(S)-Reticuline (BioDeep_00000000834)

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds

代谢物信息卡片

7-ISOQUINOLINOL, 1,2,3,4-TETRAHYDRO-1-((3-HYDROXY-4-METHOXYPHENYL)METHYL)-6-METHOXY-2-METHYL-, (1S)-

化学式: C19H23NO4 (329.16269980000004)
中文名称: 牛心果碱, 牛心果鹼, 番荔枝碱
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.6%

分子结构信息

SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)O)O)OC
InChI: InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3

描述信息

(S)-Reticuline is an endogenous precursor of morphine (PMID: 15383669). (S)-Reticuline is a key intermediate in the synthesis of morphine, the major active metabolite of the opium poppy. "Endogenous morphine" has been long isolated and authenticated by mass spectrometry in trace amounts from animal- and human-specific tissue or fluids (PMID: 15874902). Human neuroblastoma cells (SH-SY5Y) were shown capable of synthesizing morphine as well. (S)-Reticuline undergoes a change of configuration at C-1 during its transformation into salutaridinol and thebaine. From thebaine, there is a bifurcate pathway leading to morphine proceeding via codeine or oripavine, in both plants and mammals (PMID 15937106).
(S)-reticuline is the (S)-enantiomer of reticuline. It has a role as an EC 2.1.1.116 [3-hydroxy-N-methyl-(S)-coclaurine 4-O-methyltransferase] inhibitor. It is a conjugate base of a (S)-reticulinium(1+). It is an enantiomer of a (R)-reticuline.
Reticuline is a natural product found in Fumaria capreolata, Berberis integerrima, and other organisms with data available.
See also: Peumus boldus leaf (part of).
Alkaloid from Papaver somniferum (opium poppy) and Annona reticulata (custard apple)
The (S)-enantiomer of reticuline.

同义名列表

35 个代谢物同义名

7-ISOQUINOLINOL, 1,2,3,4-TETRAHYDRO-1-((3-HYDROXY-4-METHOXYPHENYL)METHYL)-6-METHOXY-2-METHYL-, (1S)-; 7-ISOQUINOLINOL, 1,2,3,4-TETRAHYDRO-1 ((3-HYDROXY-4-METHOXYPHENYL)METHYL)-6-METHOXY-2-METHYL-, (S)-; 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-,(S)-; (1S)-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol; (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol; (S)-1,2,3,4-Tetrahydro-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methylisoquinolin-7-ol; (S)-1,2,3,4-TETRAHYDRO-1-[(3-HYDROXY-4-METHOXYPHENYL)METHYL]-6-METHOXY-2-METHYLISOQUINOLIN-7-OL; (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol; (1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol; 5-21-06-00046 (Beilstein Handbook Reference); reticuline hydrochloride, (+,-)-isomer; reticuline, 14C-labeled, (+,-)-isomer; reticuline, (+,-)-isomer; reticuline perchlorate; reticuline, (R)-isomer; RETICULINE, S-(+)-; (S)-(+)-reticuline; (R,S)-Reticuline; S-(+)-Reticuline; (+,-)-reticuline; RETICULINE, (+)-; L-(+)-Reticuline; RETICULINE [MI]; UNII-X35Z551WT4; (S)-Reticulene; (S)-Reticuline; (+)-Reticuline; d-Reticuline; S-RETICULINE; Reticuline; X35Z551WT4; Reticulin; Reticline; REN; (S)-Reticuline

数据库引用编号

31 个数据库交叉引用编号

ChEBI: CHEBI:16718
ChEBI: CHEBI:26533
KEGG: C02105
PubChem: 439653
PubChem: 10233
HMDB: HMDB0003601
Metlin: METLIN6967
ChEMBL: CHEMBL235212
Wikipedia: Reticuline
MeSH: reticuline
MeSH: Reticulin
ChemIDplus: 0000485198
MetaCyc: S-RETICULINE
KNApSAcK: C00001910
foodb: FDB002089
chemspider: 388724
CAS: 485-19-8
CAS: 1699-46-3
medchemexpress: HY-N1356
PMhub: MS000011174
MetaboLights: MTBLC16718
PubChem: 5187
PDB-CCD: REN
3DMET: B01532
NIKKAJI: J12.961E
KEGG: C12328
PubChem: 582718
RefMet: (S)-Reticuline
KNApSAcK: 16718
LOTUS: LTS0181650
wikidata: Q6122828

