Sugiol

Last updated
Sugiol
Sugiol.svg
Names
IUPAC name
(4aS,10aS)-6-Hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C20H28O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-10,12,18,21H,6-8,11H2,1-5H3/t18-,20+/m0/s1
    Key: IPEHJNRNYPOFII-AZUAARDMSA-N
  • CC(C)C1=C(C=C2C(=C1)C(=O)C[C@@H]3[C@@]2(CCCC3(C)C)C)O
Properties
C20H28O2
Molar mass 300.442 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sugiol is a phenolic abietane derivative of ferruginol and can be used as a biomarker for specific families of conifers. [1] The presence of sugiol can be used to identify the Cupressaceae s.1., podocarpaceae , and Araucaraiaceae families of conifers. [2] The polar terpenoids are among the most resistant molecules to degradation besides n-alkanes and fatty acids, [1] affording them high viability as biomarkers due to their longevity in the sedimentary record. Significant amounts of sugiol has been detected in fossil wood dated to the Eocene and Miocene periods, as well as a sample of Protopodocarpoxylon dated to the middle Jurassic. [1]

Contents

Background

Sugiol is a naturally occurring phenolic diterpenoid. [1] Diterpenoids are a group of secondary metabolites with 20 carbons. [3] Acyclic diterpenes are uncommon, due to the way that they are assembled, and include important molecules such as phytol. [3] Sugiol has three six-membered rings, one of which is aromatic (ring C), and differs from ferruginol only by an addition of an oxo group bound to ring B. It may also be classified as an abietane, a class of tricyclic diterpenoids that share the same basic structure and are commonly found in the resin of conifers among other terrestrial plants. [4]

Aromatic abietanes that contain an aromatic carbon ring, such as sugiol and ferruginol, have exhibited a variety of interesting properties that have made them of high interest to the pharmacological community. [4] Sugiol specifically has demonstrated anti-tumor, anti-microbial, antioxidant, and anti-viral activities. [5]

Sugiol has been shown to inhibit the oncogenic protein STAT3, which is constituently on in malignant tumors. Sugiol directly inhibits the enzyme transketolase, leading to a build up of reactive oxygen species (ROS) and stress-induced cell death. [5] Reactive oxygen species are highly reactive, and can damage cellular mechanisms by oxidizing critical molecules.

Sugiol downregulates inflammatory genes such as NF-κB, COX-2, TNF-alpha, IL-1beta, and IL-6. [5]

Sugiol prevents virus triggered cytopathic effects as a result of H1N1 in MDCK cells for up to 72 hours. [5] It has also been shown to possess significant neutralizing activity against gram-positive and gram-negative bacteria, with slightly higher activity against gram-positive organisms. [5]

Many plant derived compounds have demonstrated potential as therapeutic tools. [5] In one study sugiol showed efficacy in treating Leishmania infantum, a parasite that can cause Leishmaniasis in humans. [6] Free sugiol was able to induce cell-death in the parasitic bacteria, and when encased in cell walls obtained from yeast was able to enter a parasitized macrophage and inhibit the L. infantum within. [6]

Because sugiol has shown so many protective effects in therapeutic trials, it is likely that in plants it acts as a chemical defense agent. [7] Sugiol present in the resins of conifers may help to protect the plant against ROS generated during metabolism, as well as against any pathogenic viruses or bacteria.

Reaction pathways

Diterpenes are commonly synthesized from the precursor molecule geranylgeranyl pyrophosphate (GGPP). GGPP's hydrocarbon backbone can be rearranged into different structures that may be further rearranged or added to in order to create precursors for different families of diterpenoid compounds. [8] This precursor molecule may be synthesized through the mevalonic acid pathway or the deoxyxylulose pathway. [4] These pathways produce isopentenyl pyrophosphate, which can be rearranged into GGPP. The cyclization of GGPP and the subsequent reorganizations into different precursors is controlled by a large family of enzymes known as diterpene syntheses (diTPS). [9]

To synthesize sugiol a plant must first synthesize GGPP through either of the previously mentioned pathways, (mevalonic acid or the deoxyxylulose pathway), then rearrange GGPP into the molecule mitiradiene. [4] After formation of an intermediate compound abietatriene, a cytochrome P450 enzyme can then attach an oxygen molecule to the intermediate. This produces ferruginol, which can then be modified to sugiol by sugiol synthase. [8]

