User:JamieLittman/Ferruginol
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[edit]Ferruginol is a natural phenol and a meroterpene (a chemical compound containing a terpenoid substructure) that has been isolated from specific conifer species including Cupressaceae and Podocarpaceae. The terpenoid part is a diterpene of the abietane chemical class. The terpenoid part is a diterpene of the abietane chemical class. It was first identified in 1939 by Brandt and Neubauer as the main component in the resin of the Miro tree (Podocarpus ferrugneus).[1] As a biomarker, the presence of Ferruginol in fossils, mainly resin, is used to describe the density of these conifers in that particular biosphere throughout time.
Additionally, research published in 2005 found that this and other compounds of the class from Sequoia have anti-tumor and anti-inflammatory properties. Studies have shown in vitro human colon, breast, and lung tumor reduction and reduction in oncogene transformed cells as well. Specific activity of tumor growth inhibition (GI) is 2-5 micrograms/milliliter.[2] Ferruginol has also been found to have antibacterial activity and gastroprotective effects.[3][4] [5]
Background
[edit]Ferruginol is a phenolic abietene, a type of tricyclic diterpenoid derived from terrestrial plants. It has a molecular composition of C20H30O with a molecular weight of 286. Along with their presence in the Verbenaceae family, they are found in a variety of conifer families including Podocarpaceae, the ancient Araucariaceae, and the extinct Cheirolepidiaceae. They are particularly useful as a biomarker because of their concentration in the Cupressaceae family.[6] In these conifers, it acts as a plant metabolite, along with some protective and antibacterial roles.
Preservation
[edit]As a polar terpenoid, Ferruginol was thought to have poor preservation potential. However, the discovery of resin fossils provided unaltered natural diterpenoids that can be used to understand botanical diversity during a given geological age. Analysis of macrofossils or clay sediments is also used to identify the presence of Ferruginol, though these samples may not be fully preserved. Comparing results from fossilized coal or clay from the same region as resin fossils can help suggest the original biological precursors of these samples. Additionally, the diagenetic alterations of fossils can be used to understand the environmental changes in the time after they were formed.[7] General abietane diterpenoid abietic acids have been connected to the diagenetic products simonellite and retene. Since microbial and abiotic degradation make it so most biomarkers are only able to identify a general conifer, it is especially useful to find resinous samples. [8]
Due to the improved preservation of Ferruginol and other diterpenoids in fossil resin, they have been found to be underrepresented in sediment samples when compared to angiosperms, whose leaf waxes are more free to disperse throughout the sample. Even in regions known to have a high abundance of conifers, sediment samples have been found to contain little to no unaltered diterpenoids.[6]
The presence of Ferruginol has also been used in more modern samples as a biological tracers. For example, analyzing the honeybee product propolis helps establish the main botanical source collected by the bees. [9]
Measurement
[edit]
The sample preparation to measure Ferruginol abundance varies depending on form the sample initially takes, though generally follows the same structure. After physically crushing the sample, BSTFA is used to transform molecules into TMS (trimethyl-silyl) derivatives. It is then chemically extracted into neutral, aromatic, and polar fractions using specified eluents, often hexane, dichloromethane, and methanol, respectively.[6] The aromatic fractions are then analyzed using gas chromatography with mass spectrometry (GC-MS), and library data along with fragmentation patterns are used to identify the molecular makeup of each notable peak and their relative concentration in the sample. Ferruginol can be identified with a molecular weight of 286 m/z.[7]
Along with GC-MS, Ferruginol has also been analyzed using TOF-SIMS with samples collected from still living organisms.
