Biogenic substance

{{short description|Product made by or of life forms}} [[File:Petroleum sample.jpg|thumb|Crude oil, a transformed biogenic substance]] [[File:Hevea gum dripping in a cup.jpg|thumb|Natural gum, a secretion from ''Hevea brasiliensis'']] A '''biogenic substance''' is a product made by or of life forms. While the term originally was specific to metabolite compounds that had toxic effects on other organisms,<ref name="Bhadury_2004" /> it has developed to encompass any constituents, secretions, and metabolites of plants or animals.<ref>{{cite book | first1 = Raju | last1 = Francis | first2 = D Sakthi | last2 = Kumar | name-list-style = vanc |title=Biomedical Applications of Polymeric Materials and Composites|publisher=John Wiley & Sons|date=2016}}</ref> In context of molecular biology, biogenic substances are referred to as biomolecules. They are generally isolated and measured through the use of chromatography and mass spectrometry techniques.<ref name="Lukman_2014" /><ref name="Albrecht_1971" /> Additionally, the transformation and exchange of biogenic substances can by modelled in the environment, particularly their transport in waterways.<ref name="Leonov_2011" />

The observation and measurement of biogenic substances is notably important in the fields of geology and biochemistry. A large proportion of isoprenoids and fatty acids in geological sediments are derived from plants and chlorophyll, and can be found in samples extending back to the Precambrian.<ref name="Albrecht_1971" /> These biogenic substances are capable of withstanding the diagenesis process in sediment, but may also be transformed into other materials.<ref name="Albrecht_1971" /> This makes them useful as biomarkers for geologists to verify the age, origin and degradation processes of different rocks.<ref name="Albrecht_1971" />

Biogenic substances have been studied as part of marine biochemistry since the 1960s,<ref name="Burja_2001" /> which has involved investigating their production, transport, and transformation in the water,<ref name="Leonov_2011" /> and how they may be used in industrial applications.<ref name="Burja_2001" /> A large fraction of biogenic compounds in the marine environment are produced by micro and macro algae, including cyanobacteria.<ref name="Burja_2001" /> Due to their antimicrobial properties they are currently the subject of research in both industrial projects, such as for anti-fouling paints,<ref name="Bhadury_2004" /> or in medicine.<ref name="Burja_2001" />

== History of discovery and classification == thumb|Biogenic sediment: limestone containing fossils During a meeting of the New York Academy of Sciences' Section of Geology and Mineralogy in 1903, geologist Amadeus William Grabau proposed a new rock classification system in his paper 'Discussion of and Suggestions Regarding a New Classification of Rocks'.<ref name="Hovey_1903">{{Cite journal| vauthors = Hovey EO |date=1903-12-18|title=New York Academy of Sciences. Section of Geology and Mineralogy |journal=Science|language=en|volume=18|issue=468|pages=789–790|doi=10.1126/science.18.468.789|s2cid=140651030 |issn=0036-8075|url=https://zenodo.org/record/1518304}}</ref> Within the primary subdivision of "Endogenetic rocks" – rocks formed through chemical processes – was a category termed "Biogenic rocks", which was used synonymously with "Organic rocks". Other secondary categories were "Igneous" and "Hydrogenic" rocks.<ref name="Hovey_1903" />

In the 1930s German chemist Alfred E. Treibs first detected biogenic substances in petroleum as part of his studies of porphyrins.<ref name="Albrecht_1971">{{cite journal | vauthors = Albrecht P, Ourisson G | title = Biogenic substances in sediments and fossils | journal = Angewandte Chemie | volume = 10 | issue = 4 | pages = 209–25 | date = April 1971 | pmid = 4996804 | doi = 10.1002/anie.197102091 }}</ref> Based on this research, there was a later increase in the 1970s in the investigation of biogenic substances in sedimentary rocks as part of the study of geology.<ref name="Albrecht_1971" /> This was facilitated by the development of more advanced analytical methods, and led to greater collaboration between geologists and organic chemists in order to research the biogenic compounds in sediments.<ref name="Albrecht_1971" />

