Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

Acta Pharmacologica Sinica

Volumn 33, Issue 10, 2012, Pages 1217-1245

  Jiang, Cheng Shi ^a   Liang, Lin Fu ^a   Guo, Yue Wei ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

inhibitor; natural products; obesity; phytochemistry; protein tyrosine phosphatase 1B (PTP1B); structure activity relationship (SAR); type 2 diabetes

Indexed keywords

3' (3 METHYLBUT 2 ENYL) 3',4',7 TRIHYDROXYFLAVANE; 5,7 DIHYDROXY 8,2' DIMETHOXYFLAVANONE; 8(1,1 DIMETHYLALLYL) 5' (3 METHYLBUT 2 ENYL) 3',4',5,7 TETRAHYDROXYFLAVONOL; BROMOPHENOL; BROUSSOCHALCONE A; COUMARIN DERIVATIVE; FLAVONOID; GLISOFLAVONE; GLYCYRRHISOFLAVONE; KARANJIN; KUWANON J; KUWANON R; KUWANON V; LICOCHALCONE A; LICOCHALCONE C; LICOCHALCONE E; LICOFLAVONE A; LIGNAN; MYRICETIN 3 O BETA DEXTRO GLUCURONIDE; NATURAL PRODUCT; PHENOL DERIVATIVE; PHENOLIC ACID; PONGAMOL; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; QUERCETIN; QUERCETIN 3 O BETA DEXTRO GLUCURONIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; URALENOL; WOGONIN;

DIABETES MELLITUS; DRUG ACTIVITY; DRUG ISOLATION; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HUMAN; IC 50; METABOLITE; NONHUMAN; OBESITY; PROTEIN FUNCTION; REVIEW; STRUCTURE ACTIVITY RELATION;

DIABETES MELLITUS, TYPE 2; ENZYME INHIBITORS; HUMANS; MOLECULAR STRUCTURE; OBESITY; PLANT PREPARATIONS; PLANTS, MEDICINAL; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84867205473     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1038/aps.2012.90     Document Type: Review

References (218)

1. WHO. Diabetes. Available from: http://www.who.int/mediacentre/factsheets/ fs312/en/index.html.
2. Eberhardt MS, Ogden C, Engelgau M, Cadwell B, Hedley AA, Saydah SH. Prevalence of overweight and obesity among adults with diagnosed diabetes-United States, 1988-1994 and 1999-2002. MMWR 2004; 53: 1066-8.
3. Risérus U, Willett WC, Hu FB. Dietary fats and prevention of type 2 diabetes. Prog Lipid Res 2009; 48: 44-51.
4. Newman DJ, Cragg GM. Natural products as sources of new drugs over the last 25 years. J Nat Prod 2007; 70: 461-77.
5. Jung M, Park M, Lee HC, Kang YH, Kang ES, Kim SK. Antidiabetic agents from medicinal plants. Curr Med Chem 2006; 13: 1203-18.
6. Zhang S, Zhang ZY. PTP1B as a drug target: recent developments in PTP1B inhibitor discovery. Drug Discov Today 2007; 12: 373-81.
7. Alonso A, Sasin J, Bottini N, Friedberg I, Friedberg I, Osterman A, et al. Protein tyrosine phosphatases in the human genome. Cell 2004; 117: 699-711.
8. Lessard L, Stuible M, Tremblay ML. The two faces of PTP1B in cancer. Biochim Biophys Acta 2010; 1804: 613-9.
9. Combs AP. Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity, and cancer. J Med Chem 2010; 53: 2333-44.
10. Nichols AJ, Mashal RD, Balkan B. Toward the discovery of small molecule PTP1B inhibitors for the treatment of metabolic diseases. Drug Dev Res 2006; 67: 559-66.
11. Taylor SD, Hill B. Recent advances in protein tyrosine phosphatase 1B inhibitors. Expert Opin Invest Drugs 2004; 13: 199-214.
12. Taylor SD. Inhibitors of protein tyrosine phosphatase 1B (PTP1B). Curr Top Med Chem 2003; 3: 759-82.
13. Lee S, Wang Q. Recent development of small molecular specific inhibitor of protein tyrosine phosphatase 1B. Med Res Rev 2007; 27: 553-73.
14. Mohler ML, He Y, Wu Z, Hwang DJ, Miller DD. Recent and emerging anti-diabetes targets. Med Res Rev 2009; 29: 125-95.
15. Thareja S, Aggarwal S, Bhardwaj TR, Kumar M. Protein tyrosine phosphatase 1B inhibitors: A molecular level legitimate approach for the management of diabetes mellitus. Med Res Rev 2012; 32: 459-517.
16. Cebula RE, Blanchard JL, Boisclair MD, Pal K, Bockovich NJ. Synthesis and phosphatase inhibitory activity of analogs of sulfircin. Bioorg Med Chem Lett 1997; 7: 2015-20.
17. Chen RM, Hu LH, An TY, Li J, Shen Q. Natural PTP1B inhibitors from Broussonetia papyrifera. Bioorg Med Chem Lett 2002; 12: 3387-90.
18. Zhang ZY. Protein-tyrosine phosphatases: Biological function, structural characteristics, and mechanism of catalysis. Crit Rev Biochem Mol Biol 1998; 33: 1-52.
19. Wang WQ, Sun JP, Zhang ZY. An overview of the protein tyrosine phosphatase superfamily. Curr Top Med Chem 2003; 3: 739-48.
20. Barford D, Flint AJ, Tonks NK. Crystal structure of human protein tyrosine phosphatase 1B. Science 1994; 263: 1397-404.
21. Zhang ZY, Maclean D, McNamara DJ, Sawyer TK, Dixon JE. Protein tyrosine phosphatase substrate specificity: size and phosphotyrosine positioning requirements in peptide substrates. Biochemistry 1994; 33: 2285-90.
22. Palmer ND, Bento JL, Mychaleckyj JC, Langefeld CD, Campbell JK, Norris JM, et al. Association of protein tyrosine phosphatase 1B gene polymorphisms with measures of glucose homeostasis in Hispanic Americans: the insulin resistance atherosclerosis study (IRAS) family study. Diabetes 2004; 53: 3013-9.
23. Elchebly M, Payette P, Michaliszyn E, Cromlish W, Collins S, Loy AL, et al. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science 1999; 283: 1544-8.
