Hydrogenation of curcumin (1), a chemopreventive agent from Turmeric (Curcuma longa L.) yielded three major compounds: 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione (2), 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (3), and 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol (4). Incubation of compound (2) with Beauveria bassiana ATCC 7159 afforded the hexahydrocurcumin (3) as the sole metabolite while biotransformation of curcumin (1) with B. bassiana gave metabolites 2-4 along with the curcumin-4'-O-4″'-O-methyl-β-D-glucopyranoside (5) and octahydrocurcumin-4'-O-4″'-O-methyl-β-D-glucopyranoside (6). The bioconversion of curcumin (1) with Rhizopus oryzae ATCC 11145 yielded analogs 2-4 while no transformation of curcumin (1) was observed with Aspergillus niger ATCC 16888. The preparation, structural elucidation and biological activities of these metabolites are reported herein.
BachmeierB, NerlichAG, IancuCM, CilliM, SchleicherE, VenéR, Dell'EvaR, JochumM, AlbiniA, PfefferU. (2007) The chemopreventive polyphenol Curcumin prevents hematogenous breast cancer metastases in immunodeficient mice. Cellular Physiology and Biochemistry: International Journal of Experimental Cellular Physiology, Biochemistry, and Pharmacology, 19, 137–152.
2.
ZhouH, BeeversCS, HuangS. (2011) The targets of curcumin. Current Drug Targets, 12, 332–347.
3.
GhoshS, BanerjeeS, SilPC. (2015) The beneficial role of curcumin on inflammation, diabetes and neurodegenerative disease: A recent update. Food and Chemical Toxicology, 83, 111–124
4.
SinghP, PandeyKB, RizviSI. (2016) Curcumin: the yellow molecule with pleiotropic biological effects. Letters in Drug Design & Discovery, 13, 170–177
5.
AliBH, MarrifH, NoureldayemSA, BakheitAO, BlundenG. (2006) Some biological properties of curcumin: A review. Natural Product Communications, 1, 509–521.
6.
AvasaralaS, ZhangF, LiuG, WangR, LondonSD, LondonL. (2013) Curcumin modulates the inflammatory response and inhibits subsequent fibrosis in a mouse model of viral-induced acute respiratory distress syndrome. PLoS ONE, 8, e57285.
7.
SomparnP, PhisalaphongC, NakornchaiS, UnchernS, MoralesN. (2007) Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives. Biological & Pharmaceutical Bulletin, 30, 74–78
8.
LeeS, HuangW, LinWW, LeeS, ChenC. (2005) Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs. Bioorganic & Medicinal Chemistry, 13, 6175–6181.
9.
DewprashadB, HadirL. (2009) Developing an invisible message about relative acidities of alcohols in the natural products henna, turmeric, rose petals, and vitamin A. Journal of Chemical Education, 87, 36–39.
10.
ChandranB, GoelA. (2012) A randomized, pilot study to assess the efficacy and safety of curcumin in patients with active rheumatoid arthritis. Phytotherapy Research, 26, 1719–1725
NiamsaN, SittiwetC. (2009) Antimicrobial activity of Curcuma longa aqueous extract. Journal of Pharmacology and Toxicology, 4, 173–177
13.
AlrawaiqNS, AbdullahA. (2014) A review of antioxidant polyphenol curcumin and its role in detoxification. International Journal of PharmTech Research, 6, 280–289.
IresonC, JonesD, OrrS, CoughtrieM, BoocockD, WilliamsM, FarmerP, StewardW, GescherA. (2002) Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiology, Biomarkers & Prevention: A Publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 11, 105–111.
16.
GarceaG, BerryD, JonesD, SinghR, DennisonA, FarmerP, SharmaR, StewardW, GescherA. (2005) Consumption of the putative chemopreventive agent curcumin by cancer patients: assessment of curcumin levels in the colorectum and their pharmacodynamic consequences. Cancer Epidemiology, Biomarkers & Prevention: A Publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 14, 120–125
17.
PanM, HuangT, LinJ. (1999) Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metabolism and Disposition: The Biological Fate of Chemicals, 27, 486–494
18.