Researchers additionally began to investigate the production of compounds by microorganisms in the marine environment during the early 1960s.<ref name="Burja_2001" /> By 1975, different research areas had developed in the study of marine biochemistry. These were "marine toxins, marine bioproducts and marine chemical ecology".<ref name="Burja_2001" /> Following this in 1994, Teuscher and Lindequist defined biogenic substances as "chemical compounds which are synthesised by living organisms and which, if they exceed certain concentrations, cause temporary or permanent damage or even death of other organisms by chemical or physicochemical effects" in their book, Biogene Gifte.<ref name="Bhadury_2004" /><ref>{{Cite book| vauthors = Teuscher E, Lindequist U |title=Biogene Gifte Biologie - Chemie; Pharmakologie - Toxikologie; mit 2500 Strukturformeln und 62 Tabellen |year=2010 |isbn=978-3-8047-2438-9|edition=3., neu bearb. und erw. Aufl|location=Stuttgart|oclc=530386916}}</ref> This emphasis in research and classification on the toxicity of biogenic substances was partly due to the cytotoxicity-directed screening assays that were used to detect the biologically active compounds.<ref name="Burja_2001" /> The diversity of biogenic products has since been expanded from cytotoxic substances through the use of alternative pharmaceutical and industrial assays.<ref name="Burja_2001" />

== In the environment ==

=== Hydroecology === 300px|thumb|Model of movement of marine compounds Through studying the transport of biogenic substances in the Tatar Strait in the Sea of Japan, a Russian team noted that biogenic substances can enter the marine environment due to input from either external sources, transport inside the water masses, or development by metabolic processes within the water.<ref name="Leonov_2011">{{Cite journal| vauthors = Leonov AV, Pishchal'nik VM, Arkhipkin VS |date=2011|title=Estimation of biogenic substance transport by water masses in Tatar Strait |journal=Water Resources|language=en|volume=38|issue=1|pages=72–86|doi=10.1134/S009780781006103X |bibcode=2011WRes...38...72L |s2cid=129565443}}</ref> They can likewise be expended due to biotransformation processes, or biomass formation by microorganisms. In this study the biogenic substance concentrations, transformation frequency, and turnover were all highest in the upper layer of the water. Additionally, in different regions of the strait the biogenic substances with the highest annual transfer were constant. These were O2, DOC, and DISi, which are normally found in large concentrations in natural water.<ref name="Leonov_2011" /> The biogenic substances that tend to have lower input through the external boundaries of the strait and therefore least transfer were mineral and detrital components of N and P. These same substances take active part in biotransformation processes in the marine environment and have lower annual output as well.<ref name="Leonov_2011" />

=== Geological sites === thumb|Oncolitic limestone: the spheroidal oncolites are formed via deposition of calcium carbonate by cyanobacteria<ref>{{cite journal | vauthors = Corsetti FA, Awramik SM, Pierce D | title = A complex microbiota from snowball Earth times: microfossils from the Neoproterozoic Kingston Peak Formation, Death Valley, USA | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 100 | issue = 8 | pages = 4399–404 | date = April 2003 | pmid = 12682298 | pmc = 153566 | doi = 10.1073/pnas.0730560100 | bibcode = 2003PNAS..100.4399C | doi-access = free }}</ref><ref>{{cite book | vauthors = Riding R | date = 1991 | title = Calcareous Algae and Stromatolites | page = 32 | publisher = Springer-Verlag Press }}</ref> Organic geochemists also have an interest in studying the diagenesis of biogenic substances in petroleum and how they are transformed in sediment and fossils.<ref name="Albrecht_1971" /> While 90% of this organic material is insoluble in common organic solvents – called kerogen – 10% is in a form that is soluble and can be extracted, from where biogenic compounds can then be isolated.<ref name="Albrecht_1971" /> Saturated linear fatty acids and pigments have the most stable chemical structures and are therefore suited to withstanding degradation from the diagenesis process and being detected in their original forms.<ref name="Albrecht_1971" /> However, macromolecules have also been found in protected geological regions.<ref name="Albrecht_1971" /> Typical sedimentation conditions involve enzymatic, microbial and physicochemical processes as well as increased temperature and pressure, which lead to transformations of biogenic substances.<ref name="Albrecht_1971" /> For example, pigments that arise from dehydrogenation of chlorophyll or hemin can be found in many sediments as nickel or vanadyl complexes.<ref name="Albrecht_1971" /> A large proportion of the isoprenoids in sediments are also derived from chlorophyll. Similarly, linear saturated fatty acids discovered in the Messel oil shale of the Messel Pit in Germany arise from organic material of vascular plants.<ref name="Albrecht_1971" />