24. Klaman LD, Boss O, Peroni OD, Kim JK, Martino JL, Zabolotny JM, et al. Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein-tyrosine phosphatase 1B-deficient mice. Mol Cell Biol 2000; 20: 5479-89.
25. Cheng A, Uetani N, Simoncic PD, Chaubey VP, Lee-Loy A, McGlade CJ, et al. Attenuation of leptin action and regulation of obesity by protein tyrosine phosphatase 1B. Dev Cell 2002; 2: 497-503.
26. Xie L, Lee SY, Andersen JN, Waters S, Shen K, Guo XL, et al. Cellular effects of small molecule PTP1B inhibitors on insulin signaling. Biochemistry 2003; 42: 12792-804.
27. Crozier A, Jaganath IB, Clifford MN. Dietary phenolics: chemistry, bioavailability and effects on health. Nat Prod Rep 2009; 26: 1001-43.
28. Veitch NC, Grayer RJ. Flavonoids and their glycosides, including anthocyanins. Nat Prod Rep 2011; 28: 1626-95.
29. Yoon G, Lee W, Kim SN, Cheon SH. Inhibitory effect of chalcones and their derivatives from Glycyrrhiza inflata on protein tyrosine phosphatase 1B. Bioorg Med Chem Lett 2009; 19: 5155-7.
30. Jeon JH, Kim MR, Jun JG. Concise synthesis of licochalcone A through water-accelerated [3,3]-sigmatropic rearrangement of an aryl prenyl ether. Synthesis 2011; 2011: 370-6.
31. Nielsen SF, Chen M, Theander TG, Kharazmi A, Christensen SB. Synthesis of antiparasitic licorice chalcones. Bioorg Med Chem Lett 1995; 5: 449-52.
32. Na Y, Cha JH, Yoon HG, Kwon Y. A concise synthesis of licochalcone E and its regio-isomer, licochalcone F. Chem Pharm Bull 2009; 57: 607-9.
33. Li S, Li W, Wang Y, Asada Y, Koike K. Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities. Bioorg Med Chem Lett 2010; 20: 5398-401.
34. Hoang DM, Ngoc TM, Dat NT, Ha DT, Kim YH, Luong HV, et al. Protein tyrosine phosphatase 1B inhibitors isolated from Morus bombycis. Bioorg Med Chem Lett 2009; 19: 6759-61.
35. Zhang J, Shen Q, Lu JC, Li JY, Liu WY, Yang JJ, et al. Phenolic compounds from the leaves of Cyclocarya paliurus (Batal.) Ijinskaja and their inhibitory activity against PTP1B. Food Chem 2010; 119: 1491-6.
36. Wagner H, Danninger H, Seligmann O, Farkas L. Synthese von glucuroniden der flavonoid-reihe, I. Erste synthese eines natürlich vorkommenden flavonoid-glucuronids (quercetin-3-β-D-glucuronid). Chem Ber 1970; 103: 3674-7.
37. Min BS. Revision of structures of flavanoids from Scutellaria indica and their protein tyrosine phosphatase 1B inhibitory activity. Nat Prod Sci 2006; 12: 205-9.
38. Huang WH, Chien PY, Yang CH, Lee AR. Novel synthesis of flavonoids of Scutellaria baicalensis Georgi. Chem Pharm Bull 2003; 51: 339-40.
39. Lee MS, Kim CH, Hoang DM, Kim BY, Sohn CB, Kim MR, et al. Genistein-derivatives from Tetracera scandens stimulate glucoseuptake in L6 myotubes. Biol Pharm Bull 2009; 32: 504-8.
40. Rao KSRM, Iyer CSR, Iyer PR. Synthesis of alpinum isoflavone, derrone and related pyranoisoflavones. Tetrahedron 1987; 43: 3015-9.
41. Punitha R, Manoharan S. Antihyperglycemic and antilipidperoxidative effects of Pongamia pinnata (Linn.) Pierre flowers in alloxan induced diabetic rats. J Ethnopharmacol 2006; 105: 39-46.
42. Tamrakar AK, Yadav PP, Tiwari P, Maurya R, Srivastava AK. Identification of pongamol and karanjin as lead compounds with antihyperglycemic activity from Pongamia pinnata fruits. J Ethnopharmacol 2008; 118: 435-9.
43. Goel A, Dixit M. Amberlyst 15-catalyzed efficient synthesis of 5-acetyl-4-hydroxy-coumarone and 5-acetyl-6-hydroxy-coumarone: Crucial precursors for several naturally occurring furanoflavones. Synlett 2004; 2004: 1990-4.
44. Yadav PP, Ahmad G, Maurya R. An efficient route for commercially viable syntheses of furan-and thiophene-anellated β-hydroxychalcones. Tetrahedron Lett 2005; 46: 5621-4.
45. Hossain MA, Das AK, Salehuddin SM. Synthesis of karanjin, naturally occurring furanoflavone. Pak J Sci Ind Res 2003; 46: 31-2.
46. Bae EY, Na M, Njamen D, Mbafor JT, Fomum ZT, Cui L, et al. Inhibition of protein tyrosine phosphatase 1B by prenylated isoflavonoids isolated from the stem bark of Erythrina addisoniae. Planta Med 2006; 72: 945-8.
47. Na M, Jang J, Njamen D, Mbafor JT, Fomum ZT, Kim BY, et al. Protein tyrosine phosphatase-1B inhibitory activity of isoprenylated flavonoids isolated from Erythrina mildbraedii. J Nat Prod 2006; 69: 1572-6.
48. Jang J, Na M, Thuong PT, Njamen D, Mbafor JT, Fomum ZT, et al. Prenylated flavonoids with PTP1B inhibitory activity from the root bark of Erythrina mildbraedii. Chem Pharm Bull 2008; 56: 85-8.
49. Cui L, Ndinteh DT, Na M, Thuong PT, Silike-Muruumu J, Njamen D, et al. Isoprenylated flavonoids from the stem bark of Erythrina abyssinica. J Nat Prod 2007; 70: 1039-42.
50. Cui L, Thuong PT, Lee HS, Ndinteh DT, Mbafor JT, Fomum ZT, et al. Flavanones from the stem bark of Erythrina abyssinica. Bioorg Med Chem 2008; 16: 10356-62.
