diarylheptanoids

Summary

Summary: A group of compounds consisting of two aromatic rings separated by seven carbons (HEPTANES) and having various substituents. The best known member is CURCUMIN.

Top Publications

  1. Kang H, Ryong Kim J, Jeong T, Choi S, Ryu Y, Taeg Oh G, et al. Cyclic diarylheptanoids inhibit cell-mediated low-density lipoprotein oxidation. Nat Prod Res. 2006;20:139-43 pubmed
    Two cyclic diarylheptanoids, garugamblin-3 (1) and acerogenin L (2), isolated from the MeOH extract of the fruits of Alnus japonica Steud...
  2. Jin W, Cai X, Na M, Lee J, Bae K. Diarylheptanoids from Alnus hirsuta inhibit the NF-kB activation and NO and TNF-alpha production. Biol Pharm Bull. 2007;30:810-3 pubmed
    Six diarylheptanoids (1-6) from the stem bark of Alnus hirsuta were investigated for their inhibitory activity against LPS-induced NF-kB activation and NO and TNF-alpha production...
  3. Jiang H, Timmermann B, Gang D. Use of liquid chromatography-electrospray ionization tandem mass spectrometry to identify diarylheptanoids in turmeric (Curcuma longa L.) rhizome. J Chromatogr A. 2006;1111:21-31 pubmed
    LC-ESI-MS/MS coupled to DAD analysis was used as an on-line tool for identification of diarylheptanoids in fresh turmeric rhizome extracts...
  4. Kuroyanagi M, Shimomae M, Nagashima Y, Muto N, Okuda T, Kawahara N, et al. New diarylheptanoids from Alnus japonica and their antioxidative activity. Chem Pharm Bull (Tokyo). 2005;53:1519-23 pubmed
    ..fractions were purified by silica gel column chromatography and HPLC using an ODS column to give four new diarylheptanoids along with known diarylheptanoids and flavonoids...
  5. Han J, Lee W, Kim J, Son J, Kwon O, Lee H, et al. Effect of 5-O-Methylhirsutanonol on nuclear factor-kappaB-dependent production of NO and expression of iNOS in lipopolysaccharide-induced RAW264.7 cells. J Agric Food Chem. 2008;56:92-8 pubmed
    b>Diarylheptanoids are known to have anti-inflammatory and anti-atherosclerotic activities in various cell types, including macrophages...
  6. Matsumoto T, Nakamura S, Nakashima S, Yoshikawa M, Fujimoto K, Ohta T, et al. Diarylheptanoids with inhibitory effects on melanogenesis from the rhizomes of Curcuma comosa in B16 melanoma cells. Bioorg Med Chem Lett. 2013;23:5178-81 pubmed publisher
    ..From the methanolic extract, three new diarylheptanoids, diarylcomosols I-III, were isolated together with 12 known diarylheptanoids...
  7. Luo J, Rui W, Jiang M, Tian Q, Ji X, Feng Y. Separation and identification of diarylheptanoids in supercritical fluid extract of Alpinia officinarum by UPLC-MS-MS. J Chromatogr Sci. 2010;48:795-801 pubmed
    ..electrospray ionization (ESI(+)) tandem mass spectrometry (MS) was developed to identify and characterize the diarylheptanoids in the supercritical fluid extract (SFE) of Alpinia officinarum...
  8. Lee C, Jang E, Kim Y, Myung S, Kim W, Lee M. Diarylheptanoid hirsutenone enhances apoptotic effect of TRAIL on epithelial ovarian carcinoma cell lines via activation of death receptor and mitochondrial pathway. Invest New Drugs. 2012;30:548-57 pubmed publisher
    ..b>Diarylheptanoids such as hirsutenone and oregonin have been shown to have anti-inflammatory and anti-tumor effects...
