fatty alcohols

Summary

Summary: Usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4 carbons, derived from natural fats and oils, including lauryl, stearyl, oleyl, and linoleyl alcohols. They are used in pharmaceuticals, cosmetics, detergents, plastics, and lube oils and in textile manufacture. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)

Top Publications

  1. Hull J, Lee J, Matsumoto S. Gqalpha-linked phospholipase Cbeta1 and phospholipase Cgamma are essential components of the pheromone biosynthesis activating neuropeptide (PBAN) signal transduction cascade. Insect Mol Biol. 2010;19:553-66 pubmed publisher
    ..In vivo RNA interference-mediated knockdown analyses revealed that BmPLCbeta1, BmGq1, and unexpectedly, BmPLCgamma, are part of the PBAN signal transduction cascade...
  2. Zheng Y, Li L, Liu Q, Yang J, Wang X, Liu W, et al. Optimization of fatty alcohol biosynthesis pathway for selectively enhanced production of C12/14 and C16/18 fatty alcohols in engineered Escherichia coli. Microb Cell Fact. 2012;11:65 pubmed publisher
    ..Though bioproduction of fatty alcohols has been carried out in engineered E...
  3. Marazzi G, Cacciotti L, Pelliccia F, Iaia L, Volterrani M, Caminiti G, et al. Long-term effects of nutraceuticals (berberine, red yeast rice, policosanol) in elderly hypercholesterolemic patients. Adv Ther. 2011;28:1105-13 pubmed publisher
    ..The purpose of this study was to examine the efficacy, safety, and tolerability of a nutraceutical-based protocol in elderly hypercholesterolemic patients previously intolerant to statins...
  4. Domergue F, Vishwanath S, Joubès J, Ono J, Lee J, Bourdon M, et al. Three Arabidopsis fatty acyl-coenzyme A reductases, FAR1, FAR4, and FAR5, generate primary fatty alcohols associated with suberin deposition. Plant Physiol. 2010;153:1539-54 pubmed publisher
    ..consisting of phenolics, glycerol, and a variety of fatty acid derivatives, including C18:0-C22:0 primary fatty alcohols. An eight-member gene family encoding alcohol-forming fatty acyl-coenzyme A reductases (FARs) has been ..
  5. Musto D, Martorelli L, Russo M, Esposito G, Amato M, Esposito P, et al. [Non-alcoholic hepatic steatosis: the role of policosanols in associated hyperlipidemia]. Minerva Gastroenterol Dietol. 2010;56:389-95 pubmed
    ..The purpose of this study was to evaluate the efficacy of policosanols in the treatment of associated hyperlipidemia in patients with non-alcoholic fatty liver disease (NAFLD)...
  6. Backes J, Gibson C, Ruisinger J, Moriarty P. Modified-policosanol does not reduce plasma lipoproteins in hyperlipidemic patients when used alone or in combination with statin therapy. Lipids. 2011;46:923-9 pubmed publisher
    ..Consistent with recent clinical trial data, MP demonstrated an excellent safety profile but produced no significant effects on major lipoproteins when used as monotherapy or when given with concomitant statin therapy. ..
  7. Ohnuma T, Anan E, Hoashi R, Takeda Y, Nishiyama T, Ogura K, et al. Dietary diacetylene falcarindiol induces phase 2 drug-metabolizing enzymes and blocks carbon tetrachloride-induced hepatotoxicity in mice through suppression of lipid peroxidation. Biol Pharm Bull. 2011;34:371-8 pubmed
    ..These results suggest that the protective effects of falcarindiol against CCl(4) toxicity might, in part, be explained by anti-lipid peroxidation activity associated with the induction of the GSTs including GSTA4...
  8. Youngquist J, Schumacher M, Rose J, Raines T, Politz M, Copeland M, et al. Production of medium chain length fatty alcohols from glucose in Escherichia coli. Metab Eng. 2013;20:177-86 pubmed publisher
    ..Microbial synthesis of fatty alcohols is an attractive process because it can control the distribution of chain lengths and utilize low cost ..