分类词条

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

136 个相关的物种来源信息

246713 - Aconitum seravschanicum:
796729 - Actinodaphne acuminata:
796729 - Actinodaphne acuminata: 10.1515/ZNB-2009-0717
2803977 - Aniba canelilla: 10.1139/V93-149
49314 - Annona cherimola:
49314 - Annona cherimola: 10.1021/NP50037A038
2029787 - Annona emarginata:
2029787 - Annona emarginata: 10.1021/NP50046A037
301703 - Annona glabra: 10.1021/NP100247R
1123437 - Annona purpurea:
301862 - Annona reticulata:
2743202 - Annona spinescens:
2743202 - Annona spinescens: 10.1021/NP960223W
301693 - Annona squamosa:
99306 - Arctomecon humilis: 10.1016/0305-1978(90)90032-B
99307 - Argemone albiflora: 10.1007/BF00598384
54796 - Argemone mexicana:
54796 - Argemone mexicana: 10.1515/ZNC-2003-7-813
99340 - Argemone ochroleuca: 10.1007/BF00598384
99325 - Argemone platyceras: 10.1007/BF00598384
12948 - Aristolochia gigantea: 10.3390/MOLECULES15129462
225833 - Artabotrys hexapetalus: 10.1002/PCA.2800040204
225833 - Artabotrys hexapetalus: 10.1021/NP010036K
1636225 - Artabotrys monteiroae: 10.1002/PCA.2800040204
1636225 - Artabotrys monteiroae: 10.1021/NP010036K
2651905 - Artabotrys venustus: 10.1021/NP50046A007
22774 - Berberis: 10.1016/0031-9422(90)85265-H
203270 - Berberis aquifolium:
659592 - Berberis aristata:
13601 - Berberis bealei:
258147 - Berberis canadensis: 10.1007/BF00631016
258149 - Berberis chilensis:
1433312 - Berberis heteropoda:
1112794 - Berberis integerrima:
1439896 - Berberis nummularia: 10.1007/BF00630533
2602253 - Berberis oblonga:
33814 - Berberis stolonifera:
121720 - Berberis thunbergii:
258209 - Berberis vulgaris:
258211 - Berberis wilsoniae:
39279 - Bongardia chrysogonum: 10.1021/NP50064A024
13393 - Cananga odorata: 10.1021/NP0005208
46963 - Caulophyllum thalictroides: 10.1016/J.JPBA.2011.07.028
379217 - Cissampelos capensis: 10.3390/MOLECULES16043001
1857144 - Clematis parviloba: 10.1007/S12272-009-1111-7
3442 - Coptis japonica: 10.1074/JBC.M002439200
3442 - Coptis japonica: 10.1074/JBC.M705082200
581246 - Corydalis cava: 10.1021/NP50071A022
404570 - Corydalis incisa: 10.1021/NP50071A022
54424 - Corydalis taliensis: 10.1515/ZNB-2007-0915
2902606 - Corydalis ternata: 10.1016/J.BMCL.2010.06.035
2902606 - Corydalis ternata: 10.1021/NP50071A022
38913 - Corydalis uniflora: 10.3109/13880208809053911
458692 - Corydalis yanhusuo: 10.1021/NP50071A022
518845 - Croton celtidifolius: 10.1055/S-2006-957745
765397 - Croton hemiargyreus: 10.1002/(SICI)1099-1565(199909/10)10:5<254::AID-PCA462>3.0.CO;2-Q
306952 - Cymbopetalum brasiliense: 10.1055/S-2007-969787
128651 - Damburneya salicifolia: 10.1021/NP960195H
610223 - Dehaasia hainanensis: 10.1177/1934578X0700200115
1127147 - Delphinium caeruleum: 10.1016/J.PHYTOCHEM.2004.03.017
1127184 - Delphinium pentagynum: 10.1016/J.PHYTOCHEM.2004.03.017
1179221 - Desmos chinensis: 10.3390/MOLECULES21070890
54418 - Dicentra peregrina: 10.1201/B16160-69
3845 - Erythrina variegata: 10.1248/YAKUSHI1947.93.12_1671
3845 - Erythrina variegata: 10.1248/YAKUSHI1947.93.12_1674
3467 - Eschscholzia californica: 10.1002/JLAC.1990199001104
1053349 - Fumaria capreolata: 10.1007/BF00269216
367484 - Fumaria vaillantii:
1533087 - Glaucium corniculatum:
1353837 - Glaucium fimbrilligerum:
56853 - Glaucium flavum: 10.1007/BF00630233