Sugiol may then be formed through the modification of ferruginol according to the following reaction [10] driven by the enzyme sugiol synthase. [8]

Ferruginol + 2 O2 + 2 NADPH → 2 H+ + 3 H2O + 2 NADP+ + Sugiol

Plant sources

Melia azedarach flowers, of the family meliaceae. Low levels of Sugiol has been detected in this family of angiosperms. Melia azedarach flower.JPG
Melia azedarach flowers, of the family meliaceae. Low levels of Sugiol has been detected in this family of angiosperms.
Chamaecyparis lawsonia, a conifer species in the family Cupressaceae. This family has been observed to contain sugiol Chamaecyparis lawsoniana 'Winston Churchill' (Cupressaceae) detail.jpg
Chamaecyparis lawsonia, a conifer species in the family Cupressaceae. This family has been observed to contain sugiol

Abietanes may fall into one of two classes, either regular or phenolic. Regular abietanes are common across all conifers, whereas phenolic abietanes are usually found in more specific families and are mostly absent from pinaceae. [2] There are a few exceptions to this, including detection of ferruginol and its derivative in Cedrus atlantica and Pinus sylvestris . [2]

Sugiol has been detected in Cupressaceae, Taxodiaceae, Podocarpaceae, and many other conifer families. [2] It has not been significantly detected in Pinaceae. [2] Similar phenolic abietanes have also been detected in cedars (genus Cedrus ), pines (genus Pinus ), monkey puzzle (genus Araucaria ), and torreya (genus Torreya ). [2] Sugiol has also been detected in certain angiosperm genera such as Inula and Melia , [2] but is much more prevalent in conifers. This allows for these organisms to be excluded from the list of species for which sugiol is a biomarker. The enzyme sugiol synthase has also been isolated from Salvia militiorrhiza , an angiosperm that contains high levels of phenolic diterpenes and is commonly utilized in traditional Chinese medicine. [8]

Preservation

Organic compounds originally in living organisms can be preserved in the rock record if certain requirements are met. Proper preservation requires ample supply of organic material, high burial of that organic matter, and that the organic matter is then polymerized and not degraded. The more degraded a biomolecule is the less specific of a biomarker it becomes, as multiple molecules may have the same hydrocarbon skeleton after diagenesis. [11] However, polar terpenoids such as sugiol may be preserved in their unaltered forms in fossil conifers, potentially due to plant resins that protect them from degradation. [11]

In samples obtained from a Pliocene fossilized forest most molecules had been significantly degraded, but phenolic abietanes including sugiol remained intact and identifiable. [12] Even in samples that had been approximately 37.7% decomposed as determined by comparing cellulose content, trace amounts of sugiol and more than 10% ferruginol were detected via GC/MS. [12] Sugiol will remain detectable in a sample long after it has lost its anatomical identifiers, making it extremely useful in identifying extremely old or decomposed plant fossils. [1]

In a study of preserved fossil wood and buried samples from a middle Jurassic forest located in Poland, a negative correlation was observed between the preservation of anatomical features of the plant samples versus the chemical features. [1] It was hypothesized that the rapid mineralization processes required to preserve biomolecules degraded the organic matter, but either extracted or trapped chemical biomarkers in the clay mineral matrix during the early stages of mineralization, protecting those molecules from breakdown. [1] Burial of samples in anaerobic sediments decreased biodegradation and increased preservation of biomarkers including sugiol. [1] Sugiol was significantly more abundant in less oxidized samples. [1] Additionally, the antimicrobial properties of sugiol [5] could help to decelerate biodegradation of itself and other natural products by decreasing microbe driven breakdown. [1]

Measurement techniques

A graphical recreation of the mass spectra of sugiol. Originally obtained from a gas chromatography column and single quadrupole mass spectrometer in positive ionization mode, with an ionization energy of 70 eV and a mass resolution of 0.0001 Da. Recreation of mass spectra of sugiol.png
A graphical recreation of the mass spectra of sugiol. Originally obtained from a gas chromatography column and single quadrupole mass spectrometer in positive ionization mode, with an ionization energy of 70 eV and a mass resolution of 0.0001 Da.

