Piceatannol Research Summary

Piceatannol, a hydroxylated analogue of resveratrol, exhibits a variety of biological activities, including antioxidant, anti-inflammatory, and anticancer effects. It can inhibit cancer cell growth, induce apoptosis, and affect cell cycle regulation by modulating gene expression and interfering with signaling pathways such as NF-kappaB and JAK-STAT. Piceatannol's ability to bind estrogen receptors suggests a role in the growth of estrogen-dependent cancer cells. However, its bioavailability and toxicity remain concerns due to rapid metabolism in the liver.

Studies have shown that piceatannol can enhance the anticancer effects of other chemotherapy drugs, increase eNOS expression in endothelial cells for vascular health, and mitigate inflammation in ocular diseases. It also demonstrates potential for skin lightening applications by inhibiting melanogenesis. Piceatannol's interactions with TNFα/NFκB pathway and Fas-mediated apoptosis indicate its potential in modulating immune responses and inducing cell death in leukemia cells. Its binding to specific receptors on brain cell membranes may also contribute to neuroprotective effects associated with Alzheimer's disease.

Due to its promising antitumor, antioxidant, and anti-inflammatory properties, piceatannol continues to be a valuable subject of research, with studies suggesting it could be developed into a beneficial nutritional and pharmacological agent. However, further research is needed to fully understand its effects in humans.

References:

1. Resveratrol, pterostilbene, and piceatannol in vaccinium berries
2. Investigation of monomeric and oligomeric wine stilbenoids in red wines by ultra-high-performance liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry
3. Biological activity of piceatannol: leaving the shadow of resveratrol
4. Postharvest UV-C-irradiated grapes as a potential source for producing stilbene-enriched red wines
5. Analysis of some stilbenes in Italian wines by liquid chromatography/tandem mass spectrometry
6. Determination of stilbene derivatives in Burgundy red wines by ultra-high-pressure liquid chromatography
7. Characterisation of stilbenes in California almonds (Prunus dulcis) by UHPLC-MS
8. Extract of passion fruit (Passiflora edulis) seed containing high amounts of piceatannol inhibits melanogenesis and promotes collagen synthesis
9. The protective effects of piceatannol from passion fruit (Passiflora edulis) seeds in UVB-irradiated keratinocytes
10. Anti-platelet aggregation activity of stilbene derivatives from Rheum undulatum
11. A new stilbene diglycoside from Rheum undulatum
12. Medicinal mushroom Ganoderma lucidum as a potent elicitor in production of t-resveratrol and t-piceatannol in peanut calluses
13. Directly suspended droplet microextraction with in injection-port derivatization coupled to gas chromatography-mass spectrometry for the analysis of polyphenols in herbal infusions, fruits and functional foods
14. Analysis of selected stilbenes in Polygonum cuspidatum by HPLC coupled with CoulArray detection
15. Isolation and identification of stilbenes in two varieties of Polygonum cuspidatum
16. Crystal and molecular structure of piceatannol; scavenging features of resveratrol and piceatannol on hydroxyl and peroxyl radicals and docking with transthyretin
17. Phosphoinositide 3-kinase is a novel target of piceatannol for inhibiting PDGF-BB-induced proliferation and migration in human aortic smooth muscle cells
18. Syk contributes to PDGF-BB-mediated migration of rat aortic smooth muscle cells via MAPK pathways
19. Inhibition of mast cell Fc epsilon R1-mediated signaling and effector function by the Syk-selective inhibitor, piceatannol
20. Piceatannol, a Syk-selective tyrosine kinase inhibitor, attenuated antigen challenge of guinea pig airways in vitro
21. Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor
22. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship
23. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents
24. Inhibition of mitochondrial proton F0F1-ATPase/ATP synthase by polyphenolic phytochemicals
25. Mechanism of inhibition of bovine F1-ATPase by resveratrol and related polyphenols
26. Piceatannol, a stilbene phytochemical, inhibits mitochondrial F0F1-ATPase activity by targeting the F1 complex
27. On the structure of the stator of the mitochondrial ATP synthase
28. The molecular mechanism of ATP synthesis by F1F0-ATP synthase
29. Binding of phytopolyphenol piceatannol disrupts β/γ subunit interactions and rate-limiting step of steady-state rotational catalysis in Escherichia coli F1-ATPase
30. A simple and sensitive HPLC-UV method for the quantification of piceatannol analog trans-3,5,3',4'-tetramethoxystilbene in rat plasma and its application for a pre-clinical pharmacokinetic study
31. Determination of piceatannol in rat serum and liver microsomes: pharmacokinetics and phase I and II biotransformation
32. Small transthyretin (TTR) ligands as possible therapeutic agents in TTR amyloidoses
33. Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats
34. In vitro evidence for the formation of reactive intermediates of resveratrol in human liver microsomes
35. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1
36. Resveratrol analog, 3,4,5,4'-tetrahydroxystilbene, differentially induces pro-apoptotic p53/Bax gene expression and inhibits the growth of transformed cells but not their normal counterparts
37. Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes
38. Generation of the human metabolite piceatannol from the anticancer-preventive agent resveratrol by bacterial cytochrome P450 BM3
39. Resveratrol is rapidly metabolized in athymic (nu/nu) mice and does not inhibit human melanoma xenograft tumor growth
40. In-vitro sulfation of piceatannol by human liver cytosol and recombinant sulfotransferases
41. Glucuronidation of piceatannol by human liver microsomes: major role of UGT1A1, UGT1A8 and UGT1A10
42. Effect of natural analogues of trans-resveratrol on cytochromes P4501A2 and 2E1 catalytic activities
43. Effect of natural phenols on the catalytic activity of cytochrome P450 2E1
44. In silico and biochemical analyses identify quinone reductase 2 as a target of piceatannol
45. PP2 and piceatannol inhibit PrP106-126-induced iNOS activation mediated by CD36 in BV2 microglia
46. Neurotoxicity of a prion protein fragment
47. Pathogenesis of prion diseases: current status and future outlook
48. CD36 participates in PrP(106-126)-induced activation of microglia
49. Fibrillar beta-amyloid-stimulated intracellular signaling cascades require Vav for induction of respiratory burst and phagocytosis in monocytes and microglia
50. CD36, a scavenger receptor involved in immunity, metabolism, angiogenesis, and behavior
51. Involvement of heme oxygenase-1 expression in neuroprotection by piceatannol, a natural analog and a metabolite of resveratrol, against glutamate-mediated oxidative injury in HT22 neuronal cells
52. Vasorelaxant effect of stilbenes from rhizome extract of rhubarb (Rheum undulatum) on the contractility of rat aorta
53. Spleen tyrosine kinase participates in Src-mediated migration and proliferation by PDGF-BB in rat aortic smooth muscle cells