1317845 - Glossocalyx brevipes: 10.1021/NP50041A025
63805 - Glossocalyx longicuspis: 10.1021/NP50041A025
296858 - Greenwayodendron oliveri: 10.1021/NP50022A020
402552 - Guatteria juruensis: 10.1016/S0305-1978(02)00164-3
63807 - Gyrocarpus americanus: 10.1021/NP50043A011
2833575 - Hernandia cordigera: 10.1007/BF00571044
121082 - Hernandia nymphaeifolia:
9606 - Homo sapiens: -
235797 - Huberantha cerasoides: 10.1021/NP070293A
152353 - Hypserpa nitida: 10.1016/J.BMCL.2007.08.027
432643 - Isopyrum thalictroides: 10.1016/S0031-9422(00)00068-6
74877 - Laureliopsis philippiana: 10.1016/0031-9422(82)83185-3
190079 - Laurobasidium lauri:
85223 - Laurus nobilis: 10.1021/NP50023A008
168833 - Leontice leontopetalum: 10.1021/NP50046A044
492004 - Leptadenia reticulata: 10.1016/S0040-4020(01)80794-8
545644 - Lindera aggregata: 10.3184/030823408X320674
332435 - Lindera glauca: 10.1021/NP50036A045
155293 - Lindera megaphylla: 10.1021/NP50108A001
943092 - Lindera pulcherrima var. hemsleyana: 10.1002/JSSC.201000243
155299 - Litsea cubeba:
1504449 - Litsea elliptica: 10.1071/CH9901949
384306 - Litsea garciae:
384309 - Litsea lancifolia: 10.3390/MOLECULES16043119
56857 - Macleaya cordata: 10.1016/J.MOLP.2017.05.007
86725 - Magnolia biondii: 10.1055/S-2007-969876
349509 - Magnolia obovata: 10.3390/MOLECULES18077739
85864 - Magnolia officinalis: 10.1016/J.FITOTE.2011.01.021
3411 - Magnolia salicifolia:
248829 - Meconopsis cambrica: 10.1016/0040-4020(66)80085-6
235758 - Miliusa velutina: 10.1016/S0305-1978(99)00083-6
489341 - Monocyclanthus vignei: 10.1021/NP50077A016
493334 - Monodora junodii: 10.1016/J.PHYTOCHEM.2006.07.011
384321 - Neolitsea aciculata: 10.1021/NP50036A042
2803928 - Neolitsea acuminatissima: 10.1002/JCCS.199200031
2803928 - Neolitsea acuminatissima: 10.1021/NP010236W
1609886 - Neolitsea konishii: 10.1002/JCCS.199200031
1609886 - Neolitsea konishii: 10.1021/NP010236W
2592295 - Ocotea fasciculata: 10.1016/S0378-8741(98)00044-0
881612 - Ocotea velloziana: 10.1016/0031-9422(94)00961-R
306934 - Oxandra xylopioides: 10.1016/S0031-9422(00)81765-3
461616 - Pachygone ovata: 10.1021/NP50004A007
357465 - Papaver armeniacum:
215227 - Papaver bracteatum: 10.1016/0040-4020(66)80085-6
33128 - Papaver rhoeas: 10.1016/0040-4020(66)80085-6
3469 - Papaver somniferum: 10.1016/0040-4020(66)80085-6
3469 - Papaver somniferum: 10.1016/S0031-9422(00)84526-4
63812 - Peumus boldus: 10.1002/JLAC.1990199001104
128687 - Phoebe formosana: 10.1016/0021-9673(94)89083-8
105756 - Polyalthia: 10.1021/NP070293A
63813 - Siparuna brasiliensis: 10.1016/S0031-9422(00)00222-3
152367 - Stephania cephalantha:
1924984 - Stephania pierrei:
527508 - Stephania venosa: 10.1021/NP50054A017
1501474 - Stephania viridiflavens: 10.1016/J.PHYTOL.2011.11.001
150094 - Thalictrum flavum: 10.1021/NP50045A018
1277777 - Thalictrum foliolosum: 10.1021/NP50021A003
1277777 - Thalictrum foliolosum: 10.1021/NP50045A018
79802 - Thalictrum tuberosum: 10.1016/0031-9422(93)85104-Y
295132 - Trepobates: 10.1021/NP50064A031
174969 - Uvaria: 10.1016/S0305-1978(97)00101-4
174962 - Uvaria dulcis: 10.1016/S0305-1978(97)00101-4
2743314 - Xylopia laevigata: 10.3390/MOLECULES21070890
992813 - Xylopia parviflora: 10.1016/J.PHYTOCHEM.2006.07.011
992813 - Xylopia parviflora: 10.1021/NP50074A018

