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A distal enhancer guides the negative selection of toxic glycoalkaloids during tomato domestication
This study identified a distal enhancer GE1, which acts as the key regulator controlling steroidal glycoalkaloids metabolism by modulating the GAME gene cluster and guides negative selection of steroidal glycoalkaloids production during tomato domestication.
- Feng Bai
- , Peng Shu
- & Mingchun Liu
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Article
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Biosynthesis of the highly oxygenated tetracyclic core skeleton of Taxol
Despite intensive investigation, stepwise reactions from diol to Taxol tetracyclic core skeleton remain unclear. Here, authors fill this gap by identifying two P450s and confirming the reaction order.
- Chengshuai Yang
- , Yan Wang
- & Zhihua Zhou
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Article
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Multiple independent losses of the biosynthetic pathway for two tropane alkaloids in the Solanaceae family
Hyoscyamine and scopolamine (HS) are two tropane alkaloids with medicinal significance produced by distantly related lineages in the Solanaceae family. Here, the authors assemble the genome of three HS-producing and one non-HS-producing species within Solanaceae, and reveal the evolution of the biosynthetic pathway.
- Jiao Yang
- , Ying Wu
- & Jianquan Liu
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Biosynthesis of barley wax β-diketones: a type-III polyketide synthase condensing two fatty acyl units
Barley plants coat their organs with waxy diketones to protect against late-summer droughts. These diketones are formed by two enzymes, one diverting common fatty acids from normal metabolism and the other one linking two fatty acid units together.
- Yulin Sun
- , Alberto Ruiz Orduna
- & Reinhard Jetter
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Deciphering triterpenoid saponin biosynthesis by leveraging transcriptome response to methyl jasmonate elicitation in Saponaria vaccaria
Methyl jasmonate triggers saponin production in Saponaria vaccaria. Using transcriptome data and heterologous expression, the authors identify P450s and glycosyltransferases that modify triterpenoids. They also discover the pathway for UDP-D-fucose biosynthesis.
- Xiaoyue Chen
- , Graham A. Hudson
- & Henrik V. Scheller
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Discovery of isoflavone phytoalexins in wheat reveals an alternative route to isoflavonoid biosynthesis
Isoflavones are mostly found in the legumes, and little is known about their formation outside of this family. Here, the authors discover an isoflavone synthase gene in wheat, found in a pathogen-induced gene cluster encoding isoflavone biosynthesis.
- Guy Polturak
- , Rajesh Chandra Misra
- & Anne Osbourn
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Characterization of the horse chestnut genome reveals the evolution of aescin and aesculin biosynthesis
Horse chestnut (Aesculus chinensis) is a tree species that can produce medicinal compounds such as aescin and aesculin. Here, the authors assemble its genome, identify key genes involved in the biosynthesis of these two group of compounds, and achieve the de novo synthesis of aesculin in E. coli.
- Wei Sun
- , Qinggang Yin
- & Shilin Chen
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Understanding the mechanism of red light-induced melatonin biosynthesis facilitates the engineering of melatonin-enriched tomatoes
Melatonin is a physiological regulator in many organisms including plants. Here, the authors demonstrate a molecular mechanism of red light-induced melatonin biosynthesis in tomato fruit which could guide the engineering of melatonin-enriched tomatoes.
- Zixin Zhang
- , Xin Zhang
- & Yang Zhang
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Characterization of two O-methyltransferases involved in the biosynthesis of O-methylated catechins in tea plant
Tea contains catechins such as (−)-epigallocatechin gallate (EGCG) which have antioxidant activity and potential health benefits. Here the authors characterise two enzymes that produce O-methylated EGCG, a modified form found in some tea cultivars that has improved bioavailability.
- Ji-Qiang Jin
- , Fu-Rong Qu
- & Liang Chen
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Functional divergence of CYP76AKs shapes the chemodiversity of abietane-type diterpenoids in genus Salvia
Functional divergence of CYP76AK subfamily, accompanied by oxidation variations at C-20, leads to diverse abietane-type diterpenoids in Salvia species. Enzyme activity loss contributes to this unique chemical diversity within the lineage.
- Jiadong Hu
- , Shi Qiu
- & Wansheng Chen
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A BAHD-type acyltransferase concludes the biosynthetic pathway of non-bitter glycoalkaloids in ripe tomato fruit
During tomato fruit ripening, bitter and toxic steroidal glycoalkaloids (SGAs) are converted to nonbitter and less toxic forms, but proposed acylating enzyme in pathway remain unknown. Here, authors report BAHD-type acyltransferase that catalyze acylation step in biosynthesis of non-bitter SGAs in tomato.
