Microbial transformation of chalcone (1), 4-hydroxychalcone (2) and 4′-hydroxychalcone (3), 1,1-diphenylmethane (4), 1,3-diphenylacetone (5), 1,3-diphenylpropane (6), bibenzyl (7), (E)-stilbene (8a)- and (Z)-stilbenes (8b), and phenylcyclohexane (9), (1R,2S)-1-phenyl-2-hydroxycyclohexane (9a) and (1S,2R)-1-phenyl-2-hydroxycyclohexane (9b), and a naturally occurring bis-bibenzyl, marchantin A (10) were performed by using Aspergillus niger TBUYN-2 and the other Aspergillus strains, and Neurospora crassa which were capable to hydrogenation and epoxidation of a conjugated double bond, and direct hydroxylation and hydroperoxidation on benzene ring, and hydroxylation and carbonization on cyclohexane ring. Aspergillus species converted chalcone (1) to dihydrochalcone (1a) almost quantitatively.
FurusawaM., HashimotoT., NomaY., AsakawaY. (2005) Highly efficient production of nootkatone, the grapefruit aroma from valencene by biotransformation. Chemical and Pharmaceutical Bulletin, 53, 1513–1514.
2.
(a) NomaY., AtakapaY. (2010) Microbial transformation of (-)-nopol benzyl ether: Direct dihydroxylation of benzene ring. Natural Product Communications, 5, 1339–1341; (b) Asakawa Y, Noma Y. (2010) Biotransformation of sesquiterpenoids. In Comprehensive Natural Products II. Chemistry and Biology, Mander L, Liu HW (Eds.), Elsevier, Oxford, 3, 856–859; (c) Noma Y, Asakawa Y. (2010) Biotransformation of monoterpenoids by microorganisms, insects, and mammals. In Handbook of Essential Oils. Baser KHC, Buchbauer G. (Eds.) CRC Press, Boca Raton, Florida.585–736; (d) Asakawa Y, Noma Y. (2010) Biotransformation of sesquiterpenoids, ionones, damascones, adamantanes, and aromatic compounds by green algae, fungi, and mammals. In Handbook of Essential Oils. Baser KHC, Buchbauer G. (Eds.) CRC Press, Boca Raton, Florida. 737–841.
3.
(a) NomaY., AsakawaY. (1994) Chapter XIII: Dunaliella tertiolecta (green microalga): culture and biotransformation of terpenoids and related compounds. In Biotechnology in Agriculture and Forestry. Medical and Aromatic Plants VII. (BjajY.P.S. (Ed.), Springer, Berlin, 28, 185–202; (b) Noma Y, Asakawa Y. (1994) Chapter XI. Euglena gracilis Z: Biotransformation of terpenoids and related compounds. In Biotechnology in Agriculture and Forestry. Medical and Aromatic Plants X. (Bjaj YPS. (Ed.), Springer, Berlin, 41, 194–237; (c) Noma Y, Asakawa Y. (1995) Chapter V: Aspergillus spp.: Biotransformation of terpenoids and related compounds. In Biotechnology in Agriculture and Forestry. Medical and Aromatic Plants VII. (Bjaj YPS. (Ed.), Springer, Berlin, 33, 62–95.
4.
(a) LeyJ., FreiherrK., KrammerG., ReindersG. (2008) Aroma compositions of alkamides with hesperetin and/or 4-hydroxydihydrochalcones and salts thereof for enhancing sweet sensory impressions. United States Patent Application Publication, US2008/0242740 A1; (b) Janeczko T, Gladkowski W, Kostrzewa-Suslow E. (2013) Microbial transformation of chalcones to produce food sweetener derivatives. Journal of Molecular Catalysis B: Enzymatic, 98, 55–61.
5.
(a) NomaY., YokoyamaT., HasimotoT., ItoT., AsakawaY. (2011) Mirobial transformation of Aromatic compounds. The 55th Symposium on the Chemisstry of Terpeens, Essential Oils and Aromatics, Tsukuba, Japan, Novermber 19–21, 383–385; (b) Noma Y, Hamauzu M, Hasimoto T, Asakawa Y. (2011) Mirobial transformation of Aromatic compounds. The 55th Symposium on the Chemisstry of Terpeens, Essential Oils and Aromatics, Tsukuba, Japan, Novermber 19–21, pp.380–382; (c) Noma Y, Hashimoto T, Ludwiczuk A, Asakawa Y. (2010) Microbial biotransformation of kawapyrones, stilbenes and chalcone. 7th Internaational Symposium on Chromatoraphy and Natural Product. Lublin, Poland, June, 52; (d) Noma Y, Asakawa Y. (2010) Highly efficient microbial one pot production of dihydrochalchone from benzalacetophenone. 7th Internaational Symposium on Chromatoraphy and Natural Products. Lublin, Poland, June 14–17, 157.
6.
BarradasS., Hernandez-TorresG., UrbanoA., CarrenoM.C. (2012) Total synthesis of natural p-quinol cochinchinenone. Organic Letters, 14, 5952–5955.
7.
AlcaideB., AlmendrosP., QuirosM.T., LopezR., MenendezM.I., Sochacka-CwiklaA. (2012) Unveiling the reactivity of propargylic hydroperoxides under gold catalysis. Journal of American Chemical Society, 135, 898–905.
8.
ColbonP., RuanJ., PurdieM., XiaoJ. (2010) Direct acylation of aryl chlorides with aldehydes by palladium-pyrrolidine co-catalysis. Organic Letters, 12, 3670–3673.
9.
ComptonB.J., LarsenD.S., LarsenL., WeaversR.T. (2008) Reactive diene for synthesis of substituted catechols. Tetrahedron Letters, 49, 219–221.
10.
AsakawaY. (1971) Chemical constituents of Alnus sieboldiana (Betulaceae). II. Isolation and structures of flavonoids and stilbenes. Bulletin of Chemical Society of Japan, 44, 2761–2766.
11.
(a) NomaY., ItoT., LudwiczukA., AsakawaY. (2010) Microbial transformation of stilbenes and stilbene oxides. The 54th Symposium on the Chemisstry of Terpeens, Essential Oils and Aromatics, Yamanashi, Japan, October 23–25, 60–162.
12.
NomaY., HasimotoT., ImagawaH., AsakawaY. (2011) Microbial transformato of phenylcyclohexane and realated compounds. The 56th Symposium on the Chemisstry of Terpeens, Essential Oils and Aromatics, Kagoshima, Japan, October 27–29,. 117–119.
13.
(a) AsakawaY., LudwiczukA., NagashimaF. (2013) Chemical constituents of bryophytes. Bio- and chemical diversity, biological activity, and chemosystematics. In Progress in the Chemistry of Organic Natural Products, Vol. 95, KinghornA.D., FalkH., KobayashiJ. (Eds). Springer, Vienna, Austria. 1–796. b) Asakawa Y, Ludwiczuk A, Toyota M. (2014) Chemical analysis of bryophytes. In Handbook of Chemical and Biological Plant Analytical Methods II. Hostettmann K, Stuppner H, Marston A, Chen S. (Eds). John Wiley & Sons Ltd. London, 753–805. (c) Asakawa Y. (2016) Bryophytes:Structures, Biological Activities, and Bio- and Total Synthesis. In: Recent Advances in Polyphenol, Vol 5, Yoshida K, Cheynier V, Quideau S. (Eds.), John Wiley & Sons, London, pp. 36–66.
14.
GhaniN.A., LudwiczukA., IsmailN.D., AsakawaY. (2016) Volatile components of the stressed liverwort Conocephalum conicum. Natural Product Communications, 11, 103–104.