  9. Teerawanichpan P, Robertson A, Qiu X. A fatty acyl-CoA reductase highly expressed in the head of honey bee (Apis mellifera) involves biosynthesis of a wide range of aliphatic fatty alcohols. Insect Biochem Mol Biol. 2010;40:641-9 pubmed publisher
    ..One of the cDNAs coding for a fatty acyl-CoA reductase (AmFAR1) involved in the synthesis of fatty alcohols was isolated and characterized...

More Information

Publications62

  1. Rosenblat G, Meretski S, Segal J, Tarshis M, Schroeder A, Zanin Zhorov A, et al. Polyhydroxylated fatty alcohols derived from avocado suppress inflammatory response and provide non-sunscreen protection against UV-induced damage in skin cells. Arch Dermatol Res. 2011;303:239-46 pubmed publisher
    ..The present study tested the ability of unique lipid molecules, polyhydroxylated fatty alcohols (PFA), extracted from avocado, to reduce UVB-induced damage and inflammation in skin...
  2. Tan X, Yao L, Gao Q, Wang W, Qi F, Lu X. Photosynthesis driven conversion of carbon dioxide to fatty alcohols and hydrocarbons in cyanobacteria. Metab Eng. 2011;13:169-76 pubmed publisher
    ..Here we describe the biosynthesis of fatty alcohols in a genetically engineered cyanobacterial system through heterologously expressing fatty acyl-CoA reductase ..
  3. Rinthong P, Zhu S, Komatsu K, Chanama S, De Eknamkul W. Genetic variation of Croton stellatopilosus Ohba based on non-coding DNA sequences of ITS, trnK and trnL-F regions. J Nat Med. 2011;65:641-5 pubmed publisher
    ..209-0.492, 0.319-0.896 and 0.442-1.000% (w/w) dry weight, respectively. The results indicated that there is a correlation between the plaunotol contents and non-coding DNA sequences of ITS, trnK and trnL-F regions of C. stellatopilosus...
  4. Baliga M, Haniadka R, Pereira M, D Souza J, Pallaty P, Bhat H, et al. Update on the chemopreventive effects of ginger and its phytochemicals. Crit Rev Food Sci Nutr. 2011;51:499-523 pubmed publisher
    ..The above-mentioned mechanisms of ginger seem to be promising for cancer prevention; however, further clinical studies are warranted to assess the efficacy and safety of ginger...
  5. Hofvander P, Doan T, Hamberg M. A prokaryotic acyl-CoA reductase performing reduction of fatty acyl-CoA to fatty alcohol. FEBS Lett. 2011;585:3538-43 pubmed publisher
    ..The Marinobacter fatty acyl reductase studied has a wide substrate range in comparison to what can be found among enzymes so far studied in eukaryotes...
  6. Brooke D, Shelley E, Roberts C, Denny W, Sutherland R, Butt A. Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells. Bioorg Med Chem. 2011;19:7033-43 pubmed publisher
    ..A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships...
  7. Vishwanath S, Kosma D, Pulsifer I, Scandola S, Pascal S, Joubès J, et al. Suberin-associated fatty alcohols in Arabidopsis: distributions in roots and contributions to seed coat barrier properties. Plant Physiol. 2013;163:1118-32 pubmed publisher
    ..consists of polymerized phenolics, glycerol, and a variety of fatty acid derivatives, including primary fatty alcohols. We have conducted an in-depth analysis of the distribution of the C18:0 to C22:0 fatty alcohols in ..
  8. Lee C, Park G, Kim C, Jang J. [6]-Gingerol attenuates ?-amyloid-induced oxidative cell death via fortifying cellular antioxidant defense system. Food Chem Toxicol. 2011;49:1261-9 pubmed publisher
    ..These results suggest that [6]-gingerol exhibits preventive and/or therapeutic potential for the management of AD via augmentation of antioxidant capacity...
  9. Willis R, Wahlen B, Seefeldt L, Barney B. Characterization of a fatty acyl-CoA reductase from Marinobacter aquaeolei VT8: a bacterial enzyme catalyzing the reduction of fatty acyl-CoA to fatty alcohol. Biochemistry. 2011;50:10550-8 pubmed publisher
    b>Fatty alcohols are of interest as a renewable feedstock to replace petroleum compounds used as fuels, in cosmetics, and in pharmaceuticals...