Bioactivity
[edit]Ferruginol has also been noted for its potential as an anti-cancer drug. Against ovarian cancer cells, it induced apoptosis, limited migration, and caused cell cycle arrest. This impact on cancer cells was dose-dependent, with higher doses of Ferruginol more successfully inhibiting migration.[11] When studied against human prostate cancer cells, Ferruginol similarly induced cell death by suppressing survival signaling pathways.[12] Beyond anti-cancer activity, studies with mice showed that Ferruginol had anti-inflammatory properties against induced ulcerative colitis[13] and acted as a gastroprotective agent against gastro lesions.[14]
Biomarker Case Study: Brazil
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The Araripe Basin in Brazil is well known for the diverse and well-preserved collection of fossils. Despite this, the Ipubi Formation in the central Santana Group is only poorly explored. To better understand the paleoflora, researchers at Universidade Federal Rural de Pernambuco analyzed amber resin from the black shales that make up the collection site. Palynological content had been used to date the Ipubi Formation as Aptian-Albian (125–100.5 mya), and the amber samples were thought to be allochthonous, having swept in from nearby conifer sources. Along with GC-MS analysis, 3C-CPMAS-NMR was used to further understand the sample. The terpenoids analyzed were separated into three groups: monoterpenes, sesquiterpenoids, and diterpenoids. Diterpenoids of the abietanic class were the most abundant in the amber, though they are widely present in all conifer families and therefore less useful in identifying specific contributing species. The detection of Ferruginol helped limit the biological origin to the familes Cupressaceae, Podocarpaceae and Cheirolepidiaceae. Further more, the absence callitrisates, kauranes and phyllocladanes excluded Cupressaceae as the source. Therefore, the possible botanical sources of the amber collected in the Ipubi Formation were identified as Podocarpaceae and Cheirolepidiaceae. The results from the amber samples are consistent with environmental conditions determined from a separate analysis of the bituminous shale.[16]
References
[edit]- ^ Brandt, C. W.; Neubauer, L. G. (1939-01-01). "221. Miro resin. Part I. Ferruginol". Journal of the Chemical Society (Resumed) (0): 1031–1037. doi:10.1039/JR9390001031. ISSN 0368-1769.
- ^ Son, Kh; Oh, Hm; Choi, Sk; Han, Dc; Kwon, Bm (Apr 2005). "Anti-tumor abietane diterpenes from the cones of Sequoia sempervirens". Bioorganic & Medicinal Chemistry Letters. 15 (8): 2019–21. doi:10.1016/j.bmcl.2005.02.057. PMID 15808460.
- ^ E.C.J. Smith; G.W. Kaatz; E.M. Williamson; S. Gibbons. "P-168: The Resistance Modifying Activity of Ferruginol" (PDF). Archived from the original (PDF) on October 9, 2007.
{{cite journal}}: Cite journal requires|journal=(help) - ^ C. Flores; J. Alarcón; J. Becerra; M. Bittner; M. Hoeneisen; M. Silva (2001). "EXTRACTABLE COMPOUNDS OF NATIVE TREES: CHEMICAL AND BIOLOGICAL STUDY I: Bark of Prumnopytis andina (Podocarpaceae) and Austrocedrus chilensis (Cupressaceae)". Bol. Soc. Chil. Quím. 46 (1). doi:10.4067/S0366-16442001000100010.
- ^ Areche, Carlos; Theoduloz, Cristina; Yáñez, Tania; Souza-Brito, Alba R. M.; Barbastefano, VíCtor; De Paula, DéBora; Ferreira, Anderson L.; Schmeda-Hirschmann, Guillermo; Rodríguez, Jaime A. (2008). "Gastroprotective activity of ferruginol in mice and rats: effects on gastric secretion, endogenous prostaglandins and non-protein sulfhydryls". Journal of Pharmacy and Pharmacology. 60 (2): 245–51. doi:10.1211/jpp.60.2.0014. hdl:10533/139107. PMID 18237473.
- ^ a b c "Conifer and angiosperm biomarkers in clay sediments and fossil plants from the Miocene Clarkia Formation, Idaho, USA". Organic Geochemistry. 36 (6): 907–922. 2005-06-01. doi:10.1016/j.orggeochem.2004.12.004. ISSN 0146-6380.
