Catalogue Number
BF-P3026
Analysis Method
HPLC,NMR,MS
Specification
98%
Storage
-20℃
Molecular Weight
492.47
Appearance
Yellow needle crystal
Botanical Source
Neopicrorhiza scrophulariiflora
Structure Type
Terpenoids
Category
Standards;Natural Pytochemical;API
SMILES
C1=CC=C(C=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3C4C(C=CO3)C(C5C4(O5)CO)O)O)O)O
Synonyms
picroside-1/PicrosideI/2-Propenoic acid, 3-phenyl-, (1aS,1bS,2S,5aR,6S,6aS)-2-(β-D-glucopyranosyloxy)-1a,1b,2,5a,6,6a-hexahydro-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-6-yl ester, (2E)-/β-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl 6-O-[(2E)-1-oxo-3-phenyl-2-propen-1-yl]-/6'-O-trans-cinnamoylcatalpol/(1aS,1bS,2S,5aR,6S,6aS)-6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-2-yl 6-O-[(2E)-3-phenyl-2-propenoyl]-β-D-glucopyranoside/picrosides I/Picroside I/(1aS,1bS,2S,5aR,6S,6aS)-2-(β-D-Glucopyranosyloxy)-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-6-yl (2E)-3-phenylacrylate
IUPAC Name
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]oxan-2-yl]methyl (E)-3-phenylprop-2-enoate
Density
1.6±0.1 g/cm3
Solubility
Methanol; Water
Flash Point
253.2±26.4 °C
Boiling Point
739.1±60.0 °C at 760 mmHg
Melting Point
InChl
InChI=1S/C24H28O11/c25-11-24-16-13(17(27)21(24)35-24)8-9-31-22(16)34-23-20(30)19(29)18(28)14(33-23)10-32-15(26)7-6-12-4-2-1-3-5-12/h1-9,13-14,16-23,25,27-30H,10-11H2/b7-6+/t13-,14-,16-,17+,18-,19+,20-,21+,22+,23+,24-/m1/s1
InChl Key
XZGPUOQGERGURE-LUVHZPKESA-N
WGK Germany
RID/ADR
HS Code Reference
2938900000
Personal Projective Equipment
Correct Usage
For Reference Standard and R&D, Not for Human Use Directly.
Meta Tag
provides coniferyl ferulate(CAS#:27409-30-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
MSDS
27038441
Expression analysis of primary and secondary metabolic pathways genes vis-à-vis shoot regeneration revealed developmental regulation of picroside-I biosynthesis in Picrorhiza kurroa. Picroside-I (P-I) is an important iridoid glycoside used in several herbal formulations for treatment of various disorders. P-I is synthesized in shoots of Picrorhiza kurroa and Picrorhiza scrophulariiflora. Current study reports on understanding P-I biosynthesis in different morphogenetic stages, viz. plant segment (PS), callus initiation (CI), callus mass (CM), shoot primordia (SP), multiple shoots (MS) and fully developed (FD) stages of P. kurroa. Expression analysis of genes involved in primary and secondary metabolism revealed that genes encoding HMGR, PMK, DXPS, ISPE, GS, G10H, DAHPS and PAL enzymes of MVA, MEP, iridoid and shikimate/phenylpropanoid pathways showed significant modulation of expression in SP, MS and FD stages in congruence with P-I content compared to CM stage. While HK, PK, ICDH, MDH and G6PDH showed high expression in MS and FD stages of P. kurroa, RBA, HisK and CytO showed high expression with progress in regeneration of shoots. Quantitative expression analysis of secondary metabolism genes at two temperatures revealed that 7 genes HMGR, PMK, DXPS, GS, G10H, DAHPS and PAL showed high transcript abundance (32-87-folds) in FD stage derived from leaf and root segments at 15 °C compared to 25 °C in P. kurroa. Further screening of these genes at species level showed high expression pattern in P. kurroa (6-19-folds) vis-à-vis P. scrophulariiflora that was in corroboration with P-I content. Therefore, current study revealed developmental regulation of P-I biosynthesis in P. kurroa which would be useful in designing a suitable genetic intervention study by targeting these genes for enhancing P-I production.
Gene expression; Morphogenetic stages; P-I; Picrorhiza kurroa; Picrorhiza scrophulariiflora; Primary metabolism; Secondary metabolism.