  10. Matsumoto S, Hull J, Ohnishi A, Moto K, Fónagy A. Molecular mechanisms underlying sex pheromone production in the silkmoth, Bombyx mori: characterization of the molecular components involved in bombykol biosynthesis. J Insect Physiol. 2007;53:752-9 pubmed
    ..Characterization of these, and other, key molecules will facilitate our understanding of the precise mechanisms underlying lepidopteran sex pheromone production...
  11. Ohnishi A, Hashimoto K, Imai K, Matsumoto S. Functional characterization of the Bombyx mori fatty acid transport protein (BmFATP) within the silkmoth pheromone gland. J Biol Chem. 2009;284:5128-36 pubmed publisher
  12. Mahady G, Pendland S, Yun G, Lu Z, Stoia A. Ginger (Zingiber officinale Roscoe) and the gingerols inhibit the growth of Cag A+ strains of Helicobacter pylori. Anticancer Res. 2003;23:3699-702 pubmed
    ..Since Helicobacter pylori (HP) is the primary etiological agent associated with dyspepsia, peptic ulcer disease and the development of gastric and colon cancer, the anti-HP effects of ginger and its constituents were tested in vitro...
  13. Ramirez Ahumada M, Timmermann B, Gang D. Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases. Phytochemistry. 2006;67:2017-29 pubmed
    ..These activities may shunt phenylpropanoid pathway intermediates away from the production of curcuminoids and gingerols, thereby potentially playing a regulatory role in the biosynthesis of these compounds...
  14. Greyling A, De Witt C, Oosthuizen W, Jerling J. Effects of a policosanol supplement on serum lipid concentrations in hypercholesterolaemic and heterozygous familial hypercholesterolaemic subjects. Br J Nutr. 2006;95:968-75 pubmed
    ..An intake of 20 mg/d policosanol for 12 weeks had no significant effect on serum lipid levels in hypercholesterolaemic and heterozygous familial hypercholesterolaemic patients when compared with placebo intake...
  15. Cubeddu L, Cubeddu R, Heimowitz T, Restrepo B, Lamas G, Weinberg G. Comparative lipid-lowering effects of policosanol and atorvastatin: a randomized, parallel, double-blind, placebo-controlled trial. Am Heart J. 2006;152:982.e1-5 pubmed
    ..This trial was designed to rigorously establish the lipid-lowering efficacy of policosanol as monotherapy and its potential additive and possibly synergistic effects when added to statin therapy...
  16. Shukla Y, Prasad S, Tripathi C, Singh M, George J, Kalra N. In vitro and in vivo modulation of testosterone mediated alterations in apoptosis related proteins by [6]-gingerol. Mol Nutr Food Res. 2007;51:1492-502 pubmed
    ..Thus, [6]-gingerol shows its protective effects in both in vivo and in vitro prostate cancer models by modulation of proteins involved in apoptosis pathway...
  17. Leal W, Chen A, Ishida Y, Chiang V, Erickson M, Morgan T, et al. Kinetics and molecular properties of pheromone binding and release. Proc Natl Acad Sci U S A. 2005;102:5386-91 pubmed
    ..Fluorescence studies shed light on the contributions of Trp-37 and Trp-127 emissions to the overall fluorescence...
  18. Hilmarsson H, Traustason B, Kristmundsdottir T, Thormar H. Virucidal activities of medium- and long-chain fatty alcohols and lipids against respiratory syncytial virus and parainfluenza virus type 2: comparison at different pH levels. Arch Virol. 2007;152:2225-36 pubmed
    Recent studies have shown that some lipids and fatty alcohols have microbicidal activities against a broad variety of pathogens...
  19. Wang Y, Jones P, Pischel I, Fairow C. Effects of policosanols and phytosterols on lipid levels and cholesterol biosynthesis in hamsters. Lipids. 2003;38:165-70 pubmed
    ..Results suggest that, although phytosterols reduce T-C and HDL-C levels, policosanols have no significant favorable effect in changing lipid levels in hamsters...