51. Cui L, Lee HS, Ndinteh DT, Mbafor JT, Kim YH, Le TVT, et al. New prenylated flavanones from Erythrina abyssinica with protein tyrosine phosphatase 1B (PTP1B) inhibitory activity. Planta Med 2010; 76: 713-8.
52. Nguyen PH, Dao TT, Kim J, Phong DT, Ndinteh DT, Mbafor JT, et al. New 5-deoxyflavonoids and their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity. Bioorg Med Chem 2011; 19: 3378-83.
53. Nguyen PH, Le TV, Thuong PT, Dao TT, Ndinteh DT, Mbafor JT, et al. Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica. Bioorg Med Chem Lett 2009; 19: 6745-9.
54. Dao TT, Nguyen PH, Thuong PT, Kang KW, Na M, Ndinteh DT, et al. Pterocarpans with inhibitory effects on protein tyrosine phosphatase 1B from Erythrina lysistemon Hutch. Phytochemistry 2009; 70: 2053-7.
55. Na M. Inhibitory effect of constituents from Cercis chinensis on cellular aging [dissertation]. Daejeon, Korea: Chungnam National University; 2004. 114 p.
56. Farmer RL, Biddle MM, Nibbs AE, Huang X, Bergan RC, Scheidt KA. Concise syntheses of the abyssinones and discovery of new inhibitors of prostate cancer and MMP-2 expression. ACS Med Chem Lett 2010; 1: 400-5.
57. Hu LH, Qin ZL, Li C, Huang Q, Wang FH. Synthesis and fungicidal activity of flavanone derivatives containing isopentene group. Chin J Appl Chem 2003; 20: 1161-5.
58. Pelter A, Ward RS, Ashdown DHJ. The synthesis of mono-, di-, and trihydroxyisoflavones. Synthesis 1978; 1978: 843.
59. Tsukayama M, Kawamura Y, Tamaki H, Horie T. Synthesis of parvisoflavones A and B. Chem Pharm Bull 1991; 39: 1704-6.
60. Yang JH, Zhao YM, Ji CB. First total synthesis of (±)- abyssinoflavanone V. Chin Chem Lett 2008; 19: 658-60.
61. Rao GV, Swamy BN, Chandregowda V, Reddy GC. Synthesis of (±)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities. Eur J Med Chem 2009; 44: 2239-45.
62. Moriarty RM, Grubjesic S, Surve BC, Chandersekera SN, Prakash O, Naithani R. Synthesis of Abyssinone II and related compounds as potential chemopreventive agents. Eur J Med Chem 2006; 41: 263-7.
63. Maiti A, Cuendet M, Croy VL, Endringer DC, Pezzuto JM, Cushman M. Synthesis and biological evaluation of (±)-abyssinone II and its analogues as aromatase inhibitors for chemoprevention of breast cancer. J Med Chem 2007; 50: 2799-806.
64. Mohamed SEN, Thomas P, Whiting DA. Synthesis of the phytoalexin (±)-phaseollin: 3-phenylthiochromans as masked 2H-chromenes and o-prenyl phenols. J Chem Soc, Perkin Trans 1 1987; 431-7.
65. Na M, Kim KA, Oh H, Kim BY, Oh WK, Ahn JS. Protein tyrosine phosphatase 1B inhibitory activity of amentoflavone and its cellular effect on tyrosine phosphorylation of insulin receptors. Biol Pharm Bull 2007; 30: 379-81.
66. Cui L, Na M, Oh H, Bae EY, Jeong DG, Ryu SE, et al. Protein tyrosine phosphatase 1B inhibitors from Morus root bark. Bioorg Med Chem Lett 2006; 16: 1426-9.
67. Guo S, Li J, Li T, Shi D, Han L. Synthesis of three bromophenols from red algae as PTP1B inhibitors. Chin J Oceanol Limnol 2011; 29: 68-74.
68. Liu Q, Xu H, Zhang T, Fan X, Han L. A new compound as PTP1B inhibitor from the red alga Polysiphonia urceolata. Hua Xue Tong Bao 2006; 69: 708-10.
69. Shi D, Xu F, He J, Li J, Fan X, Han L. Inhibition of bromophenols against PTP1B and anti-hyperglycemic effect of Rhodomela confervoides extract in diabetic rats. Chin Sci Bull 2008; 53: 2476-9.
70. Shi DY, Xu F, Li J, Guo SJ, Su H, Han LJ. PTP1B inhibitory activities of bromophenol derivatives from algae. Zhongguo Zhong Yao Za Zhi 2008; 33: 2238-40.
71. Oh KB, Lee JH, Lee JW, Yoon KM, Chung SC, Jeon HB, et al. Synthesis and antimicrobial activities of halogenated bis(hydroxyphenyl) methanes. Bioorg Med Chem Lett 2009; 19: 945-8.
72. Oh KB, Jeon HB, Han YR, Lee YJ, Park J, Lee SH, et al. Bromophenols as Candida albicans isocitrate lyase inhibitors. Bioorg Med Chem Lett 2010; 20: 6644-8.
73. Qin J, Su H, Zhang Y, Gao J, Zhu L, Wu X, et al. Highly brominated metabolites from marine red alga Laurencia similis inhibit protein tyrosine phosphatase 1B. Bioorg Med Chem Lett 2010; 20: 7152-4.
74. Liu X, Li X, Gao L, Cui C, Li C, Li J, et al. Extraction and PTP1B inhibitory activity of bromophenols from the marine red alga Symphyocladia latiuscula. Chin J Oceanol Limnol 2011; 29: 686-90.
75. Balaydin HT, Akbaba Y, Menzek A, ahin E, Göksu S. First and short syntheses of biologically active, naturally occurring brominated mono-and dibenzyl phenols. ARKIVOC 2009; 2009: 75-87.
76. Chung TW, Moon SK, Chang YC, Ko JH, Lee YC, Cho G, et al. Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: complete regression of hepatoma growth and metastasis by dual mechanism. FASEB J 2004; 18: 1670-81.
77. He ZZ, Yan JF, Song ZJ, Ye F, Liao X, Peng SL, et al. Chemical constituents from the aerial parts of Artemisia minor. J Nat Prod 2009; 72: 1198-201.