AnandP, KunnumakkaraAB, NewmanRA, AggarwalBB. (2007) Bioavailability of curcumin: problems and promises. Molecular Pharmaceutics, 4, 807–818.
19.
ZhangX, YeM, LiR, YinJ, GuoD. (2010) Microbial transformation of curcumin by Rhizopus chinensis. Biocatalysis and Biotransformation, 28, 380–386
20.
ZengJ, YangN, LiXM, ShamiPJ, ZhanJ. (2010) 4'-O-methylglycosylation of curcumin by Beauveria bassiana. Natural Product Communications, 5, 77–80
21.
ZhangW, HuangJ, WoX, WangP. (2013) Microbial transformation of curcumin to its derivatives with a novel Pichia kudriavzevii ZJPH0802 Strain. Applied Biochemistry and Biotechnology: Part A: Enzyme Engineering and Biotechnology, 170, 1026–1037.
22.
SugiyamaY, KawakishiS, OsawaT. (1996) Involvement of the β-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin. Biochemical Pharmacology, 52, 519–525
23.
MuruganP, PariL. (2006) Antioxidant effect of tetrahydrocurcumin in streptozotocin-nicotinamide induced diabetic rats. Life Sciences, 79, 1720–1728
24.
BishtS, FeldmannG, SoniS, RaviR, KarikarC, MaitraA, MaitraA. (2007) Polymeric nanoparticle-encapsulated curcumin (“nanocurcumin”): a novel strategy for human cancer therapy. Journal of Nanobiotechnology, 5, 1–18.
25.
JirásekP, AmslingerS, HeilmannJ. (2014) Synthesis of natural and non-natural curcuminoids and their neuroprotective activity against glutamate-induced oxidative stress in HT-22 cells. Journal of Natural Products, 77, 2206–2217.
26.
SinghRP, JainDA. (2012) Antimicrobial activity of hydrogenated derivatives of curcumin. Journal of Pharmacy Research, 5, 3650–3653.
27.
WagnerCE, MarshallPA, CahillTM, MohamedZ. (2013) Visually following the hydrogenation of curcumin to tetrahydrocurcumin in a natural product experiment that enhances student understanding of nmr spectroscopy. Journal of Chemical Education, 90, 930–933.
28.
GroganGJ, HollandHL. (2000) The biocatalytic reactions of Beauveria spp. Journal of Molecular Catalysis B Enzymatic, 9, 1–32.
29.
SimanjuntaP, PranaTK, WulandariD, DharmawanA, SumitroE, HendriyantMR. (2010) Chemical studies on a curcumin analogue produced by endophytic fungal transformation. Asian Journal of Applied Sciences, 3, 60–66
30.
ParshikovIA, WoodlingKA, SutherlandJB. (2015) Biotransformations of organic compounds mediated by cultures of Aspergillus niger. Applied Microbiology and Biotechnology, 99, 6971–6986.
31.
MartinGDA. (2010) Biotransformation Reactions by Rhizopus spp. Current Organic Chemistry, 14, 1–14.
32.
KondratyukT, ParkE, YuR, van BreemenR, AsolkarR, MurphyB, FenicalW, PezzutoJ. (2012) Novel marine phenazines as potential cancer chemopreventive and anti-inflammatory agents. Marine Drugs, 10, 451–464.
33.
MartinGDA, NarvaezJ, MartiA. (2013) Synthesis and bioconversions of formestane. Journal of Natural Products, 76, 1966–1969.
34.
SongLL, KosmederJW 2nd, LeeSK, GerhäuserC, LantvitD, MoonRC, MoriartyRM, PezzutoJM. (1999) Cancer chemopreventive activity mediated by 4'-bromoflavone, a potent inducer of phase II detoxification enzymes. Cancer Research, 59, 578–85.
35.
SchuppP, Kohlert-SchuppC, WhitefieldS, EngemannA, RohdeS, HemscheidtT, PezzutoJ, KondratyukT, ParkE, MarlerL, RostamaB, WrightA. (2009) Cancer chemopreventive and anticancer evaluation of extracts and fractions from marine macro- and microorganisms collected from Twilight Zone waters around Guam. Natural Product Communications, 4, 1717–1728.