Additionally, alkanes and isoprenoids are found in soluble extracts of Precambrian rock, indicating the probable existence of biological material more than three billion years ago.<ref name="Albrecht_1971" /> However, there is the potential that these organic compounds are abiogenic in nature, especially in Precambrian sediments. While Studier et al.'s (1968) simulations of the synthesis of isoprenoids in abiogenic conditions did not produce the long-chain isoprenoids used as biomarkers in fossils and sediments, traces of C9-C14 isoprenoids were detected.<ref>{{Cite journal| vauthors = Studier MH, Hayatsu R, Anders E |date=1968|title=Origin of organic matter in early solar system—I. Hydrocarbons |journal=Geochimica et Cosmochimica Acta|language=en|volume=32|issue=2|pages=151–173|doi=10.1016/S0016-7037(68)80002-X|bibcode=1968GeCoA..32..151S|hdl=2060/19670008440|hdl-access=free}}</ref> It is also possible for polyisoprenoid chains to be stereoselectively synthesised using catalysts such as Al(C2H5)3 – VCl3.<ref>{{cite book | vauthors = Natta G, Porri L, Corradini P, Morero D | date = 1967 | chapter = Crystalline Butadiene Polymer With an Isotactic 1,2-Enchainment | title = Stereoregular Polymers and Stereospecific Polymerizations | publisher = Elsevier | pages = 102–103 | isbn = 978-1-4831-9883-5 }}</ref> However, the probability of these compounds being available in the natural environment is unlikely.<ref name="Albrecht_1971" />

== Measurement == 50px|thumb|Chromatographic separation of chlorophyll The different biomolecules that make up a plant's biogenic substances – particularly those in seed exudates - can be identified by using different varieties of chromatography in a lab environment.<ref name="Lukman_2014">{{cite thesis | vauthors = Lukman A | date = 2014 | title = Biogenic Synthesis of Ag and Au Nanoparticles Using Aqueous Seed Exudates | degree = Master's | publisher = The University of Sydney | location = Sydney, Australia }}</ref> For metabolite profiling, gas chromatography-mass spectrometry is used to find flavonoids such as quercetin.<ref name="Lukman_2014" /> Compounds can then be further differentiated using reversed-phase high-performance liquid chromatography-mass spectrometry.<ref name="Lukman_2014" />

When it comes to measuring biogenic substances in a natural environment such as a body of water, a hydroecological<ref>{{Cite journal| vauthors = Leonov AV, Chicherina OV, Semenyak LV |date=2011|title=Mathematical modeling of marine environment pollution processes by petroleum hydrocarbons and their degradation in Caspian Sea ecosystem |journal=Water Resources|language=en|volume=38|issue=6|pages=774–798|doi=10.1134/S0097807811040075|bibcode=2011WRes...38..774L |s2cid=128535855|issn=0097-8078}}</ref> CNPSi model can be used to calculate the spatial transport of biogenic substances, in both the horizontal and vertical dimensions.<ref name="Leonov_2011" /> This model takes into account the water exchange and flow rate, and yields the values of biogenic substance rates for any area or layer of the water for any month. There are two main evaluation methods involved: measuring per unit water volume (mg/m3 year) and measuring substances per entire water volume of layer (t of element/year).<ref name="Leonov_2011" /> The former is mostly used to observe biogenic substance dynamics and individual pathways for flux and transformations, and is useful when comparing individual regions of the strait or waterway. The second method is used for monthly substance fluxes and must take into account that there are monthly variations in the water volume in the layers.<ref name="Leonov_2011" />

