Tetrahydrocannabinolic Acid Synthase, the Enzyme Controlling Marijuana
Psychoactivity, is Secreted into the Storage Cavity of the Glandular
Trichomes
http://pcp.oxfordjournals.org/content/46/9/1578.full.pdf+html
Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L.. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid.
http://www.ncbi.nlm.nih.gov/pubmed/8663284
PKS Activities and Biosynthesis of Cannabinoids and Flavonoids
in Cannabis sativa L. Plants
http://pcp.oxfordjournals.org/conte...html?sid=be26efac-d930-4a4b-8408-d1ecfbe2a538
Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway.
http://www.ncbi.nlm.nih.gov/pubmed/19454282
Phytocannabinoids in Cannabis sativa: recent studies on biosynthetic enzymes.
http://www.ncbi.nlm.nih.gov/pubmed/17712812
PMID- 17669365
OWN - NLM
STAT- MEDLINE
DA - 20070816
DCOM- 20071127
IS - 0006-291X (Print)
IS - 0006-291X (Linking)
VI - 361
IP - 3
DP - 2007 Sep 28
TI - Production of Delta(1)-tetrahydrocannabinolic acid by the biosynthetic enzyme
secreted from transgenic Pichia pastoris.
PG - 675-80
AB - Delta(1)-Tetrahydrocannabinolic acid (THCA) synthase is the enzyme that catalyzes
the oxidative cyclization of cannabigerolic acid into THCA, the acidic precursor
of Delta(1)-tetrahydrocannabinol. We developed a novel expression system for THCA
synthase using a methylotrophic yeast Pichia pastoris as a host. Under optimized
conditions, the transgenic P. pastoris secreted approximately 1.32nkat/l of THCA
synthase activity, and the culture medium, from which the cells were removed,
effectively synthesized THCA from cannabigerolic acid with a approximately 98%
conversion rate. The secreted THCA synthase was readily purified to homogeneity.
Interestingly, endoglycosidase treatment afforded a deglycosylated THCA synthase
with more catalytic activity than that of the glycosylated form. The
non-glycosylated THCA synthase should be suitable for structure-function studies
because it displayed much more activity than the previously reported native
enzyme from Cannabis sativa as well as the recombinant enzyme from insect cell
cultures.
AD - Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582,
Japan. [email protected]
FAU - Taura, Futoshi
AU - Taura F
FAU - Dono, Emi
AU - Dono E
FAU - Sirikantaramas, Supaart
AU - Sirikantaramas S
FAU - Yoshimura, Kohji
AU - Yoshimura K
FAU - Shoyama, Yukihiro
AU - Shoyama Y
FAU - Morimoto, Satoshi
AU - Morimoto S
LA - eng
PT - Journal Article
DEP - 20070724
PL - United States
TA - Biochem Biophys Res Commun
JT - Biochemical and biophysical research communications
JID - 0372516
RN - 0 (Benzoates)
RN - 0 (Recombinant Proteins)
RN - 0 (delta(1)-tetrahydrocannabinolic acid)
RN - 1972-08-3 (Tetrahydrocannabinol)
RN - 25555-57-1 (cannabigerolic acid)
RN - EC 5.3.- (Intramolecular Oxidoreductases)
RN - EC 5.3.- (delta(1)-tetrahydrocannabinolic acid synthase)
SB - IM
MH - Benzoates/metabolism
MH - Intramolecular Oxidoreductases/genetics/isolation & purification/*metabolism
MH - Pichia/classification/*genetics/metabolism
MH - Recombinant Proteins/genetics/isolation & purification/metabolism
MH - Tetrahydrocannabinol/*analogs & derivatives/biosynthesis/metabolism
MH - Time Factors
MH - Transgenes
EDAT- 2007/08/03 09:00
MHDA- 2007/12/06 09:00
CRDT- 2007/08/03 09:00
PHST- 2007/06/23 [received]
PHST- 2007/07/12 [accepted]
PHST- 2007/07/24 [aheadofprint]
AID - S0006-291X(07)01566-5 [pii]
AID - 10.1016/j.bbrc.2007.07.079 [doi]
PST - ppublish
SO - Biochem Biophys Res Commun. 2007 Sep 28;361(3):675-80. Epub 2007 Jul 24.