- Prashant D. Sonawane
- , Sachin A. Gharat
- & Asaph Aharoni
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Tapping the rhizosphere metabolites for the prebiotic control of soil-borne bacterial wilt disease
Prebiotics can be used to encourage beneficial organisms. Here, the authors select rhizosphere metabolites that can be used as prebiotics to reduce the effect of the plant pathogen Ralstonia.
- Tao Wen
- , Penghao Xie
- & Jun Yuan
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The allotetraploid horseradish genome provides insights into subgenome diversification and formation of critical traits
Horseradish is a spicy root vegetable and it also produces horseradish peroxidase, an enzyme widely used in biochemistry applications. Here, the authors report its telomere-to-telomere reference genome, reveal subgenome diversification and the effect on the biosynthesis of glucosinolates and horseradish peroxidases.
- Fei Shen
- , Shixiao Xu
- & Martin A. Lysak
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An unconventional proanthocyanidin pathway in maize
Maize has an unconventional proanthocyanidin (PA) biosynthetic pathway which produces rare stereoisomers of PA monomers and dimers, highlighting an opportunity for further improving the nutritional value of maize.
- Nan Lu
- , Ji Hyung Jun
- & Richard A. Dixon
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A cytochrome P450 CYP87A4 imparts sterol side-chain cleavage in digoxin biosynthesis
Digoxin is a heart medicine extracted from plants, but how plants synthesize it is largely unknown. Here Carroll et al. identify a novel enzyme for digoxin biosynthesis, paving the way to produce digoxin and other structurally similar drugs in microbes.
- Emily Carroll
- , Baradwaj Ravi Gopal
- & Zhen Q. Wang
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Regioselective stilbene O-methylations in Saccharinae grasses
O-methylated stilbenes are promising nutraceutical candidates. Here, the authors reveal that sorghum and wild sugarcane accumulate different types of O-methylated stilbenes due to major differences in catalytic regioselectivities of O-methyltransferases.
- Andy C. W. Lui
- , Kah Chee Pow
- & Clive Lo
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The core metabolome and root exudation dynamics of three phylogenetically distinct plant species
Root exudates display a diurnal signature, change with growth environment, and can be divided into a core metabolome common to multiple plant species, and specialized exudates produced by distinct species.
- Sarah McLaughlin
- , Kateryna Zhalnina
- & Joelle Sasse
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Revealing evolution of tropane alkaloid biosynthesis by analyzing two genomes in the Solanaceae family
Tropane alkaloids (TAs) are synthesized by some species in Solanaceae. Here, the authors assemble the genomes of two representative TAs producing species, show that gene loss shapes uneven distribution of TAs in Solanaceae, and identify a cytochrome P450 gene catalyzing N-demethylation of hyoscyamine to generate norhyoscyamine.
- Fangyuan Zhang
- , Fei Qiu
- & Zhihua Liao
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The Torreya grandis genome illuminates the origin and evolution of gymnosperm-specific sciadonic acid biosynthesis
Torreya grandis is a gymnosperm species that produces edible seeds with high level of sciadonic acid (SCA). Here, the authors assemble the genome of this species, preform methylone analysis of seeds at different developmental stages, and reveal two key genes involved in SCA biosynthesis.
- Heqiang Lou
- , Lili Song
- & Jiasheng Wu
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Genomics and biochemical analyses reveal a metabolon key to β-L-ODAP biosynthesis in Lathyrus sativus
Grass pea is a multi-stress tolerant orphan crop and developing cultivars with decreased accumulation of the neurotoxin β-L-oxalyl-2,3-diaminopropionic acid (β-L-ODAP) is one of its breeding objectives. Here, the authors assemble its genome and reveal genes involved in the biosynthesis of β-L-ODAP.
- Anne Edwards
- , Isaac Njaci
- & Peter M. F. Emmrich
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Tandemly duplicated CYP82Ds catalyze 14-hydroxylation in triptolide biosynthesis and precursor production in Saccharomyces cerevisiae
Hydroxylation at the C-14 position of triptolide is critical for its potent antitumor activity. Here, the authors report two CYP82Ds catalyze the 14-hydroxylation reaction via metabolic grid and achieve heterologous bioproduction of triptolide precursor in engineered Saccharomyces cerevisiae.
