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19351-63-4,MFCD16661163
Catalog No.:AA00APDE

19351-63-4 | SECOLOGANIN

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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00APDE
Chemical Name:
SECOLOGANIN
CAS Number:
19351-63-4
Molecular Formula:
C17H24O10
Molecular Weight:
388.3665
MDL Number:
MFCD16661163
SMILES:
O=CC[C@H]1[C@@H](C=C)[C@@H](OC=C1C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Properties
Computed Properties
 
Complexity:
576  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
10  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
8  
XLogP3:
-1.6  

Literature

Title: A 7-deoxyloganetic acid glucosyltransferase contributes a key step in secologanin biosynthesis in Madagascar periwinkle.

Journal: The Plant cell 20131001

Title: Precise RNAi-mediated silencing of metabolically active proteins in the defence secretions of juvenile leaf beetles.

Journal: Proceedings. Biological sciences 20121022

Title: Structures of alkaloid biosynthetic glucosidases decode substrate specificity.

Journal: ACS chemical biology 20120120

Title: Current approaches toward production of secondary plant metabolites.

Journal: Journal of pharmacy & bioallied sciences 20120101

Title: Strategies for engineering plant natural products: the iridoid-derived monoterpene indole alkaloids of Catharanthus roseus.

Journal: Methods in enzymology 20120101

Title: Novel carbon-carbon bond formations for biocatalysis.

Journal: Current opinion in biotechnology 20111201

Title: A new type of monoterpenoid indole alkaloid precursor from Alstonia rostrata.

Journal: Organic letters 20110715

Title: Effect of artificial reconstitution of the interaction between the plant Camptotheca acuminata and the fungal endophyte Fusarium solani on camptothecin biosynthesis.

Journal: Journal of natural products 20110425

Title: The subcellular organization of strictosidine biosynthesis in Catharanthus roseus epidermis highlights several trans-tonoplast translocations of intermediate metabolites.

Journal: The FEBS journal 20110301

Title: Rice MADS3 regulates ROS homeostasis during late anther development.

Journal: The Plant cell 20110201

Title: Pyrosequencing of the Camptotheca acuminata transcriptome reveals putative genes involved in camptothecin biosynthesis and transport.

Journal: BMC genomics 20110101

Title: A facile chemoenzymatic approach: one-step syntheses of monoterpenoid indole alkaloids.

Journal: Chemistry, an Asian journal 20101102

Title: Is a metabolic enzyme complex involved in the efficient and accurate control of Ipecac alkaloid biosynthesis in Psychotria ipecacuanha?

Journal: Plant signaling & behavior 20100701

Title: Construction and expression of a dual vector for chemo-enzymatic synthesis of plant indole alkaloids in Escherichia coli.

Journal: Natural product research 20100501

Title: Improved expression of His(6)-tagged strictosidine synthase cDNA for chemo-enzymatic alkaloid diversification.

Journal: Chemistry & biodiversity 20100401

Title: Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha.

Journal: The Journal of biological chemistry 20100305

Title: The first set of EST resource for gene discovery and marker development in pigeonpea (Cajanus cajan L.).

Journal: BMC plant biology 20100101

Title: Cell-specific expression of tryptophan decarboxylase and 10-hydroxygeraniol oxidoreductase, key genes involved in camptothecin biosynthesis in Camptotheca acuminata Decne (Nyssaceae).

Journal: BMC plant biology 20100101

Title: Strictosidine activation in Apocynaceae: towards a 'nuclear time bomb'?

Journal: BMC plant biology 20100101

Title: Comparison of 454-ESTs from Huperzia serrata and Phlegmariurus carinatus reveals putative genes involved in lycopodium alkaloid biosynthesis and developmental regulation.

Journal: BMC plant biology 20100101

Title: Oleuropein in olive and its pharmacological effects.

Journal: Scientia pharmaceutica 20100101

Title: Metabolic reprogramming of periwinkle plant culture.

Journal: Nature chemical biology 20090301

Title: Proteins prenylated by type I protein geranylgeranyltransferase act positively on the jasmonate signalling pathway triggering the biosynthesis of monoterpene indole alkaloids in Catharanthus roseus.

Journal: Plant cell reports 20090101

Title: Comparative 454 pyrosequencing of transcripts from two olive genotypes during fruit development.

Journal: BMC genomics 20090101

Title: Assessing the limitations to terpenoid indole alkaloid biosynthesis in Catharanthus roseus hairy root cultures through gene expression profiling and precursor feeding.

Journal: Biotechnology progress 20090101

Title: The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha.

Journal: The Journal of biological chemistry 20081212

Title: Rigorous biogenetic network for a group of indole alkaloids derived from strictosidine.

Journal: Molecules (Basel, Switzerland) 20080827

Title: 3D-Structure and function of strictosidine synthase--the key enzyme of monoterpenoid indole alkaloid biosynthesis.

Journal: Plant physiology and biochemistry : PPB 20080301

Title: The leaf epidermome of Catharanthus roseus reveals its biochemical specialization.

Journal: The Plant cell 20080301

Title: Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst.

Journal: Microbial cell factories 20080101

Title: Spatial distribution and hormonal regulation of gene products from methyl erythritol phosphate and monoterpene-secoiridoid pathways in Catharanthus roseus.

