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Information on EC 4.2.3.106 - (E)-beta-ocimene synthase
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4.2.3.106 (E)-beta-ocimene synthaseIUBMB Comments
Widely distributed in plants, which release beta-ocimene when attacked by herbivorous insects.
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Word Map
- 4.2.3.106
-
volatile
-
terpene
-
terpenoids
-
e-beta-ocimene
-
monoterpene
-
scent
-
floral
- herbivory
- myrcene
- lunatus
-
z-3-hexenyl
-
insect-induced
- lewisii
-
enemies
-
gaertn
-
plant-insect
- reductoisomerase
-
bumblebee
-
urticae
-
tetranychus
- littoralis
-
guild
- 1-deoxy-d-xylulose
- agriculture
The enzyme appears in viruses and cellular organisms
Synonyms
ama0a23, AtTPS03, beta-ocimene synthase, CsTPS6FN, CsTPS6PK, EbetaOS, EBOS, JsTPS, LjEbetaOS, MtEBOS, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ama0a23
AtTPS03
-
-
-
-
beta-ocimene synthase
-
-
-
-
EBOS
LjEbetaOS
-
-
-
-
MtEBOS
-
-
-
-
MTSL4
TPS03
ama0a23
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = (E)-beta-ocimene + diphosphate
-
-
-
-
geranyl diphosphate = (E)-beta-ocimene + diphosphate
protein does not contain the RRx8W motif,suggesting that the reaction mechanism does not proceed via an RR-dependent isomerization of geranyl diphosphate to 3S-linalyl diphosphate
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PATHWAY SOURCE
PATHWAYS
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [(E)-beta-ocimene-forming]
Widely distributed in plants, which release beta-ocimene when attacked by herbivorous insects.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(E)-beta-ocimene + diphosphate
-
-
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
-
products are 97% (E)-beta-ocimene plus 2% (Z)-beta-ocimene and 1% myrcene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
product formation does not proceed via an RR-dependent isomerization of geranyl diphosphate to 3S-linalyl diphosphate
97% (E)-beta-ocimene plus minor amounts of (Z)-beta-ocimene and myrcene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
-
products of Arabidopsis thaliana TPS10 are 56% beta-myrcene, 20% (E)-beta-ocimene, and less than 5% each of (+)-limonene, (-)-limonene, 2-carene, and tricyclene and an unknown monoterpene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
-
94% (E)-beta-ocimene plus 4% (Z)-beta-ocimene and 2% myrcene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
-
main products are 56% beta-myrcene and 20% (E)-beta-ocimene plus minor amounts of (-)-limonene, (+)-limnonene, 2-carene and tricyclene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
Q5CD81
-
97.2% (E)-beta-ocimene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
Q5CD81
-
97.2% (E)-beta-ocimene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
G0Y7D1
-
products are alpha-thujene and (+)-sabinene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
-
products are 98% (E)-beta-ocimene plus 2% (Z)-beta-ocimene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
-
98% (E)-beta-ocimene plus 2% (Z)-beta-ocimene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
-
products are 97.5% (E)-beta-ocimene plus 2% (Z)-beta-ocimene and 0.5% myrcene
-
?
geranyl diphosphate
(E)-beta-ocimene + diphosphate
-
97.5% of (E)-beta-ocimene plus 2% (Z)-beta-ocimene and 0.5% myrcene
-
?
additional information
?
-
enzyme shows both (E)-beta-ocimene and (E,E)-alpha-farnesene synthase activities
-
-
-
additional information
?
-
the enzyme shows no activity with farnesyl diphosphate. Reaction products are identified by GC-MS analysis
-
-
-
additional information
?
-
Q5CD81
no substrate: farnesyl diphosphate and geranylgeranyl diphosphate
-
-
-
additional information
?
-
Q5CD81
no substrate: farnesyl diphosphate and geranylgeranyl diphosphate
-
-
-
additional information
?
-
-
in vivo emission of E-beta-ocimene from flowers is very low, but southern race Mimulus lewisii flowers emit significantly more E-beta-ocimene than northern race flowers
-
-
-
additional information
?
-
in vivo emission of E-beta-ocimene from flowers is very low, but southern race Mimulus lewisii flowers emit significantly more E-beta-ocimene than northern race flowers
-
-
-
additional information
?
-
GC-MS analysis of floral volatiles and enzyme reaction product
-
-
-
additional information
?
-
-
GC-MS analysis of floral volatiles and enzyme reaction product
-
-
-
additional information
?
-
-
no substrates: farnesyl diphosphate or geranylgeranyl diphosphate.
-
-
-
additional information
?
-
no substrates: farnesyl diphosphate or geranylgeranyl diphosphate.