PMID- 16511162
OWN - NLM
STAT- MEDLINE
DA - 20060302
DCOM- 20060818
LR - 20091118
IS - 1744-3091 (Electronic)
IS - 1744-3091 (Linking)
VI - 61
IP - Pt 8
DP - 2005 Aug 1
TI - Crystallization of Delta1-tetrahydrocannabinolic acid (THCA) synthase from
Cannabis sativa.
PG - 799-801
AB - Delta1-Tetrahydrocannabinolic acid (THCA) synthase is a novel oxidoreductase that
catalyzes the biosynthesis of the psychoactive compound THCA in Cannabis sativa
(Mexican strain). In order to investigate the structure-function relationship of
THCA synthase, this enzyme was overproduced in insect cells, purified and finally
crystallized in 0.1 M HEPES buffer pH 7.5 containing 1.4 M sodium citrate. A
single crystal suitable for X-ray diffraction measurement was obtained in 0.09 M
HEPES buffer pH 7.5 containing 1.26 M sodium citrate. The crystal diffracted to
2.7 A resolution at beamline BL41XU, SPring-8. The crystal belonged to the
primitive cubic space group P432, with unit-cell parameters a = b = c = 178.2 A.
The calculated Matthews coefficient was approximately 4.1 or 2.0 A3 Da(-1)
assuming the presence of one or two molecules of THCA synthase in the asymmetric
unit, respectively.
AD - Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Fukuoka
812-8582, Japan.
FAU - Shoyama, Yoshinari
AU - Shoyama Y
FAU - Takeuchi, Ayako
AU - Takeuchi A
FAU - Taura, Futoshi
AU - Taura F
FAU - Tamada, Taro
AU - Tamada T
FAU - Adachi, Motoyasu
AU - Adachi M
FAU - Kuroki, Ryota
AU - Kuroki R
FAU - Shoyama, Yukihiro
AU - Shoyama Y
FAU - Morimoto, Satoshi
AU - Morimoto S
LA - eng
PT - Journal Article
DEP - 20050730
PL - England
TA - Acta Crystallogr Sect F Struct Biol Cryst Commun
JT - Acta crystallographica. Section F, Structural biology and crystallization
communications
JID - 101226117
RN - 1972-08-3 (Tetrahydrocannabinol)
RN - EC 5.3.- (Intramolecular Oxidoreductases)
RN - EC 5.3.- (delta(1)-tetrahydrocannabinolic acid synthase)
SB - IM
MH - Cannabis/*enzymology
MH - Crystallization
MH - Intramolecular Oxidoreductases/*chemistry
MH - Tetrahydrocannabinol/biosynthesis/chemistry
PMC - PMC1952348
OID - NLM: PMC1952348
EDAT- 2006/03/03 09:00
MHDA- 2006/08/19 09:00
CRDT- 2006/03/03 09:00
PHST- 2005/06/07 [received]
PHST- 2005/07/22 [accepted]
PHST- 2005/07/30 [epublish]
AID - S1744309105023365 [pii]
AID - 10.1107/S1744309105023365 [doi]
PST - ppublish
SO - Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Aug 1;61(Pt 8):799-801.
Epub 2005 Jul 30.
PMID- 15190053
OWN - NLM
STAT- MEDLINE
DA - 20040913
DCOM- 20041025
LR - 20061115
IS - 0021-9258 (Print)
IS - 0021-9258 (Linking)
VI - 279
IP - 38
DP - 2004 Sep 17
TI - The gene controlling marijuana psychoactivity: molecular cloning and heterologous
expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.
PG - 39767-74
AB - Delta(1)-tetrahydrocannabinolic acid (THCA) synthase is the enzyme that catalyzes
oxidative cyclization of cannabigerolic acid into THCA, the precursor of
Delta(1)-tetrahydrocannabinol. We cloned a novel cDNA (GenBank trade mark
accession number AB057805) encoding THCA synthase by reverse transcription and
polymerase chain reactions from rapidly expanding leaves of Cannabis sativa. This
gene consists of a 1635-nucleotide open reading frame, encoding a 545-amino acid
polypeptide of which the first 28 amino acid residues constitute the signal
peptide. The predicted molecular weight of the 517-amino acid mature polypeptide
is 58,597 Da. Interestingly, the deduced amino acid sequence exhibited high
homology to berberine bridge enzyme from Eschscholtzia californica, which is
involved in alkaloid biosynthesis. The liquid culture of transgenic tobacco hairy
roots harboring the cDNA produced THCA upon feeding of cannabigerolic acid,
demonstrating unequivocally that this gene encodes an active THCA synthase.
