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Harpagide

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-H1001

  • Specification : 98%

  • CAS number : 05-08-26

  • Formula : C15H24O10

  • Molecular Weight : 364.35

  • PUBCHEM ID : 10044294

  • Volume : 20mg

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Catalogue Number

BF-H1001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

364.35

Appearance

White crystal

Botanical Source

roots of Scrophularia ningpoensis Hemsl.

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O

Synonyms

4a,5,7-Trihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl hexopyranoside/Hexopyranoside, 1,4a,5,6,7,7a-hexahydro-4a,5,7-trihydroxy-7-methylcyclopenta[c]pyran-1-yl

IUPAC Name

(1S,4aS,5R,7S)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,7-triol

Density

1.7±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

339.1±31.5 °C

Boiling Point

637.1±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6-,7-,8-,9+,10-,11-,12+,13+,14+,15-/m1/s1

InChl Key

XUWSHXDEJOOIND-YYDKPPGPSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:6926-08-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30940474

Abstract

The neuronal apoptosis program associated with spinal cord injury (SCI) has a severe impact on spinal cord function, which leads to further secondary and permanent neuronal damage that may cause irreparable damage to the central nervous system. Activation of the Wnt/β-catenin signaling pathway is effective in reducing apoptosis and preventing SCI. Harpagide is one of the main active constituents of the iridoid class of molecules, which have neuroprotective effects after SCI. In this study, we demonstrated that harpagide attenuated neuronal apoptosis via activation of the Wnt/β-catenin signaling pathway. This resulted in a promotion of axonal regeneration and an inhibition of glial scar formation, which ultimately improved functional behavioral recovery after SCI in rats. Specifically, the administration of harpagide after SCI increased the expression levels of β-catenin, c-myc and cyclin D1 proteins in spinal cord neurons, as well as increased the number of motor neurons and reduced the size of the SCI lesion area. In addition, the administration of harpagide after SCI also decreased the protein expression levels as well as the number of cells immuno-stained for the pro-apoptotic proteins Bax and cleaved-caspase 3. The expression level of the anti-apoptotic protein Bcl-2 was also increased. When the Wnt /β-catenin signaling pathway was inhibited, a weakened anti-apoptotic effect of harpagide was observed. Additionally, the application of harpagide led to an increase in NF200 staining and a reduction in GFAP staining in the SCI injury site. In summary, our study suggested that harpagide may be a promising drug for the treatment of SCI.

Copyright © 2019. Published by Elsevier Inc.

KEYWORDS

Apoptosis; Axon regeneration; Harpagide; Neuroprotection; Spinal cord injury; Wnt/β-catenin

Title

Harpagide inhibits neuronal apoptosis and promotes axonal regeneration after spinal cord injury in rats by activating the Wnt/β-catenin signaling pathway.

Author

Rong Y1, Liu W1, Zhou Z2, Gong F1, Bai J3, Fan J1, Li L1, Luo Y1, Zhou Z1, Cai W4.

Publish date

2019 May

PMID

30133513

Abstract

Harpagide and its derivatives have valuable medicinal properties, such as anti-inflammatory, analgesic and potential antirheumatic effects. There is the demand for searching plant species containing these iridoids or developing biotechnological methods to obtain the compounds. The present study investigated the effects of methyl jasmonate (MeJa, 50 μM), ethephon (Eth, 50 μM) and L-phenylalanine (L-Phe, 2.4 g/L of medium), added to previously selected variant of Murashige and Skoog medium (supplemented with plant growth regulators: 6-benzylaminopurine 1.0 mg/L, α-naphthaleneacetic acid 0.5 mg/L, gibberellic acid 0.25 mg/L) on the accumulation of harpagide and 8-O-acetyl-harpagide in Melittis melissophyllum L. agitated shoot cultures. Plant material was harvested 2 and 8 days after the supplementation. Iridoids were quantitatively analyzed by the UPLC-MS/MS method in extracts from the biomass and the culture medium. It was found that all of the variants caused an increase in the accumulation of harpagide. In the biomass harvested after 2 days, the highest harpagide content of 247.3 mg/100 g DW was found for variant F (L-Phe and Eth), and the highest 8-O-acetyl-harpagide content of 138 mg/100 g DW for variant E (L-Phe and MeJa). After 8 days, in some variants, a portion of the metabolites was released into the culture medium. Considering the total amount of the compounds (in the biomass and medium), the highest accumulation of harpagide, amounting to 619 mg/100 g DW, was found in variant F, and the highest amount of 8-O-acetyl-harpagide, of 255.4 mg/100 g DW, was found in variant H (L-Phe, MeJa, Eth) when harvested on the 8th day. These amounts were, respectively, 24.7 and 4.8 times higher than in the control culture, and were, respectively, 15 and 6.7 times higher than in the leaves of the soil-grown plant. The total amount of the two iridoids was highest for variant F (0.78% DW) and variant H (0.68% DW) when harvested on the 8th day. The results indicate that the agitated shoot cultures of M. melissophyllum can be a rich source of harpagide and 8-O-acetyl-harpagide, having a potential practical application. To the best of our knowledge we present for the first time the results of the quantitative UPLC-MS/MS analysis of harpagide and 8-O-acetyl-harpagide in M. melissophyllum shoot cultures and the enhancement of their accumulation by means of medium supplementation with elicitors and precursor.

