hinokiresinol biosynthesis
Ju C, Hwang S, Cho GS, Kondaji G, Song S, Prather PL, Choi Y, Kim WK. Differential anti-ischemic efficacy and therapeutic time window of trans- and cis-hinokiresinols: stereo-specific antioxidant and anti-inflammatory activities. Neuropharmacology. 2013 Apr;67():465–75. doi: 10.1016/j.neuropharm.2012.12.006. PMID: 23287539.; Dong LB, He J, Wang YY, Wu XD, Deng X, Pan ZH, Xu G, Peng LY, Zhao Y, Li Y, Gong X, Zhao QS. Terpenoids and norlignans from Metasequoia glyptostroboides. J Nat Prod. 2011 Feb 25;74(2):234–9. doi: 10.1021/np100694k. PMID: 21226514.; Yamamura M, Suzuki S, Hattori T, Umezawa T. Subunit composition of hinokiresinol synthase controls enantiomeric selectivity in hinokiresinol formation. Org Biomol Chem. 2010 Mar 07;8(5):1106–10. doi: 10.1039/b918656e. PMID: 20165801.; Lim H, Nam JW, Seo EK, Kim YS, Kim HP. (-)-Nyasol (cis-hinokiresinol), a norneolignan from the rhizomes of Anemarrhena asphodeloides, is a broad spectrum inhibitor of eicosanoid and nitric oxide production. Arch Pharm Res. 2009 Nov;32(11):1509–14. doi: 10.1007/s12272-009-2102-4. PMID: 20091263.; Chen TH, Liau BC, Wang SY, Jong TT. Isolation and cytotoxicity of the lignanoids from Chamaecyparis formosensis. Planta Med. 2008 Dec;74(15):1806–11. doi: 10.1055/s-0028-1088325. PMID: 19003728.; Saito K, Mitsutani T, Imai T, Matsushita Y, Fukushima K. Discriminating the indistinguishable sapwood from heartwood in discolored ancient wood by direct molecular mapping of specific extractives using time-of-flight secondary ion mass spectrometry. Anal Chem. 2008 Mar 01;80(5):1552–7. doi: 10.1021/ac7021162. PMID: 18232669.; Suzuki S, Yamamura M, Hattori T, Nakatsubo T, Umezawa T. The subunit composition of hinokiresinol synthase controls geometrical selectivity in norlignan formation. Proc Natl Acad Sci U S A. 2007 Dec 26;104(52):21008–13. PMID: 18093914; PMCID: PMC2409257.; Song MC, Yang HJ, Bang MH, Kim DK, Jeong TS, Kim JP, Baek NI. Antioxidant and antiatherogenic activity of cis-Hinokiresinol from Trapa pseudoincisa. Arch Pharm Res. 2007 Nov;30(11):1392–7. doi: 10.1007/bf02977362. PMID: 18087806.; Imai T, Nomura M, Matsushita Y, Fukushima K. Hinokiresinol is not a precursor of agatharesinol in the norlignan biosynthetic pathway in Japanese cedar. J Plant Physiol. 2006 Dec;163(12):1221–8. doi: 10.1016/j.jplph.2006.05.012. PMID: 16884819.; Bae EA, Park EK, Yang HJ, Baek NI, Kim DH. Hinokiresinol inhibits IgE-induced mouse passive cutaneous anaphylaxis reaction. Planta Med. 2006 Nov;72(14):1328–30. doi: 10.1055/s-2006-947264. PMID: 17051467.; Skytte DM, Nielsen SF, Chen M, Zhai L, Olsen CE, Christensen SB. Antimalarial and antiplasmodial activities of norneolignans. Syntheses and SAR. J Med Chem. 2006 Jan 12;49(1):436–40. doi: 10.1021/jm0508235. PMID: 16392829.; Suzuki S, Yamamura M, Shimada M, Umezawa T. A heartwood norlignan, (E)-hinokiresinol, is formed from 4-coumaryl 4-coumarate by a Cryptomeria japonica enzyme preparation. Chem Commun (Camb). 2004 Dec 21;(24):2838–9. doi: 10.1039/b409686j. PMID: 15599432.; Jeong SJ, Higuchi R, Ono M, Kuwano M, Kim YC, Miyamoto T. cis-hinokiresinol, a norlignan from Anemarrhena asphodeloides, inhibits angiogenic response in vitro and in vivo. Biol Pharm Bull. 2003 Dec;26(12):1721–4. doi: 10.1248/bpb.26.1721. PMID: 14646178.; Park HJ, Lee JY, Moon SS, Hwang BK. Isolation and anti-oomycete activity of nyasol from Anemarrhena asphodeloides rhizomes. Phytochemistry. 2003 Nov;64(5):997–1001. doi: 10.1016/s0031-9422(03)00462-x. PMID: 14561517.; Suzuki S, Nakatsubo T, Umezawa T, Shimada M. First in vitro norlignan formation with Asparagus officinalis enzyme preparation. Chem Commun (Camb). 2002 May 21;(10):1088–9. doi: 10.1039/b200217e. PMID: 12122678.; MATSUDA H, SATO N, YAMAZAKI M, NARUTO S, KUBO M. Testosterone 5.ALPHA.-Reductase Inhibitory Active Constituents from Anemarrhenae Rhizoma. Biological & Pharmaceutical Bulletin. 2001;24(5):586–7. doi: 10.1248/bpb.24.586.; Minami E, Taki M, Takaishi S, Iijima Y, Tsutsumi S, Akiyama T. Stereochemistry of cis- and trans-hinokiresinol and their estrogen-like activity. Chem Pharm Bull (Tokyo). 2000 Mar;48(3):389–92. doi: 10.1248/cpb.48.389. PMID: 10726863.; Lee HJ, Ryu JH. Hinokiresinol: a novel inhibitor of LTB4 binding to the human neutrophils. Planta Med. 1999 May;65(4):391. doi: 10.1055/s-2006-960799. PMID: 10364852.; Jeong SJ, Ahn NH, Kim YC, Inagaki M, Miyamoto T, Higuchi R. Norlignans with Hyaluronidase Inhibitory Activity from Anemarrhena asphodeloides. Planta Med. 1999 May;65(4):367–8. doi: 10.1055/s-2006-960789. PMID: 17260262.; Iida Y, Oh K, Saito M, Matsuoka H, Kurata H, Natsume M, Abe H. Detection of Antifungal Activity in Anemarrhena asphodeloides by Sensitive BCT Method and Isolation of Its Active Compound. J. Agric. Food Chem. 1999 Jan 05;47(2):584–7. doi: 10.1021/jf980707t.; Oketch-Rabah HA, Dossaji SF, Christensen SB, Frydenvang K, Lemmich E, Cornett C, Olsen CE, Chen M, Kharazmi A, Theander T. Antiprotozoal compounds from Asparagus africanus. J Nat Prod. 1997 Oct;60(10):1017–22. doi: 10.1021/np970217f. PMID: 9358645.; Whiting DA. Lignans, neolignans, and related compounds. Nat Prod Rep. 1987 Oct;4(5):499–525. doi: 10.1039/np9870400499. PMID: 2833712.; Nikaido T, Ohmoto T, Kinoshita T, Sankawa U, Nishibe S, Hisada S. Inhibition of cyclic AMP phosphodiesterase by lignans. Chem Pharm Bull (Tokyo). 1981 Dec;29(12):3586–92. doi: 10.1248/cpb.29.3586. PMID: 6280885.