Gas chromatography/mass spectroscopy

Gas chromatography (GC) and mass spectrometry (MS) are commonly used to detect and identify sugiol in a sample. GC/MS is highly specific and sensitive and allows for identification of a wide range of analytes. [13] After extraction from the original sample, which could be the resin of a living plant, or a preserved rock sample, the sample can be ionized and the components identified through their representative spectra. Analysis of fragmentation patterns can also be used to identify a compound by connecting each peak in the mass spectra to the masses of significant fragmentation products of the molecule, as well as the molecular ion, which is the largest significant peak in the spectra.

When identifying sugiol in a sample, full-scan monitoring is commonly used to scan the full range of masses from 50 to 650 Da. [1] [14] This allows for detection of compounds with a wide range of molecular masses when attempting to make an identification based on chemical composition. Electron impact ionization is also commonly used to break apart and ionize the samples before they are passed to the mass spectrometer. [1] [14]

The molecular ion peak for sugiol appears as a small peak at an m/z ratio of 300.2084. [15] The largest peak in the mass spectra appears at a m/z ratio of 285.1849, [15] and corresponds to a fragmentation product with a formula of C19H25O2. This fragmentation product has one less ring and an H2O molecule bound to the newly open carbon chain. Another significant peak is at m/z 257.1536, and corresponds to another fragmentation product with a single ring, and a formula of C17H21O2. [16] Further significant peaks appear at m/z's of 217 [15] and 243, [15] corresponding to formulas of C13H15O2 and C15H19O2, respectively. [15]

Derivitization

Trimethylsilyl functional group used in derivitization reactions for GC/MS sample preparation. Trimethylsilyl group.PNG
Trimethylsilyl functional group used in derivitization reactions for GC/MS sample preparation.

Sugiol is a protic molecule. Protic molecules are those that have protic groups or hydrogen molecules that readily leave the molecule, such as -OH, -NH, and -HF. These molecules can complicate GC/MS data by increasing peak tailing and affecting the ease with which they can be separated by the GC. [13] In order to avoid this effect, protic molecules are often subjected to derivatization reactions, in which the offending protons are replaced by a different functional group. [13] A commonly used replacement group is trimethylsilyl (TMS), which produces trimethylsilyl derivatives of the original protic molecules. Another commonly used group is tert-butyldimethylsilyl (TBDMS), also used to derivatize hydroxyl and amine protic groups. [13] Diazomethane has also been used to form methyl esters from carboxylic acids. [13]

Case studies

The combination of the longevity of sugiol in environmental samples and its presence in only specific families of plants make it an excellent biomarker. Detection of sugiol in combination with other biomarkers like ferruginol or other diterpenes can also help to bolster the identification of the sample, as well as to narrow the scope of possible identities to only a few specific conifer families. Sugiol has been utilized in the identification of extinct plant taxa such as Protopodocarpoxylon, [1] and Taxodioxylori gypsaceum. [12]

Identification of Protopodocarpoxylon

Protopodocarpoxylon is an extinct genus of conifer tracheophytes, now often found as fossilized woods. [1] In a 2007 study, extraction and identification of biomarkers from fossil woods collected in south-central Poland allowed for the identification of the sample as Protopodocarpoxylon Eckhold [1] . Samples of the wood were collected from clays and carbonate concretions then cleaned of contaminants before being pulverized, and the organics extracted. [1] The extracts were derivatized with TMS and then subjected to gas chromatography-mass spectrometry (GC-MS) analysis. [1]

Multiple abietanes were detected in the analyzed samples, with ferruginol, sugiol, simonellite, and dehydroabietane present in all four of the samples tested. [1] Sugiol and ferruginol were both detected as unaltered natural products. [1] There was a dramatic difference in detected abundance of sugiol and ferruginol in samples that were more oxidized, but the biomarkers were still detectable in both cases. [1]

The unknown fossil wood samples were determined to contain aliphatic lipids (n-alkanols and n-alkanoic acids), diterpenoids (abietanes, labdanes, and totaranes), triterpenoids (lupane and hopane), and steroids. [1] The presence of long chain n-alkanes, ferruginol, sugiol, and dehydroabietic acid were considered and the sample was determined to be a conifer plant, in either the Podocarpaceae , Cupressaceae , or Araucariaceae family. [1] All of these chemical identifiers, combined with distinct morphological features characteristic of tracheids allowed for the assignment of Protopodocarpoxylon to the sample. [1]

The presence of multiple biomarkers, each of which correspond to different groups of organisms allows potential identities to be narrowed down. When combined with phenotypic characteristics, specific biomarkers like sugiol become very strong tools in identifying unknown organisms.