Overexpression of the recombinant THCA synthase was achieved using a
baculovirus-insect expression system. The purified recombinant enzyme contained
covalently attached FAD cofactor at a molar ratio of FAD to protein of 1:1. The
mutant enzyme constructed by changing His-114 of the wild-type enzyme to Ala-114
exhibited neither absorption characteristics of flavoproteins nor THCA synthase
activity. Thus, we concluded that the FAD binding residue is His-114 and that the
THCA synthase reaction is FAD-dependent. This is the first report on molecular
characterization of an enzyme specific to cannabinoid biosynthesis.
AD - Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, 812-8582,
Japan.
FAU - Sirikantaramas, Supaart
AU - Sirikantaramas S
FAU - Morimoto, Satoshi
AU - Morimoto S
FAU - Shoyama, Yoshinari
AU - Shoyama Y
FAU - Ishikawa, Yu
AU - Ishikawa Y
>FAU - Wada, Yoshiko
AU - Wada Y
FAU - Shoyama, Yukihiro
AU - Shoyama Y
FAU - Taura, Futoshi
AU - Taura F
LA - eng
SI - GENBANK/AB057805
PT - Journal Article
PT - Research Support, Non-U.S. Gov't
DEP - 20040609
PL - United States
TA - J Biol Chem
JT - The Journal of biological chemistry
JID - 2985121R
RN - 0 (DNA, Complementary)
RN - 1972-08-3 (Tetrahydrocannabinol)
RN - EC 5.3.- (Intramolecular Oxidoreductases)
RN - EC 5.3.- (delta(1)-tetrahydrocannabinolic acid synthase)
SB - IM
MH - Amino Acid Sequence
MH - Animals
MH - Base Sequence
MH - Cannabis/chemistry/enzymology/*genetics/metabolism
MH - Cells, Cultured
MH - Cloning, Molecular
MH - DNA, Complementary
MH - Insects
MH - Intramolecular Oxidoreductases/*genetics/*metabolism
MH - Molecular Sequence Data
MH - Oxidation-Reduction
MH - Plant Roots/physiology
MH - Tetrahydrocannabinol/*biosynthesis/chemistry
MH - Tobacco
MH - Transfection
EDAT- 2004/06/11 05:00
MHDA- 2004/10/27 09:00
CRDT- 2004/06/11 05:00
PHST- 2004/06/09 [aheadofprint]
AID - 10.1074/jbc.M403693200 [doi]
AID - M403693200 [pii]
PST - ppublish
SO - J Biol Chem. 2004 Sep 17;279(38):39767-74. Epub 2004 Jun 9.
PMID- 9862135
OWN - NLM
STAT- MEDLINE
DA - 19990128
DCOM- 19990128
LR - 20061115
IS - 0031-9422 (Print)
IS - 0031-9422 (Linking)
VI - 49
IP - 6
DP - 1998 Nov
TI - Purification and characterization of cannabichromenic acid synthase from Cannabis
sativa.
PG - 1525-9
AB - Cannabichromenic acid synthase was purified to apparent homogeneity by sequential
column chromatography including DEAE-cellulose, phenyl-Sepharose CL-4B, and
hydroxylapatite. The enzyme catalysed the oxidocyclization of cannabigerolic acid
and cannabinerolic acid to cannabichromenic acid. The K(m) values for both
substrates were in the same order of magnitude although the Vmax value for the
former was higher than that for the latter. These results suggested that
cannabichromenic acid is predominantly formed from cannabigerolic acid rather
than cannabinerolic acid. The enzyme required neither molecular oxygen nor
hydrogen peroxide, indicating that the cannabichromenic acid synthase reaction
proceeds through direct dehydrogenation without hydroxylation.
