Jatrowediol, a lathyrane diterpene from Jatropha weddelliana

Brum, Rosenei L.; Cavalheiro, Alberto José; Monachè, Franco Delle; Vencato, Ivo

doi:10.1590/s0103-50532001000200022

Cited by 11 publications

(8 citation statements)

References 4 publications

(4 reference statements)

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“…NMR spectra identical to those reported in the literature were observed also for compounds 10 [ 65 ], 11 [ 66 ], 12 [ 67 ], 13 [ 68 ], 14 [ 69 , 70 ], 15 [ 71 ], 16 [ 72 , 73 ], 17 [ 74 ], 18 [ 74 ], 19 [ 75 ], and 20 [ 75 ].…”

Section: Methodssupporting

confidence: 82%

Alvaxanthone, a Thymidylate Synthase Inhibitor with Nematocidal and Tumoricidal Activities

Maj

Mori²,

Sobich

et al. 2020

Molecules

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With the aim to identify novel inhibitors of parasitic nematode thymidylate synthase (TS), we screened in silico an in-house library of natural compounds, taking advantage of a model of nematode TS three-dimensional (3D) structure and choosing candidate compounds potentially capable of enzyme binding/inhibition. Selected compounds were tested as (i) inhibitors of the reaction catalyzed by TSs of different species, (ii) agents toxic to a nematode parasite model (C. elegans grown in vitro), (iii) inhibitors of normal human cell growth, and (iv) antitumor agents affecting human tumor cells grown in vitro. The results pointed to alvaxanthone as a relatively strong TS inhibitor that causes C. elegans population growth reduction with nematocidal potency similar to the anthelmintic drug mebendazole. Alvaxanthone also demonstrated an antiproliferative effect in tumor cells, associated with a selective toxicity against mitochondria observed in cancer cells compared to normal cells.

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Section: Methodssupporting

confidence: 82%

Alvaxanthone, a Thymidylate Synthase Inhibitor with Nematocidal and Tumoricidal Activities

Maj

Mori²,

Sobich

et al. 2020

Molecules

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“…Compound exhibiting inhibition less than 50% at 50 mM is considered as inactive. As summarized in Table 3, jatropholane diterpenes (8)(9)(10)(11)(12)(13) did not inhibit TrxR, while lathyrane (1-7) and rhamnofolane (15)(16)(17)(18)(19)(20)(21) diterpenes showed moderate inhibitory activities with IC 50 values ranging from 6.8 to 39.1 mM. Compounds 17 and 19 represented the most active compounds with IC 50 values at 9.4 and 6.8 mM, respectively.…”

Section: Resultsmentioning

confidence: 97%

“…As summarized in Table 3, jatropholane diterpenes (8)(9)(10)(11)(12)(13) did not inhibit TrxR, while lathyrane (1-7) and rhamnofolane (15)(16)(17)(18)(19)(20)(21) diterpenes showed moderate inhibitory activities with IC 50 values ranging from 6.8 to 39.1 mM. Compound exhibiting inhibition less than 50% at 50 mM is considered as inactive.…”

Section: Resultsmentioning

confidence: 99%

Natural thioredoxin reductase inhibitors from Jatropha integerrima

et al. 2015

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Nine new diterpenoids, jatrointelones A-I (1-9), including seven lathyranes (1-7) and two jatropholanes (8 and 9), along with 12 known analogues (10-21) were isolated from the trunks of Jatropha integerrima.The structures were elucidated by spectroscopic analysis, and the absolute configurations of 1-7 were determined by combination of single crystal X-ray diffraction, CD analysis (exciton chirality and Rh 2 (OCOCF 3 ) 4 -induced methods), and chemical correlations. All of the isolates were screened for inhibitory activity against thioredoxin reductase (TrxR), which is a potential target for cancer chemotherapy with redox balance and antioxidant functions. Compounds 1, 3, 6, 7, and 15-21 exhibited stronger activity than the positive control, curcumin (IC 50 ¼ 25.0 mM), in which 17 and 19 represented the most active compounds with IC 50 values of 9.4 and 6.8 mM, respectively. The active diterpenoids represent the rare examples of non-aromatic TrxR inhibitors from nature, and a preliminary structureactivity relationship is also proposed.