Journal: Plant molecular biology 20070901

Title: Structure-based engineering of strictosidine synthase: auxiliary for alkaloid libraries.

Journal: Chemistry & biology 20070901

Title: Chemoselective derivatization of alkaloids in periwinkle.

Journal: Chemical communications (Cambridge, England) 20070821

Title: UV-B-induced signaling events leading to enhanced-production of catharanthine in Catharanthus roseus cell suspension cultures.

Journal: BMC plant biology 20070101

Title: Redesign of a central enzyme in alkaloid biosynthesis.

Journal: Chemistry & biology 20061101

Title: Paratunamides A-D, oxindole alkaloids from Cinnamodendron axillare.

Journal: Journal of natural products 20061001

Title: Development of a kinetic metabolic model: application to Catharanthus roseus hairy root.

Journal: Bioprocess and biosystems engineering 20060501

Title: The structure of Rauvolfia serpentina strictosidine synthase is a novel six-bladed beta-propeller fold in plant proteins.

Journal: The Plant cell 20060401

Title: Effects of terpenoid precursor feeding on Catharanthus roseus hairy roots over-expressing the alpha or the alpha and beta subunits of anthranilate synthase.

Journal: Biotechnology and bioengineering 20060220

Title: [Molecular mechanisms and chemotaxonomy in the indole alkaloids derived from secologanin. (One drop in the sea, the sea in one drop)].

Journal: Acta pharmaceutica Hungarica 20060101

Title: Localization of tabersonine 16-hydroxylase and 16-OH tabersonine-16-O-methyltransferase to leaf epidermal cells defines them as a major site of precursor biosynthesis in the vindoline pathway in Catharanthus roseus.

Journal: The Plant journal : for cell and molecular biology 20051101

Title: Alkaloids from Alangium javanicum and Alangium grisolleoides that mediate Cu2+-dependent DNA strand scission.

Journal: Journal of natural products 20050801

Title: Biogenetically inspired enantioselective approach to Indolo[2,3-a]- and benzo[a]quinolizidine alkaloids from a synthetic equivalent of secologanin.

Journal: Organic letters 20050707

Title: [Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20050101

Title: Metabolic discrimination of Catharanthus roseus leaves infected by phytoplasma using 1H-NMR spectroscopy and multivariate data analysis.

Journal: Plant physiology 20040801

Title: Biosynthesis of camptothecin. In silico and in vivo tracer study from [1-13C]glucose.

Journal: Plant physiology 20040101

Title: Comparison of extraction methods for secologanin and the quantitative analysis of secologanin from Symphoricarpos albus using 1H-NMR.

Journal: Phytochemical analysis : PCA 20040101

Title: Two chromone-secoiridoid glycosides and three indole alkaloid glycosides from Neonauclea sessilifolia.

Journal: Phytochemistry 20030201

Title: Transient expression of strictosidine synthase in tobacco leaves by vacuum infiltration.

Journal: Sheng wu hua xue yu sheng wu wu li xue bao Acta biochimica et biophysica Sinica 20021101

Title: Synthesis and absolute configuration of a new 3,4-dihydro-beta-carboline-type alkaloid, 3,4-dehydro-5(S)-5-carboxystrictosidine, isolated from Peruvian Uña de Gato (Uncaria tomentosa).

Journal: Chemical & pharmaceutical bulletin 20021001

Title: Effect of precursor feeding on alkaloid accumulation by a tryptophan decarboxylase over-expressing transgenic cell line T22 of Catharanthus roseus.

Journal: Journal of biotechnology 20020626

Title: Vomilenine reductase--a novel enzyme catalyzing a crucial step in the biosynthesis of the therapeutically applied antiarrhythmic alkaloid ajmaline.

Journal: Bioorganic & medicinal chemistry 20020601

Title: Investigation of Pictet-Spengler type reactions of secologanin with histamine and its benzyl derivative.

Journal: Journal of natural products 20020501

Title: Cantleyoside-dimethyl-acetal and other iridoid glucosides from Pterocephalus perennis--antimicrobial activities.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101

Title: [Diversity and selectivity in biomolecules].

Journal: Acta pharmaceutica Hungarica 20011201

Title: Inactivation of cytochrome P450 by the food-derived complex phenol oleuropein.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20011101

Title: Why are the terpenoid indole alkaloids of type I homochiral?

Journal: Chirality 20010801

Title: Investigation of the coupling reaction of tetraacetylsecologanin with oxotryptamine and its derivative.

Journal: Journal of natural products 20010801

Title: Isolation and structure of korolkoside, a bis-iridoid glucoside from Lonicera korolkovii.

Journal: Journal of natural products 20010801

Title: Biotransformation of tryptamine and secologanin into plant terpenoid indole alkaloids by transgenic yeast.

Journal: Applied microbiology and biotechnology 20010801

Title: Regio- and stereoselectivity in the coupling reaction of secologanin with dopamine derivatives.

Journal: Journal of natural products 20010301

Title: Inoue K. Yakugaku Zasshi. 2005;125(1):31-49. doi:10.1248/yakushi.125.31

Title: Irmler S, et al. Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J. 2000;24(6):797-804.

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