AD - Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
FAU - Morimoto, S
AU - Morimoto S
FAU - Komatsu, K
AU - Komatsu K
FAU - Taura, F
AU - Taura F
FAU - Shoyama, Y
AU - Shoyama Y
LA - eng
PT - Journal Article
PL - UNITED STATES
TA - Phytochemistry
JT - Phytochemistry
JID - 0151434
RN - EC 1.- (Oxidoreductases)
RN - EC 1.3.99.- (cannabichromenic acid synthase)
SB - IM
MH - Cannabis/*enzymology
MH - Chromatography, Gel
MH - Electrophoresis, Polyacrylamide Gel
MH - Isoelectric Point
MH - Kinetics
MH - Molecular Weight
MH - Oxidoreductases/chemistry/*isolation & purification/metabolism
MH - Substrate Specificity
EDAT- 1998/12/23
MHDA- 1998/12/23 00:01
CRDT- 1998/12/23 00:00
AID - S0031-9422(98)00278-7 [pii]
PST - ppublish
SO - Phytochemistry. 1998 Nov;49(6):1525-9.
PMID- 5583149
OWN - NLM
STAT- MEDLINE
DA - 19680509
DCOM- 19680509
LR - 20001218
IS - 0009-2363 (Print)
IS - 0009-2363 (Linking)
VI - 15
IP - 7
DP - 1967 Jul
TI - Tetrahydrocannabinolic acid, a genuine substance of tetrahydrocannabinol.
PG - 1075-6
FAU - Yamauchi, T
AU - Yamauchi T
FAU - Shoyama, Y
AU - Shoyama Y
FAU - Aramaki, H
AU - Aramaki H
FAU - Azuma, T
AU - Azuma T
FAU - Nishioka, I
AU - Nishioka I
LA - eng
PT - Journal Article
PL - JAPAN
TA - Chem Pharm Bull (Tokyo)
JT - Chemical & pharmaceutical bulletin
JID - 0377775
SB - IM
MH - Cannabis/*analysis
MH - Chromatography
MH - Spectrum Analysis
EDAT- 1967/07/01
MHDA- 1967/07/01 00:01
CRDT- 1967/07/01 00:00
PST - ppublish
SO - Chem Pharm Bull (Tokyo). 1967 Jul;15(7):1075-6.
Psychoactivity, is Secreted into the Storage Cavity of the Glandular
Trichomes
http://pcp.oxfordjournals.org/content/46/9/1578.full.pdf+html
Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L.. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid.
http://www.ncbi.nlm.nih.gov/pubmed/8663284
PKS Activities and Biosynthesis of Cannabinoids and Flavonoids
in Cannabis sativa L. Plants
http://pcp.oxfordjournals.org/conte...html?sid=be26efac-d930-4a4b-8408-d1ecfbe2a538
Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway.
http://www.ncbi.nlm.nih.gov/pubmed/19454282
Phytocannabinoids in Cannabis sativa: recent studies on biosynthetic enzymes.
http://www.ncbi.nlm.nih.gov/pubmed/17712812
PMID- 17669365
OWN - NLM
STAT- MEDLINE
DA - 20070816
DCOM- 20071127
IS - 0006-291X (Print)
IS - 0006-291X (Linking)
VI - 361
IP - 3
DP - 2007 Sep 28
TI - Production of Delta(1)-tetrahydrocannabinolic acid by the biosynthetic enzyme
secreted from transgenic Pichia pastoris.
PG - 675-80
AB - Delta(1)-Tetrahydrocannabinolic acid (THCA) synthase is the enzyme that catalyzes
the oxidative cyclization of cannabigerolic acid into THCA, the acidic precursor
of Delta(1)-tetrahydrocannabinol. We developed a novel expression system for THCA
synthase using a methylotrophic yeast Pichia pastoris as a host. Under optimized
conditions, the transgenic P. pastoris secreted approximately 1.32nkat/l of THCA
synthase activity, and the culture medium, from which the cells were removed,
effectively synthesized THCA from cannabigerolic acid with a approximately 98%
conversion rate. The secreted THCA synthase was readily purified to homogeneity.
Interestingly, endoglycosidase treatment afforded a deglycosylated THCA synthase
with more catalytic activity than that of the glycosylated form. The
non-glycosylated THCA synthase should be suitable for structure-function studies
because it displayed much more activity than the previously reported native
enzyme from Cannabis sativa as well as the recombinant enzyme from insect cell
cultures.