Identification of Taxodioxylori gypsaceum

A fossilized sample of Taxodioxylon gypsaceum wood Taxodioxylon gypsaceum Creta Belgio Naturalis.JPG
A fossilized sample of Taxodioxylon gypsaceum wood

Taxodioxylon gysaceum is an extinct species of conifer presently found as fossil wood. [12]

Samples of the same wood in various stages of degradation were collected from a forest in Italy, originally existing during the Pliocene period. [12] These samples were milled and filtered into different fractions by coarseness before steam distillation was utilized to extract terpenes. The extraction was then analyzed through GC/MS. [12] The comparative degree of degradation was determined by analysis of holocellulose contents in each sample. [12] Holocellulose refers to the fraction of plant biomass that includes cellulose and hemicellulose but excludes lignin. These carbohydrates are broken down during decomposition, and so their concentrations can be used as a measure of the degree of degradation.

A variety of terpenes were detected in the degraded lignite samples, including more than 10% ferruginol, between 5 and 10% podocarpodiol, and less than 5% of sugiol. [12] These compounds were hypothesized to have become more prevalent in the degraded sample due to preferential decomposition of other compounds. [12] The presence of these terpenes in this sample suggest that the organism belongs to the Cupressaceae, Podocarpaceae, or Taxodiaceae families. [12] Given the specific combination of terpenes present, the sample was identified as Taxodioxylon gypsaceum [12] . This combination of terpenes has also been detected in other samples known to be Taxodioxylon gypsaceum, further supporting this identification. [12]

The yields of terpenes retrieved from these samples were higher than other species that also contain phenolic diterpenes, suggesting that high percentages of sesquiterpenes and diterpenes are an additional biomarker for Taxodioxylon gypsaceum [12] .

Related Research Articles

<span class="mw-page-title-main">Salvinorin A</span> Chemical compound

Salvinorin A is the main active psychotropic molecule in Salvia divinorum. Salvinorin A is considered a dissociative hallucinogen.

The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.

<span class="mw-page-title-main">Terpene</span> Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.

<span class="mw-page-title-main">Electron ionization</span> Ionization technique

Electron ionization is an ionization method in which energetic electrons interact with solid or gas phase atoms or molecules to produce ions. EI was one of the first ionization techniques developed for mass spectrometry. However, this method is still a popular ionization technique. This technique is considered a hard ionization method, since it uses highly energetic electrons to produce ions. This leads to extensive fragmentation, which can be helpful for structure determination of unknown compounds. EI is the most useful for organic compounds which have a molecular weight below 600 amu. Also, several other thermally stable and volatile compounds in solid, liquid and gas states can be detected with the use of this technique when coupled with various separation methods.

<span class="mw-page-title-main">Cupressaceae</span> Cypress family of conifers

Cupressaceae or the cypress family is a family of conifers. The family includes 27–30 genera, which include the junipers and redwoods, with about 130–140 species in total. They are monoecious, subdioecious or (rarely) dioecious trees and shrubs up to 116 m (381 ft) tall. The bark of mature trees is commonly orange- to red-brown and of stringy texture, often flaking or peeling in vertical strips, but smooth, scaly or hard and square-cracked in some species. The family reached its peak of diversity during the mesozoic era.

<span class="mw-page-title-main">Abietic acid</span> Chemical compound

Abietic acid is a diterpenoid found in coniferous trees. It is supposed to exist as a defend the host plant from insect attack or various wounds. Chemically, it is a complicated molecule featuring two alkene groups and a carboxylic acid within a chiral tricyclic framework. As the major component of rosin, it is a commercially important. Historically speaking, it was a major component of naval stores. It is the most common of the resin acids. Another common resin acid is pimaric acid, which converts to abietic acid upon heating.

