Chapter 7 Phenethylisoquinoline Alkaloids

Kametani, Tetsuji; Koizumi, Masao

doi:10.1016/s1876-0813(08)60224-9

Cited by 3 publications

(3 citation statements)

References 62 publications

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“…Isotope trace analysis had shown that these substrates derive from phenylalanine and tyrosine, respectively ( Fig. 1 ) ( 2 , 5 ). However, so far, the details for 4-HPAA and 4-HDCA biosynthesis as well as for the origin of dopamine have remained unclear in both BIA and PIA accumulating plants ( 23 ).…”

Section: Resultsmentioning

confidence: 99%

“…S1 ) has been approved by the US Food and Drug Administration for the therapy of chronic myeloid leukemia ( 1 , 2 ). The great potential of PIAs is constrained by their sporadic occurrence to the conifer genus Cephalotaxus ( 3 , 4 ), the monocot family Colchicaceae , and the dicot genus Phelline ( 5 ) . For instance, HHT is uniquely found in Cephalotaxus which is endemic to East Asia ( 5 ).…”

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confidence: 99%

“…The great potential of PIAs is constrained by their sporadic occurrence to the conifer genus Cephalotaxus ( 3 , 4 ), the monocot family Colchicaceae , and the dicot genus Phelline ( 5 ) . For instance, HHT is uniquely found in Cephalotaxus which is endemic to East Asia ( 5 ). Although HHT has been generated by chemical synthesis ( 6 ), extraction from plants has remained the only commercial source of HHT.…”

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Elucidation of the 1-phenethylisoquinoline pathway from an endemic conifer Cephalotaxus hainanensis

Qiao

Zhang

et al. 2022

Proc. Natl. Acad. Sci. U.S.A.

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Cephalotaxines harbor great medical potential, but their natural source, the endemic conifer Cephalotaxus is highly endangered, creating a conflict between biotechnological valorization and preservation of biodiversity. Here, we construct the whole biosynthetic pathway to the 1-phenethylisoquinoline scaffold, as first committed compound for phenylethylisoquinoline alkaloids (PIAs), combining metabolic modeling, and transcriptome mining of Cephalotaxus hainanensis to infer the biosynthesis for PIA precursor. We identify a novel protein, Ch PSS, driving the Pictet–Spengler condensation and show that this enzyme represents the branching point where PIA biosynthesis diverges from the concurrent benzylisoquinoline-alkaloids pathway. We also pinpoint Ch DBR as crucial step to form 4-hydroxydihydrocinnamaldehyde diverging from lignin biosynthesis. The elucidation of the early PIA pathway represents an important step toward microbe-based production of these pharmaceutically important alkaloids resolving the conflict between biotechnology and preservation of biodiversity.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Elucidation of the 1-phenethylisoquinoline pathway from an endemic conifer Cephalotaxus hainanensis

Qiao

Zhang

et al. 2022

Proc. Natl. Acad. Sci. U.S.A.

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The Phenethylisoquinolines

Shamma¹,

Moniot²

1978

Isoquinoline Alkaloids Research 1972–1977

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Synthesis of the 1-Phenethyltetrahydroisoquinoline Alkaloids (+)-Dysoxyline, (+)-Colchiethanamine, and (+)-Colchiethine

2012

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Asymmetric total syntheses of the 1-phenethyl-1,2,3,4-tetrahydroisoquinoline alkaloids (+)-dysoxyline (1), (+)-colchiethanamine (2), and (+)-colchiethine (3) are described. In the synthetic routes, coupling of a key, enatiomerically pure 1-(sulfonylmethyl)tetrahydroisoquinoline with aromatic aldehydes, performed by using the Julia-Kocienski reaction, afforded the corresponding 1-(β-styryl)-substituted tetrahydroisoquinolines with complete retention of the absolute configuration at the C1 carbon atom. Functionalization of the products generated in these processes by using four- or five-step sequences gave the target alkaloids 1-3.

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Chapter 7 Phenethylisoquinoline Alkaloids

Cited by 3 publications

References 62 publications

Elucidation of the 1-phenethylisoquinoline pathway from an endemic conifer Cephalotaxus hainanensis

Elucidation of the 1-phenethylisoquinoline pathway from an endemic conifer Cephalotaxus hainanensis

The Phenethylisoquinolines

Synthesis of the 1-Phenethyltetrahydroisoquinoline Alkaloids (+)-Dysoxyline, (+)-Colchiethanamine, and (+)-Colchiethine

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