In the study of geochemistry, biogenic substances can be isolated from fossils and sediments through a process of scraping and crushing the target rock sample, then washing with 40% hydrofluoric acid, water, and benzene/methanol in the ratio 3:1.<ref name="Albrecht_1971" /> Following this, the rock pieces are ground and centrifuged to produce a residue. Chemical compounds are then derived through various chromatography and mass spectrometry separations.<ref name="Albrecht_1971" /> However, extraction should be accompanied by rigorous precautions to ensure there is no amino acid contaminants from fingerprints,<ref>{{cite book | vauthors = Eglinton G, Scott PM, Belsky T, Burlingame AL, Richter W, Calvin M | date = 1966 | chapter = Occurrence of Isoprenoid Alkanes in a Precambrian Sediment | title = Advances in Organic Geochemistry 1964 | publisher = Elsevier | pages = 41–74 | isbn = 978-0-08-011577-1 }}</ref> or silicone contaminants from other analytical treatment methods.<ref name="Albrecht_1971" />

== Applications == 200px|thumb|Cyanobacteria extracts inhibiting the growth of ''Micrococcus luteus''

=== Anti-fouling paints === Metabolites produced by marine algae have been found to have many antimicrobial properties.<ref name="Bhadury_2004">{{cite journal | vauthors = Bhadury P, Wright PC | title = Exploitation of marine algae: biogenic compounds for potential antifouling applications | journal = Planta | volume = 219 | issue = 4 | pages = 561–78 | date = August 2004 | pmid = 15221382 | doi = 10.1007/s00425-004-1307-5 | bibcode = 2004Plant.219..561B | s2cid = 34172675 }}</ref> This is because they are produced by the marine organisms as chemical deterrents and as such contain bioactive compounds. The principal classes of marine algae that produce these types of secondary metabolites are Cyanophyceae, Chlorophyceae and Rhodophyceae.<ref name="Bhadury_2004" /> Observed biogenic products include polyketides, amides, alkaloids, fatty acids, indoles and lipopeptides.<ref name="Bhadury_2004" /> For example, over 10% of compounds isolated from ''Lyngbya majuscula'', which is one of the most abundant cyanobacteria, have antifungal and antimicrobial properties.<ref name="Bhadury_2004" /><ref name="Burja_2001">{{cite journal| vauthors = Burja AM, Banaigs B, Abou-Mansour E, Burgess JG, Wright PC |date=2001|title=Marine cyanobacteria—a prolific source of natural products |journal=Tetrahedron|language=en|volume=57|issue=46|pages=9347–9377|doi=10.1016/S0040-4020(01)00931-0 }}</ref> Additionally, a study by Ren et al. (2002) tested halogenated furanones produced by ''Delisea pulchra'' from the Rhodophyceae class against the growth of ''Bacillus subtilis''.<ref name="Ren_2002">{{cite journal | vauthors = Ren D, Sims JJ, Wood TK | title = Inhibition of biofilm formation and swarming of Bacillus subtilis by (5Z)-4-bromo-5-(bromomethylene)-3-butyl-2(5H)-furanone | journal = Letters in Applied Microbiology | volume = 34 | issue = 4 | pages = 293–9 | date = 2002 | pmid = 11940163 | doi = 10.1046/j.1472-765x.2002.01087.x | bibcode = 2002LAppM..34..293R | s2cid = 20485554 | citeseerx = 10.1.1.701.7622 }}</ref><ref name="Bhadury_2004" /> When applied at a 40 μg/mL concentration, the furanone inhibited the formation of a biofilm by the bacteria and reduced the biofilm's thickness by 25% and the number of live cells by 63%.<ref name="Ren_2002" />