- Yifeng Zhang
- , Jie Gao
- & Luqi Huang
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The natural pyrazolotriazine pseudoiodinine from Pseudomonas mosselii 923 inhibits plant bacterial and fungal pathogens
Natural antimicrobial metabolites produced by soil microorganisms can be used as green pesticides. Here, the authors isolated a Pseudomonas mosselii strain 923 from rice rhizosphere soils and identify the compound pyrazolotriazine pseudoiodinine inhibits the growth of plant bacterial and fungal pathogens.
- Ruihuan Yang
- , Qing Shi
- & Gongyou Chen
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Uncovering a miltiradiene biosynthetic gene cluster in the Lamiaceae reveals a dynamic evolutionary trajectory
A diterpenoid biosynthetic gene cluster (BGC) has been identified in a few species in the Lamiaceae (mint) family, but its origin and evolution remain unclear. Here, the authors report assembly of genomes of three species within the family and reveal the dynamic evolutionary trajectory of the BGC.
- Abigail E. Bryson
- , Emily R. Lanier
- & Björn Hamberger
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Alkaloid binding to opium poppy major latex proteins triggers structural modification and functional aggregation
Opium poppy accumulates alkaloids in the specialized cytoplasm of laticifers known as latex. Here the authors show that the binding of alkaloids to the abundant major latex proteins triggers quaternary structural modification that mediates a functional role for protein aggregation.
- Natali Ozber
- , Samuel C. Carr
- & Peter J. Facchini
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A gene cluster in Ginkgo biloba encodes unique multifunctional cytochrome P450s that initiate ginkgolide biosynthesis
Although ginkgo terpenoids have been studied extensively for their pharmaceutical properties, knowledge on their biosynthesis remains limited. Here, the authors identify five multifunctional cytochrome P450s that catalyze the generation of the tert-butyl group and one of the lactone rings towards the biosynthesis of ginkgolides.
- Victor Forman
- , Dan Luo
- & Irini Pateraki
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Tripterygium wilfordii cytochrome P450s catalyze the methyl shift and epoxidations in the biosynthesis of triptonide
How triptonide is made in the medicinal plant Tripterygium wilfordii is largely unknown. Here, the authors report the identification and characterization of a suite of cytochrome P450s and show their function in catalyzing the formation of triptonide from miltriadiene in tobacco and baker’s yeast.
- Nikolaj Lervad Hansen
- , Louise Kjaerulff
- & Johan Andersen-Ranberg
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Catalytic innovation underlies independent recruitment of polyketide synthases in cocaine and hyoscyamine biosynthesis
Cocaine is a tropane alkaloid produced by Erythroxylum novogranatense. Here the authors identify two polyketide synthases involved in cocaine biosynthesis and provide insight into the parallel evolution of these enzymes in tropane alkaloids-producing plants.
- Tian Tian
- , Yong-Jiang Wang
- & Sheng-Xiong Huang
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Biocatalytic routes to stereo-divergent iridoids
Iridoid compounds are an important class of natural products. Here, the authors report on the discovery and engineering of nepetalactol-related short chain reductases and their application for the biosynthesis of nepetalactol or nepetalactone stereoisomers, as a versatile system for the production of the iridoid natural product scaffold.
- Néstor J. Hernández Lozada
- , Benke Hong
- & Sarah E. O’Connor
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Metabolomics-guided discovery of cytochrome P450s involved in pseudotropine-dependent biosynthesis of modified tropane alkaloids
Cytochrome P450s drive the structural diversity of plant alkaloids, many of which have biotechnological uses. Here the authors use reverse genetics and metabolomics to identify two Atropa belladonna cytochrome P450s that synthesize pseudotropine-derived alkaloids.
- Radin Sadre
- , Thilani M. Anthony
- & Cornelius S. Barry
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A role for ascorbate conjugates of (+)-catechin in proanthocyanidin polymerization
Proanthocyanidins are natural polymers of flavan-3-ols produced by plants. Here the authors provide genetic and biochemical evidence for the involvement of ascorbate linked flavan-3-ol oligomers in the extension of the proanthocyanidin chain.