78. Lee YS, Kang IJ, Won MH, Lee JY, Kim JK, Lim SS. Inhibition of protein tyrosine phosphatase 1β by hispidin derivatives isolated from the fruiting body of Phellinus linteus. Nat Prod Commun 2010; 5: 1927-30.
79. Yao XS, Li J, Hong K, Tang JS, Gao H, Gao LX, et al. Application of 2-acetylamino gentisic acid to preparing insulin sensitizer. China patent CN 101919835 A. 2010 December 22.
80. Seo C, Yim JH, Lee HK, Oh H. PTP1B inhibitory secondary metabolites from the Antarctic lichen Lecidella carpathica. Mycology 2011; 2: 18-23.
81. Seo C, Choi YH, Ahn JS, Yim JH, Lee HK, Oh H. PTP1B inhibitory effects of tridepside and related metabolites isolated from the Antarctic lichen Umbilicaria antarctica. J Enzyme Inhib Med Chem 2009; 24: 1133-7.
82. Seo C, Sohn JH, Ahn JS, Yim JH, Lee HK, Oh H. Protein tyrosine phosphatase 1B inhibitory effects of depsidone and pseudodepsidone metabolites from the Antarctic lichen Stereocaulon alpinum. Bioorg Med Chem Lett 2009; 19: 2801-3.
83. Oh H, Kim BS, Bae EY, Kim MS, Kim BY, Lee HB, et al. Inhibition of PTP1B by metabolites from Micromucor ramannianus var angulisporus CRM000232. J Antibiot 2004; 57: 528-31.
84. Fürstner A, Konetzki I. Total synthesis of caloporoside. J Org Chem 1998; 63: 3072-80.
85. Fürstner A. Total syntheses and biological assessment of macrocyclic glycolipids. Eur J Org Chem 2004; 2004: 943-58.
86. Seo C, Sohn JH, Oh H, Kim BY, Ahn JS. Isolation of the protein tyrosine phosphatase 1B inhibitory metabolite from the marine-derived fungus Cosmospora sp SF-5060. Bioorg Med Chem Lett 2009; 19: 6095-7.
87. Baumgartner RR, Steinmann D, Heiss EH, Atanasov AG, Ganzera M, Stuppner H, et al. Bioactivity-guided isolation of 1,2,3,4,6-penta-O-galloyl-D- glucopyranose from Paeonia lactiflora roots as a PTP1B inhibitor. J Nat Prod 2010; 73: 1578-81.
88. Baumgartner RR, Steinmann D, Heiss EH, Atanasov AG, Ganzera M, Stuppner H, et al. Bioactivity-guided isolation of 1,2,3,4,6-penta-O-galloyl-D- glucopyranose from Paeonia lactiflora roots as a PTP1B inhibitor. J Nat Prod 2010; 73: 1742.
89. Na M, Hoang DM, Njamen D, Mbafor JT, Fomum ZT, Thuong PT, et al. Inhibitory effect of 2-arylbenzofurans from Erythrina addisoniae on protein tyrosine phosphatase-1B*. Bioorg Med Chem Lett 2007; 17: 3868-71.
90. Feng Y, Carroll AR, Addepalli R, Fechner GA, Avery VM, Quinn RJ. Vanillic acid derivatives from the green algae Cladophora socialis as potent protein tyrosine phosphatase 1B inhibitors. J Nat Prod 2007; 70: 1790-2.
91. Seo C, Sohn JH, Park SM, Yim JH, Lee HK, Oh H. Usimines A-C, bioactive usnic acid derivatives from the Antarctic lichen Stereocaulon alpinum. J Nat Prod 2008; 71: 710-2.
92. Hawranik DJ, Anderson KS, Simmonds R, Sorensen JL. The chemoenzymatic synthesis of usnic acid. Bioorg Med Chem Lett 2009; 19: 2383-5.
93. Otani T, Sugimoto Y, Aoyagi Y, Igarashi Y, Furumai T, Saito N, et al. New Cdc25B tyrosine phosphatase inhibitors, nocardiones A and B, produced by Nocardia sp TP-A0248: taxonomy, fermentation, isolation, structural elucidation and biological properties. J Antibiot 2000; 53: 337-44.
94. Tanada Y, Mori K. Synthesis and absolute configuration of nocardione A and B, furano-o-naphthoquinone-type metabolites of Nocardia sp with antifungal, cytotoxic, and enzyme inhibitory activities. Eur J Org Chem 2001; 2001: 4313-9.
95. Yang H, Lu W, Bao JX, Aisa HA, Cai JC. Total synthesis of (±)-nocardione A and (±)-nocardione B, two Cdc25B tyrosine phosphatase inhibitors. Chin Chem Lett 2001; 12: 883-6.
96. Clive DL, Fletcher SP. Synthesis of (+)-nocardione A-use of formal radical cyclization onto a benzene ring. Chem Commun 2003; (19): 2464-5.
97. Clive DL, Fletcher SP, Liu D. Formal radical cyclization onto benzene rings: A general method and its use in the synthesis of entnocardione A. J Org Chem 2004; 69: 3282-93.
98. Seo C, Choi YH, Sohn JH, Ahn JS, Yim JH, Lee HK, et al. Ohioensins F and G: Protein tyrosine phosphatase 1B inhibitory benzonaphthoxanthenones from the Antarctic moss Polytrichastrum alpinum. Bioorg Med Chem Lett 2008; 18: 772-5.
99. Wang Y, Shang XY, Wang SJ, Mo SY, Li S, Yang YC, et al. Structures, biogenesis, and biological activities of pyrano[4,3-c]isochromen-4-one derivatives from the fungus Phellinus igniarius. J Nat Prod 2007; 70: 296-9.
100. Murray RD. Coumarins. Nat Prod Rep 1989; 6: 591-624.
101. Murray RDH. Coumarins. Nat Prod Rep 1995; 12: 477-505.
102. Estévez-Braun A, González AG. Coumarins. Nat Prod Rep 1997; 14: 465-75.
103. Umezawa T. Diversity in lignan biosynthesis. Phytochem Rev 2003; 2: 371-90.
104. Kim YC, Oh H, Kim BS, Kang TH, Ko EK, Han YM, et al. In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia. Planta Med 2005; 71: 87-9.
