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the upper left corner and a random sequence is shown in the upper right. Each amino acid is designated by a capital letter. Typical antibodies recognize the linear sequence (from left to right) indicated in the horizontal boxes, which is |
unique to each sequence. When the peptides aggregate to form pathological oligomers, they line up in a parallel, in-register fashion, shown below. This gives rise to steric zippers that run up and down the sheet perpendicular to the sequence, shown |
in vertical boxes. Aggregation-dependent, disease-specific antibodies recognize the steric zippers from many different amyloid sequences. Zippers from F and V amino acids are shown in boxes, but there are potentially 20 different zippers; one for each of the 20 amino |
acids. The fact that a completely random sequence can form the same type of steric zipper as is found in Aß amyloid in Alzheimer’s disease means we can use a non-human, random peptide sequence as a vaccine to produce a |
protective immune response that has a very low potential for autoimmune side effects. Vaccines based on non-human peptides, like diphtheria and pertussis toxin, are so safe they routinely are given to infants. There is no reason to expect that a |
vaccine for AD that targets the disease-specific steric zippers wouldn’t be as safe and free of side effects. A goal of the research funded by Cure Alzheimer’s Fund is to do the preclinical investigations that are a necessary prelude to |
Aliphatic alcohols occur naturally in free form (component of the cuticular lipids) but more usually in esterified (wax esters) or etherified form (glyceryl ethers). Several alcohols belong to aroma compounds which are found in environmental or food systems (see the |
website: Flavornet). They are found with normal, branched (mono- or isoprenoid), saturated or unsaturated of various chain length and sometimes with secondary or even tertiary alcoholic function. An unusual phenolic alcohol is found as a component of glycolipids in Mycobacteria. |
Some cyclic alcohols have been described in plants. A classification according to the carbon-chain structure is given below. 1 - Normal-chain alcohols The carbon chain may be fully saturated or unsaturated (with double and/or triple bonds), it may also be |
substituted with chlorine, bromine or sulfate groups. Some acetylenic alcohols have been also described. Among the most common, some are listed below 9-methyl-1-hendecanol (anteisolauryl alcohol) 11-methyl-1-tridecanol (anteisomyristyl alcohol) 14-methyl-1-pentadecanol (isopalmityl alcohol) 13-methyl-1-pentadecanol (an... |
Free fatty alcohols are not commonly found in epicuticular lipids of insects, although high molecular weight alcohols have been reported in honeybees (Blomquist GJ et al., Insect Biochem 1980, 10, 313). Long-chain alcohols also have been reported in the defensive |
secretions of scale insects (Byrne DN et al., Physiol Entomol 1988, 13,267). Typically, insects more commonly produce lower molecular weight alcohols. Honeybees produce alcohols of 17–22 carbons, which induce arrestment in parasitic varroa mites (Donze G et al., Arch Insect |
Biochem Physiol 1998, 37, 129). Two female-specific fatty alcohols, docosanol (C22) and eicosanol (C20), which have been found in epicuticle of Triatoma infestans (a vector of Chagas disease in South America), are able to trigger copulation in males (Cocchiararo-Bastias L |
et al., J Chem Ecol 2011, 37, 246). Hexadecyl acetate is found in the web of some spiders (Pholcidae) to attract females (Schulz S, J Chem Ecol 2013, 39, 1). Long-chain alcohols (C18, C24, C28) from the femoral glands in |
the male lizard Acanthodactylus boskianus play a role in chemical communication as a scent marking pheromone (Khannoon ER et al., Chemoecology 2011, 21, 143). Various fatty alcohols are found in the waxy film that plants have over their leaves and |
fruits. Among them, octacosanol (C28:0) is the most frequently cited. Policosanol is a natural mixture of higher primary aliphatic alcohols isolated and purified from sugar cane (Saccharum officinarum, L.) wax, whose main component is octacosanol but contains also hexacosanol (C26:0) |
and triacontanol or melissyl alcohol (C30:0). Policosanol is also extracted from a diversity of other natural sources such as beeswax, rice bran, and wheat germ (Irmak S et al., Food Chem 2006, 95, 312) but is also present in the |