- Keji Yu
- , Richard A. Dixon
- & Changqing Duan
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Article
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A Catharanthus roseus Fe(II)/α-ketoglutarate-dependent dioxygenase catalyzes a redox-neutral reaction responsible for vindolinine biosynthesis
Catharanthus roseus is the source for anticancer drug vinblastine and other medicinal monoterpenoid indole alkaloids. Here the authors characterize an Fe/2OG dioxygenase, vindolinine synthase, which catalyzes an unusual redox-neutral reaction leading to alkaloid diversity.
- Jasmine Ga May Eng
- , Mohammadamin Shahsavarani
- & Yang Qu
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A functionally conserved STORR gene fusion in Papaver species that diverged 16.8 million years ago
The STORR gene fusion event is a key step in the evolution of benzylisoquinoline alkaloid metabolism in opium poppy. Here, the authors combine phylogenetic, transcriptomic, metabolomic, biochemical and genomic analyses to show the STORR gene fusion occurred only once between 16.8-24.1 million years ago in Papaver species.
- Theresa Catania
- , Yi Li
- & Ian A. Graham
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Deletion and tandem duplications of biosynthetic genes drive the diversity of triterpenoids in Aralia elata
Unlike Panax species, which can produce dammarane-type saponins, Aralia elata can only synthesize oleananetype saponins. Here, the authors reveal that the loss of the dammaranediol synthase-encoding gene and tandem duplication of triterpene biosynthetic genes drive structural divergences of saponins between the two genera.
- Yu Wang
- , He Zhang
- & Yuhua Li
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A peroxisomal heterodimeric enzyme is involved in benzaldehyde synthesis in plants
Benzaldehyde is a simple aromatic aldehyde that attracts pollinators, has antifungal properties and contributes to flavor in many plants. Here the authors show that benzaldehyde is synthesized in petunia via the benzoic acid β-oxidative pathway by a peroxisomal heterodimeric enzyme consisting of α and β subunits.
- Xing-Qi Huang
- , Renqiuguo Li
- & Natalia Dudareva
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Activation of the plant mevalonate pathway by extracellular ATP
Products of the mevalonate pathway support plant development. Here the authors show that the extracellular ATP receptor P2K1 phosphorylates mevalonate kinase and this affects the mevalonate pathway.
- Sung-Hwan Cho
- , Katalin Tóth
- & Gary Stacey
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Identification of a diarylpentanoid-producing polyketide synthase revealing an unusual biosynthetic pathway of 2-(2-phenylethyl)chromones in agarwood
2-(2-Phenylethyl)chromones (PECs) contribute to the distinctive fragrance of agarwood. Here the authors identify a diarylpentanoid-producing polyketide synthase from Aquilaria sinensis and show how it catalyzes PEC formation.
- Xiao-Hui Wang
- , Bo-Wen Gao
- & She-Po Shi
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Comment
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Biotechnological development of plants for space agriculture
The logistical and practical challenges of supplying food for long-term space missions are substantial. In this comment, the authors discuss potential biotechnological approaches that could be used to aid the production of food crops in space.
- Yongming Liu
- , Gengxin Xie
- & Maozhi Ren
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Article
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A chromosome-level Camptotheca acuminata genome assembly provides insights into the evolutionary origin of camptothecin biosynthesis
Camptothecin is a monoterpene indole alkaloid with anti-tumor activity. Here, the authors assemble the genome of the camptothecin producing plant Camptotheca acuminata and provide insights into the evolutionary origin of camptothecin biosynthesis by comparing to the vinblastine and vincristine biosynthetic pathway in Catharanthus roseus.
- Minghui Kang
- , Rao Fu
- & Jianquan Liu
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Article
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Analysis of the Coptis chinensis genome reveals the diversification of protoberberine-type alkaloids
Coptis chinensis represents an early-diverging eudicot lineage with diverse medicinal applications. Here, the authors report its chromosome-scale genome assembly, infer a single ancient whole-genome duplication, and characterize the function of CYP719 in diversification of protoberberine-type alkaloids.
- Yifei Liu
- , Bo Wang
- & Jing Nie
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Article
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Structure-based engineering of substrate specificity for pinoresinol-lariciresinol reductases
Pinoresinol–lariciresinol reductases (PLRs) are enzymes involved in the lignan biosynthesis. Here, crystal structures of three PLRs in the apo, substrate-bound and product-bound states, and accompanying mutagenesis provide insight into PLRs catalytic mechanism and suggest a strategy for PLR engineering.
