Molecular Cloning of anO-Methyltransferase from Adventitious Roots ofCarapichea ipecacuanha

Metabolic engineering for the production of plant isoquinoline alkaloids

“…The knowledge acquired on these pathways showed that it involves a restricted number of enzyme families catalysing coupling reactions and functional group modifications including Pictet‐Spenglerases, cytochrome P450, acetyl‐, O ‐ and N ‐methyltransferases, oxidoreductases and dioxygenases (Hagel and Facchini, ;). To date, only five biosynthetic genes for ipecac alkaloids, one for Amaryllidaceae alkaloids and none for the phenylethylisoquinoline alkaloids have been reported (Figure ) (Cheong et al ., ; Kilgore et al ., ; Nomura and Kutchan, ; Nomura et al ., ). As metabolic engineering requires knowledge of the pathway genes and enzymes involved, the majority of the studies focus on the benzylisoquinoline alkaloid pathways.…”

Improved Production of Plant Isoquinoline Alkaloids by Metabolic Engineering

“…6.1 and 6.2): the genes of corytuberine synthase in aporphine biosynthesis (CYP82G2, Ikezawa, Iwasa, & Sato, 2008); those of salutaridine synthase (CYP719B1, Gesell et al, 2009), salutaridine reductase (SalR, Ziegler et al, 2006), salutaridinol-7-O-acetyltransferase (SalAT, Grothe, Lenz, & Kutchan, 2001), thebaine 6-O-demethylase and codeine O-demethylase (T6ODM, CODM, Hagel & Facchini, 2010) and NADPH-dependent codeinone reductase (COR, Unterlinner, Lenz, & Kutchan, 1999) in morphinan alkaloid biosynthesis; those of chelanthifoline synthase (CYP719A5, Ikezawa, Iwasa, & Sato, 2009), stylopine synthase (CYP719A2/A3, Ikezawa, Iwasa, & Sato, 2007), (S)-cis-N-methylstylopine 14-hydroxylase (Beaudoin & Facchini, 2013), protopine 6-hydroxylase (CYP82N2v2, Takemura, Ikezawa, Iwasa, & Sato, 2013), sanguinarine reductase (Vogel, Lawson, Sippl, Conarad, & Roos, 2010) and dihydrobenzophenanthridine oxidase (DBOX, Hagel et al, 2012) in benzophenanthridine biosynthesis; those of berbamunine synthase (CYP80A1, Kraus & Kutchan, 1995) in the bis-benzylisoquinoline alkaloid pathway; those of O-methyltransferases (Dang & Facchini, 2012) and a short-chain dehydrogenase/reductase (PSSDR1, Winzer et al, 2012)) in noscapine biosynthesis and those of O-methyltransferases in emetine biosynthesis (IpeOMT1/2/3, CiOMT, Cheong, Takemura, Yoshimatsu, & Sato, 2011;Nomura & Kutchan, 2010). 6.1 and 6.2): the genes of corytuberine synthase in aporphine biosynthesis (CYP82G2, Ikezawa, Iwasa, & Sato, 2008); those of salutaridine synthase (CYP719B1, Gesell et al, 2009), salutaridine reductase (SalR, Ziegler et al, 2006), salutaridinol-7-O-acetyltransferase (SalAT, Grothe, Lenz, & Kutchan, 2001), thebaine 6-O-demethylase and codeine O-demethylase (T6ODM, CODM, Hagel & Facchini, 2010) and NADPH-dependent codeinone reductase (COR, Unterlinner, Lenz, & Kutchan, 1999) in morphinan alkaloid biosynthesis; those of chelanthifoline synthase (CYP719A5, Ikezawa, Iwasa, & Sato, 2009), stylopine synthase (CYP719A2/A3, Ikezawa, Iwasa, & Sato, 2007), (S)-cis-...…”

Late stages in the biosynthesis of ipecac alkaloids - cephaeline, emetine and psychotrine in Alangium lamarckii Thw. (Alangiaceae)

“…Proemetine then reacts with another dopamine molecule to form 7'-O-demethylcephaeline (11). The final products are then produced with a 7'-O-methylation to make cephaeline and a 6'-O-methylation successively to make emetine [21][22][23][24][25][26] (Scheme 1 and 2). The presence of ipecoside, an acetylated derivative of the first proposed intermediate lends credence to the proposed pathway.…”

“…We have also established the stereochemistry at the two asymmeteric centres of biphenylbisbenzylisoquinoline alkaloids as exemplified by tiliacorine, tiliacorinine and nortilacorinine 13,14 . The early stages of the biosynthesis of these alkaloids have been studied [24][25][26][27][28][29][30][31][32] . The bioconversion of these bases has not yet been studied.…”