fruits, leaves, and surfaces of plants and whole seeds. A complex policosanol mixture has been identified in peanut (Cherif AO et al., J Agric Food Chem 2010, 58, 12143). More than 20 aliphatic alcohols were identified (C14-C30) and four unsaturated |
alcohols (C20-24). The total policosanol content of the whole peanut samples varied from 11 to 54 mg/100 g of oil. This mixture was shown to have cholesterol-lowering effects in rabbits (Arruzazabala ML et al., Biol Res 1994, 27, 205). Octacosanol |
was also able to suppress lipid accumulation in rats fed on a high-fat diet (Kato S et al., Br J Nutr 1995, 73, 433) and to inhibit platelet aggregation (Arruzazabala ML et al., Thromb Res 1993, 69, 321). The effectiveness |
of policosanol is still questionable but it has been approved as a cholesterol-lowering drug in over 25 countries (Carbajal D et al., Prostaglandins Leukotrienes Essent Fatty Acids 1998, 58, 61), and it is sold as a lipid-lowering supplement in more |
than 40 countries. More recent studies in mice question about any action on improvement of lipoprotein profiles (Dullens SPJ et al., J Lipid Res 2008, 49, 790). The authors conclude that individual policosanols, as well as natural policosanol mixtures, have |
no potential for reducing coronary heart disease risk through effects on serum lipoprotein concentrations. Furthermore, sugar cane policosanol at doses of 20 mg daily has shown no lipid lowering effects in subjects with primary hypercholesterolemia (Francini-Pesenti F et al., Phytother |
Res 2008, 22, 318). It must be noticed that, for the most part, positive results have been obtained by only one research group in Cuba. Outside Cuba, all groups have failed to validate the cholesterol-lowering efficacy of policosanols (Marinangeli C |
et al., Crit Rev Food Sci Nutr 2010, 50, 259). Independent studies are required before evaluating the exact value of the therapeutic benefits of that mixture. An unsaturated analogue of octacosanol, octacosa-10, 19-dien-1-ol was synthesized and was as effective as |
policosanol in inhibiting the upregulation of HMGCoA reductase (Oliaro-Bosso S et al., Lipids 2009, 44, 907). This work opens promising perspectives for the design of new antiangiogenic compounds (Thippeswamy G et al., Eur J Pharmacol 2008, 588, 141). An unsaturated |
analogue of octacosanol, octacosa-10, 19-dien-1-ol was synthesized and was as effective as policosanol in inhibiting the upregulation of HMGCoA reductase (Oliaro-Bosso S et al., Lipids 2009, 44, 907). This work opens promising perspectives for the design of new antiangiogenic compounds. |
1-Octanol and 3-octanol are components of the mushroom flavor (Maga JA, J Agric Food Chem 1981, 29, 1). Many alcohols in the C10 to C18 range, and their short-chain acid esters are potent sex or aggregation pheromones. They are mainly |
found as components of specialized defensive glands, pheromone glands or glands of the reproductive system. A series of C22 up to C28 saturated n-alcohols, with even carbon numbers predominating, and a maximum at C26 and C28, has been identified in |
the cyanobacterium Anabaena cylindrica (Abreu-Grobois FA et al., Phytochemistry 1977, 16, 351). Several authors have reported high contents of the 22:0 alcohol in sediments where an algal origin is plausible. For example, the major alcohol in a sample of the |
lacustrine Green River Shale of Eocene age is also 22:0 which comprises over 50% of the alcohols present (Sever JR et al., Science 1969, 164, 1052) Long-chain alcohols are known as major surface lipid components (waxes) with chains from C20 |
up to C34 carbon atoms, odd carbon-chain alcohols being found in only low amounts. Very long-chain methyl-branched alcohols (C38 to C44) and their esters with short-chain acids were shown to be present in insects, mainly during metamorphosis. A series of |
long-chain alkanols (more than 23 carbon atoms) were identified in settling particles and surface sediments from Japanese lakes and were shown to be produced by planktonic bacteria being thus useful molecular markers (Fukushima K et al., Org Geochem 2005, 36, |
311). Cutin and suberin contain as monomer saturated alcohols from C16 to C22 up to 8% of the total polymers. C18:1 alcohol (oleyl alcohol) is also present. Long-chain di-alcohols (1,3-alkanediols) have been described in the waxes which impregnate the matrix |
