasia (HGPIN) and well-differentiated adenocarcinoma (WDA), according to the age in the control groups. Celecoxib treatment decreased the WDA incidence in the late response group. GTN led to a significant healthy tissue increase, and an LGPIN and HGPIN decrease in the immediate response group. In the late response group, GTN led to healthy area increase and there was no occurrence of WDA. AR and ERα immunoexpressions were reduced by both treatments in the immediate response groups. However, only GTN was able to decrease the ERα level in the late response group. Regarding COX-2 immunoreactivity, both treatments reduced the frequency of this enzyme. We can conclude that the prostate anterior lobe is a good model to study prostate cancer, considering its slow progression. Both treatments led to cancer delay in the prostate anterior lobe. However, GTN pointed towards a better treatment spectrum in the signaling pathways in the prostate microenvironment, particularly in ERα.

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“…Regarding goniothalamin (GTN), astyryl lactone compound isolated from the plants of the Goniothalamus genus and found in an enantiomeric form (R), it has demonstrated selective toxicity against different cancer cell lineages (Sam et al 1987, Al-Qubaisi et al 2011. According to Vendramini-Costa et al (2010) both enantiomerically pure (R) and racemic (racGTN) forms showed antiproliferative features in an Ehrlich solid tumor model mice.…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory therapies in TRAMP mice: delay in PCa progression

Kido¹,

Montico²,

Sauce³

et al. 2016

Endocrine-Related Cancer

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The aim of this study was to characterize the structural and molecular biology as well as evaluate the immediate and late responses of prostatic cancer in the transgenic adenocarcinoma of the mouse prostate (TRAMP) model after treatment with goniothalamin (GTN) and celecoxib. The treated mice received GTN (150 mg/kg, gavage) or celecoxib (10 mg/kg, gavage) from 8 to 12 weeks of age. They were killed at different ages: the immediate-response groups at 12 weeks and the late-response groups at 22 weeks. The ventral prostate was collected for light microscopy, immunohistochemistry, western blotting, TUNEL, and ELISA. Morphological analyses indicated that GTN treatment delayed the progression of prostatic adenocarcinoma, leading to a significant decrease of prostatic lesion frequency in both experimental period responses to this treatment, mainly high-grade prostatic intraepithelial neoplasia and well-differentiated adenocarcinoma. Also, the celecoxib treatment showed a particular decrease in the proliferative processes (PCNA) in both the experimental periods. Despite celecoxib diminishing the COX2 and IGFR1 levels, GTN presented higher action spectrum considering the decrease of a greater molecular number involved in the proliferative and inflammatory processes in prostatic cancer. Goniothalamin attenuated the pro-inflammatory response in TRAMP prostatic microenvironment, delaying prostate cancer (PCa) progression. Celecoxib treatment was efficient in the regulation of COX2 in the TRAMP mice, mainly in the advanced disease grade. Finally, we concluded that inflammatory process control in early grades of PCa was crucial for the downregulation of the signaling pathways involved in the proliferative processes in advanced cancer grades.

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Goniothalamin oxide: An embryotoxic compound from (annonaceae)

Cited by 82 publications

References 8 publications

De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations

De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations

Steroidal hormone and morphological responses in the prostate anterior lobe in different cancer grades after Celecoxib and Goniothalamin treatments in TRAMP mice

Anti-inflammatory therapies in TRAMP mice: delay in PCa progression

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