AD - Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582,
Japan. [email protected]
FAU - Taura, Futoshi
AU - Taura F
FAU - Dono, Emi
AU - Dono E
FAU - Sirikantaramas, Supaart
AU - Sirikantaramas S
FAU - Yoshimura, Kohji
AU - Yoshimura K
FAU - Shoyama, Yukihiro
AU - Shoyama Y
FAU - Morimoto, Satoshi
AU - Morimoto S
LA - eng
PT - Journal Article
DEP - 20070724
PL - United States
TA - Biochem Biophys Res Commun
JT - Biochemical and biophysical research communications
JID - 0372516
RN - 0 (Benzoates)
RN - 0 (Recombinant Proteins)
RN - 0 (delta(1)-tetrahydrocannabinolic acid)
RN - 1972-08-3 (Tetrahydrocannabinol)
RN - 25555-57-1 (cannabigerolic acid)
RN - EC 5.3.- (Intramolecular Oxidoreductases)
RN - EC 5.3.- (delta(1)-tetrahydrocannabinolic acid synthase)
SB - IM
MH - Benzoates/metabolism
MH - Intramolecular Oxidoreductases/genetics/isolation & purification/*metabolism
MH - Pichia/classification/*genetics/metabolism
MH - Recombinant Proteins/genetics/isolation & purification/metabolism
MH - Tetrahydrocannabinol/*analogs & derivatives/biosynthesis/metabolism
MH - Time Factors
MH - Transgenes
EDAT- 2007/08/03 09:00
MHDA- 2007/12/06 09:00
CRDT- 2007/08/03 09:00
PHST- 2007/06/23 [received]
PHST- 2007/07/12 [accepted]
PHST- 2007/07/24 [aheadofprint]
AID - S0006-291X(07)01566-5 [pii]
AID - 10.1016/j.bbrc.2007.07.079 [doi]
PST - ppublish
SO - Biochem Biophys Res Commun. 2007 Sep 28;361(3):675-80. Epub 2007 Jul 24.
PMID- 16511162
OWN - NLM
STAT- MEDLINE
DA - 20060302
DCOM- 20060818
LR - 20091118
IS - 1744-3091 (Electronic)
IS - 1744-3091 (Linking)
VI - 61
IP - Pt 8
DP - 2005 Aug 1
TI - Crystallization of Delta1-tetrahydrocannabinolic acid (THCA) synthase from
Cannabis sativa.
PG - 799-801
AB - Delta1-Tetrahydrocannabinolic acid (THCA) synthase is a novel oxidoreductase that
catalyzes the biosynthesis of the psychoactive compound THCA in Cannabis sativa
(Mexican strain). In order to investigate the structure-function relationship of
THCA synthase, this enzyme was overproduced in insect cells, purified and finally
crystallized in 0.1 M HEPES buffer pH 7.5 containing 1.4 M sodium citrate. A
single crystal suitable for X-ray diffraction measurement was obtained in 0.09 M
HEPES buffer pH 7.5 containing 1.26 M sodium citrate. The crystal diffracted to
2.7 A resolution at beamline BL41XU, SPring-8. The crystal belonged to the
primitive cubic space group P432, with unit-cell parameters a = b = c = 178.2 A.
The calculated Matthews coefficient was approximately 4.1 or 2.0 A3 Da(-1)
assuming the presence of one or two molecules of THCA synthase in the asymmetric
unit, respectively.
AD - Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Fukuoka
812-8582, Japan.
