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Papaver somniferum L. taxonomy, uses and new insight in poppy alkaloid pathways

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Abstract

Since ancient times, opium poppy (Papaver somniferum L.) is known for its medicinal properties, related to its secondary metabolite content. Its most important secondary metabolites, called benzylisoquinoline alkaloids (BIAs), are still essential in pharmaceutical field. Few of them, like morphine, have specific clinical application but also effects on CNS. Not all poppy cultivars are able to biosynthesize morphine in high amount, making this plant useful for other purposes like food uses. For this reason it is crucial to deeply understand the origin of poppy, its possible use and have a deep knowledge of the BIA biosynthesis. These aspects are crucial for the final use of P. somniferum. This review aims to summarize the state-of-the-art on its taxonomy and origin beside its uses and BIA biosynthetic pathways, its most important metabolites. The review focuses on conflicting or unsolved questions about enzymatic localization, role of different plant organs in the biosynthesis, and storage and external conditions that influence the alkaloid production, highlighting the significant involvement of transcription factors. Behind this review, there is the firm belief that only a deep knowledge of alkaloid biosynthetic processes could lead to the characterization of undefined step and to the development of engineering cultivars optimizing the potential uses of P. somniferum. The goal is answer in more sustainable way to ever-increasing worldwide request of such products, in particular morphine and derivates, obtaining high morphine content cultivars useful for pharmaceutical market or no morphine producing cultivars appreciated as food. Devising cultivars with different BIA content could lead to decrease, or even avoid, illicit use and illegal extraction, confining only low alkaloid content cultivars to consumers market.

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Abbreviations

3′OHase:

3′-Hydroxylase

3′OMT:

3′-O-methyltransferase

3OHase:

Tyrosine/tyramine 3-hydroxylase

4′OMT:

3′-hydroxyl-N-methylcoclaurine 4′-O-methyltransferase

4HPAA:

4 Hydroxyphenylacetic acid

4HPPDC:

4-Hydroxyphenylpuruvate decarboxylase

6OMT:

Norcoclaurine 6-O-methyltransferase

7OMT:

Reticuline 7-O-methyltransferase

AC:

Adenylyl cyclase

AFLP:

Amplified fragment length polymorphism

AMP:

Adenosine monophosphate

AMPc:

Adenosine monophosphate cyclic

BBE:

Berberine bridge enzyme

BIAs:

Benzylisoquinoline alkaloids

CAS:

Canadine synthase

CFS:

Cheilanthifoline synthase

CNMT:

Coclaurine N-methyltransferase

CNS:

Central nervous system

CODM:

Codeine O-demethylase

CoOMT:

Columbamine O-methyltransferase

COR:

Codeinone reductase

CPVO:

Community Plant Variety Office

CYP:

Cytochrome P450 enzyme family

CYP82Y1:

N-methylcanadine 1-hydroxylase

CYP80B:

(S)-N-methylcoclaurine 3′-hydroxylase isozyme

Cys:

Cysteine

DA:

Dopamine

DBOX:

Dihydrosanguinarine oxidase

EFSA:

European Food Safety Authority

ER:

Endoplasmic reticulum

EST:

Expressed sequence tag

FT–ICR–MS:

Fourier-transform–ion-cyclotron resonance–mass spectrometry

GC:

Gas chromatography

GPCR:

G protein–coupled receptors

HPLC:

High performance liquid chromatography

MeJa:

Methyl jasmonate

MIA:

Monoterpenoid indole alkaloid

MLP15:

Major latex proteins

MSH:

N-methylstylopine 14-hydroxylase

N7OMT:

Norreticuline 7-O-methyltransferase

NAc:

Nucleus accumbens

NCS:

Norcoclaurine synthase

NMCH:

N-methylcoclaurine 3′-hydroxylase

NOS:

Noscapine synthase

Nuclear factor-κB:

Nuclear factor kappa-light-chain-enhancer of activated B cells

OR receptors:

Receptors for endogenous opiates

ORL1:

Opioid receptor-like

P6H:

Protopine 6-hydroxylase

PKA:

Protein kinase A

PKC:

Protein kinase C

PPH:

Protopine-6-hydroxylase

RAPD:

Random amplified polymorphic DNA

RFLP:

Restriction fragment length polymorphism

ROS:

Reactive oxygen species

RSP:

Restriction site polymorphism

RVM:

Rostral ventromedial medulla

SalAT:

Salutaridinol 7-O-acetyltransferase

SalR:

Salutaridine reductase

SanR:

Sanguinarine reductase

SAT:

(7S)-salutaridinol 7-O-acetyltransferase

SNPs:

Single nucleotide polymorphism

SOMT1:

Scoulerine 9-O-methyltransferase

SOR:

7-Oxidoreductase

SPS:

Stylopine synthase

STOX:

(S)-tetrahydroxyprotoberberineoxidase

STRs:

Short tandem repeat

STS:

Salutaridine synthase

StySyn:

Sstylopine synthase

T6ODM:

Thebaine 6-O-demethylase

TFBSs:

Transcription factor binding bites

TFs:

Transcription factors

TNMT:

Tetrahydroprotoberberine N-methyltransferase

TYDC:

Tyrosine/DOPA decarboxylase

UHPLC–ESI–QTOF–MS:

Ultra high performance liquid chromatography–electrospray ionization–quadrupole time-of-flight–mass spectrometry

VNTRs:

Variable number of tandem repeat or minisatellites

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Acknowledgements

Authors would like to thank the Czech Minstry of Agriculture, Projects NAZV QK1720263 and RO0417 for the support.

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Authors and Affiliations

  1. Department of Science, University of Basilicata, v.le dell’Ateneo Lucano, 10, 85100, Potenza, Italy

    Fabiana Labanca & Luigi Milella

  2. Plant Genetics and Breeding Methods, Division of Crop Genetics and Breeding, Crop Research Institute, Drnovska 507, 161 06, Prague 6, Czech Republic

    Fabiana Labanca & Jaroslava Ovesnà

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  1. Fabiana Labanca
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  2. Jaroslava Ovesnà
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Correspondence to Luigi Milella.

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Labanca, F., Ovesnà, J. & Milella, L. Papaver somniferum L. taxonomy, uses and new insight in poppy alkaloid pathways. Phytochem Rev 17, 853–871 (2018). https://doi.org/10.1007/s11101-018-9563-3

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