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Hardwickiic acid

$1,120

  • Brand : BIOFRON

  • Catalogue Number : BN-O1594

  • Specification : 98%(HPLC)

  • CAS number : 1782-65-6

  • Formula : C20H28O3

  • Molecular Weight : 316.43452

  • PUBCHEM ID : 6451316

  • Volume : 5mg

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Catalogue Number

BN-O1594

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

316.43452

Appearance

Powder

Botanical Source

This product is isolated and purified from the herbs of Hardwickia pinnata

Structure Type

Diterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1CCC2(C(C1(C)CCC3=COC=C3)CCC=C2C(=O)O)C

Synonyms

1-Naphthalenecarboxylic acid, 5-[2-(3-furanyl)ethyl]-3,4,4a,5,6,7,8,8a-octahydro-5,6,8a-trimethyl-, (4aR,5S,6R,8aR)-/(-)-Hardwickiic acid/(4aR,5S,6R,8aR)-5-[2-(3-Furyl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1-naphthalenecarboxylic acid/(-)-Hardwickic acid

IUPAC Name

(4aR,5R,6R,8aR)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Density

1.1±0.1 g/cm3

Solubility

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

Flash Point

212.2±21.2 °C

Boiling Point

427.2±18.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)/t14-,17-,19-,20+/m1/s1

InChl Key

HHWOKJDCJVESIF-JRJVTICQSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:1782-65-6) 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

26944237

Abstract

Ethnopharmacological relevance: Croton urucurana (Euphorbiaceae) is popularly used in Brazil to treat inflammatory processes, pain, and gastric ulcers.

Aim of study: To evaluate the anti-inflammatory and antinociceptive properties of the methanol extract from the bark of C. urucurana (MECu) in mice and identify its chemical constituents.

Materials and methods: The extract was characterized by UHPLC-DAD-ESI-Q-TOF-MS/MS. Extract doses of 25, 100, and 400mg/kg were employed in the biological assays. Evaluation of anti-inflammatory activity was based on paw edema and leukocyte recruitment into the peritoneal cavity of mice, both induced by carrageenan. Abdominal writhing caused by acetic acid and duration of formalin-induced paw-licking were the models employed to evaluate antinociceptive activity.

Results: Ten compounds were identified in the extract: (+)-gallocatechin (1), procyanidin B3 (2), (+)-catechin (3), (-)-epicatechin (4), tembetarine (5), magnoflorine (6), taspine (7), methyl-3-oxo-12-epi-barbascoate (8), methyl-12-epi-barbascoate (9), and hardwickiic acid (10). This is the first report of compounds 2, 4, 6, 7, and 10 in C. urucurana and compound 5 in the genus Croton. In addition to inhibiting paw edema and leukocyte recruitment (particularly of polymorphonuclear cells) into the peritoneal cavity of mice, MECu reduced the number of abdominal writhings induced by acetic acid and the duration of formalin-induced paw licking.

Conclusions: The methanol extract of C. urucurana bark exhibited anti-inflammatory and antinociceptive properties, corroborating its use in folk medicine. These effects may be related to the presence of diterpenes, alkaloids, and flavonoids.

KEYWORDS

(+)-Catechin (PubChem CID: 9064); (+)-gallocatechin (PubChem CID: 65084); (−)-epicatechin (PubChem CID: 72276); Euphorbiaceae; Inflammation; Medicinal plants; Methyl-3-oxo-12-epi-barbascoate (8) methyl-12-epi-barbascoate (9); Pain; Sangra-d'agua; hardwickiic acid (PubChem CID: 161454); magnoflorine (PubChem CID: 73337); procyanidin B3 (PubChem CID: 146798); taspine (PubChem CID: 215159); tembetarine (PubChem CID: 167718).

Title

Anti-inflammatory and Antinociceptive Activities of Croton Urucurana Baillon Bark

Author

Katia Wolff Cordeiro 1, Josyelen Lousada Felipe 2, Kauê Franco Malange 2, Pamela Rafaela do Prado 3, Patricia de Oliveira Figueiredo 3, Fernanda Rodrigues Garcez 3, Karine de Cassia Freitas 2, Walmir Silva Garcez 3, Mônica Cristina Toffoli-Kadri 4

Publish date

2016 May 13

PMID

30525440

Abstract

For an affliction that debilitates an estimated 50 million adults in the United States, the current chronic pain management approaches are inadequate. The Centers for Disease Control and Prevention have called for a minimization in opioid prescription and use for chronic pain conditions, and thus, it is imperative to discover alternative non-opioid based strategies. For the realization of this call, a library of natural products was screened in search of pharmacological inhibitors of both voltage-gated calcium channels and voltage-gated sodium channels, which are excellent targets due to their well-established roles in nociceptive pathways. We discovered (-)-hardwickiic acid ((-)-HDA) and hautriwaic acid (HTA) isolated from plants, Croton californicus and Eremocarpus setigerus, respectively, inhibited tetrodotoxin-sensitive sodium, but not calcium or potassium, channels in small diameter, presumptively nociceptive, dorsal root ganglion (DRG) neurons. Failure to inhibit spontaneous postsynaptic excitatory currents indicated a preferential targeting of voltage-gated sodium channels over voltage-gated calcium channels by these extracts. Neither compound was a ligand at opioid receptors. Finally, we identified the potential of both (-)-HDA and HTA to reverse chronic pain behavior in preclinical rat models of HIV-sensory neuropathy, and for (-)-HDA specifically, in chemotherapy-induced peripheral neuropathy. Our results illustrate the therapeutic potential for (-)-HDA and HTA for chronic pain management and could represent a scaffold, that, if optimized by structure-activity relationship studies, may yield novel specific sodium channel antagonists for pain relief.

KEYWORDS

(−)-hardwickiic acid; HIV-associated sensory neuropathy; Natural products; chemotherapy-induced peripheral neuropathy; hautriwaic acid; non-opioid; voltage-gated sodium channels.

Title

(-)-Hardwickiic Acid and Hautriwaic Acid Induce Antinociception via Blockade of Tetrodotoxin-Sensitive Voltage-Dependent Sodium Channels

Author

Song Cai, Shreya S Bellampalli, Jie Yu 1, Wennan Li, Yingshi Ji 2, E M Kithsiri Wijeratne, Angie Dorame, Shizhen Luo, Zhiming Shan 3, May Khanna 4, Aubin Moutal, John M Streicher, A A Leslie Gunatilaka, Rajesh Khanna 4

Publish date

2019 Mar 20;

PMID

14510607

Abstract

Three new neoclerodane diterpenoids, divinatorins A-C (7-9), have been isolated from the leaves of Salvia divinorum. The compounds were identified by spectroscopic methods as derivatives of the antibiotic (-)-hardwickiic acid (10), which was also isolated, along with four other known terpenoids. Neither the crude extract nor 7-9 displayed antimicrobial activity.

Title

Divinatorins A-C, New Neoclerodane Diterpenoids From the Controlled Sage Salvia Divinorum

Author

Andrea K Bigham 1, Thomas A Munro, Mark A Rizzacasa, Roy M Robins-Browne

Publish date

2003 Sep


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