FAU - Shoyama, Yoshinari
AU - Shoyama Y
FAU - Takeuchi, Ayako
AU - Takeuchi A
FAU - Taura, Futoshi
AU - Taura F
FAU - Tamada, Taro
AU - Tamada T
FAU - Adachi, Motoyasu
AU - Adachi M
FAU - Kuroki, Ryota
AU - Kuroki R
FAU - Shoyama, Yukihiro
AU - Shoyama Y
FAU - Morimoto, Satoshi
AU - Morimoto S
LA - eng
PT - Journal Article
DEP - 20050730
PL - England
TA - Acta Crystallogr Sect F Struct Biol Cryst Commun
JT - Acta crystallographica. Section F, Structural biology and crystallization
communications
JID - 101226117
RN - 1972-08-3 (Tetrahydrocannabinol)
RN - EC 5.3.- (Intramolecular Oxidoreductases)
RN - EC 5.3.- (delta(1)-tetrahydrocannabinolic acid synthase)
SB - IM
MH - Cannabis/*enzymology
MH - Crystallization
MH - Intramolecular Oxidoreductases/*chemistry
MH - Tetrahydrocannabinol/biosynthesis/chemistry
PMC - PMC1952348
OID - NLM: PMC1952348
EDAT- 2006/03/03 09:00
MHDA- 2006/08/19 09:00
CRDT- 2006/03/03 09:00
PHST- 2005/06/07 [received]
PHST- 2005/07/22 [accepted]
PHST- 2005/07/30 [epublish]
AID - S1744309105023365 [pii]
AID - 10.1107/S1744309105023365 [doi]
PST - ppublish
SO - Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Aug 1;61(Pt 8):799-801.
Epub 2005 Jul 30.
PMID- 15190053
OWN - NLM
STAT- MEDLINE
DA - 20040913
DCOM- 20041025
LR - 20061115
IS - 0021-9258 (Print)
IS - 0021-9258 (Linking)
VI - 279
IP - 38
DP - 2004 Sep 17
TI - The gene controlling marijuana psychoactivity: molecular cloning and heterologous
expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.
PG - 39767-74
AB - Delta(1)-tetrahydrocannabinolic acid (THCA) synthase is the enzyme that catalyzes
oxidative cyclization of cannabigerolic acid into THCA, the precursor of
Delta(1)-tetrahydrocannabinol. We cloned a novel cDNA (GenBank trade mark
accession number AB057805) encoding THCA synthase by reverse transcription and
polymerase chain reactions from rapidly expanding leaves of Cannabis sativa. This
gene consists of a 1635-nucleotide open reading frame, encoding a 545-amino acid
polypeptide of which the first 28 amino acid residues constitute the signal
peptide. The predicted molecular weight of the 517-amino acid mature polypeptide
is 58,597 Da. Interestingly, the deduced amino acid sequence exhibited high
homology to berberine bridge enzyme from Eschscholtzia californica, which is
involved in alkaloid biosynthesis. The liquid culture of transgenic tobacco hairy
roots harboring the cDNA produced THCA upon feeding of cannabigerolic acid,
demonstrating unequivocally that this gene encodes an active THCA synthase.
Overexpression of the recombinant THCA synthase was achieved using a
baculovirus-insect expression system. The purified recombinant enzyme contained
covalently attached FAD cofactor at a molar ratio of FAD to protein of 1:1. The
mutant enzyme constructed by changing His-114 of the wild-type enzyme to Ala-114
exhibited neither absorption characteristics of flavoproteins nor THCA synthase
activity. Thus, we concluded that the FAD binding residue is His-114 and that the
THCA synthase reaction is FAD-dependent. This is the first report on molecular
characterization of an enzyme specific to cannabinoid biosynthesis.
AD - Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, 812-8582,
Japan.
FAU - Sirikantaramas, Supaart
AU - Sirikantaramas S
FAU - Morimoto, Satoshi
AU - Morimoto S
FAU - Shoyama, Yoshinari
AU - Shoyama Y
FAU - Ishikawa, Yu
AU - Ishikawa Y
>FAU - Wada, Yoshiko
AU - Wada Y
FAU - Shoyama, Yukihiro
AU - Shoyama Y
FAU - Taura, Futoshi
AU - Taura F
LA - eng
SI - GENBANK/AB057805
PT - Journal Article
PT - Research Support, Non-U.S. Gov't
DEP - 20040609
PL - United States
TA - J Biol Chem
JT - The Journal of biological chemistry
JID - 2985121R
RN - 0 (DNA, Complementary)
RN - 1972-08-3 (Tetrahydrocannabinol)
RN - EC 5.3.- (Intramolecular Oxidoreductases)
RN - EC 5.3.- (delta(1)-tetrahydrocannabinolic acid synthase)
SB - IM
MH - Amino Acid Sequence
MH - Animals
MH - Base Sequence
MH - Cannabis/chemistry/enzymology/*genetics/metabolism
MH - Cells, Cultured
MH - Cloning, Molecular
MH - DNA, Complementary
MH - Insects
MH - Intramolecular Oxidoreductases/*genetics/*metabolism
MH - Molecular Sequence Data
MH - Oxidation-Reduction
MH - Plant Roots/physiology
MH - Tetrahydrocannabinol/*biosynthesis/chemistry
MH - Tobacco
MH - Transfection
EDAT- 2004/06/11 05:00
MHDA- 2004/10/27 09:00
CRDT- 2004/06/11 05:00
PHST- 2004/06/09 [aheadofprint]
AID - 10.1074/jbc.M403693200 [doi]
AID - M403693200 [pii]
PST - ppublish
SO - J Biol Chem. 2004 Sep 17;279(38):39767-74. Epub 2004 Jun 9.