  20. Fu H, Yabe Y, Asahi K, Hayashi Y, Murata H, Eguchi H, et al. (2E,6Z,10E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol (Plaunotol) increases cyclooxygenase-2 expression via nuclear factor kappaB and cyclic AMP response element in rat gastric epithelial cells. Eur J Pharmacol. 2005;524:38-43 pubmed
    ..In conclusion, plaunotol induced COX-2 expression and increased PGE(2) production in serum-starved RGM1 cells via activation of the NF-kappaB and CRE sites of Cox-2 gene promoters...
  21. Affuso F, Ruvolo A, Micillo F, Sacca L, Fazio S. Effects of a nutraceutical combination (berberine, red yeast rice and policosanols) on lipid levels and endothelial function randomized, double-blind, placebo-controlled study. Nutr Metab Cardiovasc Dis. 2010;20:656-61 pubmed publisher
    ..We evaluated the effects of a nutraceutical combination (NC), consisting of 500 mg berberine, 200mg red yeast rice and 10mg policosanols, on cholesterol levels and endothelial function in patients with hypercholesterolemia...
  22. Czepa A, Hofmann T. Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree. J Agric Food Chem. 2003;51:3865-73 pubmed
    ..04 mmol/kg, thus demonstrating that this acetylenic diol significantly contributes to the bitter taste of the carrot products investigated...
  23. Stavri M, Gibbons S. The antimycobacterial constituents of dill (Anethum graveolens). Phytother Res. 2005;19:938-41 pubmed
    ..The three known compounds exhibited antibacterial activity against a panel of rapidly growing mycobacteria with minimum inhibitory concentration (MIC) values in the range 2-128 microg/mL...
  24. Hauss F, Liu J, Michelucci A, Coowar D, Morga E, Heuschling P, et al. Dual bioactivity of resveratrol fatty alcohols: differentiation of neural stem cells and modulation of neuroinflammation. Bioorg Med Chem Lett. 2007;17:4218-22 pubmed
    The synthesis of resveratrol fatty alcohols (RFAs), a new class of small molecules presenting strong potential for the treatment of neurological diseases, is described...
  25. Marinangeli C, Kassis A, Jain D, Ebine N, Cunnane S, Jones P. Comparison of composition and absorption of sugarcane policosanols. Br J Nutr. 2007;97:381-8 pubmed
    ..05) than hamsters receiving APC1. If the cholesterol-lowering efficacy of PC mixtures is dependent on their purity and composition, then sugarcane-derived APC products should possess similar therapeutic properties as the OPC supplement...
  26. Muller T, Grandbarbe L, Morga E, Heuschling P, Luu B. Tocopherol long chain fatty alcohols decrease the production of TNF-alpha and NO radicals by activated microglial cells. Bioorg Med Chem Lett. 2004;14:6023-6 pubmed
    The synthesis of a series of Tocopherol long chain Fatty Alcohols (TFA) and their biological activities on the modulation of microglial activation are described...
  27. Gräter F, Xu W, Leal W, Grubmuller H. Pheromone discrimination by the pheromone-binding protein of Bombyx mori. Structure. 2006;14:1577-86 pubmed
    ..While BmorPBP might filter out other physiologically irrelevant compounds hitting the sensillar lymph, discrimination between the natural pheromone compounds must be achieved by molecular interactions with their cognate receptors...
  28. Jiang H, Somogyi A, Timmermann B, Gang D. Instrument dependence of electrospray ionization and tandem mass spectrometric fragmentation of the gingerols. Rapid Commun Mass Spectrom. 2006;20:3089-100 pubmed
  29. Jiang H, Solyom A, Timmermann B, Gang D. Characterization of gingerol-related compounds in ginger rhizome (Zingiber officinale Rosc.) by high-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2005;19:2957-64 pubmed
    ..This study demonstrated that LC/ESI-MS/MS is a powerful on-line tool for identification of gingerol-related compounds, especially for thermally labile compounds that cannot be readily detected by GC/MS analysis...
  30. Kobaek Larsen M, Christensen L, Vach W, Ritskes Hoitinga J, Brandt K. Inhibitory effects of feeding with carrots or (-)-falcarinol on development of azoxymethane-induced preneoplastic lesions in the rat colon. J Agric Food Chem. 2005;53:1823-7 pubmed
    ..The present study provides a new perspective on the known epidemiological associations between high intake of carrots and reduced incidence of cancers...