<span class="mw-page-title-main">Gas chromatography–mass spectrometry</span> Analytical method

Gas chromatography–mass spectrometry (GC–MS) is an analytical method that combines the features of gas-chromatography and mass spectrometry to identify different substances within a test sample. Applications of GC–MS include drug detection, fire investigation, environmental analysis, explosives investigation, food and flavor analysis, and identification of unknown samples, including that of material samples obtained from planet Mars during probe missions as early as the 1970s. GC–MS can also be used in airport security to detect substances in luggage or on human beings. Additionally, it can identify trace elements in materials that were previously thought to have disintegrated beyond identification. Like liquid chromatography–mass spectrometry, it allows analysis and detection even of tiny amounts of a substance.

Diterpenes are a class of terpenes composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and anti-inflammatory.

<span class="mw-page-title-main">Cholestane</span> Chemical compound

Cholestane is a saturated tetracyclic triterpene. This 27-carbon biomarker is produced by diagenesis of cholesterol and is one of the most abundant biomarkers in the rock record. Presence of cholestane, its derivatives and related chemical compounds in environmental samples is commonly interpreted as an indicator of animal life and/or traces of O2, as animals are known for exclusively producing cholesterol, and thus has been used to draw evolutionary relationships between ancient organisms of unknown phylogenetic origin and modern metazoan taxa. Cholesterol is made in low abundance by other organisms (e.g., rhodophytes, land plants), but because these other organisms produce a variety of sterols it cannot be used as a conclusive indicator of any one taxon. It is often found in analysis of organic compounds in petroleum.

<span class="mw-page-title-main">Ferruginol</span> Chemical compound

Ferruginol is a natural phenol with a terpenoid substructure. Specifically, it is a diterpene of the abietane chemical class, meaning it is characterized by three fused six-membered rings and alkyl functional groups. Ferruginol was first identified in 1939 by Brandt and Neubauer as the main component in the resin of the Miro tree and has since been isolated from other conifer species in the families Cupressaceae and Podocarpaceae. 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.

<span class="mw-page-title-main">Totarol</span> Chemical compound

Totarol is a naturally produced diterpene that is bioactive. It was first isolated by McDowell and Easterfield from the heartwood of Podocarpus totara, a conifer tree found in New Zealand. Podocarpus totara was investigated for unique molecules due to the tree's increased resistance to rotting. Recent studies have confirmed totarol's unique antimicrobial and therapeutic properties. Consequently, totarol is a candidate for a new source of drugs and has been the goal of numerous syntheses.

<span class="mw-page-title-main">Taxodone</span> Chemical compound

Taxodone is a naturally occurring diterpenoid found in Taxodium distichum, Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.

<span class="mw-page-title-main">Quinone methide</span> Chemical compound

A quinone methide is a type of conjugated organic compound that contain a cyclohexadiene with a carbonyl and an exocyclic methylidene or extended alkene unit. It is analogous to a quinone, but having one of the double bonded oxygens replaced with a carbon. The carbonyl and methylidene are usually oriented either ortho or para to each other. There are some examples of transient synthetic meta quinone methides.

<span class="mw-page-title-main">18-Norabietane</span> Chemical compound

18-Norabietane is a diterpene perhydrogenated phenanthrene derivative. It occurs in the mineral fichtelite, one of the abietanes. Like many "fossil compounds", it is saturated and devoid of oxygen-containing functional groups. Its presence is usually analyzed by gas chromatography–mass spectrometry.

<span class="mw-page-title-main">Abietane</span> Chemical compound

Abietane is an organic compound with the formula C20H36. It is a tricyclic, saturated hydrocarbon with an elaborate stereochemistry. It is a colorless solid. It is of little biochemical interest except as a reference structure of the abietanes,

<span class="mw-page-title-main">Levopimaric acid</span> Chemical compound

Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as antibacterial, cardiovascular and antioxidant. Levopimaric acid accounts for about 18 to 25% of pine oleoresin. The production of oleoresin by conifer species is an important component of the defense response against insect attack and fungal pathogen infection.

