Degradation of Jatropha curcas phorbol esters derived from Jatropha oil cake and their tumor-promoting activity

Nakao, Motoyuki; Hasegawa, Go; Yasuhara, Tadashi; Ishihara, Yoko

doi:10.1016/j.ecoenv.2014.07.009

Cited by 12 publications

(12 citation statements)

References 14 publications

(21 reference statements)

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“…For the 4,12-dideoxyphorbol of m/z 329, the elimination of one water molecule generates the ion of m/z 311 commonly found in samples containing PEs since it is related to the main degradation product of the phorbol nucleus [8,9]. In a second fragmentation route, via a rearrangement [1,3], H occurs the elimination of ethanol group (HC ≡ COH, 42 Da). The proposed fragmentation mechanisms from ionization in two different sites are shown in Fig.…”

Section: Discussionmentioning

confidence: 99%

“…To PEs quantification, non-toxic J. curcas leaf extracts were chosen as matrix, and it was spiked with PDA at different concentration levels (1,5,10,15,20,25, and 30 μg/mL). Selected reaction monitoring (SRM) mode was used for the quantification experiments (transition of m/z 431 to 391).…”

Section: Analytical Performancementioning

confidence: 99%

“…J atropha curcas L. is an oilseed plant found in tropical and subtropical regions [1]. Its seeds consist of 30-40% of oil which makes it useful for biodiesel production.…”

Section: Introductionmentioning

confidence: 99%

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Molecularly Imprinted Polymer-Coated Probe Electrospray Ionization Mass Spectrometry Determines Phorbol Esters and Deoxyphorbol Metabolites in Jatropha curcas Leaves

Silva

Carvalho

Vaz

et al. 2019

J. Am. Soc. Mass Spectrom.

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In this study, a molecularly imprinted polymer-coated probe electrospray ionization mass spectrometry (MIPCPESI-MS) method was developed for detection of phorbol esters (PEs) and deoxyphorbol metabolites in Jatropha curcas leaves. Such an approach was established by sticking on a metallic needle a molecularly imprinted polymer to particularly design a MIP-coated probe for selective sampling and ioni zation of PEs and deoxyphorbol metabolites. By a subsequent application of a high voltage and methanol, as spray solvent, ESI was generated for direct and rapid analysis under ambient and open-air conditions. MIP-coated probe exhibited a high sampling capacity of the PEs and its metabolites in methanolic extracts of J. curcas leaves compared with the non-imprinted polymer (NIP)-coated probe. MIPCPESI-MS allowed the detection of phorbol 12,13-diacetate (PDA) from J. curcas leaves with minimal sample preparation, and with detection limit and quantification reaching 0.28 μg/mL and 0.92 μg/mL, respectively. Also, good linearity was obtained with R 2 > 0.99 and precision and accuracy values between 4.06-13.49% and − 1.60 to − 15.26%, respectively. The current method was successfully applied to screening methanolic extracts of six different J. curcas leaf genotypes (three toxic and three non-toxic). PDA and three PE deoxyphorbol metabolites were identified only from toxic genotypes, in which PDA was determined with concentration ranging from 222.19 ± 23.55 to 528.23 ± 19.72 μg/g. All these findings support that the MIPCPESI-MS method developed here has a high potential for the analysis of PEs in plant extracts enabling differentiation of toxic and non-toxic genotypes earlier in the leaves.

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Section: Discussionmentioning

confidence: 99%

Section: Analytical Performancementioning

confidence: 99%

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Molecularly Imprinted Polymer-Coated Probe Electrospray Ionization Mass Spectrometry Determines Phorbol Esters and Deoxyphorbol Metabolites in Jatropha curcas Leaves

Silva

Carvalho

Vaz

et al. 2019

J. Am. Soc. Mass Spectrom.

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“…Regular solvent renewal is of utmost importance to ensure good yields. 18 However, such results are contrary to Zimila et al, 10 where adding modifiers slightly reduced the extraction capacity of pure MeOH. These differences are presumably due to differences in the matrix composition.…”