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Luiz Henrique Alves Guerra, Silvana Gisele Pegorin Campos, Sebastião Roberto Taboga, Patricia Simone Leite Vilamaior. Prostatic morphological changes throughout life: Cytochemistry as a tool to reveal tissue aging markers. Microscopy research and technique. 2024 Jan; ?(?):. doi: 10.1002/jemt.24489. [PMID: 38186358]
Maaya Yamada, Ryuichi Minoda Sada, Eriko Kashihara, Gosuke Okubo, Sho Matsushita, Atsushi Manabe, Shunsuke Tagawa, Hiroyuki Akebo, Hirofumi Miyake, Kazuhiro Hatta. TAFRO syndrome with a fatal clinical course following BNT162b2 mRNA (Pfizer-BioNTech) COVID-19 vaccination: A case report. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy. 2022 Jul; 28(7):1008-1011. doi: 10.1016/j.jiac.2022.04.005. [PMID: 35428576]
Hirofumi Watanabe, Fumiyoshi Fujishima, Noriko Fukuhara, Shinji Taniuchi, Kensuke Joh, Hironobu Sasano. Advanced extramedullary hematopoiesis with a marked increase in reticulin fibers and hemorrhage on various organs: the first autopsy case report. Medical molecular morphology. 2022 Mar; 55(1):68-75. doi: 10.1007/s00795-021-00300-x. [PMID: 34396490]
Daoyi Guo, Sijia Kong, Yue Sun, Xun Li, Hong Pan. Development of an artificial biosynthetic pathway for biosynthesis of (S)-reticuline based on HpaBC in engineered Escherichia coli. Biotechnology and bioengineering. 2021 12; 118(12):4635-4642. doi: 10.1002/bit.27924. [PMID: 34427913]
J Maquet, E Bories, M B Nogier, C Beck, G Aizel, A Toledano, S Faguer, K Paricaud, G Pugnet, G Moulis, L Astudillo, L Sailler. [TAFRO syndrome and cutaneous necrotizing vasculitis]. La Revue de medecine interne. 2021 Feb; 42(2):134-139. doi: 10.1016/j.revmed.2020.10.384. [PMID: 33218790]
Yi Li, Thilo Winzer, Zhesi He, Ian A Graham. Over 100 Million Years of Enzyme Evolution Underpinning the Production of Morphine in the Papaveraceae Family of Flowering Plants. Plant communications. 2020 03; 1(2):100029. doi: 10.1016/j.xplc.2020.100029. [PMID: 32685922]
Nozomu Kurose, Ken-Ichi Mizutani, Motona Kumagai, Akihiro Shioya, Xin Guo, Satoko Nakada, Shino Fujimoto, Hiroshi Kawabata, Yasufumi Masaki, Kazue Takai, Sadao Aoki, Masaru Kojima, Shigeo Nakamura, Masatoshi Kida, Sohsuke Yamada. An extranodal histopathological analysis of idiopathic multicentric Castleman disease with and without TAFRO syndrome. Pathology, research and practice. 2019 Mar; 215(3):410-413. doi: 10.1016/j.prp.2018.12.025. [PMID: 30642741]
P O Awoniran, D O Adeyemi. Ethanol extract of Curcuma longa rhizome mitigates potassium bromate-induced liver changes in the Wistar rat: Histological, histochemical and immunohistochemical assessments. Morphologie : bulletin de l'Association des anatomistes. 2018 Dec; 102(339):276-288. doi: 10.1016/j.morpho.2018.07.004. [PMID: 30195667]
Seth J Corey, Jyoti Jha, Elizabeth A McCart, William B Rittase, Jeffy George, Joseph J Mattapallil, Hrishikesh Mehta, Mungunsukh Ognoon, Michelle A Bylicky, Thomas A Summers, Regina M Day. Captopril mitigates splenomegaly and myelofibrosis in the Gata1low murine model of myelofibrosis. Journal of cellular and molecular medicine. 2018 09; 22(9):4274-4282. doi: 10.1111/jcmm.13710. [PMID: 29971909]
Matthew R Bennett, Mark L Thompson, Sarah A Shepherd, Mark S Dunstan, Abigail J Herbert, Duncan R M Smith, Victoria A Cronin, Binuraj R K Menon, Colin Levy, Jason Micklefield. Structure and Biocatalytic Scope of Coclaurine N-Methyltransferase. Angewandte Chemie (International ed. in English). 2018 08; 57(33):10600-10604. doi: 10.1002/anie.201805060. [PMID: 29791083]