covering all organs of plants (Vermeer CP et al., Phytochemistry 2003, 62, 433). These compounds forming about 11% of the leaf cuticular waxes of Ricinus communis were identified as homologous unbranched alcohols ranging from C22 to C28 with hydroxyl group |
at the carbon atoms 1 and 3. In the leaf cuticular waxes of Myricaria germanica (Tamaricaceae) several alkanediols were identified (Jetter R, Phytochemistry 2000, 55, 169). Hentriacontanediol (C31) with one hydroxyl group in the 12-position and the second one in |
positions from 2 to 18 is the most abundant diol (9% of the wax). Others were far less abundant : C30-C34 alkanediols with one hydroxyl group on a primary and one on a secondary carbon atom, C25-C43 b-diols and C39-C43 |
g-diols. Very-long-chain 1,5-alkanediols ranging from C28 to C38, with strong predominance of even carbon numbers, were identified in the cuticular wax of Taxus baccata (Wen M et al., Phytochemistry 2007, 68, 2563). The predominant diol had 32 carbon atoms (29% |
of the total). Long-chain saturated C30-C32 diols occur in most marine sediments and in a few instances, such as in Black Sea sediments, they can be the major lipids (de Leeuw JW et al., Geochim Cosmochim Acta 1981, 45, 2281). |
A microalgal source for these compounds was discovered when Volkman JK et al. (Org Geochem 1992, 18, 131) identified C30-C32 diols in marine eustigmatophytes from the genus Nannochloropsis. Two nonacosanetriols (7,8,11-nonacosanetriol and 10,12,15-nonacosanetriol) have been isolated from the outer fleshy |
layer (sarcotesta) of the Ginkgo biloba "fruit" (Zhou G et al., Chem Phys Lipids 2012, 165, 731). They exhibited slight activity of antithrombin and moderate activities of platelet aggregation in vitro. The chief lipid fraction in the uropygial gland excretion |
of the domestic hen is a diester wax. The unsaponifiable fraction consists of a series of three homologous compounds, which have been named the uropygiols and identified as 2,3-alkanediols containing 22-24 carbon atoms. These fatty alcohols are esterified by saturated |
normal C22-C24 fatty acids (Haahti E et al., J Lipid Res 1967, 8, 131). - Unsaturated alcohols Some fatty alcohols have one double bond (monounsaturated). Their general formula is: The unique double bond may be found in different positions: at |
the C6: i.e. cis-6-octadecen-1-ol (petroselenyl alcohol), C9 i.e cis-9-octadecen-1-ol (oleyl alcohol) and C11 i.e cis-11-octadecen-1-ol (vaccenyl alcohol). Some of these alcohols have insect pheromone activity. As an example, 11-eicosen-1-ol is a major component of the alarm pheromone secreted by the |
sting apparatus of the worker honeybee. In zooplankton, the cis-11-docosen-1-ol (22:1 (n-11) alcohol) is not only present in high proportion in wax esters (54 to 83%) but may be also predominant in free form (75-94% of free alcohols) in ctenophores |
(Graeve M et al., Mar Biol 2008, 153, 643). This presence is unexplained because pathways for conversion and catabolism of fatty alcohols in ctenophores are still unknown. Some short-chain unsaturated alcohols are components of mushroom flavor, such as 1-octen-3-ol, t2-octen-1-ol, |
and c2-octen-1-ol (Maga JA, J Agric Food Chem 1981, 29, 1). An acetoxy derivative of a 16-carbon alcohol with one double bond, gyptol (10-acetoxy cis-7-hexadecen-1-ol), was described to be a strong attractive substance secreted by a female moth (Porthetria dispar, |
"gypsy moth"). A fatty alcohol with two double bonds, bombykol (tr-10,cis-12-hexadecadien-1-ol), was also shown to be excreted as a very strong attractive substance by the female of silk-worm (Bombyx mori). This first discovery of a pheromone was made by Butenandt |
A et al. (Z Naturforsch 1959, 14, 283) who was formerly Nobel laureate (in 1939) for his work in sex hormones. Another pheromone, 8,10-dodecadienol (codlemone), is secreted by the codling moth Cydia pomonella, has been used for monitoring and mating |
in apple and pear orchards in the USA and Europe. This molecule was also used to monitor the population of the pea moth Cydia nigricana. Likewise, 7,9-dodecadienol, the female pheromone of the European grapewine moth Lobesia botrana, was used to |