  9. Su J, Sripanidkulchai K, Suksamrarn A, Hu Y, Piyachuturawat P, Sripanidkulchai B. Pharmacokinetics and organ distribution of diarylheptanoid phytoestrogens from Curcuma comosa in rats. J Nat Med. 2012;66:468-75 pubmed publisher
    ..Previous studies reported that it has phytoestrogenic activity, and several diarylheptanoids were found to be the active constituents...

More Information

Publications62

  1. Yadav D, Singh S, Verma R, Saxena K, Verma R, Murthy P, et al. Antifilarial diarylheptanoids from Alnus nepalensis leaves growing in high altitude areas of Uttarakhand, India. Phytomedicine. 2013;20:124-32 pubmed publisher
    ..Platyphyllenone (A), alusenone (B), hirustenone (C) and hirsutanonol (D) are important biologically active diarylheptanoids present in Alnus nepalensis...
  2. Tantikanlayaporn D, Robinson L, Suksamrarn A, Piyachaturawat P, Blair H. A diarylheptanoid phytoestrogen from Curcuma comosa, 1,7-diphenyl-4,6-heptadien-3-ol, accelerates human osteoblast proliferation and differentiation. Phytomedicine. 2013;20:676-82 pubmed publisher
    ..We conclude that DPHD promotes human osteoblast function in vitro effectively at nanomolar concentrations, making it a promising compound to protect bone in menopausal women...
  3. Choi S, Jeong M, Kang M, Lee D, Joo S, Lee C, et al. Effect of topical application and intraperitoneal injection of oregonin on atopic dermatitis in NC/Nga mice. Exp Dermatol. 2010;19:e37-43 pubmed publisher
    ..The results presented in this report suggest that ORE might be beneficial in the treatment of AD. ..
  4. Sodsai A, Piyachaturawat P, Sophasan S, Suksamrarn A, Vongsakul M. Suppression by Curcuma comosa Roxb. of pro-inflammatory cytokine secretion in phorbol-12-myristate-13-acetate stimulated human mononuclear cells. Int Immunopharmacol. 2007;7:524-31 pubmed
    ..These results indicated that C. comosa and its diarylheptanoids have anti-inflammatory properties which could be exploited for clinical use.
  5. Winuthayanon W, Piyachaturawat P, Suksamrarn A, Ponglikitmongkol M, Arao Y, Hewitt S, et al. Diarylheptanoid phytoestrogens isolated from the medicinal plant Curcuma comosa: biologic actions in vitro and in vivo indicate estrogen receptor-dependent mechanisms. Environ Health Perspect. 2009;117:1155-61 pubmed publisher
    b>Diarylheptanoids isolated from Curcuma comosa Roxb. have been recently identified as phyto estrogens. However, the mechanism underlying their actions has not yet been identified...
  6. Nhiem N, Kiem P, Minh C, Kim N, Park S, Lee H, et al. Diarylheptanoids and flavonoids from viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. J Nat Prod. 2013;76:495-502 pubmed publisher
    Three new diarylheptanoids, (3S,5R)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (1), (3S,5S)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (2), and (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one (3), four ..
  7. Yao H, Zhou G, Wu Q, Lei G, Chen D, Chen J, et al. Mistletonone, a novel antioxidative diarylheptanoid from the branches and leaves of Viscum coloratum. Molecules. 2007;12:312-7 pubmed
    ..The compound showed significant scavenging effects on hydroxyl radicals and superoxide anion radicals in the direct assay using the electron spin resonance (ESR) technique...
  8. An N, Zou Z, Tian Z, Luo X, Yang S, Xu L. Diarylheptanoids from the rhizomes of Alpinia officinarum and their anticancer activity. Fitoterapia. 2008;79:27-31 pubmed
    Two new diarylheptanoids (1, 2), together with two known analogs (3, 4), were isolated from the rhizomes of Alpinia officinarum...