-
-
-
additional information
?
-
no substrate: farnesyl diphosphate
-
-
-
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
in vivo emission of E-beta-ocimene from flowers is very low, but southern race Mimulus lewisii flowers emit significantly more E-beta-ocimene than northern race flowers
-
-
-
additional information
?
-
W6A3F2
in vivo emission of E-beta-ocimene from flowers is very low, but southern race Mimulus lewisii flowers emit significantly more E-beta-ocimene than northern race flowers
-
-
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0026
(2E,6E)-farnesyl diphosphate
accession Columbia, 30°C, pH not specified in the publication
0.0067
geranyl diphosphate
accession Columbia, 30°C, pH not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0048
(2E,6E)-farnesyl diphosphate
accession Columbia, 30°C, pH not specified in the publication
0.034
geranyl diphosphate
accession Columbia, 30°C, pH not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.82
(2E,6E)-farnesyl diphosphate
accession Columbia, 30°C, pH not specified in the publication
5.12
geranyl diphosphate
accession Columbia, 30°C, pH not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
deduced protein does not contain the RRx8W motif; member of a subfamily of the terpene synthase family designated the Tps-g group, which lacks the RRx8W motif; memeber of TPSg group of terpene synthases
UniProt
brenda
i.e. Erythranthe lewisii, southern race distributed in the Sierra Nevada
UniProt
brenda
; deduced protein contains a modification of the conserved RRx8W motif of plant monoterpene synthases. The N-terminal sequence indicates the presence of a plastid transit peptide
UniProt
brenda
member of TPSb group of angiosperm monoterpene and hemiterpene synthases
UniProt
brenda
member oft the TPSb subfamily of angiosperm monoterpene synthases; the tandem arginine motif RRX8W is conserved in the deduced protein of TPS10; bifunctional myrcene/(E)-beta-ocimene synthase
SwissProt
brenda
member of the Tps-b subfamily containing a RRx8W motif
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
Q5CD81
abundant in flower, amount decreases towards fruit development
brenda
Q5CD81
abundant in flower, amount decreases towards fruit development
brenda
(E)-b-ocimene is released from leaves of both undamaged and insect-damaged plants, but at levels two-fold higher in insect-damaged M.edicago truncatula
brenda
maximum TPS transcript accumulation is observed in flower petals, analysis of JsTPS expression in different developmental stages and in different floral part by semiquantitative RT-PCR. Unopened flower (buds) emit no beta-ocimene or farnesene. Senescence initiated in Jasminnum sambac flower after 24 h of petal opening, while low emission of linalool and beta-ocimene is detected until the abscission of floral tissue. beta-Ocimene is not detected in any other floral tissue except petals with a very lowamount of emission
brenda
additional information
transcriptome analysis of trichomes of the cannabis hemp variety Finola reveals sequences of all stages of terpene biosynthesis. Major terpene compounds such as beta-myrcene, (E)-beta-ocimene, (-)-limonene, (+)-alpha-pinene, beta-caryophyllene, and alpha-humulene. Transcripts associated with terpene biosynthesis are highly expressed in trichomes compared to non-resin producing tissues. Relative composition of terpene profiles in Cannabis sativa var. Finola pistillate flowers, overview
brenda
additional information
during the life span of Jasminum sambac flower, clear variations in monoterpene emission between the day and night periods are observed for linalool and beta-ocimene that continue to emituntil next morning
brenda
additional information
-
during the life span of Jasminum sambac flower, clear variations in monoterpene emission between the day and night periods are observed for linalool and beta-ocimene that continue to emituntil next morning
brenda
additional information
no constitutive expression in flowers, stems or roots
brenda
additional information
-
transcripts of MtEBOS are not detected via RNA blots in stems, flowers, and roots
brenda
additional information
transcripts of MtEBOS are not detected via RNA blots in stems, flowers, and roots
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
N-terminal sequence indicates the presence of a plastid transit peptide
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
transcriptome analysis of trichomes of the cannabis hemp variety Finola reveal sequences of all stages of terpene biosynthesis. Nine cannabis terpene synthases (CsTPS) are identified in subfamilies TPS-a and TPS-b. Functional characterization identified mono- and sesqui-TPS, whose products collectively comprise most of the terpenes of Finola resin, including major compounds such as beta-myrcene, (E)-beta-ocimene, (-)-limonene, (+)-alpha-pinene, beta-caryophyllene, and alpha-humulene
physiological function
evolution
the taxa closely related to Mimulus lewisii have evolved several diff erent pollination syndromes, including hummingbird pollination and self pollination (autogamy), floral scent variation contributing to species diversification in this clade, E-beta-ocimene emission within this Mimulus clade does only occur in Mimulus lewisii, given the very low E-beta-ocimene emission in vivo, Mimulus parishii has a fully functional ocimene synthase enzyme in vitro, the other taxa do not emit E-beta- ocimene from flowers, overview