control this important pest in vineyards. A fatty triol with one double bond, avocadene (16-heptadecene-1,2,4-triol) is found in avocado fruit (Persea americana) and has been tested for anti-bacterial and anti-inflammatory properties. These properties are likely related with the curative effects |
of avocado described for a number of ailments (diarrhea, dysentery, abdominal pains and high blood pressure). Several others heptadecanols with one primary and two secondary alcohol functions and with one double or triple bond have been identified in the leaves |
of Persea americana (Lee TH et al., Food Chem 2012, 132, 921). One or two of these alcohol groups may be acetylated. These compounds may be related to the known antifungal activity of Persea leaves. Long-chain alkenols (C37 to C39) |
with 2 to 4 double bonds, the reduced form of the alkenones, have been described in the benthic haptophyte Chrysotila lamellosa (Rontani JF et al., Phytochemistry 2004, 65, 117). al., 1986). C30 to C32 alcohols having one or two double |
bonds are significant constituents of the lipids of marine eustigmatophytes of the genus Nannochloropsis (Volkman JK et al., Org Geochem 1992, 18, 131). These microalgae could be partially the source of the alkenols found in some marine sediments. Two chlorinated |
derivatives of unusual alcohols were described in a red alga Gracilaria verrucosa (Shoeb M et al., J Nat Prod 2003, 66, 1509). Both compounds have a C12 aliphatic chain chlorinated in position 2 and with one double bond at carbon |
2 (compound 1 : 2-chlorododec-2-en-1-ol) or two double bonds at carbon 2 and 11 (compound 2 : 2-chlorododec-2,11-dien-1-ol). - Acetylenic alcohols Natural acetylenic alcohols and their derivatives have been isolated from a wide variety of plant species, fungi and invertebrates. |
Pharmacological studies have revealed that many of them display chemical and medicinal properties. Monoacetylenic alcohols : were isolated from culture of Clitocybe catinus (Basidiomycetes) and the study of their structure revealed the presence of two or three hydroxyl groups (Armone |
A et al., Phytochemistry 2000, 53, 1087). One of these compounds is shown below. Acetylenic alcohols have been also described in a tropical sponge Reniochaline sp (Lee HS et al., Lipids 2009, 44, 71). One of the two described in |
that species is shown below, it exhibited a significant growth effect against human tumor cell lines. Polyacetylenic alcohols : Several examples with different chain lengths, unsaturation degrees, and substitution have been reported from terrestrial plants and marine organisms. Food plants |
of the Apiaceae (Umbellifereae) plant family such as carrots, celery and parsley, are known to contain several bioactive bisacetylenic alcohols. The main plant sources of these compounds are Angelica dahurica, Heracleum sp and Crithmum maritimum (falcarindiol, falcarinol), red ginseng (Panax |
ginseng) (panaxacol, panaxydol, panaxytriol), Cicuta virosa (virol A), and Clibadium sylvestre (cunaniol). All these compounds display antibiotic or cytotoxic activities. Polyacetylenes have been isolated from the stems of Oplopanax elatus (Araliaceae), plant used in Korean and Chinese traditional medicine for |
anti-inflammatory and analgesic purposes (Yang MC et al., J Nat Prod 2010, 73, 801). Among the most efficient in inhibiting the formation of nitric oxide in LPS-induced cells is a seventeen-carbon diyne diol with an epoxy cycle, oploxyne A. Other |
parent compounds without the epoxy group were also described. J. Sci. Food Agric. 2003, 83, 1010). Falcarinl has potent anticancer properties on primary mammary epithelial cells and was compared with that of b-carotene. These results might be important in developing |
new cancer treatments with simple and common vegetables. At high concentrations, falcarinol is capable to induce contact dermatitis. Falcarinol, a seventeen-carbon diyne fatty alcohol (1,9-heptadecadiene-4,6-diyn-3-ol), was first isolated from Falcaria vulgaris (Bohlmann F et al., Chem Ber 1966, 99, 3552) |
as well as from Korean ginseng (Takahashi et al., Yakugaku Zasshi 1966, 86, 1053). It was also isolated from carrot (Hansen SL et al. Falcarinol protects the vegetable from fungal diseases, it showed biphasic activity, having stimulatory effects between 0.01 |
and 0.05 µg per ml and inhibitory effects between 1 and 10 µg per ml, whereas b-carotene showed no effect in the concentration range 0.001–100 µg per ml (Hansen SL et al., J Sci Food Agric 2003, 83, 1010). Experiments |