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“…These data imply that casbene is biosynthesized in most organs of Jatropha, regardless of their developmental stages. Lathyrane-type diterpenes and phorbol were found in various tissues of other Euphorbiaceae plants, e.g., jatrowediol from J. weddelliana stems (Brum et al 2001), multi done from J. multi da stems (Das et al 2009), and sapintoxin A from unripe S. indicum fruit (Taylor et al 1981). us, the JcCSH gene is expected to be involved in the biosynthesis of a broad range of diterpenes, including phorbol.…”

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confidence: 99%

Characterization of the casbene synthase homolog from Jatropha (<i>Jatropha curcas</i> L.)

Nakano

Ohtani

Polsri

et al. 2012

Plant Biotechnology

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Abstracte high oil content of Jatropha (Jatropha curcas L.) seeds makes Jatropha an attractive resource for the production of sustainable bioenergy. However, the Jatropha seed kernels also contain antinutrients and various toxins that persist in the oil and seed cakes and pose a safety risk. Since phorbol esters (PEs) are the major contributor to toxicity, a better understanding of PE biosynthesis is expected to elucidate an e ective strategy for the utilization of Jatropha plants. In this study, a Jatropha curcas casbene synthase homolog (JcCSH) with high sequence similarity to casbene synthases (CSs) from Ricinus communis, Euphorbia esula, and Sapium sebiferum was cloned from Jatropha leaf tissue. CS has been hypothesized to catalyze the rst step of phorbol biosynthesis. JcCSH encodes a protein that contains a chloroplast transit peptide and a DDXXD motif that is conserved among known terpene cyclases. JcCSH was expressed in seedlings, mature leaves, and the esh of developing fruits, but not in developing seeds. Our results suggest that JcCSH is widely involved in casbene biosynthesis in various tissues other than seeds. Key words:Casbene synthase, Jatropha (Jatropha curcas L.), phorbol ester.Recently, Jatropha (Jatropha curcas L.) has attracted much attention as a potential resource for the production of sustainable bioenergy, following concerns about the depletion of fossil fuels and global warming. Jatropha, a perennial shrub that originated in Mexico and Central America and belongs to the Euphorbiaceae family, is widely distributed between the tropics of Cancer and Capricorn.e seed kernels are rich in oil (44-62%) and proteins (22-35%), making this plant a favorable feedstock not only for biodiesel but also for protein (Makkar et al. 1998). However, it is hard to utilize the Jatropha seed cakes for animal feed a er extracting the oil, because several antinutrients and various toxins, such as curcin, trypsin inhibitors, and phorbol esters (PEs), are contained in the seed kernels (Makkar et al. 1998). Among these harmful substances, the major contributor to toxicity is PEs (Makkar et al. 1998). PEs are tetracyclic diterpenoids that occur in the seeds, sap, and latex of plants of the ymelaeaceae and Euphobiaceae families. Six PE derivatives were identified from Jatropha oil and their structures were solved by nuclear magnetic resonance (NMR) analysis. They were all found to contain 12-hydroxy-16-deoxyphorbol (Adolf et al. 1984;Haas et al. 2002). Since a PE isolated from Jatropha is known to have tumor-promoting activity (Hirota et al. 1988), it is critical to eliminate the risk of PEs toxicity if Jatropha is to be used commercially. One e ective means of doing so is to shut down and/or modify the biosynthesis of PEs at the molecular level.PEs are composed of a tetracyclic diterpene, named tiglian, and two fatty acids, which are esterified to C13 and C16 of the tiglian skeleton (Haas et al. 2002). The biosynthetic pathway of PEs is currently poorly understood. The only presumed step is the first cyclization of...

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Jatrowediol, a lathyrane diterpene from Jatropha weddelliana

Cited by 11 publications

References 4 publications

Alvaxanthone, a Thymidylate Synthase Inhibitor with Nematocidal and Tumoricidal Activities

Alvaxanthone, a Thymidylate Synthase Inhibitor with Nematocidal and Tumoricidal Activities

Natural thioredoxin reductase inhibitors from Jatropha integerrima

Characterization of the casbene synthase homolog from Jatropha (<i>Jatropha curcas</i> L.)

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