- Ying Xiao
- , Kai Shao
- & Wansheng Chen
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Subtelomeric assembly of a multi-gene pathway for antimicrobial defense compounds in cereals
The genomic organization and origin of the avenacin biosynthetic gene cluster remain unknown. Here, the authors assemble the genome of diploid oat Avena strigosa, reveal the structure and organization of the consecutive genes, characterize the last two missing pathway steps, and investigate the origin of the pathway in cereals.
- Yan Li
- , Aymeric Leveau
- & Anne Osbourn
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Two chemically distinct root lignin barriers control solute and water balance
Defects in the Casparian strip, a fine band of lignin that seals root endodermal cells and plays roles in nutrient homeostasis, activate a signaling pathway leading to over-lignification. Here, the authors show that this process leads to the deposition of compensatory lignin that is chemically distinct from Casparian strip lignin.
- Guilhem Reyt
- , Priya Ramakrishna
- & David E. Salt
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Versatility in acyltransferase activity completes chicoric acid biosynthesis in purple coneflower
Biosynthetic pathway of chicoric acid in purple coneflower has not been fully elucidated, though the compound has been shown to have potential health benefits. Here, the authors report the involvement of both BAHD and SCPL acyltransferases in its biosynthesis and show the pathway is unique to Echinacea species.
- Rao Fu
- , Pingyu Zhang
- & Yang Zhang
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Article
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The biosynthetic pathway of potato solanidanes diverged from that of spirosolanes due to evolution of a dioxygenase
One goal of potato breeding is to reduce the accumulation of toxic solanidane glycoalkaloids. Here the authors show that potato DPS, a 2-oxoglutarate dependent dioxygenase, catalyzes ring rearrangement of a biosynthetic precursor to differentiate solanidanes from spirosolanes that are found in other solanaceous plants.
- Ryota Akiyama
- , Bunta Watanabe
- & Masaharu Mizutani
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Expansion within the CYP71D subfamily drives the heterocyclization of tanshinones synthesis in Salvia miltiorrhiza
Salvia miltiorrhiza is a medicinal plant that can produce the bioactive tanshinones. Here, the authors report the improved genome assembly and reveal the possible roles of three CYP71Ds in catalyzing the reactions leading to the formation of the characteristic furan D-ring of transhinones.
- Ying Ma
- , Guanghong Cui
- & Luqi Huang
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Article
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Chromosome-level genome assembly of Ophiorrhiza pumila reveals the evolution of camptothecin biosynthesis
Ophiorrhiza pumila is a medicinal plant that can produce the anti-cancer monoterpene indole alkaloid (MIA) camptothecin. Here, the authors report its genome assembly and propose a working model for MIA evolution and biosynthesis through comparative genomics, synteny, and metabolic gene cluster analyses.
- Amit Rai
- , Hideki Hirakawa
- & Mami Yamazaki
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Docking of acetyl-CoA carboxylase to the plastid envelope membrane attenuates fatty acid production in plants
In plants, light-dependent activation fatty acid synthesis (FAS) is mediated in part by acetyl-CoA carboxylase (ACCase). Here the authors identify a family of genes encoding carboxyltransferase interactors that attenuate FAS in the light by docking acetyl-CoA carboxylase to the plastid envelope.
- Yajin Ye
- , Krisztina Nikovics
- & Jay J. Thelen
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Article
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Genome-enabled discovery of anthraquinone biosynthesis in Senna tora
Anthraquinones are aromatic polyketides and have been used for treating various diseases, but the biosynthetic pathway is unclear. Here, the authors assemble the genome of an anthraquinone-producing medicinal plant Senna tora and show the evidences that CHS-like genes may be involved in anthraquinone biosynthesis.
- Sang-Ho Kang
- , Ramesh Prasad Pandey
- & Jae Kyung Sohng
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A cellulose synthase-derived enzyme catalyses 3-O-glucuronosylation in saponin biosynthesis
Saponins such as glycyrrhizin, a natural sweetener found in licorice root, are a class of triterpenoids synthesized that are characterized by a glucoronic acid moiety at the C-3 position. Here the authors show that saponin glucuronosylation is catalyzed by cellulose-synthase like enzymes and reconstitute glycyrrhizin synthesisin yeast.
- Soo Yeon Chung
- , Hikaru Seki
- & Toshiya Muranaka
Phytoalexin sakuranetin attenuates endocytosis and enhances resistance to rice blast