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, Hirota; Suttajit, Maitree; Rawangkan, Anchalee; Iida, Keisuke; Limtrakul, Pornngarm; Umsumarng, Sonthaya; Suganuma, Masami

doi:10.1007/s00432-017-2341-6

Cited by 15 publications

(12 citation statements)

References 46 publications

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“…On the other hand, Hirota et al (2017) reported the identification of DHP as the fundamental structural core which is derived from 12-deoxy-16-hydroxy-phorbol-4 - [12 ,14 -butadienyl]-6 -[16 ,18 ,20 -nonatrienyl + were also reported in J. curcas seeds (Wink et al, 2000). Even more so, Haas, Sterk & Mittelbach (2002) reported the identification of diterpenes named Jatropha factors C 2 to C 6 through ESI-MS m/z 711 [M+H] + and of DHP (m/z of 365 [M+H] + ).…”

Section: Discussionmentioning

confidence: 99%

“…In Mexico, Brazil and India, non-toxic varieties of this species have been identified with very low or non-detectable levels of phorbol esters (PEs) in seeds ( Laviola et al, 2010 ; Martínez-Herrera, Chel-Guerrero & Martínez-Ayala, 2004 ; Kumar, Anand & Reddy, 2011 ). PEs are known as Jatropha factors because each one of them has the same nucleus diterpene moiety, namely, 12-deoxy-16-hydroxy-phorbol (DHP) which is coupled to unstables intramolecular diterpenes (named C 1 –C 6 factors) ( Hirota et al, 2017 ).…”

Section: Introductionmentioning

confidence: 99%

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Chemical analysis of callus extracts from toxic and non-toxic varieties of Jatropha curcas L.

Leyva-Padrón

Vanegas‐Espinoza

Evangelista‐Lozano

et al. 2020

PeerJ

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Jatropha curcas L. belongs to Euphorbiaceae family, and it synthesizes flavonoid and diterpene compounds that have showed antioxidant, anti-inflammatory, anticancer, antiviral, antimicrobial, antifungal and insecticide activity. Seeds of this plant accumulate phorbol esters, which are tigliane type diterpenes, reported as toxic and, depending on its concentration, toxic and non-toxic varieties has been identified. The aim of this work was to characterize the chemical profile of the extracts from seeds, leaves and callus of both varieties (toxic and non-toxic) of Jatropha curcas, to verify the presence of important compounds in dedifferentiated cells and consider the possibility of using these cultures for the massive production of metabolites. Callus induction was obtained using NAA (1.5 mg L−1) and BAP (1.5 mg L−1) after 21 d for both varieties. Thin layer chromatography analysis showed differences in compounds accumulation in callus from non-toxic variety throughout the time of culture, diterpenes showed an increase along the time, in contrast with flavonoids which decreased. Based on the results obtained through microQTOF-QII spectrometer it is suggested a higher accumulation of phorbol esters, derived from 12-deoxy-16-hydroxy-phorbol (m/z 365 [M+H]+), in callus of 38 d than those of 14 d culture, from both varieties. Unlike flavonoids accumulation, the MS chromatograms analysis allowed to suggest lower accumulation of flavonoids as the culture time progresses, in callus from both varieties. The presence of six glycosylated flavonoids is also suggested in leaf and callus extracts derived from both varieties (toxic and non-toxic), including: apigenin 6-C-α-L-arabinopyranosyl-8-C-β-D-xylopyranoside (m/z 535 [M+H]+), apigenin 4′-O-rhamnoside (m/z 417 [M+H]+), vitexin (m/z 433 [M+H]+), vitexin 4′-O-glucoside-2″-O-rhamnoside (m/z 741 [M+H]+), vicenin-2 (m/z 595 [M+H]+), and vicenin-2,6″-O-glucoside (m/z 757 [M+H]+).

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemical analysis of callus extracts from toxic and non-toxic varieties of Jatropha curcas L.

Leyva-Padrón

Vanegas‐Espinoza

Evangelista‐Lozano

et al. 2020

PeerJ

View full text Add to dashboard Cite

show abstract

“…On the other hand, Hirota et al (2017) reported the identification of DHP as the fundamental structural core which is derived from 12-deoxy-16-hydroxy-phorbol-4'-[12',14'-butadienyl]-6'- [16',18',20'-nonatrienyl (Wink et al, 2000). Even more so, Haas, Sterk & Mittelbach, (2002) reported the identification of diterpenes named Jatropha factors C 2 to C 6 through ESI-MS m/z 711 [M+H] + and of DHP (m/z of 365 [M+H] + ).…”

Section: Discussionmentioning

confidence: 99%

“…In Mexico, Brazil and India, it have been identified non-toxic varieties of this species with very low or non-detectable levels of phorbol esters (PEs) in seeds (Laviola et al, 2010;Martínez-Herrera, Chel-Guerrero & Martínez-Ayala, 2004;Kumar, Anand & Reddy, 2011). PEs are known as Jatropha factors because each one of them has the same nucleus diterpene moiety, namely, 12deoxy-16-hydroxy-phorbol (DHP) which is coupled to unstables intramolecular diterpenes (named C 1 -C 6 factors) (Hirota et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Peer Review #2 of "Chemical analysis of callus extracts from toxic and non-toxic varieties of Jatropha curcas L. (v0.2)"

2020

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“…For example, they can induce acute toxic effects in animals and insets and cause skin irritant and promote tumors in human beings (Becker and Makkar, 1998;Devappa et al, 2012;Katole et al, 2011;Li et al, 2010;Rug and Ruppel, 2000). In contrast, recent studies revealed phorbol esters can exhibit antimicrobial and antitumor activities when applied at low concentrations (Devappa et al, 2013b;Fujiki et al, 2017). The diverse bioactivities of phorbol esters are not only dependent on dosage effects but also associated with varied structures among phorbol esters and their derivates.…”

Section: Introductionmentioning

confidence: 99%

Tissue-specific accumulation profiles of phorbol esters inJatropha curcasand gene induction in response to abiotic and biotic stresses

Zhang

Fan

Dai

et al. 2020

Preprint

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Jatropha curcas L. (J. curcas), a shrub plant of the Euphorbiaceae family, has received enormous attention as a promising biofuel plant for the production of biodiesel and medical potential in ethnopharmacology. However, the tumor-promoter toxin phorbol esters present in J. curcas raises concerns for health and environmental risk as its large-scale cultivation limits the use of meal obtained after oil extraction for animal feed. Here, we determined the variation of phorbol ester profiles and contents in eight J. curcas tissues by high performance liquid chromatography (HPLC) and found phorbol esters present in all parts of the plant except the seed shell. We showed tissue-specific patterns of accumulation of phorbol esters and associated terpenoids at the transcriptomic level with high transcript levels in reproductive and young tissues. Genes involved in the same module of terpenoids biosynthesis were positively correlated. We further present diverse abiotic and biotic stresses that had different effects on the accumulation of transcripts in terpenoids shared and branched terpenoid pathways in plant seedlings. The fine-tuning of terpenoids biosynthesis may link with ecological functions in plants under extreme environments and defense against pathogens.

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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

Cited by 15 publications

References 46 publications

Chemical analysis of callus extracts from toxic and non-toxic varieties of Jatropha curcas L.

Chemical analysis of callus extracts from toxic and non-toxic varieties of Jatropha curcas L.

Peer Review #2 of "Chemical analysis of callus extracts from toxic and non-toxic varieties of Jatropha curcas L. (v0.2)"

Tissue-specific accumulation profiles of phorbol esters inJatropha curcasand gene induction in response to abiotic and biotic stresses

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