gentiopicrin

1H,3H-pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)-

CAS: 20831-76-9 C16 H20 O9 MW: 356.32820000

Identification

Namegentiopicrin
IUPAC(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
CAS Number20831-76-9
EINECS244-070-2
FDA UNII0WE09Z21RC
Molecular FormulaC16 H20 O9
Molecular Weight356.32820000
MDL NumberMFCD00075700
Nikkaji NumberJ40.726G

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 191.00 °C. @ 760.00 mm Hg
Boiling Point 667.80 °C. @ 760.00 mm Hg (est)
Flash Point 477.00 °F. TCC ( 247.10 °C. ) (est)
logP (o/w) -3.170 (est)
Soluble in water, 1e+006 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for gentiopicrin usage levels up tonot for fragrance use.
Recommendation for gentiopicrin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

(3S,4R)-4- ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one gentiopicroside 1H,3H- pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)- PubMed: Evaluation of antioxidant and antibacterial activity of methanolic extracts of Gentiana kurroo royle. PubMed: Comparative study on "long-dan", "qin-jiao" and their adulterants by HPLC analysis. PubMed: [Optimum harvest study of Gentiana crassicaulis in Ludian]. PubMed: [Simultaneous determination of five iridoids in gentianae macrophyllae radix and their local variety by HPLC]. PubMed: Pharmacokinetic and excretion study of three secoiridoid glycosides and three flavonoid glycosides in rat by LC-MS/MS after oral administration of the Swertia pseudochinensis extract. PubMed: Metabolic discrimination of Swertia mussotii and Swertia chirayita known as "Zangyinchen" in traditional Tibetan medicine by (1)H NMR-based metabolomics. PubMed: Hepatoprotective effects of secoiridoid-rich extracts from Gentiana cruciata L. against carbon tetrachloride induced liver damage in rats. PubMed: Evaluation of anticonvulsant, sedative, anxiolytic, and phytochemical profile of the methanol extract from the aerial parts of Swertia corymbosa (Griseb.) wight ex C.B. Clarke. PubMed: Simultaneous determination of six index constituents and comparative analysis of four ethnomedicines from genus Gentiana using a UPLC-UV-MS method. PubMed: A rapid and sensitive UFLC-MS/MS method for the simultaneous determination of gentiopicroside and swertiamarin in rat plasma and its application in pharmacokinetics. PubMed: Application of quantitative 1H-NMR method to determination of gentiopicroside in Gentianae radix and Gentianae scabrae radix. PubMed: Attenuation of reserpine-induced pain/depression dyad by gentiopicroside through downregulation of GluN2B receptors in the amygdala of mice. PubMed: [Efficient method for analyzing absorbed ingredients of traditional Chinese medicine genitana macrophyllae radix]. PubMed: Combination of UHPLC/Q-TOF-MS, NMR spectroscopy, and ECD calculation for screening and identification of reactive metabolites of gentiopicroside in humans. PubMed: Anti-diabetic activity of Swertia corymbosa (Griseb.) Wight ex C.B. Clarke aerial parts extract in streptozotocin induced diabetic rats. PubMed: New analytical method for the study of the metabolism of gentiopicroside in rats after oral administration by LC-TOF-MS following picolinoyl derivatization. PubMed: [Comparative study on pharmacokinetics of gentiopicroside and gentianae radix extract in rats]. PubMed: Rapid preparative separation of six bioactive compounds from Gentiana crassicaulis Duthie ex Burk. using microwave-assisted extraction coupled with high-speed counter-current chromatography. PubMed: Microbial biotransformation of gentiopicroside by the endophytic fungus Penicillium crustosum 2T01Y01. PubMed: Preparation, characterization, and in vivo pharmacokinetics of nanostructured lipid carriers loaded with oleanolic acid and gentiopicrin. PubMed: Rigenolide A, a new secoiridoid glucoside with a cyclobutane skeleton, and three new acylated secoiridoid glucosides from Gentiana rigescens Franch. PubMed: [Simultaneous determination of five constituents in eight Qingyedan species derived from Swertia plants by HPLC]. PubMed: Identification and determination of major constituents in a traditional Chinese medicine compound recipe Xiongdankaiming tablet using HPLC-PDA/ESI-MS(n) and HPLC-UV/ELSD. PubMed: Identification of bio-active metabolites of gentiopicroside by UPLC/Q-TOF MS and NMR. PubMed: Inhibition of vascular smooth muscle cell proliferation by Gentiana lutea root extracts. PubMed: Spatial variation profiling of four phytochemical constituents in Gentiana straminea (Gentianaceae). PubMed: Isolation and identification of constituents with activity