  31. Nakagawa T, Sakurai T, Nishioka T, Touhara K. Insect sex-pheromone signals mediated by specific combinations of olfactory receptors. Science. 2005;307:1638-42 pubmed
    ..The same effects were also observed for general ORs. Both odorant and pheromone signaling pathways are mediated by means of a common mechanism in insects...
  32. Coowar D, Bouissac J, Hanbali M, Paschaki M, Mohier E, Luu B. Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres. J Med Chem. 2004;47:6270-82 pubmed
    ..neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared...
  33. Steen E, Kang Y, Bokinsky G, Hu Z, Schirmer A, McClure A, et al. Microbial production of fatty-acid-derived fuels and chemicals from plant biomass. Nature. 2010;463:559-62 pubmed publisher
    ..we demonstrate the engineering of Escherichia coli to produce structurally tailored fatty esters (biodiesel), fatty alcohols, and waxes directly from simple sugars...
  34. Butt A, Roberts C, Seawright A, Oelrichs P, Macleod J, Liaw T, et al. A novel plant toxin, persin, with in vivo activity in the mammary gland, induces Bim-dependent apoptosis in human breast cancer cells. Mol Cancer Ther. 2006;5:2300-9 pubmed
    ..Due to the unique structure of the compound, persin could represent a novel class of microtubule-targeting agent with potential specificity for breast cancers...
  35. Doan T, Carlsson A, Hamberg M, Bulow L, Stymne S, Olsson P. Functional expression of five Arabidopsis fatty acyl-CoA reductase genes in Escherichia coli. J Plant Physiol. 2009;166:787-96 pubmed publisher
    ..The five functional FAR enzymes yielded distinctly different compositions of fatty alcohols when expressed in E...
  36. Zick S, Djuric Z, Ruffin M, Litzinger A, Normolle D, Alrawi S, et al. Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects. Cancer Epidemiol Biomarkers Prev. 2008;17:1930-6 pubmed publisher
    ..We conducted a clinical trial with 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol, examining the pharmacokinetics and tolerability of these analytes and their conjugate metabolites...
  37. Tripathi S, Maier K, Bruch D, Kittur D. Effect of 6-gingerol on pro-inflammatory cytokine production and costimulatory molecule expression in murine peritoneal macrophages. J Surg Res. 2007;138:209-13 pubmed
  38. Shukla Y, Singh M. Cancer preventive properties of ginger: a brief review. Food Chem Toxicol. 2007;45:683-90 pubmed
    ..A number of mechanisms that may be involved in the chemopreventive effects of ginger and its components have been reported from the laboratory studies in a wide range of experimental models...
  39. Miyoshi N, Nakamura Y, Ueda Y, Abe M, Ozawa Y, Uchida K, et al. Dietary ginger constituents, galanals A and B, are potent apoptosis inducers in Human T lymphoma Jurkat cells. Cancer Lett. 2003;199:113-9 pubmed
    ..In conclusion, the results from this study provide biological evidence that ginger-specific constituents other than curcuminoids are potential anticancer agents...
  40. Ueki S, Miyoshi M, Shido O, Hasegawa J, Watanabe T. Systemic administration of [6]-gingerol, a pungent constituent of ginger, induces hypothermia in rats via an inhibitory effect on metabolic rate. Eur J Pharmacol. 2008;584:87-92 pubmed publisher
  41. Klusák V, Havlas Z, Rulísek L, Vondrasek J, Svatos A. Sexual attraction in the silkworm moth. Nature of binding of bombykol in pheromone binding protein--an ab initio study. Chem Biol. 2003;10:331-40 pubmed
    ..All of these interactions are well defined and cannot be considered as nonspecific hydrophobic interactions, one of the major conclusions of this work...
  42. Menendez R, Marrero D, Mas R, Fernández I, Gonzalez L, Gonzalez R. In vitro and in vivo study of octacosanol metabolism. Arch Med Res. 2005;36:113-9 pubmed
    ..Scarce data about the metabolism of octacosanol and the other fatty alcohols composing policosanol have been published.
  43. Dulin M, Hatcher L, Sasser H, Barringer T. Policosanol is ineffective in the treatment of hypercholesterolemia: a randomized controlled trial. Am J Clin Nutr. 2006;84:1543-8 pubmed
    ..Recent studies have challenged these findings, but there have been no trials conducted in North America that have examined the ability of sugar cane-derived policosanol to lower cholesterol...