- ^ a b "Polar aromatic biomarkers of Miocene-aged Chukurovo resinite and correlation with a progenitor macrofossil". International Journal of Coal Geology. 75 (3): 166–174. 2008-08-05. doi:10.1016/j.coal.2008.05.003. ISSN 0166-5162.
- ^ "Sesqui- and diterpenoid biomarkers preserved in Taxodium-rich Oligocene oxbow lake clays, Weisselster basin, Germany". Organic Geochemistry. 26 (1–2): 105–115. 1997-01-01. doi:10.1016/S0146-6380(96)00133-7. ISSN 0146-6380.
- ^ Popova, Milena; Trusheva, Boryana; Cutajar, Simone; Antonova, Daniela; Mifsud, David; Farrugia, Claude; Bankova, Vassya (2012-05-XX). "Identification of the Plant Origin of the Botanical Biomarkers of Mediterranean type Propolis". Natural Product Communications. 7 (5): 1934578X1200700. doi:10.1177/1934578X1200700505. ISSN 1934-578X.
{{cite journal}}: Check date values in:|date=(help) - ^ "Biomarker signatures of Cretaceous Gondwana amber from Ipubi Formation (Araripe Basin, Brazil) and their palaeobotanical significance". Journal of South American Earth Sciences. 98: 102413. 2020-03-01. doi:10.1016/j.jsames.2019.102413. ISSN 0895-9811.
- ^ Xiong, Wen-Dong; Gong, Jian; Xing, Chao (2017-11-01). "Ferruginol exhibits anticancer effects in OVCAR‑3 human ovary cancer cells by inducing apoptosis, inhibition of cancer cell migration and G2/M phase cell cycle arrest Retraction in /10.3892/mmr.2021.11868". Molecular Medicine Reports. 16 (5): 7013–7017. doi:10.3892/mmr.2017.7484. ISSN 1791-2997.
- ^ "Ferruginol suppresses survival signaling pathways in androgen-independent human prostate cancer cells". Biochimie. 90 (6): 843–854. 2008-06-01. doi:10.1016/j.biochi.2008.01.011. ISSN 0300-9084.
- ^ Zhu, Xiao-Yan; Zhang, Chun-Ling; Lin, Yukiat; Dang, Min-Yan (2020). "Ferruginol alleviates inflammation in dextran sulfate sodium-induced colitis in mice through inhibiting COX-2, MMP-9 and NF-κB signaling". Asian Pacific Journal of Tropical Biomedicine. 10 (7): 308. doi:10.4103/2221-1691.284945. ISSN 2221-1691.
{{cite journal}}: CS1 maint: unflagged free DOI (link) - ^ Areche, Carlos; Theoduloz, Cristina; Yáñez, Tania; Souza-Brito, Alba R M; Barbastefano, Víctor; de Paula, Débora; Ferreira, Anderson L; Schmeda-Hirschmann, Guillermo; Rodríguez, Jaime A (2008-02-01). "Gastroprotective activity of ferruginol in mice and rats: effects on gastric secretion, endogenous prostaglandins and non-protein sulfhydryls†". Journal of Pharmacy and Pharmacology. 60 (2): 245–251. doi:10.1211/jpp.60.2.0014. ISSN 0022-3573.
- ^ "Biomarker signatures of Cretaceous Gondwana amber from Ipubi Formation (Araripe Basin, Brazil) and their palaeobotanical significance". Journal of South American Earth Sciences. 98: 102413. 2020-03-01. doi:10.1016/j.jsames.2019.102413. ISSN 0895-9811.
- ^ "Biomarker signatures of Cretaceous Gondwana amber from Ipubi Formation (Araripe Basin, Brazil) and their palaeobotanical significance". Journal of South American Earth Sciences. 98: 102413. 2020-03-01. doi:10.1016/j.jsames.2019.102413. ISSN 0895-9811.