evolution
the enzyme is a member of the terpene synthase (TPS) superfamily, CsTPSFN TPS-b subfamily
physiological function
enzyme is involved in the herbivore-induced indirect defense response of spider mite-infested Lotus japonicus via de novo formation and emission (E)-beta-ocimene
physiological function
differences in the relative emissions of (E)-beta-ocimene and (E,E)-alpha-farnesene from accession Wassilewskija, a high-(E)-beta-ocimene emitter, and accession Columbia, a trace-(E)-beta-ocimene emitter, are attributed to allelic variation of closely related, tandem-duplicated terpene synthase genes, TPS02 and TPS03. The Wassilewskija genome contains a functional allele of TPS02 but not of TPS03, while the opposite is the case for Columbia. Recombinant proteins of the functional Wassilewskija TPS02 and Columbia TPS03 genes both show (E)-beta-ocimene and (E,E)-alpha-farnesene synthase activities. Differential subcellular compartmentalization of the two enzymes in plastids and the cytosol is responsible for the ecotype-specific differences in (E)-beta-ocimene/(E,E)-alpha-farnesene emission
physiological function
E-beta-ocimene, a monoterpene produced by ocimene synthase (OS) in Mimulus lewisii, is a floral scent important in attracting the species' bumblebee pollinators
physiological function
floral scent of Jasminum sambac (Oleaceae) includes three major benzenoid esters: benzylacetate, methylbenzoate, and methylsalicylate, and three major terpene compounds viz. (E)-beta-ocimene, linalool and alpha-farnesene, analysis of concentrations and emission rates of benzenoids and terpenoids during the developmental stages of the flowers, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
Sequence
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CLONED/commentary
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
gene CsTPS6FN, sequence comparisons and phylogenetic analysis, RT-PCR expression analysis
gene OS, genotyping and genomic analysis, sequence comparisons, quantitative RT-PCR expression analysis, recombinant overexpression in Escherichia coli strain BL21
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
induced in plants infested with two-spotted spider mites (Tetranychus urticae), coinciding with increasing emissions of (E)-beta-ocimene as well as other volatiles, (Z)-3-hexenyl acetate and (E)-4,8-dimethyl-1,3,7-nonatriene, by the infested plants. Mechanical wounding of the leaves or application of alamethicin also induces transiently increased levels of EbOS transcripts in Lotus japonicus. Wounding or alamethicin does not result in elevated release of (E)-beta-ocimene; transcripts of LjEbOS are induced in plants infested with two-spotted spider mites, Tetranychus urticae, coinciding with increasing emissions of (E)-beta-ocimene as well as other volatiles, (Z)-3-hexenyl acetate and (E)-4,8-dimethyl-1,3,7-nonatriene, by the infested plants. Mechanical wounding of the leaves or application of alamethicin, a potent fungal elicitor of plant volatile emission, also induces transiently increased levels of transcripts, but not elevated release of (E)-beta-ocimene
mRNA is detected first in mature flower buds, and its level increases until it peaks on day 4 after anthesis. Over the next 3 days, mRNA levels decline sharply by 40% and decrease slowly thereafter; only slight variations in monoterpene synthase mRNA levels during the daily light/dark cycle
transcripts accumulate in leaves in response to exogenous jasmonic acid treatments, lepidopteran herbivory, and lepidopteran oral secretions
-
transcripts are upregulated in response to mechanical wounding and treatment with jasmonic acid, concurrent with induced emission of (E)-beta-ocimene
treatment with 1-aminocyclopropane-1-carboxylic acid does not cause an increase in transcripts
treatment with the ethylene precursor, 1-aminocyclopropane-1-carboxylic acid does not cause an increase in transcripts
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
when lima bean plants that have previously been placed downwind of transgenic tobacco plants that are constitutively overexpressing (E)-beta-ocimene synthase are infested by spider mites in an open-flow tunnel, they are more defensive to spider mites and more attractive to predatory mites, in comparison to the infested plants that have been placed downwind of wild-type tobacco plants. Similarly, when the transgenic tobacco-downwind maize plants are infested with Mythimna separata larvae, this results in reduced larval growth and greater attraction of parasitic wasps Cotesia kariyai. In a greenhouse experiment, lima bean plants placed near the transgenic tobacco plants are more attractive when damaged by spider mites, in comparison to the infested plants that have been placed near the wild-type plants. Volatile organic compounds emitted from infested receiver plants affect their conspecific neighboring plants to prime indirect defenses in response to herbivory
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Bohlmann, J.; Martin, D.; Oldham, N.J.; Gershenzon, J.
Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase
Arch. Biochem. Biophys.
375
261-269
2000
Arabidopsis thaliana, Arabidopsis thaliana (Q9ZUH4)
brenda
Dudareva, N.; Martin, D.; Kish, C.M.; Kolosova, N.; Gorenstein, N.; Fäldt, J.; Miller, B.; Bohlmann, J.
(E)-beta-Ocimene and myrcene synthase genes of floral scent biosynthesis in snapdragon: function and expression of three terpene synthase genes of a new terpene synthase subfamily
Plant Cell
15
1227-1241
2003
Antirrhinum majus (Q84NC8)
brenda
Navia-Gine, W.G.; Yuan, J.S.; Mauromoustakos, A.; Murphy, J.B.; Chen, F.; Korth, K.L.
Medicago truncatula (E)-beta-ocimene synthase is induced by insect herbivory with corresponding increases in emission of volatile ocimene
Plant Physiol. Biochem.
47
416425
2009
Medicago truncatula (Q5UB07)
-
brenda
Arimura, G.; Ozawa, R.; Kugimiya, S.; Takabayashi, J;, Bohlmann, J.
Herbivore-induced defense response in a model legume. Two-spotted spider mites induce emission of (E)-beta-ocimene and transcript accumulation of (E)-beta-ocimene synthase in Lotus japonicus
Plant Physiol.
135
1976-1983
2004
Lotus japonicus, Lotus japonicus (Q672F7)
brenda
Huang, M.; Abel, C.; Sohrabi, R.; Petri, J.; Haupt, I.; Cosimano, J.; Gershenzon, J.; Tholl, D.
Variation of herbivore-induced volatile terpenes among Arabidopsis ecotypes depends on allelic differences and subcellular targeting of two terpene synthases, TPS02 and TPS03
Plant Physiol.
153
1293-1310
2010
Arabidopsis thaliana (A4FVP2)
brenda
Navia-Gine, W.G.; Yuan, J.S.; Mauromoustakos, A.; Murphy, J.B.; Chen, F.; Korth, K.L.
Medicago truncatula (E)-beta-ocimene synthase is induced by insect herbivory with corresponding increases in emission of volatile ocimene
Plant Physiol. Biochem.
47
416-425
2009
Medicago truncatula, Medicago truncatula (Q5UB07)
brenda
Shimada, T.; Endo, T.; Fujii, H.; Hara, M.; Omura, M.
Isolation and characterization of (E)-beta-ocimene and 1,8 cineole synthases in Citrus unshiu Marc
Plant Sci.
168
987-995
2005
Citrus unshiu (Q5CD81), Citrus unshiu Marc (Q5CD81)
-
brenda
Faeldt, J.; Arimura, G.; Gershenzon, J.; Takabayashi, J.; Bohlmann, J.
Functional identification of AtTPS03 as (E)-beta-ocimene synthase: a monoterpene synthase catalyzing jasmonate- and wound-induced volatile formation in Arabidopsis thaliana
Planta
216
745-751
2003
Arabidopsis thaliana (A4FVP2), Arabidopsis thaliana
brenda
Chang, Y.; Chu, F.
Molecular cloning and characterization of monoterpene synthases from Litsea cubeba (Lour.) Persoon
Tree Genet. Genomes
7
835-844
2011
Litsea cubeba (G0Y7D1)
-
brenda
Muroi, A.; Ramadan, A.; Nishihara, M.; Yamamoto, M.; Ozawa, R.; Takabayashi, J.; Arimura, G.
The composite effect of transgenic plant volatiles for acquired immunity to herbivory caused by inter-plant communications
PLoS ONE
6
e24594
2011
Phaseolus lunatus (B1P189)
brenda
Peng, F.; Byers, K.; Bradshaw, H.J.
Less is more Independent loss-of-function ocimene synthase alleles parallel pollination syndrome diversification in monkeyflowers (Mimulus)
Am. J. Bot.
104
1055-1059
2017
Erythranthe lewisii, Erythranthe lewisii (W6A3F2)
brenda
Bera, P.; Mukherjee, C.; Mitra, A.
Enzymatic production and emission of floral scent volatiles in Jasminum sambac
Plant Sci.
256
25-38
2017
Jasminum sambac (A0A1B0WVE7), Jasminum sambac
brenda
Booth, J.; Page, J.; Bohlmann, J.
Terpene synthases from Cannabis sativa
PLoS ONE
12
e0173911
2017
Cannabis sativa (A0A1V0QSH1)
brenda
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