105. Xiao K, Song QH, Zhang SW, Xuan LJ. Water-soluble constituents of the root barks of Fraxinus rhynchophylla (Chinese drug Qinpi). J Asian Nat Prod Res 2008; 10: 205-10.
106. Pahari P, Rohr J. Total synthesis of psoralidin, an anticancer natural product. J Org Chem 2009; 74: 2750-4.
107. Yang S, Min Kyun N, Jang JP, Kim KA, Kim BY, Sung NJ, et al. Inhibition of protein tyrosine phosphatase 1B by lignans from Myristica fragrans. Phytother Res 2006; 20: 680-2.
108. He ZZ, Yan JF, Liao X, Zhang WY, Ji JX, Ding LS. Novel lignan compound and application thereof. China patent CN 101805325 A. 2010. August 18.
109. Takano S, Shimazaki Y, Ogasawara K. Enantiocontrolled synthesis of natural (+)-bakuchiol. Tetrahedron Lett 1990; 31: 3325-6.
110. Araki S, Bustugan Y. Short synthesis of (±)-bakuchiol via a geranylindium reagent. J Chem Soc, Perkin Trans 1 1991; 2395-7.
111. Du XL, Chen HL, Feng HJ, Li YC. Stereoselective total synthesis of natural (S)-bakuchiol and its enantiomer. Helv Chim Acta 2008; 91: 371-8.
112. Chen H, Li Y. Simple and convenient synthesis of (±)-bakuchiol. Lett Org Chem 2008; 5: 467-9.
113. Esumi T, Shimizu H, Kashiyama A, Sasaki C, Toyota M, Fukuyama Y. Efficient construction of a chiral all-carbon quaternary center by asymmetric 1,4-addition and its application to total synthesis of (+)-bakuchiol. Tetrahedron Lett 2008; 49: 6846-9.
114. Bequette JP, Jungong CS, Novikov AV. Enantioselective synthesis of Bakuchiol using diazosulfonate C-H insertion to install the quaternary center. Tetrahedron Lett 2009; 50: 6963-4.
115. Wang JD, Dong ML, Zhang W, Shen X, Guo YW. Chemical constituents of mangrove plant Lumnitzera racemosa. Chin J Nat Med 2006; 4: 185-7.
116. Arisawa M, Ohmura K, Kobayashi A, Morita N. A cytotoxic constituent of Lysimachia japonica THUNB. (Primulaceae) and the structureactivity relationships of related compounds. Chem Pharm Bull 1989; 37: 2431-4.
117. Kolev TM, Velcheva EA, Stamboliyska BA, Spiteller M. DFT and experimental studies of the structure and vibrational spectra of curcumin. Int J Quantum Chem 2005; 102: 1069-79.
118. Li JM, Li YC, Kong LD, Hu QH. Curcumin inhibits hepatic proteintyrosine phosphatase 1B and prevents hypertriglyceridemia and hepatic steatosis in fructose-fed rats. Hepatology 2010; 51: 1555-66.
119. Pedersen U, Rasmussen PB, Lawesson SO. Synthesis of naturally occurring curcuminoids and related compounds. Liebigs Ann Chem 1985; 1985: 1557-69.
120. Qiu X, Du Y, Lou B, Zuo Y, Shao W, Huo Y, et al. Synthesis and identification of new 4-arylidene curcumin analogues as potential anticancer agents targeting nuclear factor-κB signaling pathway. J Med Chem 2010; 53: 8260-73.
121. Li YF, Hu LH, Lou FC, Li J, Shen Q. PTP1B inhibitors from Ardisia japonica. J Asian Nat Prod Res 2005; 7: 13-8.
122. Motoyoshiya J, Masue Y, Nishi Y, Aoyama H. Synthesis of hypericin via emodin anthrone derived from a two-fold Diels-Alder reaction of 1,4-benzoquinone. Nat Prod Commun 2007; 2: 67-70.
123. Li S, An TY, Li J, Shen Q, Lou FC, Hu LH. PTP1B inhibitors from Saussrurea lappa. J Asian Nat Prod Res 2006; 8: 281-6.
124. Ahmed SA, Bardshiri E, Simpson TJ. A convenient synthesis of isotopically labelled anthraquinones, chrysophanol, islandicin, and emodin. Incorporation of [methyl-2H3]chrysophanol into tajixanthone in Aspergillus variecolor. J Chem Soc, Chem Commun 1987; 12: 883-4.
125. Nicoletti TM, Raston CL, Sargent MV. A new synthesis of anthraquinones using dihydro-oxazoles and Grignard reagents derived from Mg(anthracene)(THF)3. J Chem Soc, Perkin Trans 1 1990; 133-8.
126. Bae EY, Oh H, Oh WK, Kim MS, Kim BS, Kim BY, et al. A new VHR dual-specificity protein tyrosine phosphatase inhibitor from Dendrobium moniliforme. Planta Med 2004; 70: 869-70.
127. Paululat T, Kulik A, Hausmann H, Karagouni AD, Zinecker H, Imhoff JF, et al. Grecocyclines: New angucyclines from Streptomyces sp Acta 1362. Eur J Org Chem 2010; 2010: 2344-50.
128. Paduch R, Kandefer-Szersze M, Trytek M, Fiedurek J. Terpenes: substances useful in human healthcare. Arch Immunol Ther Exp 2007; 55: 315-27.
129. Wagner KH, Elmadfa I. Biological relevance of terpenoids. Ann Nutr Metab 2003; 47: 95-106.
130. Deng M, Dong W, Jiao W, Lu R. New eremophilane sesquiterpenes from the roots of Ligularia fischeri. Helv Chim Acta 2009; 92: 495-501.
131. Shao ZY, Li J, Sim CJ, Li JY, Li ZY, Nan FJ, et al. O-methyl nakafuran-8 lactone, a new sesquiterpenoid from a Hainan marine sponge Dysidea sp. J Asian Nat Prod Res 2006; 8: 223-7.
132. Huang XC, Li J, Li ZY, Shi L, Guo YW. Sesquiterpenes from the Hainan sponge Dysidea septosa. J Nat Prod 2008; 71: 1399-403.
133. Li Y, Zhang Y, Shen X, Guo YW. A novel sesquiterpene quinone from Hainan sponge Dysidea villosa. Bioorg Med Chem Lett 2009; 19: 390-2.