54. PDGF and cardiovascular disease
55. Atherosclerosis--an inflammatory disease
56. Differential regulation of arginases and inducible nitric oxide synthase in murine macrophage cells
57. Arginase reciprocally regulates nitric oxide synthase activity and contributes to endothelial dysfunction in aging blood vessels
58. Role of neutral amino acid transport and protein breakdown for substrate supply of nitric oxide synthase in human endothelial cells
59. L-Arginine supplementation or arginase inhibition augments reflex cutaneous vasodilatation in aged human skin
60. MKP-1 switches arginine metabolism from nitric oxide synthase to arginase following endotoxin challenge
61. Oxidized low-density lipoprotein-dependent endothelial arginase II activation contributes to impaired nitric oxide signaling
62. Induction of arginase isoforms in the lung during hyperoxia
63. Piceatannol-3'-O-beta-D-glucopyranoside as an active component of rhubarb activates endothelial nitric oxide synthase through inhibition of arginase activity
64. Arginase inhibition by piceatannol-3'-O-β-D-glucopyranoside improves endothelial dysfunction via activation of endothelial nitric oxide synthase in ApoE-null mice fed a high-cholesterol diet
65. Piceatannol is more effective than resveratrol in restoring endothelial cell dimethylarginine dimethylaminohydrolase expression and activity after high-glucose oxidative stress
66. Regulation of nitric oxide synthesis by dimethylarginine dimethylaminohydrolase
67. Dimethylarginine dimethylaminohydrolase and endothelial dysfunction in failing hearts
68. Asymmetric dimethylarginine (ADMA) as a target for pharmacotherapy
69. Inhibitory effect of resveratrol derivative BTM-0512 on high glucose-induced cell senescence involves dimethylaminohydrolase/asymmetric dimethylarginine pathway
70. Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship
71. Effect of long-term piceatannol treatment on eNOS levels in cultured endothelial cells
72. Regulation of endothelium-derived nitric oxide production by the protein kinase Akt
73. Repeated and long-term treatment with physiological concentrations of resveratrol promotes NO production in vascular endothelial cells
74. The red wine phenolics piceatannol and myricetin act as agonists for estrogen receptor alpha in human breast cancer cells
75. Differential effects of resveratrol and its natural analogs, piceatannol and 3,5,4'-trans-trimethoxystilbene, on anti-inflammatory heme oxigenase-1 expression in RAW264.7 macrophages
76. Phosphorylation of Tyr342 in the linker region of Syk is critical for Fc epsilon RI signaling in mast cells
77. Direct interaction of Syk and Lyn protein tyrosine kinases in rat basophilic leukemia cells activated via type I Fc epsilon receptors
78. Polyphenol derivatives - potential regulators of neutrophil activity
79. Piceatannol suppresses endotoxin-induced ocular inflammation in rats
80. The natural history of uveitis
81. CYP1B1 and hormone-induced cancer
82. Cytochrome P450 gene polymorphism and cancer
83. Cytochrome P450 1B1: a novel anticancer therapeutic target
84. Angiotensin II-induced process of angiogenesis is mediated by spleen tyrosine kinase via VEGF receptor-1 phosphorylation
85. Cardiac myofibroblasts: a novel source of vascular endothelial growth factor (VEGF) and its receptors Flt-1 and KDR
86. Angiotensin II-induced migration of vascular smooth muscle cells is mediated by p38 mitogen-activated protein kinase-activated c-Src through spleen tyrosine kinase and epidermal growth factor receptor transactivation
87. Piceatannol Enhances the Antitumor Efficacy of Gemcitabine in Human A549 Non-Small Cell Lung Cancer Cells
88. Trimethoxy-resveratrol and piceatannol administered orally suppress and inhibit tumor formation and growth in prostate cancer xenografts
89. Tumour necrosis factor alpha: a potential target for the therapy of solid tumours
90. The transmembrane form of tumor necrosis factor is the prime activating ligand of the 80 kDa tumor necrosis factor receptor
91. ADAMs in cancer cell proliferation and progression
92. The ADAMs family of metalloproteases: multidomain proteins with multiple functions
93. Suppression of Akt/Foxp3-mediated miR-183 expression blocks Sp1-mediated ADAM17 expression and TNFα-mediated NFκB activation in piceatannol-treated human leukemia U937 cells
94. Transcription factor Sp1 induces ADAM17 and contributes to tumor cell invasiveness under hypoxia
95. CRD-BP protects the coding region of betaTrCP1 mRNA from miR-183-mediated degradation
96. Suppression of ADAM17-mediated Lyn/Akt pathways induces apoptosis of human leukemia U937 cells: Bungarus multicinctus protease inhibitor-like protein-1 uncovers the cytotoxic mechanism
97. Piceatannol enhances TRAIL-induced apoptosis in human leukemia THP-1 cells through Sp1- and ERK-dependent DR5 up-regulation
98. Biochemical effects of piceatannol in human HL-60 promyelocytic leukemia cells--synergism with Ara-C
99. Piceatannol induces Fas and FasL up-regulation in human leukemia U937 cells via Ca2+/p38alpha MAPK-mediated activation of c-Jun and ATF-2 pathways
100. Death receptor-induced cell killing
101. Piceatannol inhibits melanogenesis by its antioxidative actions
102. Structures of human transthyretin complexed with thyroxine at 2.0 A resolution and 3',5'-dinitro-N-acetyl-L-thyronine at 2.2 A resolution
103. Amyloidosis
104. Inhibition of amyloid fibril formation by polyphenols: structural similarity and aromatic interactions as a common inhibition mechanism
105. Transthyretin binding to A-Beta peptide--impact on A-Beta fibrillogenesis and toxicity
106. Specific plasma membrane binding sites for polyphenols, including resveratrol, in the rat brain