<span class="mw-page-title-main">Incensole</span> Chemical compound

Incensole is a C20 diterpene alcohol and biomarker for some plants of the Boswellia genus. It, along with its acetate ester incensole acetate, is an abundant component of frankincense, the resin collected from Boswellia trees. Incensole is used archaeologically to assist in identifying trade routes and distinguishing the identity of frankincense from other resins which may have been used together in incense and other salves. Incensole has also been deemed to be an active component in medicinal frankincense. 

The Mars Organic Molecule Analyser (MOMA) is a mass spectrometer-based instrument on board the Rosalind Franklin rover to be launched in 2028 to Mars on an astrobiology mission. It will search for organic compounds in the collected soil samples. By characterizing the molecular structures of detected organics, MOMA can provide insights into potential molecular biosignatures. MOMA will be able to detect organic molecules at concentrations as low as 10 parts-per-billion by weight (ppbw). MOMA examines solid crushed samples exclusively; it does not perform atmospheric analyses.

<span class="mw-page-title-main">Isoarborinol</span> Chemical compound

Isoarborinol is a triterpenoid ubiquitously produced by angiosperms and is thus considered a biomarker for higher plants. Though no isoarborinol-producing microbe has been identified, isoarborinol is also considered a possible biomarker for marine bacteria, as its diagenetic end product, arborane, has been found in ancient marine sediments that predate the rise of plants. Importantly, isoarborinol may represent the phylogenetic link between hopanols and sterols.

<span class="mw-page-title-main">Chamaecydin</span> Chemical compound

Chamaecydin is a chemical compound with the molecular formula C30H40O3. It is made up of three six-membered rings and two five-membered rings and has one polar hydroxyl functional group. It is well preserved in the rock record and is only found in a specific family of conifers, the swamp cypress subfamily. The presence and abundance of chamaecydin in the rock record can reveal environmental changes in ancient biomes.