PMID- 9862135
OWN - NLM
STAT- MEDLINE
DA - 19990128
DCOM- 19990128
LR - 20061115
IS - 0031-9422 (Print)
IS - 0031-9422 (Linking)
VI - 49
IP - 6
DP - 1998 Nov
TI - Purification and characterization of cannabichromenic acid synthase from Cannabis
sativa.
PG - 1525-9
AB - Cannabichromenic acid synthase was purified to apparent homogeneity by sequential
column chromatography including DEAE-cellulose, phenyl-Sepharose CL-4B, and
hydroxylapatite. The enzyme catalysed the oxidocyclization of cannabigerolic acid
and cannabinerolic acid to cannabichromenic acid. The K(m) values for both
substrates were in the same order of magnitude although the Vmax value for the
former was higher than that for the latter. These results suggested that
cannabichromenic acid is predominantly formed from cannabigerolic acid rather
than cannabinerolic acid. The enzyme required neither molecular oxygen nor
hydrogen peroxide, indicating that the cannabichromenic acid synthase reaction
proceeds through direct dehydrogenation without hydroxylation.
AD - Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
FAU - Morimoto, S
AU - Morimoto S
FAU - Komatsu, K
AU - Komatsu K
FAU - Taura, F
AU - Taura F
FAU - Shoyama, Y
AU - Shoyama Y
LA - eng
PT - Journal Article
PL - UNITED STATES
TA - Phytochemistry
JT - Phytochemistry
JID - 0151434
RN - EC 1.- (Oxidoreductases)
RN - EC 1.3.99.- (cannabichromenic acid synthase)
SB - IM
MH - Cannabis/*enzymology
MH - Chromatography, Gel
MH - Electrophoresis, Polyacrylamide Gel
MH - Isoelectric Point
MH - Kinetics
MH - Molecular Weight
MH - Oxidoreductases/chemistry/*isolation & purification/metabolism
MH - Substrate Specificity
EDAT- 1998/12/23
MHDA- 1998/12/23 00:01
CRDT- 1998/12/23 00:00
AID - S0031-9422(98)00278-7 [pii]
PST - ppublish
SO - Phytochemistry. 1998 Nov;49(6):1525-9.
PMID- 5583149
OWN - NLM
STAT- MEDLINE
DA - 19680509
DCOM- 19680509
LR - 20001218
IS - 0009-2363 (Print)
IS - 0009-2363 (Linking)
VI - 15
IP - 7
DP - 1967 Jul
TI - Tetrahydrocannabinolic acid, a genuine substance of tetrahydrocannabinol.
PG - 1075-6
FAU - Yamauchi, T
AU - Yamauchi T
FAU - Shoyama, Y
AU - Shoyama Y
FAU - Aramaki, H
AU - Aramaki H
FAU - Azuma, T
AU - Azuma T
FAU - Nishioka, I
AU - Nishioka I
LA - eng
PT - Journal Article
PL - JAPAN
TA - Chem Pharm Bull (Tokyo)
JT - Chemical & pharmaceutical bulletin
JID - 0377775
SB - IM
MH - Cannabis/*analysis
MH - Chromatography
MH - Spectrum Analysis
EDAT- 1967/07/01
MHDA- 1967/07/01 00:01
CRDT- 1967/07/01 00:00
PST - ppublish
SO - Chem Pharm Bull (Tokyo). 1967 Jul;15(7):1075-6.