of inhibiting nitric oxide production in RAW 264.7 macrophages from Gentiana triflora. PubMed: Induction of apoptosis in human pancreatic MiaPaCa-2 cells through the loss of mitochondrial membrane potential (ΔΨm) by Gentiana kurroo root extract and LC-ESI-MS analysis of its principal constituents. PubMed: In vitro inhibition and induction of human liver cytochrome P450 enzymes by gentiopicroside: potent effect on CYP2A6. PubMed: [Determination and quality assessment of 10 ingredients gentiopicroside and sweroside and so on in Tibetan medicine Jia Di (Swertia chirayita)]. PubMed: Chemical profile, radical scavenging and cytotoxic activity of yellow gentian leaves (Genitaneae luteaefolium) grown in northern regions of Montenegro. PubMed: [Callus cultivation and determination of gentiopicroside from Gentiana macrophylla]. PubMed: Hepatoprotective effects of Gentiana asclepiadea L. extracts against carbon tetrachloride induced liver injury in rats. PubMed: [Chemical constituents of Aconitum tanguticum]. PubMed: [Transdermal behavior of effective constituents in xuanbi gel plaster]. PubMed: [Quickly investigating the absorption ingredients of Gentianae Radix et Rhizoma by SEMAC]. PubMed: Gentiopicroside attenuates morphine rewarding effect through downregulation of GluN2B receptors in nucleus accumbens. PubMed: Inhibition of myeloperoxidase and antioxidative activity of Gentiana lutea extracts. PubMed: An in vitro perspective to cholinesterase inhibitory and antioxidant activity of five Gentiana species and Gentianella caucasea. PubMed: Potent Antifungal Activity of Pure Compounds from Traditional Chinese Medicine Extracts against Six Oral Candida Species and the Synergy with Fluconazole against Azole-Resistant Candida albicans. PubMed: Determination of the plasma pharmacokinetic and tissue distributions of swertiamarin in rats by liquid chromatography with tandem mass spectrometry. PubMed: [Study on the chemical constituents in roots of Gentiana dahurica]. PubMed: [Transdermal delivery of Gentiana macrophylla complex components system under micro-needle conditions]. PubMed: Introgression of the heterologous nuclear DNAs and efficacious compositions from Swertia tetraptera Maxim. into Bupleurum scorzonerifolium Willd. via somatic hybridization. PubMed: Isolation of gentiopicroside from Gentianae Radix and its pharmacokinetics on liver ischemia/reperfusion rats. PubMed: [Study on the quality and genetic diversity of Gentiana macrophylla pall of different habitats]. PubMed: Inhibitory effects of secoiridoids from the roots of Gentiana straminea on stimulus-induced superoxide generation, phosphorylation and translocation of cytosolic compounds to plasma membrane in human neutrophils. PubMed: Development and validation of a LC-ESI-MS/MS method for the determination of swertiamarin in rat plasma and its application in pharmacokinetics. PubMed: Introgression of Swertia mussotii gene into Bupleurum scorzonerifolium via somatic hybridization. PubMed: Effect of Feining on bleomycin-induced pulmonary injuries in rats. PubMed: [Preparation of gentiopicroside from the extract of Swertia mussotii Franch by preparative high performance liquid chromatography]. PubMed: Antibacterial and antifungal screening of Centaurium pulchellum crude extracts and main secoiridoid compounds. PubMed: Analysis of iridoids, secoiridoids and xanthones in Centaurium erythraea, Frasera caroliniensis and Gentiana lutea using LC-MS and RP-HPLC. PubMed: Concentrations of the active constituents of the Tibetan folk medicine Qinjiao (Gentiana sect. Cruciata) within and between taxonomic species across the Qinghai-Tibetan Plateau. PubMed: [Determination of five active constituents in aerial part of Tibetan medicine Gentiana straminea by HPLC]. PubMed: New physiological function of secoiridoids: neuritogenic activity in PC12h cells. PubMed: Anti-apoptotic activity of gentiopicroside in D-galactosamine/lipopolysaccharide-induced murine fulminant hepatic failure. PubMed: [Simultaneous determination of four constituents in wild Gentiana lawrencei from Qinghai province by RP-HPLC]. PubMed: Simultaneous determination of four iridoid and secoiridoid glycosides and comparative analysis of Radix Gentianae Macrophyllae and their related substitutes by HPLC. PubMed: DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots. PubMed: [Determination of six active components in three species of genus Swertia by HPLC multiwavelength with detection]. PubMed: Sensitive determination of gentiopicroside in medicine and bio-fluids using luminol-myoglobin chemiluminescence combined with flow injection