These characteristics then have the potential to be utilised in man-made materials, such as making anti-fouling paints without the environment-damaging chemicals.<ref name="Bhadury_2004" /> Environmentally safe alternatives are needed to TBT (tin-based antifouling agent) which releases toxic compounds into water and the environment and has been banned in several countries.<ref name="Bhadury_2004" /> A class of biogenic compounds that has had a sizeable effect against the bacteria and microalgae that cause fouling are acetylene sesquiterpenoid esters produced by ''Caulerpa prolifera'' (from the Chlorophyceae class), which Smyrniotopoulos et al. (2003) observed inhibiting bacterial growth with up to 83% of the efficacy of TBT oxide.<ref>{{cite journal | vauthors = Smyrniotopoulos V, Abatis D, Tziveleka LA, Tsitsimpikou C, Roussis V, Loukis A, Vagias C | title = Acetylene sesquiterpenoid esters from the green alga Caulerpa prolifera | journal = Journal of Natural Products | volume = 66 | issue = 1 | pages = 21–4 | date = January 2003 | pmid = 12542338 | doi = 10.1021/np0202529 | bibcode = 2003JNAtP..66...21S }}</ref> thumb|215x215px|Photobioreactor used to produce microalgae metabolites Current research also aims to produce these biogenic substances on a commercial level using metabolic engineering techniques.<ref name="Bhadury_2004" /> By pairing these techniques with biochemical engineering design, algae and their biogenic substances can be produced on a large scale using photobioreactors.<ref name="Bhadury_2004" /> Different system types can be used to yield different biogenic products.<ref name="Bhadury_2004" /> {| class="wikitable" |+Examples of photobioreactor use for biogenic compound production !Photobioreactor type !Algae species cultured !Product !Reference |- |Seaweed type polyurethane |''Scytonema sp.TISTR 8208'' |Cyclic dodecapeptide antibiotic effective against Gram-positive bacteria, filamentous fungi and pathogenic yeasts |Chetsumon et al. (1998)<ref>{{cite book | vauthors = Chetsumon A, Umeda F, Maeda I, Yagi K, Mizoguchi T, Miura Y | title = Biotechnology for Fuels and Chemicals | chapter = Broad Spectrum and Mode of Action of an Antibiotic Produced by Scytonema sp. TISTR 8208 in a Seaweed-Type Bioreactor | series = Applied Biochemistry and Biotechnology | volume = 70-72 | pages = 249–56 | date = 1998 | pmid = 9627386 | doi = 10.1007/978-1-4612-1814-2_24 | publisher = Humana Press | isbn = 978-1-4612-7295-3 | veditors = Finkelstein M, Davison BH | place = Totowa, NJ }}</ref> |- |Stirred tank |''Agardhiella subulata'' |Biomass |Huang and Rorrer (2003)<ref>{{cite journal | vauthors = Huang YM, Rorrer GL | title = Cultivation of microplantlets derived from the marine red alga Agardhiella subulata in a stirred tank photobioreactor | journal = Biotechnology Progress | volume = 19 | issue = 2 | pages = 418–27 | date = 2003-04-04 | pmid = 12675582 | doi = 10.1021/bp020123i | bibcode = 2003BioPr..19..418H | s2cid = 20653359 }}</ref> |- |Airlift |''Gyrodinium impundicum'' |Sulphated exopolysaccharides for antiviral action against encephalomyocarditis virus |Yim et al. (2003)<ref>{{cite journal | vauthors = Yim JH, Kim SJ, Ahn SH, Lee HK | title = Optimal conditions for the production of sulfated polysaccharide by marine microalga Gyrodinium impudicum strain KG03 | journal = Biomolecular Engineering | volume = 20 | issue = 4–6 | pages = 273–80 | date = July 2003 | pmid = 12919808 | doi = 10.1016/S1389-0344(03)00070-4 | series = Marine Biotechnology: Basics and Applications }}</ref> |- |Large scale outdoor |''Haematococcus pluvialis'' |Astaxanthin compound |Miguel (2000)<ref>{{Cite journal| vauthors = Olaizola M |date=2000-10-01|title=Commercial production of astaxanthin from Haematococcus pluvialis using 25,000-liter outdoor photobioreactors |journal=Journal of Applied Phycology|language=en|volume=12|issue=3|pages=499–506|doi=10.1023/A:1008159127672 |bibcode=2000JAPco..12..499O |s2cid=24973288}}</ref> |}

