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Title: Oxidation and cyclization of casbene in the biosynthesis of Euphorbia factors from mature seeds of Euphorbia lathyris L.

Authors:
; ; ; ; ; ; ; ; ORCiD logo; ; ORCiD logo;
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1288983
Grant/Contract Number:
FC02-07ER64494
Resource Type:
Journal Article: Published Article
Journal Name:
Proceedings of the National Academy of Sciences of the United States of America
Additional Journal Information:
Journal Volume: 113; Journal Issue: 34; Related Information: CHORUS Timestamp: 2017-06-24 16:20:34; Journal ID: ISSN 0027-8424
Publisher:
Proceedings of the National Academy of Sciences
Country of Publication:
United States
Language:
English

Citation Formats

Luo, Dan, Callari, Roberta, Hamberger, Britta, Wubshet, Sileshi Gizachew, Nielsen, Morten T., Andersen-Ranberg, Johan, Hallström, Björn M., Cozzi, Federico, Heider, Harald, Lindberg Møller, Birger, Staerk, Dan, and Hamberger, Björn. Oxidation and cyclization of casbene in the biosynthesis of Euphorbia factors from mature seeds of Euphorbia lathyris L.. United States: N. p., 2016. Web. doi:10.1073/pnas.1607504113.
Luo, Dan, Callari, Roberta, Hamberger, Britta, Wubshet, Sileshi Gizachew, Nielsen, Morten T., Andersen-Ranberg, Johan, Hallström, Björn M., Cozzi, Federico, Heider, Harald, Lindberg Møller, Birger, Staerk, Dan, & Hamberger, Björn. Oxidation and cyclization of casbene in the biosynthesis of Euphorbia factors from mature seeds of Euphorbia lathyris L.. United States. doi:10.1073/pnas.1607504113.
Luo, Dan, Callari, Roberta, Hamberger, Britta, Wubshet, Sileshi Gizachew, Nielsen, Morten T., Andersen-Ranberg, Johan, Hallström, Björn M., Cozzi, Federico, Heider, Harald, Lindberg Møller, Birger, Staerk, Dan, and Hamberger, Björn. Tue . "Oxidation and cyclization of casbene in the biosynthesis of Euphorbia factors from mature seeds of Euphorbia lathyris L.". United States. doi:10.1073/pnas.1607504113.
@article{osti_1288983,
title = {Oxidation and cyclization of casbene in the biosynthesis of Euphorbia factors from mature seeds of Euphorbia lathyris L.},
author = {Luo, Dan and Callari, Roberta and Hamberger, Britta and Wubshet, Sileshi Gizachew and Nielsen, Morten T. and Andersen-Ranberg, Johan and Hallström, Björn M. and Cozzi, Federico and Heider, Harald and Lindberg Møller, Birger and Staerk, Dan and Hamberger, Björn},
abstractNote = {},
doi = {10.1073/pnas.1607504113},
journal = {Proceedings of the National Academy of Sciences of the United States of America},
number = 34,
volume = 113,
place = {United States},
year = {Tue Aug 09 00:00:00 EDT 2016},
month = {Tue Aug 09 00:00:00 EDT 2016}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at 10.1073/pnas.1607504113

Citation Metrics:
Cited by: 8works
Citation information provided by
Web of Science