Eitaro Matsumura, Akira Nakagawa, Yusuke Tomabechi, Shinichi Ikushiro, Toshiyuki Sakaki, Takane Katayama, Kenji Yamamoto, Hidehiko Kumagai, Fumihiko Sato, Hiromichi Minami. Microbial production of novel sulphated alkaloids for drug discovery. Scientific reports. 2018 05; 8(1):7980. doi: 10.1038/s41598-018-26306-7. [PMID: 29789647]
Xinyao Yang, Xiaoli Gao, Yuan Cao, Qiang Guo, Shanshan Li, Zhixiang Zhu, Yunfang Zhao, Pengfei Tu, Xingyun Chai. Anti-Inflammatory Effects of Boldine and Reticuline Isolated from Litsea cubeba through JAK2/STAT3 and NF-κB Signaling Pathways. Planta medica. 2018 Jan; 84(1):20-25. doi: 10.1055/s-0043-113447. [PMID: 28651290]
Mythri Mudireddy, Daniela Barraco, Curtis A Hanson, Animesh Pardanani, Naseema Gangat, Ayalew Tefferi. The prognostic relevance of serum lactate dehydrogenase and mild bone marrow reticulin fibrosis in essential thrombocythemia. American journal of hematology. 2017 May; 92(5):454-459. doi: 10.1002/ajh.24689. [PMID: 28211153]
Eitaro Matsumura, Akira Nakagawa, Yusuke Tomabechi, Takashi Koyanagi, Hidehiko Kumagai, Kenji Yamamoto, Takane Katayama, Fumihiko Sato, Hiromichi Minami. Laboratory-scale production of (S)-reticuline, an important intermediate of benzylisoquinoline alkaloids, using a bacterial-based method. Bioscience, biotechnology, and biochemistry. 2017 Feb; 81(2):396-402. doi: 10.1080/09168451.2016.1243985. [PMID: 27740901]
Mizuho Nara, Atsushi Komatsuda, Fumiko Itoh, Hajime Kaga, Masaya Saitoh, Masaru Togashi, Yoshihiro Kameoka, Hideki Wakui, Naoto Takahashi. Two Cases of Thrombocytopenia, Anasarca, Fever, Reticulin Fibrosis/Renal Failure, and Organomegaly (TAFRO) Syndrome with High Serum Procalcitonin Levels, Including the First Case Complicated with Adrenal Hemorrhaging. Internal medicine (Tokyo, Japan). 2017; 56(10):1247-1252. doi: 10.2169/internalmedicine.56.7991. [PMID: 28502946]
Jeremy S Morris, Peter J Facchini. Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy. The Journal of biological chemistry. 2016 Nov; 291(45):23416-23427. doi: 10.1074/jbc.m116.750893. [PMID: 27634038]
Wan Nurul Nazneem Wan Othman, Sook Yee Liew, Kooi Yeong Khaw, Vikneswaran Murugaiyah, Marc Litaudon, Khalijah Awang. Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae). Bioorganic & medicinal chemistry. 2016 09; 24(18):4464-4469. doi: 10.1016/j.bmc.2016.07.043. [PMID: 27492195]
Akira Nakagawa, Eitaro Matsumura, Takashi Koyanagi, Takane Katayama, Noriaki Kawano, Kayo Yoshimatsu, Kenji Yamamoto, Hidehiko Kumagai, Fumihiko Sato, Hiromichi Minami. Total biosynthesis of opiates by stepwise fermentation using engineered Escherichia coli. Nature communications. 2016 Feb; 7(?):10390. doi: 10.1038/ncomms10390. [PMID: 26847395]
Mark A Lusco, Agnes B Fogo, Behzad Najafian, Charles E Alpers. AJKD Atlas of Renal Pathology: Fibrillary Glomerulonephritis. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2015 Oct; 66(4):e27-8. doi: 10.1053/j.ajkd.2015.08.002. [PMID: 26408242]
Limei Chang, Jillian M Hagel, Peter J Facchini. Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum. Plant physiology. 2015 Oct; 169(2):1127-40. doi: 10.1104/pp.15.01240. [PMID: 26297140]
Scott C Farrow, Jillian M Hagel, Guillaume A W Beaudoin, Darcy C Burns, Peter J Facchini. Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy. Nature chemical biology. 2015 Sep; 11(9):728-32. doi: 10.1038/nchembio.1879. [PMID: 26147354]
Isis J Trenchard, Michael S Siddiqui, Kate Thodey, Christina D Smolke. De novo production of the key branch point benzylisoquinoline alkaloid reticuline in yeast. Metabolic engineering. 2015 Sep; 31(?):74-83. doi: 10.1016/j.ymben.2015.06.010. [PMID: 26166409]
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