  9. Tung N, Kwon H, Kim J, Ra J, Ding Y, Kim J, et al. Anti-influenza diarylheptanoids from the bark of Alnus japonica. Bioorg Med Chem Lett. 2010;20:1000-3 pubmed publisher
    ..anti-influenza components from the bark of Alnus japonica resulted in the isolation of two rare acylated diarylheptanoids, named oregonoyl A (5) and oregonoyl B (6), along with nine known compounds (1-4 and 7-11)...
  10. Abas F, Hui L, Ahmad S, Stanslas J, Israf D, Shaari K, et al. Biological evaluation of curcumin and related diarylheptanoids. Z Naturforsch C. 2006;61:625-31 pubmed
    Nine derivatives of three natural diarylheptanoids, curcumin, demethoxycurcumin and bisdemethoxycurcumin, were prepared...
  11. Kang H, Son K, Yang D, Han D, Kim J, Baek N, et al. Inhibitory activity of diarylheptanoids on farnesyl protein transferase. Nat Prod Res. 2004;18:295-9 pubmed
    b>Diarylheptanoids [curcumin (1), demethoxycurcumin (2), bisdemethoxycurcumin (3), bisdimethoxymethylcurcumin (4), and 1,2-dihydrobis(de-O-methyl)curcumin (5)] were isolated from the methanolic extract of Curcuma longa L...
  12. Tabata K, Yamazaki Y, Okada M, Fukumura K, Shimada A, Sun Y, et al. Diarylheptanoids derived from Alpinia officinarum induce apoptosis, S-phase arrest and differentiation in human neuroblastoma cells. Anticancer Res. 2009;29:4981-8 pubmed
    ..previously screened many natural products for their cytotoxic effects on neuroblastoma cell lines, and two diarylheptanoids derived from Alpinia officinarum, 7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-4E-hepten-3-one (Compound 1) and ..
  13. Jiang H, Timmermann B, Gang D. Characterization and identification of diarylheptanoids in ginger (Zingiber officinale Rosc.) using high-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2007;21:509-18 pubmed
    In our continuing investigation of diarylheptanoids in Zingiberaceae plants using liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS/MS), 26 diarylheptanoids were identified from fresh ginger rhizome...
  14. Wei Q, Ma J, Cai Y, Yang L, Liu Z. Cytotoxic and apoptotic activities of diarylheptanoids and gingerol-related compounds from the rhizome of Chinese ginger. J Ethnopharmacol. 2005;102:177-84 pubmed
    ..relationship (SAR) we isolated from the rhizomes of Chinese ginger (Zingiber officinale Roscoe) five new diarylheptanoids along with 20 known diarylheptanoids and gingerol-related compounds and studied their cytotoxic and apoptotic ..
  15. Kim H, Yeom S, Kim M, Shim J, Paek I, Lee M. Nitric oxide and prostaglandin E2 synthesis inhibitory activities of diarylheptanoids from the barks of Alnus japonica steudel. Arch Pharm Res. 2005;28:177-9 pubmed
    Nine known diarylheptanoids (1-9) isolated from the barks of Alnus japonica were evaluated for their inhibitory activities on nitric oxide (NO) and prostagrandin E2 (COX-2) production in interferon-gamma (INF-gamma) and lipopolysaccharide ..
  16. Tao Q, Xu Y, Lam R, Schneider B, Dou H, Leung P, et al. Diarylheptanoids and a monoterpenoid from the rhizomes of Zingiber officinale: antioxidant and cytoprotective properties. J Nat Prod. 2008;71:12-7 pubmed publisher
    Three new diarylheptanoids and one new monoterpenoid were isolated from the rhizomes of Zingiber officinale together with four known diarylheptanoids, 5-8...
  17. Grienke U, Schmidtke M, Kirchmair J, Pfarr K, Wutzler P, Durrwald R, et al. Antiviral potential and molecular insight into neuraminidase inhibiting diarylheptanoids from Alpinia katsumadai. J Med Chem. 2010;53:778-86 pubmed publisher
    ..Among the six isolated constituents, four diarylheptanoids showed in vitro NA inhibitory activities in low micromolar ranges against human influenza virus A/PR/8/34 of ..