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  • A sensitive test system for the detection of unknown tumor promoters is reported. A description is given of the use of the system in detecting promoter activity in Euphorbia lathyris extracts before and after treatment with organic solvents in the preparation of synthetic fuels. Using both normal and ts-virus infected cells, tumor promoter-like activities were detected and identified as ingenol esters in the active fraction of the latex of E. lathyris. These activities were shown to be inactive after extraction of potential sources of fuel. Results indicate that there should be no toxicological dangers after mechanical harvesting and drying. Thismore » finding has much potential significance, both for the further processing of E. lathyris and for other possible sources of energy. (JMT)« less
  • Published and unpublished estimates of land and water requirements and energy yield were used to prepare energy budgets for 4 potential biocrude (liquid fuel) crops in the SW USA: the perennials Calotropis procera and Chrysothamnus paniculatus and the annuals Euphorbia lathyris and Grindelia camporum. Estimated annual costs are examined and discussed for an operation processing 300,000 t/yr. The cheapest energy was produced by C. paniculatus, although it required the largest land area. The paper emphasizes that selecting for biocrude content (biomass quality) of plants may be at the expense of productivity (quantity) since the 2 have been shown to bemore » inversely related in many cases. 8 references.« less
  • Particulate (15,000g) fractions from developing seeds of honesty (Lunaria annua L.) and mustard (Sinapis alba L.) synthesize radioactive very long chain monounsaturated fatty acids (gadoleic, erucic, and nervonic) from (1-{sup 14}C)oleoyl-CoA and malonyl-CoA or from oleoyl-CoA and (2-{sup 14}C)malonyl-CoA. The very long chain monounsaturated fatty acids are rapidly channeled to triacylglycerols and other acyl lipids without intermediate accumulation of their CoA thioesters. When (1-{sup 14}C)oleoyl-CoA is used as the radioactive substrate, phosphatidylcholines and other phospholipids are most extensively radiolabeled by oleoyl moieties rather than by very long chain monounsaturated acyl moieties. When (2-{sup 14}C)malonyl-CoA is used as the radioactive substrate,more » no radioactive oleic acid is formed and the newly synthesized very long chain monounsaturated fatty acids are extensively incorporated into phosphatidylcholines and other phospholipids as well as triacylglycerols. The pattern of labeling of the key intermediates of the Kennedy pathway, e.g. lysophosphatidic acids, phosphatidic acids, and diacylglycerols by the newly synthesized very long chain monounsaturated fatty acids is consistent with the operation of this pathway in the biosynthesis of triacylglycerols.« less
  • The structures of those tetracyclic triterpenols in Euphorbia lathyris latex which had not previously been known were elucidated. Many times dependent incubations were done, investigating the stability of the whole latex system and the re-suspended pellet systems. The effects of centrifugation on the biosynthesis were examined. The partitioning of the triterpenoid pool as a function of when the compounds were made was examined. A number of incubations were performed in the hopes of observing some interconversion of the individual triterpenols. The effect of several inhibitors on the biosynthesis of the triterpenoids was examined. The effects of the morpholine based fungicides,more » tridemorph and fenpropimorph were examined. The possibility that cycloartenol is made via lanosterol was investigated by synthesizing 4-R-4-{sup 3} H-mevalonic acid and incubating the latex with a mixture of this and {sup 14}C-mevalonic acid.« less
  • The structures of triterpenols, not previously been known, from Euphorbia lathyris latex are reported. A method for quantifying very small amounts of these compounds was developed. Concerning the biochemistry of the latex, no exogenous cofactors were required for the biosynthesis and the addition of compounds such as NADPAH and ATP do not stimulate the biosynthesis. The addition of DTE or a similar anti-oxidant was found to help reduce the oxidation of the latex, thus increasing the length of time that the latex remains active. The requirement of a divalent cation and the preference for Mn in the pellet was observed.more » The effect of several inhibitors on the biosynthesis of the triterpenoids was examined. Mevinolin was found to inhibit the biosynthesis of the triterpenoids from acetate, but not mevalonate. A dixon plot of the inhibition of acetate incorporation showed an I/sub 50/ concentration of 3.2 ..mu..M. Fenpropimorph was found to have little or no effect on the biosynthesis. Tridemorph was found to inhibit the biosynthesis of all of the triterpenoids with an I/sub 50/ of 4 ..mu..M. It was also observed that the cyclopropyl containing triterpenols, cycloartenol and 24-methylenecycloartenol were inhibited much more strongly than those containing an 8-9 double bond, lanosterol and 24-methylenelanosterol. The evidence indicates, but does not definetely prove, that lanosterol and 24-methylenelanosterol are not made from cycloartenol and 24-methylenecycloartenol via a ring-opening enzyme such as cycloeucalenol-obtusifoliol isomerase. The possibilty that cycloartenol is made via lanosterol was investigated by synthesizing 4-R-4-/sup 3/H-mevalonic acid and incubating latex with a mixture of this and /sup 14/C-mevalonic acid. From the /sup 3/H//sup 14/C ratio it was shown that cycloartenol and 24-methylenecycloartenol are not made via an intermediate containing as 8-9 double bond. 88 refs., 15 figs., 30 tabs.« less