=== Paleochemotaxonomy === In the field of paleochemotaxonomy the presence of biogenic substances in geological sediments is useful for comparing old and modern biological samples and species.<ref name="Albrecht_1971" /> These biological markers can be used to verify the biological origin of fossils and serve as paleo-ecological markers. For example, the presence of pristane indicates that the petroleum or sediment is of marine origin, while biogenic material of non-marine origin tends to be in the form of polycyclic compounds or phytane.<ref>{{cite journal | vauthors = Blumer M, Snyder WD | title = Isoprenoid Hydrocarbons in Recent Sediments: Presence of Pristane and Probable Absence of Phytane | journal = Science | volume = 150 | issue = 3703 | pages = 1588–9 | date = December 1965 | pmid = 17743968 | doi = 10.1126/science.150.3703.1588 | bibcode = 1965Sci...150.1588B | s2cid = 33248946 }}</ref> The biological markers also provide valuable information about the degradation reactions of biological material in geological environments.<ref name="Albrecht_1971" /> Comparing the organic material between geologically old and recent rocks shows the conservation of different biochemical processes.<ref name="Albrecht_1971" />

=== Metallic nanoparticle production === thumb|Scanning electron microscope image of silver nanoparticles Another application of biogenic substances is in the synthesis of metallic nanoparticles.<ref name="Lukman_2014" /> The current chemical and physical production methods for nanoparticles used are costly and produce toxic waste and pollutants in the environment.<ref>{{Cite journal| vauthors = Gardea-Torresdey JL, Parsons JG, Gomez E, Peralta-Videa J, Troiani HE, Santiago P, Yacaman MJ |date=2002|title=Formation and Growth of Au Nanoparticles inside Live Alfalfa Plants |journal=Nano Letters|volume=2|issue=4|pages=397–401|doi=10.1021/nl015673+|bibcode=2002NanoL...2..397G|issn=1530-6984}}</ref> Additionally, the nanoparticles that are produced can be unstable and unfit for use in the body.<ref name="Shukla_2008">{{cite journal|display-authors=6|vauthors=Shukla R, Nune SK, Chanda N, Katti K, Mekapothula S, Kulkarni RR, Welshons WV, Kannan R, Katti KV|date=September 2008|title=Soybeans as a phytochemical reservoir for the production and stabilization of biocompatible gold nanoparticles|journal=Small|volume=4|issue=9|pages=1425–36|doi=10.1002/smll.200800525|pmid=18642250 |bibcode=2008Small...4.1425S }}</ref> Using plant-derived biogenic substances aims to create an environmentally-friendly and cost-effective production method.<ref name="Lukman_2014" /> The biogenic phytochemicals used for these reduction reactions can be derived from plants in numerous ways, including a boiled leaf broth,<ref>{{cite journal | vauthors = Nune SK, Chanda N, Shukla R, Katti K, Kulkarni RR, Thilakavathi S, Mekapothula S, Kannan R, Katti KV | display-authors = 6 | title = Green Nanotechnology from Tea: Phytochemicals in Tea as Building Blocks for Production of Biocompatible Gold Nanoparticles | journal = Journal of Materials Chemistry | volume = 19 | issue = 19 | pages = 2912–2920 | date = June 2009 | pmid = 20161162 | pmc = 2737515 | doi = 10.1039/b822015h | bibcode = 2009JMCh...19.2912N }}</ref> biomass powder,<ref>{{Cite journal| vauthors = Canizal G, Schabes-Retchkiman PS, Pal U, Liu HB, Ascencio JA |date=2006|title=Controlled synthesis of Zn0 nanoparticles by bioreduction |journal=Materials Chemistry and Physics|language=en|volume=97|issue=2–3|pages=321–329|doi=10.1016/j.matchemphys.2005.08.015}}</ref> whole plant immersion in solution,<ref name="Shukla_2008" /> or fruit and vegetable juice extracts.<ref>{{Cite journal| vauthors = Canizal G, Ascencio JA, Gardea-Torresday J, Yacamán MJ |date=2001|title=Multiple Twinned Gold Nanorods Grown by Bio-reduction Techniques |journal=Journal of Nanoparticle Research|volume=3|issue=5/6|pages=475–481|doi=10.1023/A:1012578821566|bibcode=2001JNR.....3..475C|s2cid=92126604}}</ref> ''C. annuum'' juices have been shown to produce Ag nanoparticles at room temperature when treated with silver ions and additionally deliver essential vitamins and amino acids when consumed, making them a potential nanomaterials agent.<ref name="Lukman_2014" /> Another procedure is through the use of a different biogenic substance: the exudate of germinating seeds. When seeds are soaked, they passively release phytochemicals into the surrounding water, which after reaching equilibrium can be mixed with metal ions to synthesise metallic nanoparticles.<ref>{{Cite journal| vauthors = Odunfa VS |date=1979|title=Free amino acids in the seed and root exudates in relation to the nitrogen requirements of rhizosphere soil Fusaria |journal=Plant and Soil|language=en|volume=52|issue=4|pages=491–499|doi=10.1007/BF02277944|bibcode=1979PlSoi..52..491O |s2cid=34913145|issn=0032-079X}}</ref><ref name="Lukman_2014" /> ''M. sativa'' exudate in particular has had success in effectively producing Ag metallic particles, while ''L. culinaris'' is an effective reactant for manufacturing Au nanoparticles.<ref name="Lukman_2014" /> This process can also be further adjusted by manipulating factors such as pH, temperature, exudate dilution and plant origin to produce different shapes of nanoparticles, including triangles, spheres, rods, and spirals.<ref name="Lukman_2014" /> These biogenic metallic nanoparticles then have applications as catalysts, glass window coatings to insulate heat, in biomedicine, and in biosensor devices.<ref name="Lukman_2014" />