Section: -Way Interactions (Extraction Time × Stirring Rate Extraction Time × Sample:solvent Ratio Extraction Time × Extracting Solvent Smentioning

confidence: 82%

Efficient Vortex-assisted Extraction of Phorbol Esters from Jatropha Leaves and Correlation Between Leaves and Seeds in Phorbol EstersContent

et al. 2021

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This work aimed to optimise and validate the vortex-assisted extraction with high-performance liquid chromatography-ultraviolet detection (HPLC-UV) method to quantify phorbol esters (PEs) in Jatropha leaves. Additionally, to evaluate the correlation between PEs content in leaves and seeds. The results of PEs content were expressed as equivalent of the major Jatropha phorbol ester, 12-deoxy-16-hydroxyphorbol-4'-[12',14'-butadienyl]-6'-[16',18',20'-nonatrienyl]-bicyclo[3.1.0]-hexane-(13-O)-2'-[carboxylate]-(16-O)-3'-]8'-butenoic-10']ate (DHPB) . One-variable-at-time strategy and 25-1V factorial fractional design were employed to determine the effects of solvent type, volume, stirring frequency, extraction time and cycles on yield. The quantification was performed using HPLC-UV. The optimum conditions were three extractions with 2% tetrahydrofuran:dichloromethane (1:1) in methanol (THF:DCM/MeOH). The sample:solvent ratio was 1 mg:25 μL, and the vortex stirring was 2200 rpm for 5 minutes. The method showed good linearity (R2 0.999), recoveries (97 to 105%), selectivity and repeatability (RSD 1.93-7.95%). In addition, good limits of detection and quantification of 2.19 and 6.65 ng μL"1, respectively, were noted. DHPB content in leaves and seeds ranged from 0.01 to 0.38 mg g"1 and 0.41 to 1.82 mg g"1, respectively. There is a statistically significant and positive linear relationship between leaves and seeds for DHPB content. These results may have practical application in analysing and predicting the amount of PEs in Jatropha leaves for environmental safety studies and the selection of better varieties for genetic improvement. Keywords: correlation, Jatropha leaves; Jatropha seeds; phorbol esters; vortex-assisted.

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“…Although phorbol ester is easily degraded by various methods, resulting seed cake should be carefully tested for toxicity: the seed contains toxic compounds, such as phorbol ester and curcin, the latter of which is a type-1 ribosome inactivating protein (He et al 2011). One publication about DHPB reported the degradation of active DHPB by esterase KM109 from soil bacterium into non-toxic compound, with reduced cell transforming activity (Nakao et al 2015). Recently, a new method was developed for the complete utilization of seeds: briquettes of seed cake were made using a vertical extruding machine, and producer gas was obtained by gasifying the briquettes in a downdraft gasifier.…”

Section: Degradation Of Phorbol Ester For Utilization Of Seed Oil Andmentioning

confidence: 99%

Phorbol esters in seed oil of Jatropha curcas L. (saboodam in Thai) and their association with cancer prevention: from the initial investigation to the present topics

Fujiki

Suttajit

Rawangkan

et al. 2017

J Cancer Res Clin Oncol

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PurposeIn 1988, we first reported the complete chemical structure of a new type of phorbol ester, abbreviated to DHPB, found in seed oil of Jatropha curcas L. (Saboodam in Thai) and its tumor-promoting activity on mouse skin. Although this seed oil contains toxic phorbol ester, it was planned to use it as a feasible renewable oil and the extracted seed cake as fertilizer. This utilization value opened a new science of Jatropha curcas.MethodsThe main experimental results are cited from our publications, and the relevant literature screened from journals and PubMed.Results and discussionThis paper begins with our original work on the structural elucidation of a new phorbol ester, 12-deoxy-16-hydroxyphorbol (DHPB): its tumor-promoting activity was compared with that of TPA. We think that it is timely to review the following research advances with Jatropha curcas, so numerous topics are classified as follows: (1) historical development of phorbol esters in seed oil; (2) toxicity of phorbol ester based on various bioassays; (3) degradation of phorbol ester; (4) a new pharmaceutical compound in seed; and (5) tumor promotion and progression with endogeneous tumor promoters in human carcinogenesis. The discovery of phorbol ester in seed oil raised awareness of the danger of public use of seed oil and seed cake in Thailand, and also indicated the necessity of discussing the concept of primary and tertiary cancer preventions.ConclusionIt is worthwhile to study the future benefits and cancer risks of globally distributed Jatropha curcas L.

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Degradation of Jatropha curcas phorbol esters derived from Jatropha oil cake and their tumor-promoting activity

Cited by 12 publications

References 14 publications

Molecularly Imprinted Polymer-Coated Probe Electrospray Ionization Mass Spectrometry Determines Phorbol Esters and Deoxyphorbol Metabolites in Jatropha curcas Leaves

Molecularly Imprinted Polymer-Coated Probe Electrospray Ionization Mass Spectrometry Determines Phorbol Esters and Deoxyphorbol Metabolites in Jatropha curcas Leaves

Efficient Vortex-assisted Extraction of Phorbol Esters from Jatropha Leaves and Correlation Between Leaves and Seeds in Phorbol EstersContent

Phorbol esters in seed oil of Jatropha curcas L. (saboodam in Thai) and their association with cancer prevention: from the initial investigation to the present topics

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