technique. PubMed: Antimicrobial activity of Gentiana lutea L. extracts. PubMed: Changes of gentiopicroside synthesis during somatic embryogenesis in Gentiana macrophylla. PubMed: Further studies on the chemical constituents of Chinese folk medicine Gentiana apiata N.E. Br. PubMed: Gentiopicrin-producing endophytic fungus isolated from Gentiana macrophylla. PubMed: [Optimal technique of wine-processed gentian]. PubMed: [Studies on glycosides from Gentiana veitchiorum]. PubMed: [Chemical constituents from herbs of Swertia delavayi]. PubMed: Fagraldehyde, a secoiridoid isolated from Fagraea fragrans. PubMed: Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro. PubMed: [Enrichment process of gentiopicroside from the leaves of Gentiana macropylla with macroporous resin]. PubMed: Down-regulation of NR2B receptors partially contributes to analgesic effects of Gentiopicroside in persistent inflammatory pain. PubMed: [Preparative separation of gentiopicrin from Radix Gentianae by high-speed counter-current chromatography with macroporous resin]. PubMed: [Determination of iridoids and triterpenes in herb of Swertia pseudochinesis by RP-HPLC]. PubMed: [Investigation on explovitage of Gentiana straminea]. PubMed: Somatic embryogenesis pathway for plant regeneration in Qinjiao (Gentiana macrophylla Pall.). PubMed: Pharmacokinetic behavior of gentiopicroside from decoction of Radix Gentianae, Gentiana macrophylla after oral administration in rats: a pharmacokinetic comaprison with gentiopicroside after oral and intravenous administration alone. PubMed: [Preparative separation of gentiopicrin from Gentiana scabra bunge by high speed counter current chromatography]. PubMed: [Determination of three glycosides from herbs of Swertia punicea by RP-HPLC]. PubMed: [Content of gentiopicroside and loganic acid in Radix gentianae and their fingerprints]. PubMed: Quantitative analysis of iridoids, secoiridoids, xanthones and xanthone glycosides in Gentiana lutea L. roots by RP-HPLC and LC-MS. PubMed: Pharmacokinetics and bioavailability of gentiopicroside from decoctions of Gentianae and Longdan Xiegan Tang after oral administration in rats--comparison with gentiopicroside alone. PubMed: In vivo pharmacokinetic and metabolism studies of ginsenoside Rd. PubMed: Biotransformation of gentiopicroside by asexual mycelia of Cordyceps sinensis. PubMed: [Simultaneous determination of six main constituents in Swertia of Qinghai Province and Sichuan Province by HPLC]. PubMed: Screening of plant extracts for antimicrobial activity against bacteria and yeasts with dermatological relevance. PubMed: [Determination of ginsenoside rd in human plasma by LC/MS/MS]. PubMed: Genetic transformation of Gentiana macrophylla with Agrobacterium rhizogenes: growth and production of secoiridoid glucoside gentiopicroside in transformed hairy root cultures. PubMed: [Inhibition of extracts from 17 Chinese herbs on periodontal pathogenic microbes]. PubMed: Genetic transformation of Centaurium erythraea Rafn by Agrobacterium rhizogenes and the production of secoiridoids. PubMed: Effects of gentiopicroside, sweroside and swertiamarine, secoiridoids from gentian (Gentiana lutea ssp. symphyandra), on cultured chicken embryonic fibroblasts. PubMed: [Studies on the chemical constituents in root of Gentiana macrophylla from Shaanxi]. PubMed: Isolation of iridoid and secoiridoid glycosides and comparative study on Radix gentianae and related adulterants by HPLC analysis. PubMed: [HPLC fingerprinting of total glycosides of Swertia franchetiana]. PubMed: [Determination gentiopicrin in biyanqingdu granulae by SPE-HPLC]. PubMed: Mist trickling bioreactor for Centaurium erythraea Rafn growth of shoots and production of secoiridoids. PubMed: Two new iridoid glycosides from the Tibetan folk medicine Swertia franchetiana. PubMed: [Content determination of loganic acid and gentiopicroside in Tebitan herbal medicines Gentiana macrophylla and G. straminea by HPLC]. PubMed: [Determination of gentiopicroside in different morphological types of cultivated Gentiana manshurica population]. PubMed: [Determination and comparision of gentiopicroside of various parts of five species of genus Gentiana collected from Xinjiang by TLCS]. PubMed: Pharmacokinetics and tissue distribution of gentiopicroside following oral and intravenous administration in mice. PubMed: [Influence of gentian leaf blight on the output and quality of Chinese gentian]. PubMed: Simultaneous determination of some active ingredients in anti-viral preparations of traditional Chinese medicine by micellar electrokinetic chromatography. PubMed: [Comparative botanical and phytochemical investigations on the Gentiana species native to Hungary]. PubMed: Separation and determination of gentiopicroside and swertiamarin in Tibetan medicines by micellar electrokinetic electrophoresis. PubMed: Pharmacological evaluation of several major ingredients of Chinese herbal medicines in human hepatoma Hep3B cells. PubMed: Bioactivity of gentiopicroside from the aerial parts of Centaurium erythraea. PubMed: [Studies on the metabolism of gentiopicroside by rat intestinal flora]. PubMed: Effects of Gentiana lutea ssp. symphyandra on the central nervous system in mice. PubMed: Quantitative determination of secoiridoid glucosides in in vitro propagated plants of Gentiana davidii var. formosana by high performance liquid chromatography. PubMed: Smooth muscle relaxing activity of gentiopicroside isolated from Gentiana spathacea. PubMed: Quantitative determination of secoiridoid and gamma-pyrone compounds in Gentiana lutea cultured in vitro. PubMed: Secoiridoid glycosides and an antifungal anthranilate derivative from Gentiana tibetica. PubMed: Secoiridoids from Gentiana siphonantha. PubMed: Hepatoprotective principles of Swertia japonica Makino on D-galactosamine/lipopolysaccharide-induced liver injury in mice. PubMed: Acyl secoiridoids and antifungal constituents from Gentiana macrophylla. PubMed: Determination of gentiopicroside, mangiferin, palmatine, berberine, baicalin, wogonin and glycyrrhizin in the traditional Chinese medicinal preparation sann-joong-kuey-jian-tang by high-performance liquid chromatography. PubMed: [Chemical constituents of Swertia pubescens Franch]. PubMed: An acetophenone glycoside from Exacum affine. PubMed: Suppression of chemically and immunologically induced hepatic injuries by gentiopicroside in mice. PubMed: [Simultaneous determination of five bitter secoiridoid glycosides in nine Chinese Gentiana species used as the Chinese drug "long dan" by high performance liquid chromatography]. PubMed: Secoiridoid Glucosides Isolated from Gentiana gelida. PubMed: Metabolism of gentiopicroside (gentiopicrin) by human intestinal bacteria. PubMed: In vitro transformations of gentiopicroside and swertiamarin. PubMed: 6'-O-beta-D-Glucosyl Gentiopicroside: A New Secoiridoid from Gentiana asclepiadea. PubMed: [High speed liquid chromatographic determination of gentiopicroside in radix Gentianae]. PubMed: [Isolation and identification of gentiopicroside from the roots of Gentiana triflora Pall]. PubMed: [General survey on medicinal plants of the Gentianaceae family in China]. PubMed: [Comparison of the gentiopicroside content and preparation of the root of Gentiana scabra collected in different seasons and in different growing years]. PubMed: [TLC-densitometry determination of bitter glycosides in the Chinese drug longdan, radix gentianae, and its quality evaluation]. PubMed: Desorption/Chemical ionization mass spectrometry of bitter glycosides from gentiana1. PubMed: Gentiogenal, a conversion product of gentiopicrin (gentiopicroside)*. PubMed: Studies on Iridoid-related Compounds III: Gentiopicral, the Aglucone of Gentiopicroside. PubMed: A New Bitter Secoiridoid Glucoside from Gentiana scabra var. Buergeri. PubMed: Gentiogenal, a new antimicrobial iridoid derived from gentiopicrin (gentiopicroside). PubMed: Fungitoxic activity of the secoiridoid glucoside gentiopicrin (gentiopicroside). PubMed: Secoiridoids and Xanthones in the genus Centaurium. PubMed: [High-speed liquid chromatographic analysis of drugs. IX. Determination of gentiopicroside in Swertiae Herba (author's transl)]. PubMed: [High-speed liquid chromatographic analysis of drugs. VI. Rapid estimation of gentiopicroside in Gentianae scabrae radix and Gentianae radix (author's transl)]. PubMed: [Studies on crude drugs originated from Gentianaceous plants. VI. Contents of gentiopicroside in various parts of Gentiana scabra and accumulation of gentiopicroside in Gentiana triflora]. PubMed: [Studies on crude drugs originated from Gentianaceous plants. I. Determination of gentiopicroside, the bitter principle of Gentianae radix and Gentianae scabrae radix (author's transl)]. PubMed: Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis. PubMed: [On the incorporation of loganin into gentiopicroside]. PubMed: The biological conversion of sweroside into gentiopicroside and vindoline and a biogenetic aspect of some indole alkaloids. PubMed: Biosynthesis of gentiopicroside, a novel monoterpene. PubMed: Studies on gentiopicrin. PubMed: A preliminary study of the hydrolytic products of gentiopicrin by paper chromatography.