Discerning picroside-I Biosynthesis via Molecular Dissection of in Vitro Shoot Regeneration in Picrorhiza Kurroa
Neha Sharma 1 , Rajinder Singh Chauhan 1 , Hemant Sood 2
2016 Aug
30077096
Picroside I is an iridoid glycoside derived from Picrorhiza kurroa Royle ex Benth and Picrorhiza scrophulariiflora Pennell and characterized by many biological activities. In this study, a fast, selective, and sensitive UHPLC-MS/MS method was developed and validated to determine picroside I in rat plasma. Analytes were separated by using an ACQUITY UPLC® BEH C18 (2.1 × 50 mm, 1.7 μm) column at a running time of 2 min. Selected reaction monitoring (SRM) transitions were m/z 491.1 → 147.1 for picroside I and m/z 511.1 → 235.1 for the internal standard in a negative ion mode. The established UHPLC-MS/MS method achieved good linearity for picroside I within the range of 0.1-500 ng/mL. The validated method was successfully applied for the pharmacokinetic analysis of picroside I in rats after oral administration. Fifteen metabolites of picroside I were tentatively identified through ultra-high-performance chromatography/tandem quadrupole time-of-flight mass spectrometry, and four metabolites were identified by comparing with the standards. Besides, nine of these metabolites were discovered for the first time. The proposed metabolic pathways of picroside I in vivo can be divided into four parts, namely, phase I reaction of picroside I, including hydroxylation and deoxygenation; phase II reaction of picroside I, including glucuronidation, sulfation, and methylation; phase I biotransformations of metabolites, such as reduction and hydroxylation; and phase II biotransformations of metabolites, such as glucuronidation and sulfation. These results could offer insights into the effectiveness and toxicity of picroside I.
Gene expression; Morphogenetic stages; P-I; Picrorhiza kurroa; Picrorhiza scrophulariiflora; Primary metabolism; Secondary metabolism.
Metabolic Profiles and Pharmacokinetics of Picroside I in Rats by Liquid Chromatography Combined With Electrospray Ionization Tandem Mass Spectrometry
Kai Xiong 1 , Zhengcai Ju 2 , Tong Zhang 3 , Zhengtao Wang 2 , Han Han 4
2018 Sep 15
29333043
Background: Picrorhiza kurroa (PK) belongs to Scrophulariaceae family and is a representative endemic, medicinal herb, widely distributed throughout the higher altitudes of alpine Himalayas from west to east, between 3000 and 4500 m above mean sea level.
Objective: The objective of the present study is to assess the production of picroside I and picroside II from tissue cultures of PK.
Materials and methods: Auxiliary shoot tips of PK were incubated in Murashige and Skoog medium supplemented with indole-3-butyric acid and kinetin phytohormones. The callus produced was collected at different time intervals and was processed for extraction of picroside I and picroside II followed by thin layer chromatography and high-performance liquid chromatography HPLC analysis.
Results: The maximum growth index was found to be 5.109 ± 0.159 at 16-week-old callus culture. The estimation of picroside-I and picroside-II was carried out by (HPLC) analysis; quantity of secondary metabolite found to be 16.37 ± 0.0007 mg/g for PK-I and 6.34 ± 0.0012 mg/g for PK-II.
Conclusion: This is the first attempt to produce the Picroside-I and II in large amount by the tissue culture technique. It can be observed that the method of callus culture can be used in production of secondary metabolites Picroside-I and II from PK.
Summary: Picrorhiza kurroa is a high value medicinal herb due to rich source of hepatoprotective metabolites, Picroside-I and Picroside-II. The medicinal importance of P. kurroa is due to its pharmacological properties like hepatoprotective, antioxidant (particularly in liver), antiallergic and antiasthamatic, anticancer activity particularly in liver and immunomodulatory. Shoot apices which were produced a good response was inoculated on selected medium i.e., on MS medium containing 2, 4 D (mg/l) + KN (1mg/l) for induction of callus. The initiation of callus was observed after 4weeks and it was light green and fragile Maximum growth was observed with 3% w/v of sucrose supplement. The callus culture was maintained and growth index was recorded after every subculture. The growth index was calculated from the obtained final dried weight divided by initial weight.Abbreviations Used: PK-Picrorhizakurroa, IBA-Indole-3-butyricacid, KN-Kinetin, 2,4D-2,4Dichlorophenoxy acetic acid.
Picrorhiza kurroa; picroside I; picroside II; tissue cultures.
Picroside I and Picroside II From Tissue Cultures of Picrorhiza kurroa
Yamjala Ganeshkumar 1 , Ajmera Ramarao 1 , Ciddi Veeresham 1
2017 Dec