  44. Kassis A, Jones P. Lack of cholesterol-lowering efficacy of Cuban sugar cane policosanols in hypercholesterolemic persons. Am J Clin Nutr. 2006;84:1003-8 pubmed
    ..However, several animal and human trials conducted outside of Cuba that used non-Cuban mixtures have failed to reproduce the efficacy of policosanols observed in earlier studies...
  45. Syed Z, Ishida Y, Taylor K, Kimbrell D, Leal W. Pheromone reception in fruit flies expressing a moth's odorant receptor. Proc Natl Acad Sci U S A. 2006;103:16538-43 pubmed
    ..We also found an endogenous receptor in one of the sensillum types on Drosophila antenna that responds to bombykol and bombykal with sensitivity comparable to the pheromone-detecting sensilla on B. mori male antennae...
  46. Castano G, Fernandez L, Mas R, Illnait J, Fernandez J, Mesa M, et al. Comparison of the efficacy, safety and tolerability of original policosanol versus other mixtures of higher aliphatic primary alcohols in patients with type II hypercholesterolemia. Int J Clin Pharmacol Res. 2002;22:55-66 pubmed
    ..Thus, policosanol reached the efficacy criterion for LDL-C reduction in both steps, while Octa-60 failed to reach this goal. In addition, policosanol was better tolerated than Octa-60...
  47. Wang Y, Ebine N, Jia X, Jones P, Fairow C, Jaeger R. Very long chain fatty acids (policosanols) and phytosterols affect plasma lipid levels and cholesterol biosynthesis in hamsters. Metabolism. 2005;54:508-14 pubmed
    ..05) in animals fed VLCFA25 and VLCFA50 than those fed control or VLCFA25/LT or VLCFA25/PS. Results suggest that PSs can decrease total and non-HDL-C cholesterol, whereas VLCFA may increase HDL-C in hamsters...
  48. Grosse Wilde E, Svatos A, Krieger J. A pheromone-binding protein mediates the bombykol-induced activation of a pheromone receptor in vitro. Chem Senses. 2006;31:547-55 pubmed publisher
    ..This study provides evidence that both distinct pheromone receptors and PBPs play an important role in insect pheromone recognition...
  49. Nigam N, George J, Srivastava S, Roy P, Bhui K, Singh M, et al. Induction of apoptosis by [6]-gingerol associated with the modulation of p53 and involvement of mitochondrial signaling pathway in B[a]P-induced mouse skin tumorigenesis. Cancer Chemother Pharmacol. 2010;65:687-96 pubmed publisher
  50. Aktan F, Henness S, Tran V, Duke C, Roufogalis B, Ammit A. Gingerol metabolite and a synthetic analogue Capsarol inhibit macrophage NF-kappaB-mediated iNOS gene expression and enzyme activity. Planta Med. 2006;72:727-34 pubmed
  51. Yamada J, Kawai K, Tsuno N, Kitayama J, Tsuchiya T, Yoneyama S, et al. Plaunotol induces apoptosis of gastric cancer cells. Planta Med. 2007;73:1068-73 pubmed
    ..Plaunotol should be a promising new antitumor agent, and since it is already available for clinical use in Japan, its anticancer properties should be confirmed in clinical trials...
  52. Lee H, Seo E, Kang N, Kim W. [6]-Gingerol inhibits metastasis of MDA-MB-231 human breast cancer cells. J Nutr Biochem. 2008;19:313-9 pubmed
    ..In conclusion, we have shown that [6]-gingerol inhibits cell adhesion, invasion, motility and activities of MMP-2 and MMP-9 in MDA-MB-231 human breast cancer cell lines...
  53. Ratnayake A, Hemscheidt T. Olefin cross-metathesis as a tool in natural product degradation. The stereochemistry of (+)-falcarindiol. Org Lett. 2002;4:4667-9 pubmed
    ..Degradation of (+)-falcarindiol from Tetraplasandra hawaiiensis yields a meso product as shown by chiral HPLC. Hence, (+)-falcarindiol from this source has a (3R,8S)-configuration...