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Calenduloside E

$538

  • Brand : BIOFRON

  • Catalogue Number : BD-P0487

  • Specification : 98.0%(HPLC)

  • CAS number : 26020-14-4

  • Formula : C36H56O9

  • Molecular Weight : 632.84

  • PUBCHEM ID : 176079

  • Volume : 25mg

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Catalogue Number

BD-P0487

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

632.84

Appearance

Powder

Botanical Source

Structure Type

Triterpenoids

Category

SMILES

CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)O)C)C)C2C1)C)C(=O)O)C

Synonyms

(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

IUPAC Name

(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Applications

Density

1.3±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

228.6±26.4 °C

Boiling Point

750.8±60.0 °C at 760 mmHg

Melting Point

243-245 ºC (decomp)

InChl

InChI=1S/C36H56O9/c1-31(2)14-16-36(30(42)43)17-15-34(6)19(20(36)18-31)8-9-22-33(5)12-11-23(32(3,4)21(33)10-13-35(22,34)7)44-29-26(39)24(37)25(38)27(45-29)28(40)41/h8,20-27,29,37-39H,9-18H2,1-7H3,(H,40,41)(H,42,43)/t20-,21-,22+,23-,24-,25-,26+,27-,29+,33-,34+,35+,36-/m0/s1

InChl Key

IUCHKMAZAWJNBJ-RCYXVVTDSA-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#:26020-14-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30219960

Abstract

Oleanolic acid glucuronosyltransferase (OAGT) genes synthesizing the direct precursor of oleanane-type ginsenosides were discovered. The four recombinant proteins of OAGT were able to transfer glucuronic acid at C-3 of oleanolic acid that yields oleanolic acid 3-O-β-glucuronide. Ginsenosides are the primary active components in the genus Panax, and great efforts have been made to elucidate the mechanisms underlying dammarane-type ginsenoside biosynthesis. However, there is limited information on oleanane-type ginsenosides. Here, high-performance liquid chromatography analysis demonstrated that oleanane-type ginsenosides (particularly ginsenoside Ro and chikusetsusaponin IV and IVa) are the abundant ginsenosides in Panax zingiberensis, an extremely endangered Panax species in southwest China. These ginsenosides are derived from oleanolic acid 3-O-β-glucuronide, which may be formed from oleanolic acid catalyzed by an unknown oleanolic acid glucuronosyltransferase (OAGT). Transcriptomic analysis of leaves, stems, main roots, and fibrous roots of P. zingiberensis was performed, and a total of 46,098 unigenes were obtained, including all the identified homologous genes involved in ginsenoside biosynthesis. The most upstream genes were highly expressed in the leaves, and the UDP-glucosyltransferase genes were highly expressed in the roots. This finding indicated that the precursors of ginsenosides are mainly synthesized in the leaves and transported to different parts for the formation of particular ginsenosides. For the first time, enzyme activity assay characterized four genes (three from P. zingiberensis and one from P. japonicus var. major, another Panax species with oleanane-type ginsenosides) encoding OAGT, which particularly transfer glucuronic acid at C-3 of oleanolic acid to form oleanolic acid 3-O-β-glucuronide. Taken together, our study provides valuable genetic information for P. zingiberensis and the genes responsible for synthesizing the direct precursor of oleanane-type ginsenosides.

KEYWORDS

Biosynthesis; Ginsenosides; Oleanolic acid glucuronosyltransferase (OAGT); Transcriptome; Triterpenoid saponins.

Title

Transcriptome analysis of Panax zingiberensis identifies genes encoding oleanolic acid glucuronosyltransferase involved in the biosynthesis of oleanane-type ginsenosides

Author

Qing-Yan Tang 1 2, Geng Chen 1, Wan-Ling Song 1, Wei Fan 1, Kun-Hua Wei 3, Si-Mei He 1, Guang-Hui Zhang 1, Jun-Rong Tang 1, Ying Li 1, Yuan Lin 1, Sheng-Chao Yang 4

Publish date

2019 Feb;

PMID

21237343

Abstract

Background: The spermicidal activity of oleanolic acid 3-β-D-glucuronide (OAG), an active principle isolated from root extracts of Sesbania sesban, was evaluated.