134. Uyehara T, Sugimoto M, Suzuki I, Yamamoto Y. Total synthesis of (±)-nakafuran-8, a marine metabolite with antifeedant properties, based on formal bridgehead substitution of a bicyclo[2.2.2]oct-5-en-2-one system. J Chem Soc, Chem Commun 1989; 1841-2.
135. Uyehara T, Sugimoto M, Suzuki I, Yamamoto Y. Rearrangement approaches to cyclic skeletons. Part 8. Total synthesis of (±)-nakafuran-8, a marine metabolite with antifeedant properties, on the basis of bridgehead substitution of a bicyclo[2.2.2]oct-5-en-2-one system. J Chem Soc, Perkin Trans 1 1992; 1785-8.
136. Kurth MJ, Soares CJ. Asymmetric aza-Claisen rearrangement: Synthesis of (+)-dihydropallescensin-2 [(+)-penlanpallescensin]. Tetrahedron Lett 1987; 28: 1031-4.
137. Aisa A, Xin XL, Li YM; Lactucin and its preparation method and application. China patent CN 101099566 B. 2008 November 10.
138. Choi JY, Na M, Hwang IH, Lee SH, Bae EY, Kim BY, et al. Isolation of betulinic acid, its methyl ester and guaiane sesquiterpenoids with Protein Tyrosine Phosphatase 1B inhibitory activity from the roots of Saussurea lappa CB Clarke. Molecules 2009; 14: 266-72.
139. Rigby JH, Wilson JZ. Total synthesis of guaianolides: (±)-dehydrocostus lactone and (±)-estafiatin. J Am Chem Soc 1984; 106: 8217-24.
140. Yuuya S, Hagiwara H, Suzuki T, Ando M, Yamada A, Suda K, et al. Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokko lactone, eremanthin, and their derivatives. J Nat Prod 1998; 62: 22-30.
141. Fu HZ, Luo YM, Li CJ, Yang JZ, Zhang DM. Psidials A-C, three unusual meroterpenoids from the leaves of Psidium guajava L. Org Lett 2010; 12: 656-9.
142. Kim S, Na M, Oh H, Jang J, Sohn CB, Kim BY, et al. PTP1B inhibitory activity of kaurane diterpenes isolated from Siegesbeckia glabrescens. J Enzyme Inhib Med Chem 2006; 21: 379-83.
143. Na M, Oh WK, Kim YH, Cai XF, Kim S, Kim BY, et al. Inhibition of protein tyrosine phosphatase 1B by diterpenoids isolated from Acanthopanax koreanum. Bioorg Med Chem Lett 2006; 16: 3061-4.
144. Cui L, Wu X, An ZS, Li DH; Kaurane-type diterpenoid compound as well as preparation method and medical application thereof. China patent CN 101786953 A. 2010 July 28.
145. Cheng YX, Zhou WS. Study on the tetracyclic diterpenoids 5. Synthesis of ent-kaur-16-en-19-oic acid. Acta Chim Sinica 1993; 51: 819-24.
146. Ling T, Chowdhury C, Kramer BA, Vong BG, Palladino MA, Theodorakis EA. Enantioselective synthesis of the antiinflammatory agent (?)-acanthoic acid. J Org Chem 2001; 66: 8843-53.
147. Han YM, Oh H, Na M, Kim BS, Oh WK, Kim BY, et al. PTP1B inhibitory effect of abietane diterpenes isolated from Salvia miltiorrhiza. Biol Pharm Bull 2005; 28: 1795-7.
148. Kakisawa H, Inouye Y. Total syntheses of tanshinone-I, tanshinone-II, and cryptotanshinone. Chem Commun (London) 1968; 1327-8.
149. Marrero JG, Andrés LS, Luis JG. Quinone derivatives by chemical transformations of 16-hydroxycarnosol from Salvia species. Chem Pharm Bull 2005; 53: 1524-9.
150. Kate AS, Aubry I, Tremblay ML, Kerr RG. Lipidyl pseudopteranes A-F: isolation, biomimetic synthesis, and PTP1B inhibitory activity of a new class of pseudopteranoids from the Gorgonian Pseudopterogorgia acerosa. J Nat Prod 2008; 71: 1977-82.
151. Iguchi K, Shimada Y, Yamada Y. Hyrtiosal, a new sesterterpenoid with a novel carbon skeleton from the Okinawan marine sponge Hyrtios erectus. J Org Chem 1992; 57: 522-4.
152. Sun T, Wang Q, Yu Z, Zhang Y, Guo Y, Chen K, et al. Hyrtiosal, a PTP1B inhibitor from the marine sponge Hyrtios erectus, shows extensive cellular effects on PI3K/AKT activation, glucose transport, and TGFβ/Smad2 signaling. ChemBioChem 2007; 8: 187-93.
153. Du L, Shen L, Yu Z, Chen J, Guo Y, Tang Y, et al. Hyrtiosal, from the marine sponge Hyrtios erectus, inhibits HIV-1 integrase binding to viral DNA by a new inhibitor binding site. ChemMedChem 2008; 3: 173-80.
154. Basabe P, Diego A, Díez D, Marcos IS, Urones JG. Synthesis and absolute configuration of (-)-hyrtiosal. Synlett 2000; 2000: 1807-9.
155. Basabe P, Diego A, Díez D, Marcos IS, Mollinedo F, Urones JG. Hyrtiosanes from labdanes: (-)-hyrtiosal from sclareol. Synthesis 2002; 2002: 1523-9.
156. Lunardi I, Santiago GMP, Imamura PM. Synthesis of (?)-and (+)-hyrtiosal and their C-16 epimers. Tetrahedron Lett 2002; 43: 3609-11.
157. Cao S, Foster C, Lazo JS, Kingston DG. Sesterterpenoids and an alkaloid from a Thorectandra sp as inhibitors of the phosphatase Cdc25B. Bioorg Med Chem 2005; 13: 5094-8.
158. Boukouvalas J, Robichaud J, Maltais F. A unified strategy for the regiospecific assembly of homoallyl-substituted butenolides and γ-hydroxybutenolides: First synthesis of luffariellolide. Synlett 2006; 2006: 2480-2.
159. Wright AE, McCarthy PJ, Schulte GK. Sulfircin: a new sesterterpene sulfate from a deep-water sponge of the genus Ircinia. J Org Chem 1989; 54: 3472-4.