  18. Suksamrarn A, Ponglikitmongkol M, Wongkrajang K, Chindaduang A, Kittidanairak S, Jankam A, et al. Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation. Bioorg Med Chem. 2008;16:6891-902 pubmed publisher
    Three new diarylheptanoids, a 1:2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one (15), together with two synthetically known diarylheptanoids 1,..
  19. Kim J, Kim A, Chung H, Han S, Kim B, Choi J. In vitro peroxynitrite scavenging activity of diarylheptanoids from Curcuma longa. Phytother Res. 2003;17:481-4 pubmed
    ..Peroxynitrite scavenging diarylheptanoids, curcumin I (1), curcumin II (2), and curcumin III (3) were isolated as active principles...
  20. Lee C, Ko H, Seo S, Choi Y, Lee M, Myung S, et al. Diarylheptanoid hirsutenone prevents tumor necrosis factor-alpha-stimulated production of inflammatory mediators in human keratinocytes through NF-kappaB inhibition. Int Immunopharmacol. 2009;9:1097-104 pubmed publisher
    Keratinocytes may play an important role in the pathogenesis of skin disease in atopic dermatitis. Diarylheptanoids such as oregonin and hirstanonol are demonstrated to have anti-inflammatory and anti-oxidant effects...
  21. Dhuru S, Bhedi D, Gophane D, Hirbhagat K, Nadar V, More D, et al. Novel diarylheptanoids as inhibitors of TNF-? production. Bioorg Med Chem Lett. 2011;21:3784-7 pubmed publisher
    Synthesis and anti-inflammatory activity of novel diarylheptanoids [5-hydroxy-1-phenyl-7-(pyridin-3-yl)-heptan-3-ones and 1-phenyl-7-(pyridin-3-yl)hept-4-en-3-ones] as inhibitors of tumor necrosis factor-? (TNF-?) production is described ..
  22. Kim J, Lee K, Lee M, Lee H, Kim S, Surh Y. Hirsutenone inhibits phorbol ester-induced upregulation of COX-2 and MMP-9 in cultured human mammary epithelial cells: NF-kappaB as a potential molecular target. FEBS Lett. 2006;580:385-92 pubmed
    ..In summary, hirsutenone inhibits the TPA-induced upregulation of COX-2 and MMP-9 in human breast epithelial cells, possibly by targeting NF-kappaB, which may contribute to its chemopreventive effects. ..
  23. Choi S, Kim K, Kwon J, Kim S, Kim H, Lee M. Cytotoxic activities of diarylheptanoids from Alnus japonica. Arch Pharm Res. 2008;31:1287-9 pubmed publisher
    The diarylheptanoids (1-10) 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranoside (1), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-beta-D-apiofuranosyl(1-->6)-beta-D-glucopyranoside (2), 1,7-bis-(..
  24. Ma J, Jin X, Yang L, Liu Z. Diarylheptanoids from the rhizomes of Zingiber officinale. Phytochemistry. 2004;65:1137-43 pubmed
    Seven new diarylheptanoids, i.e...
  25. Jin W, Cai X, Na M, Lee J, Bae K. Triterpenoids and diarylheptanoids from Alnus hirsuta inhibit HIF-1 in AGS cells. Arch Pharm Res. 2007;30:412-8 pubmed
    ..hirsuta (Betulaceae), using an in vitro HIF-1 assay, led to the isolation of four triterpenoids (1-4) and six diarylheptanoids (5-10)...
  26. Joo S, Kim S, Choi S, Kim Y, Park H, Seo S, et al. Suppression of T cell activation by hirsutenone, isolated from the bark of Alnus japonica, and its therapeutic advantages for atopic dermatitis. Eur J Pharmacol. 2009;614:98-105 pubmed publisher
    ..Therefore, our results suggest that hirsutenone may be a new topical drug candidate, which probably acts by mimicking calcineurin inhibitor mechanisms...