with macrophage cells have shown that falcarinol (and its C-8 hydroxylated derivative, falcarindiol) reduced nitric oxide production, suggesting that these polyacetylenes are responsible for anti-inflammatory bioactivity (Metzger BT et al., J Agric Food Chem 2008, 56, 3554). Falcarindiol was first |
reported as phytochemicals in carrots (Daucus carota) (Bentley RK et al., J Chem Soc 1969, 685). Besides falcarinol, falcarindiol, and falcarindiol 3-acetate, nine additional bisacetylene alcohols were identified in Daucus carota (Schmiech L et al., J Agric Food Chem 2009, |
57, 11030). Experiments with human intestinal cells demonstrate that aliphatic C17-polyacetylenes (panaxydol, falcarinol, falcarindiol) are potential anticancer principles of carrots and related vegetables (parsley, celery, parsnip, fennel) and that synergistic interaction between bioactive polyacetylenes may be import... |
(Purup S et al., J Agric Food Chem 2009, 57, 8290). Compounds very similar to falcarinol and extracted from Panax japonicus are potent a-glucosidase inhibitors (Chan HH et al., Phytochemistry 2010, 71, 1360). These inhibitors may potentially reduce the progression |
of diabetes by decreasing digestion and absorption of carbohydrates. The water dropwort (Oenanthe crocata), which lives near streams in the Northern Hemisphere, contains a violent toxin, cicutoxin, resulting in convultions and respiratory paralysis (Uwai K et al., J Med Chem |
2000, 43, 4508). The biochemistry and bioactivity of polyacetylenes are presented in a review (Christensen LP et al., J Pharm Biomed Anal 2006, 41, 683) as well methods for the isolation and quantification of these compounds. Many other polyacetylenic alcohols |
were found in primitive marine organisms, such as sponges and ascidians. These invertebrates have no physical defenses and thus they have developed efficient chemical mechanisms such as polyacetylenic metabolites to resist predators and bacteria. A C36 linear diacetylene alcohol named |
lembehyne was found in an Indonesian marine sponge (Haliclona sp) (Aoki S et al., Tetrahedron 2000, 56, 9945) and was later able to induce neuronal differentiation in neuroblastoma cell (Aoki S et al., Biochem Biophys Res Comm 2001, 289, 558). |
Several polyacetylenic alcohols with 22 carbon atoms were isolated and identified in lipid extract from a Red Sea sponge, Callyspongia sp (Youssef DT et al., J Nat Prod 2003, 66, 679). Their physical study revealed the presence of 4 triple |
bonds and one, two or three double bonds. The structure of one of these Callyspongenols is given below. Several di- and tri-acetylenic di-alcohols with a chain of 26 up to 31 carbon atoms, named strongylodiols, have been isolated from a |
Petrosia Okinawan marine sponge (Watanabe K et al., J Nat Prod 2005, 68, 1001). Some of them have cytotoxic Several polyacetylenic alcohols with 21 carbon atoms were isolated from a marine ascidian (Polyclinidae) and were determined to have two triple |
bonds combined with a conjugated dienyne group (Gavagnin M et al., Lipids 2004, 39, 681). Some of them have an additional hydroxyl group or only three double bonds. The structure of one of these molecules is given below. Several brominated |
polyacetylenic diols with cytotoxic properties were isolated from a Philippines sponge Diplastrella sp (Lerch ML et al., J Nat Prod 2003, 66, 667). One of these molecules is shown below. A comprehensive survey of acetylenic alcohols in plant and invertebrates |
with information on their anticancer activity has been released by Dembitsky VM (Lipids 2006, 41, 883). - Sulfated alcohols Long-chain di-hydroxy alcohols in which both the primary and secondary hydroxyl groups are converted to sulfate esters and one to five |
chlorine atoms are introduced at various places have been discovered in the alga Ochromonas danica (Chrysophyceae, Chrysophyta) where they constitute 15% of the total lipids (Haines TH, Biochem J 1969, 113, 565). An example of these chlorosulfolipids is given below. |
There may be several types of chlorine addition : one at R4, two at R3 and R5 or R1 and R2, five at R1 to R5 and six at R1 to R6. Similar molecules with a 24 carbon chain was |