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 Marynowski, Leszek; Otto, Angelika; Zatoń, Michał; Philippe, Marc; Simoneit, Bernd R. T. (2007-02-12). "Biomolecules preserved in ca. 168 million year old fossil conifer wood" (PDF). Naturwissenschaften. 94 (3): 228–236. Bibcode:2007NW.....94..228M. doi:10.1007/s00114-006-0179-x. ISSN   0028-1042. PMID   17139498. S2CID   25984294.
  2. 1 2 3 4 5 6 7 Otto, Angelika; Wilde, Volker (2001-04-01). "Sesqui-, di-, and triterpenoids as chemosystematic markers in extant conifers—A review" . The Botanical Review. 67 (2): 141–238. Bibcode:2001BotRv..67..141O. doi:10.1007/BF02858076. ISSN   1874-9372. S2CID   20371074.
  3. 1 2 Talapatra, Sunil Kumar; Talapatra, Bani (2015), Talapatra, Sunil Kumar; Talapatra, Bani (eds.), "Diterpenoids (C20)" , Chemistry of Plant Natural Products: Stereochemistry, Conformation, Synthesis, Biology, and Medicine, Berlin, Heidelberg: Springer, pp. 469–510, doi:10.1007/978-3-642-45410-3_8, ISBN   978-3-642-45410-3 , retrieved 2021-05-21
  4. 1 2 3 4 González, Miguel A. (2015-04-29). "Aromatic abietane diterpenoids: their biological activity and synthesis" . Natural Product Reports. 32 (5): 684–704. doi:10.1039/C4NP00110A. ISSN   1460-4752. PMID   25643290.
  5. 1 2 3 4 5 6 7 Bajpai, Vivek K.; Sonwal, Sonam; Hwang, Seung-Kyu; Shukla, Shruti; Khan, Imran; Dey, Debasish Kumar; Chen, Lei; Simal-Gandara, Jesus; Xiao, Jianbo; Huh, Yun Suk; Han, Young-Kyu (2021-01-01). "Sugiol, a diterpenoid: Therapeutic actions and molecular pathways involved" . Pharmacological Research. 163: 105313. doi:10.1016/j.phrs.2020.105313. ISSN   1043-6618. PMID   33246173. S2CID   227191966.
  6. 1 2 Scariot, Débora Botura; Volpato, Hélito; Fernandes, Nilma de Souza; Soares, Edna Filipa Pais; Ueda-Nakamura, Tânia; Dias-Filho, Benedito Prado; Din, Zia Ud; Rodrigues-Filho, Edson; Rubira, Adley Forti; Borges, Olga; Sousa, Maria Do Céu (2019). "Activity and Cell-Death Pathway in Leishmania infantum Induced by Sugiol: Vectorization Using Yeast Cell Wall Particles Obtained From Saccharomyces cerevisiae". Frontiers in Cellular and Infection Microbiology. 9: 208. doi: 10.3389/fcimb.2019.00208 . ISSN   2235-2988. PMC   6587907 . PMID   31259161.
  7. ↑ González, Miguel A. (May 2015). "Aromatic abietane diterpenoids: their biological activity and synthesis". Natural Product Reports. 32 (5): 684–704. doi:10.1039/c4np00110a. ISSN   1460-4752. PMID   25643290.
  8. 1 2 3 4 Cui, Guanghong; Duan, Lixin; Jin, Baolong; Qian, Jun; Xue, Zheyong; Shen, Guoan; Snyder, John Hugh; Song, Jingyuan; Chen, Shilin; Huang, Luqi; Peters, Reuben J. (November 2015). "Functional Divergence of Diterpene Syntheses in the Medicinal Plant Salvia miltiorrhiza1[OPEN]". Plant Physiology. 169 (3): 1607–1618. doi:10.1104/pp.15.00695. ISSN   0032-0889. PMC   4634056 . PMID   26077765.
  9. ↑ Gong, Hai-Yan; Zeng, Ying; Chen, Xiao-Ya (2014-04-18). "Diterpene Synthases and Their Responsible Cyclic Natural Products". Natural Products and Bioprospecting. 4 (2): 59–72. doi:10.1007/s13659-014-0012-8. ISSN   2192-2195. PMC   4004862 . PMID   24858310.
  10. ↑ "Rhea- Annotated reactions database". www.rhea-db.org. Retrieved 2021-05-18.
  11. 1 2 Otto, Angelika; White, James D.; Simoneit, Bernd R. T. (2002-08-30). "Natural Product Terpenoids in Eocene and Miocene Conifer Fossils" . Science. 297 (5586): 1543–1545. Bibcode:2002Sci...297.1543O. doi:10.1126/science.1074225. ISSN   0036-8075. PMID   12202827. S2CID   41346998.
  12. 1 2 3 4 5 6 7 8 9 10 11 12 13 Staccioli, Giuseppe; Bartolini, Giuseppe (1997-08-01). "New biomarkers of the extinct speciesTaxodioxylori gypsaceum" . Wood Science and Technology. 31 (4): 311–315. doi:10.1007/BF00702618. ISSN   1432-5225. S2CID   30503274.
  13. 1 2 3 4 5 Halket, John M.; Waterman, Daniel; Przyborowska, Anna M.; Patel, Raj K. P.; Fraser, Paul D.; Bramley, Peter M. (2005-01-01). "Chemical derivatization and mass spectral libraries in metabolic profiling by GC/MS and LC/MS/MS". Journal of Experimental Botany. 56 (410): 219–243. CiteSeerX   10.1.1.563.133 . doi: 10.1093/jxb/eri069 . ISSN   0022-0957. PMID   15618298.
  14. 1 2 Simoneit, Bernd R. T.; Otto, Angelika; Oros, Daniel R.; Kusumoto, Norihisa (2019-08-21). "Terpenoids of the Swamp Cypress Subfamily (Taxodioideae), Cupressaceae, an Overview by GC-MS". Molecules (Basel, Switzerland). 24 (17): 3036. doi: 10.3390/molecules24173036 . ISSN   1420-3049. PMC   6751496 . PMID   31438610.
  15. 1 2 3 4 5 Pereira, Ricardo; Carvalho, Ismar S.; Fernandes, Antonio Carlos S.; Azevedo, Débora A. (August 2011). "Chemotaxonomical aspects of lower Cretaceous amber from Recôncavo Basin, Brazil" (PDF). Journal of the Brazilian Chemical Society. 22 (8): 1511–1518. doi: 10.1590/S0103-50532011000800015 . ISSN   0103-5053.
  16. ↑ "SUGIOLE - MS - Spectrum - SpectraBase". spectrabase.com. Retrieved 2021-05-20.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.