Title

Enhanced accumulation of harpagide and 8-O-acetyl-harpagide in Melittis melissophyllum L. agitated shoot cultures analyzed by UPLC-MS/MS.

Author

Skrzypczak-Pietraszek E1, Reiss K1, Żmudzki P2, Pietraszek J3.

Publish date

2018 Aug 22

PMID

26712566

Abstract

ETHNOPHARMACOLOGICAL RELEVANCE:
Harpagide, an iridoid glucoside, is a constituent of the root of Harpagophytum procumbens var. sublobatum (Engl.) Stapf, Devil’s claw which has been used in patients with osteoarthritis (OA). In the present study, we investigated the anti-osteoporotic potential of harpagide and its underlying mechanism of action in in vitro cell culture and in vivo bone loss animal models.

MATERIAL AND METHODS:
Harpagide was obtained from the alkalic hydrolysis of harpagoside, a major constituent of H. procumbens var. sublobatum Analysis of biomarkers for bone formation in osteoblastic MC3T3-E1 cells and bone resorption in osteoclast cells derived from mouse bone marrow cells was performed to evaluate the mechanism of action. The protective activity of harpagide against bone loss was also evaluated in ovariectomized (OVX) mouse model.

RESULTS:
Harpagide improved bone properties by stimulating the process of differentiation and maturation of osteoblast cells and suppressing the process of RANKL-induced differentiation of osteoclast cells. In OVX-induced bone loss mouse model, oral administration of harpagide significantly improved recovery of bone mineral density, trabecular bone volume, and trabecular number in the femur. Harpagide also prevented increase of trabecular separation and structure model index induced by OVX. Harpagide effectively inhibited the serum levels of biochemical markers of bone loss, including alkaline phosphatase, osteocalcin, C-terminal telopeptide, and tartrate-resistant acid phosphatase.

CONCLUSION:
Taken together, the present study demonstrates that harpagide has a potential for prevention of bone loss in OVX mice by regulating the stimulation of osteoblast differentiation and the suppression of osteoclast formation. Therefore, these findings suggest that harpagide might serve as a bioactive compound derived from H. procumbens var. sublobatum for improvement of age-dependent bone destruction disease.

Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

KEYWORDS

Anti-osteoporotic activity; H. procumbens var. sublobatum (Engl.) Stapf; Harpagide; Osteoblast; Osteoclast; Ovariectomized mice

Title

Anti-osteoporotic activity of harpagide by regulation of bone formation in osteoblast cell culture and ovariectomy-induced bone loss mouse models.

Author

Chung HJ1, Kyung Kim W2, Joo Park H2, Cho L2, Kim MR3, Kim MJ3, Shin JS3, Ho Lee J3, Ha IH3, Kook Lee S4.

Publish date

2016 Feb 17


Description :

Harpagide is a class of iridoid glycoside isolated from Scrophularia cryptophila and has antiparasitic activity, which exhibits good in vitro trypanocidal activities against African trypanosomes (T.b. rhodesiense) with an IC50 of 21 μg/mL. Harpagide exerts significant antileishmanial activity against L. donovani with an IC50 value of 2.0 μg/mL. Harpagide also possess significant anti-inflammatory activities[1][2].