==Examples== [[File:Lupeol_structure.svg|thumb|Chemical structure of lupeol, a triterpenoid derived from plants<ref>{{Cite web| work = PubChem|title=Lupeol|url=https://pubchem.ncbi.nlm.nih.gov/compound/259846|access-date=2020-11-20 }}</ref>]] *Coal and oil are possible examples of constituents which may have undergone changes over geologic time periods. *Chalk and limestone are examples of secretions (marine animal shells) which are of geologic age. *Grass and wood are biogenic constituents of contemporary origin. *Pearls, silk and ambergris are examples of secretions of contemporary origin. *Biogenic neurotransmitters.

=== Table of isolated biogenic compounds === {| class="wikitable" |+ !Chemical class !Compound !Source !Reference |- |Lipopeptide<ref name="Bhadury_2004" /> | * Lyngbyaloside * Radiosumin | * ''Lyngbya bouillonii'' * ''Plectonema radiosum'' | * Klein, Braekman, Daloze, Hoffmann & Demoulin (1997)<ref>{{Cite journal| vauthors = Klein D, Braekman JC, Daloze D, Hoffmann L, Demoulin V |date=1997|title=Lyngbyaloside, a Novel 2,3,4-Tri- O -methyl-6-deoxy-α-mannopyranoside Macrolide from Lyngbya bouillonii (Cyanobacteria) |journal=Journal of Natural Products|language=en|volume=60|issue=10|pages=1057–1059|doi=10.1021/np9702751 |bibcode=1997JNAtP..60.1057K }}</ref> * Mooberry, Stratman & Moore (1995)<ref>{{cite journal | vauthors = Mooberry SL, Stratman K, Moore RE | title = Tubercidin stabilizes microtubules against vinblastine-induced depolymerization, a taxol-like effect | journal = Cancer Letters | volume = 96 | issue = 2 | pages = 261–6 | date = September 1995 | pmid = 7585466 | doi = 10.1016/0304-3835(95)03940-X }}</ref> |- |Fatty acid<ref name="Bhadury_2004" /> | * Sulfolipid *Linolenic acid | * ''Lyngbya lagerheimii'' *''Synechococcus sp.'' | * Gustafson et al. (1989)<ref>{{cite journal | vauthors = Gustafson KR, Cardellina JH, Fuller RW, Weislow OS, Kiser RF, Snader KM, Patterson GM, Boyd MR | display-authors = 6 | title = AIDS-antiviral sulfolipids from cyanobacteria (blue-green algae) | journal = Journal of the National Cancer Institute | volume = 81 | issue = 16 | pages = 1254–8 | date = August 1989 | pmid = 2502635 | doi = 10.1093/jnci/81.16.1254 }}</ref> * Ohta et al. (1994)<ref>{{cite journal | vauthors = Ohta S, Chang T, Kawashima A, Nagate T, Murase M, Nakanishi H, Miyata H, Kondo M | display-authors = 6 | title = Anti methicillin-resistant Staphylococcus aureus (MRSA) activity by