160. Na M, Cui L, Min BS, Bae K, Yoo JK, Kim BY, et al. Protein tyrosine phosphatase 1B inhibitory activity of triterpenes isolated from Astilbe koreana. Bioorg Med Chem Lett 2006; 16: 3273-6.
161. Na M, Yang S, He L, Oh H, Kim BS, Oh WK, et al. Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata. Planta Med 2006; 72: 261-3.
162. Shi L, Zhang W, Zhou YY, Zhang YN, Li JY, Hu LH, et al. Corosolic acid stimulates glucose uptake via enhancing insulin receptor phosphorylation. Eur J Pharmacol 2008; 584: 21-9.
163. Ma M, Wang SJ, Li S, Yang YC, Shi JG, Ye F, et al. Triterpenes with protein tyrosine phosphotase 1B inhibitory activity from Macaranga adenantha. Zhongcaoyao 2006; 37: 1128-31.
164. Qian S, Li H, Chen Y, Zhang W, Yang S, Wu Y. Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B. J Nat Prod 2010; 73: 1743-50.
165. Qiu WW, Shen Q, Yang F, Wang B, Zou H, Li JY, et al. Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B. Bioorg Med Chem Lett 2009; 19: 6618-22.
166. Corey EJ, Lee J. Enantioselective total synthesis of oleanolic acid, erythrodiol, β-amyrin, and other pentacyclic triterpenes from a common intermediate. J Am Chem Soc 1993; 115: 8873-4.
167. Ramírez-Espinosa JJ, Rios MY, López-Martínez S, López-Vallejo F, Medina-Franco JL, Paoli P, et al. Antidiabetic activity of some pentacyclic acid triterpenoids, role of PTP-1B: In vitro, in silico, and in vivo approaches. Eur J Med Chem 2011; 46: 2243-51.
168. Zhang P, Hao J, Liu J, Zhang L, Sun H. Efficient synthesis of morolic acid and related triterpenes starting from betulin. Tetrahedron 2009; 65: 4304-9.
169. Flekhter O, Medvedeva N, Tolstikov GA, Galin F, Yunusov M, Mai H, et al. Synthesis of olean-18(19)-ene derivatives from betulin. Russ J Bioorg Chem 2009; 35: 233-9.
170. Xu W, Zhu C, Cheng W, Fan X, Chen X, Yang S, et al. Chemical constituents of the roots of Euphorbia micractina. J Nat Prod 2009; 72: 1620-6.
171. Kwon JH, Chang MJ, Seo HW, Lee JH, Min BS, Na M, et al. Triterpenoids and a sterol from the stem-bark of Styrax japonicaand their protein tyrosine phosphatase 1B inhibitory activities. Phytother Res 2008; 22: 1303-6.
172. Na M, Thuong PT, Hwang IH, Bae K, Kim BY, Osada H, et al. Protein tyrosine phosphatase 1B inhibitory activity of 24-norursane triterpenes isolated from Weigela subsessilis. Phytother Res 2010; 24: 1716-9.
173. Na M, Kim BY, Osada H, Ahn JS. Inhibition of protein tyrosine phosphatase 1B by lupeol and lupenone isolated from Sorbus commixta. J Enzyme Inhib Med Chem 2009; 24: 1056-9.
174. Csuk R, Schmuck K, Schäfer R. A practical synthesis of betulinic acid. Tetrahedron Lett 2006; 47: 8769-70.
175. Surendra K, Corey EJ. A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol. J Am Chem Soc 2009; 131: 13928-9.
176. Hung TM, Hoang DM, Kim JC, Jang HS, Ahn JS, Min BS. Protein tyrosine phosphatase 1B inhibitory by dammaranes from Vietnamese Giao-Co-Lam tea. J Ethnopharmacol 2009; 124: 240-5.
177. Hanson JR. Steroids: partial synthesis in medicinal chemistry. Nat Prod Rep 2010; 27: 887-99.
178. Lee HS, Hwang IH, Kim JA, Choi JY, Jang TS, Osada H, et al. Isolation of protein tyrosine phosphatase 1B inhibitory constituents from the sclerotia of Polyporus umbellatus Fries. Bull Korean Chem Soc 2011; 32: 697-700.
179. Wang L, Chen B, Shen XR, Zhou YY, Jiang DW, Li J, et al. Growth inhibition and induction of early apoptosis by arenicolsterol A, a novel cytotoxic enolic sulphated sterol from the marine annelid, Arenicola cristata. J Asian Nat Prod Res 2007; 9: 753-61.
180. Wang JR, Shen Q, Fang L, Peng SY, Yang YM, Li J, et al. Structural and stereochemical studies of five new pregnane steroids from the stem bark of Toona ciliata var pubescens. Steroids 2011; 76: 571-6.
181. Yan XH, Guo YW, Zhu XZ. Chemical constituents of the gorgonian Muricella sinensis (Verrill). Nat Prod Res Dev 2005; 17: 412-4.
182. Singh TV, Kaur R, Agnihotri KR, Bali M. Synthesis of calicoferol E. ARKIVOC 2002; 2002: 82-90.
183. Piao SJ, Zhang HJ, Lu HY, Yang F, Jiao WH, Yi YH, et al. Hippolides A-H, acyclic manoalide derivatives from the marine sponge Hippospongia lachne. J Nat Prod 2011; 74: 1248-54.
184. Mao SC, Guo YW, Shen X. Two novel aromatic valerenane-type sesquiterpenes from the Chinese green alga Caulerpa taxifolia. Bioorg Med Chem Lett 2006; 16: 2947-50.
185. Wikipedia. Berberine. Available from: http://en.wikipedia.org/wiki/ Berberine.
186. Bustanji Y, Taha MO, Yousef AM, Al-Bakri AG. Berberine potently inhibits protein tyrosine phosphatase 1B: Investigation by docking simulation and experimental validation. J Enzyme Inhib Med Chem 2006; 21: 163-71.
187. Chen C, Zhang Y, Huang C. Berberine inhibits PTP1B activity and mimics insulin action. Biochem Biophys Res Commun 2010; 397: 543-7.
188. Wikipedia. Papaverine. Available from: http://en.wikipedia.org/wiki/ Papaverine.
189. Bustanji Y, Taha MO, Al-masri IM, Mohammad MK. Docking simulations and in vitro assay unveil potent inhibitory action of papaverine against protein tyrosine phosphatase 1B. Biol Pharm Bull 2009; 32: 640-5.