  27. Han J, Lee W, Kim J, Son J, Nam K, Choi S, et al. Effects of diarylheptanoids on the tumor necrosis factor-alpha-induced expression of adhesion molecules in human umbilical vein endothelial cells. J Agric Food Chem. 2007;55:9457-64 pubmed
    ..In the present study, we report the inhibitory effects of two diarylheptanoids, 5-O-methylhirsutanonol (1) and oregonin (2), isolated from the methanolic extracts of Alnus japonica leaves, ..
  28. Bhukhai K, Suksen K, Bhummaphan N, Janjorn K, Thongon N, Tantikanlayaporn D, et al. A phytoestrogen diarylheptanoid mediates estrogen receptor/Akt/glycogen synthase kinase 3? protein-dependent activation of the Wnt/?-catenin signaling pathway. J Biol Chem. 2012;287:36168-78 pubmed publisher
    ..Our findings provide a scientific rationale for using C. comosa as a dietary supplement to prevent bone loss in postmenopausal women. ..
  29. Deguchi J, Motegi Y, Nakata A, Hosoya T, Morita H. Cyclic diarylheptanoids as inhibitors of NO production from Acer nikoense. J Nat Med. 2013;67:234-9 pubmed publisher
    ..A benzoyl ester derivative of acerogenin C showed the most potent inhibitory activity of NO production from lipopolysaccharide-activated macrophages. ..
  30. Cho S, Kwon Y, Lee J, Yon K, Lee M. Melanogenesis inhibitory activities of diarylheptanoids from Alnus hirsuta Turcz in B16 mouse melanoma cell. Arch Pharm Res. 2002;25:885-8 pubmed
    Four diarylheptanoids, (5R-1,7-bis (3,4-dihydroxyphenyl)-heptane-5-O-beta-D-glucoside (1), (5R) 1,7-bis (3,4-dihydroxyphenyl)-heptane-5-ol (2), oregonin (3), hirsutanonol (4), were isolated from the bark of Alnus hirsuta Turcz and its ..
  31. Winuthayanon W, Suksen K, Boonchird C, Chuncharunee A, Ponglikitmongkol M, Suksamrarn A, et al. Estrogenic activity of diarylheptanoids from Curcuma comosa Roxb. Requires metabolic activation. J Agric Food Chem. 2009;57:840-5 pubmed publisher
    ..We investigated the estrogenic activity of 7 naturally occurring diarylheptanoids from the extracts of C. comosa both in vitro and in vivo...
  32. Tung N, Ra J, Sohn D, Kim Y. A new diarylheptanoid from the bark of Alnus japonica. J Asian Nat Prod Res. 2010;12:921-4 pubmed publisher
    ..Their structures were elucidated on the basis of extensive spectroscopic evidence. The new compound 1 showed significant hepatoprotective activity on the basis of t-butylhydroperoxide-induced hepatocyte injury in vitro assay. ..
  33. Hoye T, Ayyad S, Beckord H, Brown S. New diarylheptanoids and a hydroxylated ottelione from Ottelia alismoides. Nat Prod Commun. 2013;8:351-8 pubmed
    Ten new diarylheptanoids (2, 3, 4, 5a-d, 6, 7, and 8) have been isolated from an extract of Ottelia alismoides. The structures of these previously unknown metabolites were determined by NMR spectroscopic analysis...
  34. Costantino V, Fattorusso E, Mangoni A, Perinu C, Teta R, Panza E, et al. Tedarenes A and B: structural and stereochemical analysis of two new strained cyclic diarylheptanoids from the marine sponge Tedania ignis. J Org Chem. 2012;77:6377-83 pubmed publisher
    Ring strain causes planar chirality in tedarenes A and B, two cyclic diarylheptanoids isolated from the marine sponge Tedania ignis. In both molecules, the chiral plane is an olefinic system, which is very rare among natural products...