also described in Ochromonas malhamensis (review in Dembitsky VM et al., Prog Lipid Res 2002, 41, 315 and in Bedke DK et al., Nat Prod Rep 2011, 28, 15). It was suggested that the chlorosulfolipids replace sulfoquinovosyl diglyceride, since when |
the later is high the former is low and vice versa. They have been associated with the human toxicity of the mussel-derived lipids (Diarrhetic Shellfish Poisoning). Several of these chlorosulfolipids have also been identified from more than 30 species of |
both freshwater and marine algae belonging to green (Chlorophyceae), brown (Phaeophyceae), red (Rhodophyceae) macrophytic algae (Mercer EI et al., Phytochemistry 1979, 18, 457), and other microalgal species (Mercer EI et al., Phytochemistry 1975, 14, 1545). Some fatty alcohols, such as |
dodecanol (lauryl or dodecyl alcohol), are used for the manufacture of detergents after sulphonation (by action of SO3 gas). The salt sodium laurylsulfate (or sodium dodecylsulfate) is a detergent and strong anionic surfactant, used in biochemistry and in the composition |
of cosmetic products (shampoos, toothpastes). 2 - Branched-chain alcohols In 1936, Stodola et al. characterized an optically active substance recovered on saponification of ‘‘purified waxes’’ of Mycobacterium tuberculosis, determined its global formula and proposed to name it phthiocerol (Stodola FH |
et al., J Biol Chem 1936, 114, 467). In 1959, after several chemical studies, its structure was determined as a mixture of C36 and C34b-glycols. It has been proposed that the term phthiocerol be reserved for the original 3-methoxy congener |
(phthiocerol A) and that the term phthioglycol be used to refer to the family of compounds (Onwueme KC et al., Prog Lipid Res 2005, 44, 259). Among the most important saturated isopranols found in plants or in geological sediments are |
those having two (tetrahydrogeraniol), three (farnesanol), or four (phytanol) isoprenoid units. Pristanol (2,6,10,14-tetramethyl-1-pentadecanol) is tetramethylated but with only three complete isoprenoid units. B - Unsaturated polyisoprenoids (prenols or polyprenols) They have the following general structure : These mo... |
several up to more than 100 isoprene residues linked head-to-tail, with a hydroxy group at one end (a-residue) and a hydrogen atom at the other (w-end). - 1. all trans forms : They have the following structure: Some important members |
of the series are as follows: Number of isoprene unit Number of carbons Long-chain trans-polyprenol (n>8) have been characterized from Eucommia ulmoides. Geraniol (from rose oil) is a monoterpene (2 isoprene units). It has a rose-like odor and is commonly |
used in perfumes and as several fruit flavors. Geraniol is also an effective mosquito repellent. Inversely, it can attract bees as it is produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the |
entrances to their hives. Farnesol is a sesquiterpene (3 isoprene units). It is the prenol that corresponds to the carbon skeleton of the simplest juvenile hormone described for the first time in insects in 1961 (Schmialek PZ, Z Naturforsch 1961, |
16b, 461; Wigglesworth VB, J Insect Physiol 1961, 7, 73). It is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, rose, and others. It is used in perfumery to emphasize the odors of sweet floral perfumes. |
It is especially used in lilac perfumes. As a pheromone, farnesol is a natural pesticide for mites. The dimorphic fungus Candida albicans has been shown to use farnesol as quorum-sensing molecule (Hornby JM et al., Appl Environ Microbiol 2001, 67, |
2982). Geranylgeraniol is a diterpene (4 isoprene units). Geraniol and geranylgeraniol are important molecules in the synthesis of various terpenes, the acylation of proteins and the synthesis of vitamins (Vitamins E and K). The covalent addition of phosphorylated derivatives of |
typical isoprenoids, farnesyl pyrophosphate and geranylgeranyl pyrophosphate, to proteins is a process (prenylation) common to G protein subunits. These isoprenylated proteins have key roles in membrane attachment leading to central functionality in cell biology and pathology. Solanesol, discovered in tobacco |
leaves in 1956 (Rowland RL et al., J Am Chem Soc 1956, 78, 4680), may be an important precursor of the tumorigenic polynuclear aromatic hydrocarbons of smoke but is also a possible side chain for plastoquinone. Solanesol is also present |
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