190. Hohmann C, Schneider K, Bruntner C, Brown R, Jones AL, Goodfellow M, et al. Albidopyrone, a new α-pyrone-containing metabolite from marine-derived Streptomyces sp NTK 227. J Antibiot 2009; 62: 75-9.
191. Schulz D, Nachtigall J, Riedlinger J, Schneider K, Poralla K, Imhoff JF, et al. Piceamycin and its N-acetylcysteine adduct is produced by Streptomyces sp GB 4-2*. J Antibiot 2009; 62: 513-8.
192. Seo C, Yim JH, Lee HK, Park SM, Sohn JH, Oh H. Stereocalpin A, a bioactive cyclic depsipeptide from the Antarctic lichen Stereocaulon alpinum. Tetrahedron Lett 2008; 49: 29-31.
193. Ghosh AK, Xu CX. A convergent synthesis of the proposed structure of antitumor depsipeptide stereocalpin A. Org Lett 2009; 11: 1963-6.
194. Choi YH, Sohn JH, Lee D, Kim JK, Kong IS, Ahn SC, et al. Chejuenolides A and B, new macrocyclic tetraenes from the marine bacterium Hahella chejuensis. Tetrahedron Lett 2008; 49: 7128-31.
195. Sun YQ, Guo YW. Gymnorrhizol, an unusual macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza. Tetrahedron Lett 2004; 45: 5533-5.
196. Sun YQ, Sun J, Guo YW. Crystal structure of 1,2,6,7,11,12- hexathiacyclopentadecane, C9H18S6. Z Kristallogr-NCS 2004; 219: 119-20.
197. Gong JX, Shen X, Yao LG, Jiang H, Krohn K, Guo YW. Total synthesis of gymnorrhizol, an unprecedented 15-membered macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza. Org Lett 2007; 9: 1715-6.
198. Huang XY, Wang Q, Liu HL, Zhang Y, Xin GR, Shen X, et al. Diastereoisomeric macrocyclic polydisulfides from the mangrove Bruguiera gymnorrhiza. Phytochemistry 2009; 70: 2096-100.
199. Hamaguchi T, Sudo T, Osada H. RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle progression at G1 phase. FEBS Lett 1995; 372: 54-8.
200. Sodeoka M, Sampe R, Kagamizono T, Osada H. Asymmetric synthesis of RK-682 and its analogs, and evaluation of their protein phosphatase inhibitory activities. Tetrahedron Lett 1996; 37: 8775-8.
201. Shinagewa S, Muroi M, Ito T, Hida T; Tetronic acid derivative, its production and use. Japan patent JP 05-43568 A. 1993 February 23.
202. Mittra A, Yamashita M, Kawasaki I, Murai H, Yoshioka T, Ohta S. A useful oxidation procedure for the preparation of 3-alkanoyltetronic acids. Synlett 1997; 1997: 909-10.
203. Schobert R, Jagusch C. Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins. J Org Chem 2005; 70: 6129-32.
204. Helaly S, Schneider K, Nachtigall J, Vikineswary S, Tan GY, Zinecker H, et al. Gombapyrones, new α-pyrone metabolites produced by Streptomyces griseoruber Acta 3662*. J Antibiot 2009; 62: 445-52.
205. Alvi KA, Nair BG, Rabenstein J, Davis G, Baker DD. CD45 tyrosine phosphatase inhibitory components from Aspergillus niger. J Antibiot 2000; 53: 110-3.
206. Seibert SF, Eguereva E, Krick A, Kehraus S, Voloshina E, Raabe G, et al. Polyketides from the marine-derived fungus Ascochyta salicorniae and their potential to inhibit protein phosphatases. Org Biomol Chem 2006; 4: 2233-40.
207. Galbraith MN, Whalley WB. The synthesis of (±)-ascochitine. Chem Commun (London) 1966; 620a-a.
208. Wang JD, Dong ML, Zhang W, Shen X, Guo YW. Chemical constituents of mangrove plant Aegiceras corniculatum. Chin J Nat Med 2006; 4: 275-7.
209. Zheng G, Lu W, Cai J. Stereoselective total synthesis of (3R,8S)-falcarindiol, a common polyacetylenic compound from umbellifers. J Nat Prod 1999; 62: 626-8.
210. Sabitha G, Bhaskar V, Reddy CS, Yadav JS. Stereoselective approaches for the total synthesis of polyacetylenic (3R,8S)-falcarindiol. Synthesis 2008; 2008: 115-21.
211. Schmiech L, Alayrac C, Witulski B, Hofmann T. Structure determination of bisacetylenic oxylipins in carrots (Daucus carota L) and enantioselective synthesis of falcarindiol. J Agric Food Chem 2009; 57: 11030-40.
212. Tamura S, Ohno T, Hattori Y, Murakami N. Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma. Tetrahedron Lett 2010; 51: 1523-5.
213. Li YF, Li J, Shen Q, Hu LH. Benzoquinones from Ardisia japonica with inhibitory activity towards human protein tyrosine phosphatase 1B (PTP1B). Chem Biodivers 2007; 4: 961-5.
214. Yadav JS, Upender V, Rao AVR. A practical preparation of functionalized alkylbenzoquinones: synthesis of maesanin and irisquinone. J Org Chem 1992; 57: 3242-5.
215. Poigny S, Guyot M, Samadi M. Total synthesis of maesanin and analogues. Tetrahedron 1998; 54: 14791-802.
216. Pfeifer J, Gerlach H. Synthese von naturstoffen mit alkyl-methoxy-1,4- benzochinon-struktur. Liebigs Ann 1995; 1995: 131-7.
217. Tsukamoto S, Takeuchi S, Ishibashi M, Kobayashi J. Manzamenones A-F from the Okinawan marine sponges Plakortis sp: novel dimeric fatty acid derivatives possessing a bicyclo[4.3.0]nonane skeleton. J Org Chem 1992; 57: 5255-60.
218. Wakuda Y, Kubota T, Shima H, Okada T, Mitsuhashi S, Aoki N, et al. Manzamenones Inhibit T-Cell Protein Tyrosine Phosphatase. Mar Drugs 2006; 4: 9-14.