  35. Hölscher D, Brand S, Wenzler M, Schneider B. NMR-based metabolic profiling of Anigozanthos floral nectar. J Nat Prod. 2008;71:251-7 pubmed publisher
    ..A linear diarylheptanoid was detected as a trace component, marking the first time this type of secondary product in Hemodoraceae has been found...
  36. Sawamura R, Shimizu T, Sun Y, Yasukawa K, Miura M, Toriyama M, et al. In vitro and in vivo anti-influenza virus activity of diarylheptanoids isolated from Alpinia officinarum. Antivir Chem Chemother. 2010;21:33-41 pubmed publisher
    b>Diarylheptanoids (AO-0002 [7-(4''-hydroxy-3''-methoxyphenyl)-1-phenyl-4E-hepten-3-one] and AO-0011 [(5S)-5-hydroxy-7-(4''-hydroxyphenyl)-1-phenyl-3-heptanone]) isolated from Alpinia officinarum have been reported to exhibit anti-influenza ..
  37. Paul A, Das S, Das J, Samadder A, Bishayee K, Sadhukhan R, et al. Diarylheptanoid-myricanone isolated from ethanolic extract of Myrica cerifera shows anticancer effects on HeLa and PC3 cell lines: signalling pathway and drug-DNA interaction. J Integr Med. 2013;11:405-15 pubmed publisher
  38. Yokosuka A, Mimaki Y, Sakagami H, Sashida Y. New diarylheptanoids and diarylheptanoid glucosides from the rhizomes of Tacca chantrieri and their cytotoxic activity. J Nat Prod. 2002;65:283-9 pubmed
    Two new diarylheptanoids (1, 2) and seven new diarylheptanoid glucosides (3-9) were isolated from the rhizomes of Tacca chantrieri...
  39. Lee S, Huang W, Lin W, Lee S, Chen C. Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs. Bioorg Med Chem. 2005;13:6175-81 pubmed
    ..These compounds, however, possess stronger potency than 1 against COX-2-derived PGE2 formation, of which hexahydrocurcumin (4) is the most potent one with an IC50 value of 0.7 microM. ..
  40. Dong S, Nikolic D, Simmler C, Qiu F, van Breemen R, Soejarto D, et al. Diarylheptanoids from Dioscorea villosa (Wild Yam). J Nat Prod. 2012;75:2168-77 pubmed publisher
    ..This quantifiable and structural guidance led to the isolation of 14 diarylheptanoids (1-14), including five new compounds (1-5) with a tetrahydropyrano core skeleton...
  41. Lee K, Kim S, Sung S, Kim Y. Inhibitory constituents of lipopolysaccharide-induced nitric oxide production in BV2 microglia isolated from Amomum tsao-ko. Planta Med. 2008;74:867-9 pubmed publisher
    ..TSAO-KO using bioactivity-guided fractionation. All thirteen compounds significantly inhibited lipopolysaccharide-induced nitric oxide production in BV2 microglial cells at concentrations ranging from 1 microM to 100 microM...
  42. Liu H, Tsim K, Chou G, Wang J, Ji L, Wang Z. Phenolic compounds from the rhizomes of Dioscorea bulbifera. Chem Biodivers. 2011;8:2110-6 pubmed publisher
    ..Their structures were elucidated by NMR and MS analyses. Compound 7 showed high antioxidant capacity in FRAP assay and DPPH radical-scavenging activity. ..
  43. Ye Q, Tan X, Zhu L, Zhao Z, Yang D, Yin S, et al. [Isolation and purification of diarylheptanoids from Alpinia officinarum Hance by high-speed counter-current chromatography]. Se Pu. 2012;30:327-31 pubmed
    Three diarylheptanoids were isolated and purified from Alpinia officinarum Hance by high-speed counter-current chromatography (HSCCC). A two-phase solvent system composed of hexane-ethyl acetate-methanol-water (2: 3: 1...