Study design: Under the Sander-Cramer test criteria, the sperm-immobilizing activity of OAG was studied using highly motile rat sperm. Sperm mortality and membrane integrity were assessed by supravital staining, hypo-osmotic swelling (HOS), transmission electron microscopy (TEM) and sperm membrane lipid peroxidation (LPO). In vitro microbicidal potential and hemolytic index of OAG were examined in Lactobacillus culture and rat red blood corpuscles (RBCs), respectively. Post-intravaginal OAG application, the in vivo contraceptive efficacy was evaluated in rats. Ames test determined the carcinogenic potential of OAG.

Results: The minimum effective concentration (MEC) of OAG was 50 mcg/mL. More than 97% of the OAG-treated sperm lost their HOS responsiveness in a dose-dependent manner. TEM and LPO revealed that OAG affected the sperm membrane integrity. OAG declined fertility to zero, was nonmutagenic and was not harmful to lactobacillus.

Conclusion: OAG has significant spermicidal activity that may be explored further.

Title

Potent spermicidal effect of oleanolic acid 3-beta-D-glucuronide, an active principle isolated from the plant Sesbania sesban Merrill

Author

Nilanjana Das 1, Poornima Chandran, Smritinath Chakraborty

Publish date

2011 Feb

PMID

10428392

Abstract

The effects of various oleanolic acid glycosides obtained from medicinal herbs on gastrointestinal transit (GIT) and ileus were investigated in fasted mice. Ileus was induced by the peritoneal-irritation or by the laparotomy with manipulation. One hour after the oral administration, three oleanolic acid 3-O-monodesmosides (oleanolic acid 3-O-glucuronide (3, 50 mg/kg), momordin Ic (4, 25 and 50 mg/kg), and momordin I (6, 25 mg/kg)) significantly accelerated GIT, but two oleanolic acid 3-O-monodesmosides (28-deglucosyl-chikusetsusaponins IV (8) and V (10)), oleanolic acid 3,28-O-bisdesmosides (momordin IIc (5), chikusetsusaponins IV (7) and V (9)), and their common aglycon (oleanolic acid (1)) (50 mg/kg) showed no significant effect. On the other hand, oleanolic acid 28-O-monodesmoside (compound O (2, 50 mg/kg)) significantly inhibited GIT. 4 (5-25 mg/kg) and 6 (12.5 and 25 mg/kg) also significantly prevented the inhibition of GIT induced by the peritoneal injection of acetic acid. 2 and 9 (50 mg/kg) significantly potentiated the inhibition of GIT, whereas 1, 3, 5, 7, 8, and 10 (50 mg/kg) showed no significant effect. 3, 4, 6, and 10 (50 mg/kg) significantly prevented the inhibition of GIT induced by laparotomy with manipulation, while 1, 2, 5, 7, 8, and 9 (50 mg/kg) showed no significant effect. These results indicate that the 3-O-glycoside moiety seems to be essential to show the GIT accelerating activity, and the 28-O-glucoside moiety reduce the activity. The accelerations of GIT by 3, 4, and 6 were completely abolished by the pretreatment with streptozotocin (100 mg/kg, i.v.), but not by the pretreatment with capsaicin (75 mg/kg in total, s.c.). These results suggest that sympathetic nervous system, but not capsaicin-sensitive sensory nerves, be involved in the enhancements of GIT by 3, 4, and 6. It is worthy to study their therapeutical effect in the prevention of the inhibition of GIT, including ileus, in clinic.

Title

Effects of oleanolic acid glycosides on gastrointestinal transit and ileus in mice

Author

Y Li 1, H Matsuda, M Yoshikawa

Publish date

1999 Jun