linolenic acid isolated from the marine microalga Chlorococcum HS-101 | journal = Bulletin of Environmental Contamination and Toxicology | volume = 52 | issue = 5 | pages = 673–80 | date = May 1994 | pmid = 7910498 | doi = 10.1007/BF00195486 | bibcode = 1994BuECT..52..673O | s2cid = 44300232 }}</ref> |- |Terpene<ref name="Burja_2001" /> | * Triterpenoid | * ''Prochlorothrix hollandica,'' Messel oil shale | * Simonin, Jürgens & Rohmer (1996),<ref>{{cite journal | vauthors = Simonin P, Jürgens UJ, Rohmer M | title = Bacterial triterpenoids of the hopane series from the prochlorophyte Prochlorothrix hollandica and their intracellular localization | journal = European Journal of Biochemistry | volume = 241 | issue = 3 | pages = 865–71 | date = November 1996 | pmid = 8944776 | doi = 10.1111/j.1432-1033.1996.00865.x }}</ref> Albrecht & Ourisson (1971)<ref name="Albrecht_1971" /> |- |Alkaloid<ref name="Bhadury_2004" /> | * Cylindrospermopsin *Welwistatin | * ''Cylindrospermopsis raciborskii'' *''Hapalosiphon welwitschii'' | * Saker & Eaglesham (1999)<ref>{{cite journal | vauthors = Saker ML, Eaglesham GK | title = The accumulation of cylindrospermopsin from the cyanobacterium Cylindrospermopsis raciborskii in tissues of the Redclaw crayfish Cherax quadricarinatus | journal = Toxicon | volume = 37 | issue = 7 | pages = 1065–77 | date = July 1999 | pmid = 10484741 | doi = 10.1016/S0041-0101(98)00240-2 | bibcode = 1999Txcn...37.1065S }}</ref> * Zhang & Smith (1996)<ref>{{cite journal | vauthors = Zhang X, Smith CD | title = Microtubule effects of welwistatin, a cyanobacterial indolinone that circumvents multiple drug resistance | journal = Molecular Pharmacology | volume = 49 | issue = 2 | pages = 288–94 | date = February 1996 | doi = 10.1016/S0026-895X(25)08710-3 | pmid = 8632761 }}</ref> |- |Ketone<ref name="Albrecht_1971" /> | * Arborinone | * Messel oil shale | * Albrecht & Ourisson (1971)<ref name="Albrecht_1971" /> |}

== Abiogenic (opposite) == An '''abiogenic''' substance or process does not result from the present or past activity of living organisms. Abiogenic products may, e.g., be minerals, other inorganic compounds, as well as simple organic compounds (e.g. extraterrestrial methane, see also abiogenesis).

== References == {{reflist}}

{{DEFAULTSORT:Biogenic Substance}} Category:Biosphere Category:Geological processes Category:Natural materials Category:Organic compounds Category:Phycology Category:Paleobiology