  44. Sun Y, Tabata K, Matsubara H, Kitanaka S, Suzuki T, Yasukawa K. New cytotoxic diarylheptanoids from the rhizomes of Alpinia officinarum. Planta Med. 2008;74:427-31 pubmed publisher
    ..of the cytotoxic MeOH extract from the rhizomes of Alpinia officinarum Hance led to the isolation of two new diarylheptanoids named alpinoid D (1) and E (2), together with fifteen known diarylheptanoids (3 - 17)...
  45. Yin J, Han N, Liu Z, Xu X, Zhang B, Kadota S. The in vitro anti-osteoporotic activity of some diarylheptanoids and lignans from the rhizomes of Dioscorea spongiosa. Planta Med. 2008;74:1451-3 pubmed publisher
    Three diarylheptanoids and three lignans from the 90 % ethanol fraction of the rhizomes of DIOSCOREA SPONGIOSA were isolated and subjected to IN VITRO experiments to investigate their activity on osteoblasts and osteoclasts...
  46. Konno K, Miura M, Toriyama M, Motohashi S, Sawamura R, Watanabe W, et al. Antiviral activity of diarylheptanoid stereoisomers against respiratory syncytial virus in vitro and in vivo. J Nat Med. 2013;67:773-81 pubmed publisher
    ..virus activity and anti-respiratory syncytial virus (RSV) activity, respectively, than the other isolated diarylheptanoids. In this study, we synthesized an enantiomer (AO-0503) and racemate (AO-0504) of AO-0011 and an enantiomer (..
  47. Mshvildadze V, Legault J, Lavoie S, Gauthier C, Pichette A. Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera. Phytochemistry. 2007;68:2531-6 pubmed
    ..Platyphylloside (4) exerted the strongest cytotoxic activity of all isolated compounds with IC(50) values ranging from 10.3 to 13.8 microM. ..
  48. Jo H, Choi S, Jung S. Protective effects of a compound isolated from Alnus japonica on oxidative stress-induced death in transformed retinal ganglion cells. Food Chem Toxicol. 2013;56:425-35 pubmed publisher
    ..Hirsutenone treatment led to a reduction in NMDA-induced IPL and TUNEL staining of the GCL. In conclusion, hirsutenone isolated from A. japonica may act as neuroprotective agent for conditions such as glaucoma. ..
  49. Siddiqui I, Ahmad V, Zahoor A, Ahmed A, Khan S, Khan A, et al. Two new diarylheptanoids from Alnus nitida. Nat Prod Commun. 2010;5:1787-8 pubmed
    Two new diarylheptanoids, trivially named nitidone A and nitidone B, have been isolated from Alnus nitida...
  50. Jeong M, Choi S, Kim J, Kim J, Kim E, Park K, et al. Atopic dermatitis-like skin lesions reduced by topical application and intraperitoneal injection of Hirsutenone in NC/Nga mice. Clin Dev Immunol. 2010;2010:618517 pubmed publisher
    ..These results suggest that HIR might be an effective treatment for AD. ..
  51. Fang Z, Wills M. Asymmetric transfer hydrogenation of functionalized acetylenic ketones. J Org Chem. 2013;78:8594-605 pubmed publisher
    ..In several cases, excellent enantioselectivities and yields were achieved. ..
  52. Lee O, Kim J, Choi Y, Lee M, Park G, Oh C. Efficacy of oregonin investigated by non-invasive evaluation in a B16 mouse melanoma model. Exp Dermatol. 2013;22:842-4 pubmed publisher
    ..Based on survival rates after transplantation, the control group showed less than 50% survival after 20 days, while the treatment groups showed at least 50% survival up to the 41st day. ..
  53. Cakir S, Stokes S, Sygula A, Mead K. Evidence for pi-stacking as a source of stereocontrol in the synthesis of the core pyranochromene ring system common to calyxin I, calyxin J, and epicalyxin J. J Org Chem. 2009;74:7529-32 pubmed publisher
    ..Further, our results show that stereocontrol is under kinetic control, and calculations suggest that a favorable pi-stacking interaction may be the source of this stereocontrol. ..