TABLE 1

Comprehensive summary of compounds reported to form diconjugates such as diglucuronides and sulfoglucuronides

Specific comments relating to identified metabolites along with the relevant references are noted. A “+” sign indicates that the specific type of metabolite has been reported.

Compounds	Diglucuronide(s)	Diglucuronide Type	Sulfoglucuronide(s)	Comments	Reference
24-Norlithocholic acid	+	Discrete			Shattuck et al., 1986
4-Hydroxy droloxifene	+	Discrete		Primary metabolite of droloxifene	O'Donnell et al., 1998
Androsterone	+	Linked		Second glucuronic acid moiety is linked to the 2′carbon of the first glucuronic acid moiety	Murai et al., 2005
ARQ501	+	Discrete	+		Miao et al., 2009
Benzo[a]pyrene diphenol	+	Discrete		UGT1A1, UGT1A9. Multiple diglucuronides identified in rat bile	Lilienblum et al., 1985; Lind, 1985; Bevan and Sadler, 1992; Bock et al., 1992; Gschaidmeier et al., 1995; Bock et al., 1999
Bevirimat	+	Discrete			Wen et al., 2007
Bilirubin	+	Discrete		The first diglucuronide to be identified	Billing et al., 1957; Schmid, 1957
Bisphenol A			+		Pritchett et al., 2002
Chrysene-3,6-diphenol	+	Discrete		UGT1A6, UGT1A7	Bock et al., 1992, 1999
Crocetin	+	Discrete			Asai et al., 2005
Daidzein	+	Discrete	+	Metabolites identified in human plasma	Adlercreutz et al., 1995; Hosoda et al., 2010
Dehydroepiandrosterone	+	Linked			Murai et al., 2008
Di-demethylated methoxychlor			+	Secondary metabolite of methoxychlor	Ohyama et al., 2004
Diflunisal	+	Discrete		Acyl migration of the first glucuronide thought to be re-requisite for second glucuronidation step	King and Dickinson, 1991
Dihydrotestosterone	+	Linked		UGT1A8	Murai et al., 2006
Dihydroxy-1,2,7,8-tetrachlorodibenzo-p-dioxin	+	Discrete			Hakk et al., 2001
Dihydroxydibutyl ether	+	Discrete			Corbic et al., 1982
Diosmetin	+	Discrete			Boutin et al., 1993
Enterodiol	+	Discrete	+		Adlercreutz et al., 1995
Epiandrosterone	+	Linked		Similar observations for dehydroepiandrosterone. Second glucuronic acid moiety is linked to the 2′carbon of the first glucuronic acid moiety	Murai et al., 2008
Equol	+	Discrete	+		Adlercreutz et al., 1995
Estradiol	+	Linked			Murai et al., 2005
Estriol	+	Linked			Murai et al., 2005
Estrone	+	Linked		Second glucuronic acid moiety is linked to the 2′carbon of the first glucuronic acid moiety	Murai et al., 2005
Ethinyl estradiol	+	Linked	+	Also identified after administration of mestranol	Newburger et al., 1983
Ferulic acid			+		Zhao et al., 2003
Genistein	+	Discrete	+	Circulating metabolites in human plasma	Hosoda et al., 2010
Glycyrrhetinic acid			+		Jing et al., 2008
Hesperetin	+	Discrete	+	Human urinary metabolites	Mullen et al., 2008; Bredsdorff et al., 2010
Hydroxy efavirenz			+	Primary metabolite of efavirenz	Mutlib et al., 1999
Hydroxy naveglitazar			+	Primary metabolite of naveglitazar	Yi et al., 2007
Morphine	+	Discrete			Yeh et al., 1977
Nalmefene	+	Discrete		Diglucuronides identified in dog urine	Dixon et al., 1989
Naringenin	+	Discrete		Urinary metabolites	Mullen et al., 2008; Bredsdorff et al., 2010
O-Desmethyl naproxen		Discrete	+	Primary metabolite of naproxen, no diglucuronides observed	Jaggi et al., 2002
Phytoestrogens	+	Discrete	+	More than one of each type identified in human urine	Clarke et al., 2002
Posaconazole	+	Discrete			Krieter et al., 2004
Quercetin			+	Similar observations for methyl quercetin. Quercetin sulfoglucuronide identified in human urine	Graf et al., 2005 Hong and Mitchell, 2004
Resorcinol			+		Kim and Matthews, 1987
Resveratrol	+	Discrete	+	More than one sulfoglucuronide identified	Azorin-Ortuno et al., 2010
Resveratrol	+	Discrete		One glucuronidation occurred to a C atom alpha to a phenolic hydroxy group	Burkon and Somoza, 2008
Rooperol	+	Discrete		Similar results for 2-, 3-, 4-, hydroxyl rooperol analogs	Kruger et al., 1994; Coetzee et al., 1996
Testosterone	+	Linked		Second glucuronic acid moiety is linked to the 2′carbon of the first glucuronic acid moiety	Murai et al., 2005