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Lappaconitine

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-L4008

  • Specification : 98%(HPLC)

  • CAS number : 32854-75-4

  • Formula : C32H44N2O8

  • Molecular Weight : 584.7

  • PUBCHEM ID : 5281279

  • Volume : 25mg

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Catalogue Number

BF-L4008

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

584.7

Appearance

White needle crystal

Botanical Source

Aconitum bulleyanum,Aconitum leucostomum,Aconitum sinomontanum

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCN1CC2(CCC(C34C2CC(C31)C5(CC(C6CC4C5(C6OC)O)OC)O)OC)OC(=O)C7=CC=CC=C7NC(=O)C

Synonyms

LAPPACONITINE/(1a,14a,16b)-20-Ethyl-1,14,16-trimethoxyaconitane-4,8,9-triol 4-[2-(Acetylamino)benzoate]/acetyl-10-deoxysepaconitine/(1α,14α,16β)-20-Ethyl-8,9-dihydroxy-1,14,16-trimethoxyaconitan-4-yl 2-acetamidobenzoate/Benzoic acid, 2-(acetylamino)-, (1α,14α,16β)-20-ethyl-8,9-dihydroxy-1,14,16-trimethoxyaconitan-4-yl ester/N-Acetylpuberanidine/lappaconintine/Aconitum kusnezoffii Reichb

IUPAC Name

[(1S,2S,3S,4S,5R,6S,8S,9R,13S,16S,17S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl] 2-acetamidobenzoate

Density

1.4±0.1 g/cm3

Solubility

Methanol

Flash Point

389.7±32.9 °C

Boiling Point

720.7±60.0 °C at 760 mmHg

Melting Point

217-218ºC

InChl

InChI=1S/C32H44N2O8/c1-6-34-16-29(42-28(36)18-9-7-8-10-21(18)33-17(2)35)12-11-25(40-4)31-23(29)14-20(26(31)34)30(37)15-22(39-3)19-13-24(31)32(30,38)27(19)41-5/h7-10,19-20,22-27,37-38H,6,11-16H2,1-5H3,(H,33,35)/t19-,20+,22+,23-,24+,25+,26?,27+,29-,30+,31+,32+/m1/s1

InChl Key

NWBWCXBPKTTZNQ-BAERZWJTSA-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#:32854-75-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29926144

Abstract

Lappaconitine is a representative C18-diterpenoid alkaloid extracted from Aconitum sinomontanum Nakai and has been prescribed as a pain relief medicine in China for more than 30 years. This study evaluated its antihypersensitivity activity in the rat models of neuropathic and cancer pains and explored its underlying mechanisms. Subcutaneous injection of cumulative doses of lappaconitine produced dose-dependent mechanical antiallodynia and thermal antihyperalgesia in spinal nerve ligation-induced neuropathic rats. The cumulative dose-response analysis exhibited their Emax values of 53.3 and 58.3% MPE, and ED50 values of 1.1 and 1.6 mg/kg. Single intrathecal lappaconitine dose in neuropathy also dose- and time-dependently blocked mechanical allodynia, with an Emax of 66.1% MPE and an ED50 of 0.8 μg. Its multiple twice-daily intrathecal administration over 7 days did not induce mechanical antiallodynic tolerance. Subcutaneous cumulative doses of lappaconitine also produced dose-dependent blockade of mechanical allodynia in the rat bone cancer pain model induced by tibia implantation of cancer cells, with the Emax of 57.9% MPE and ED50 of 2.0 mg/kg. Furthermore, lappaconitine treatment stimulated spinal dynorphin A expression in neuropathic rats, and in primary cultures of microglia but not neurons or astrocytes. Intrathecal pretreatment with the specific microglia depletor liposome-encapsulated clodronate, dynorphin A antibody, and κ-opioid receptor antagonist GNTI totally suppressed intrathecal and subcutaneous lappaconitine-induced mechanical antiallodynia. This study suggests that lappaconitine exhibits antinociception through directly stimulating spinal microglial dynorphin A expression. Graphical Abstract

KEYWORDS

Bone cancer pain; Dynorphin a; Lappaconitine; Neuropathic pain; Spinal microglia.

Title

Lappaconitine, a C18-diterpenoid Alkaloid, Exhibits Antihypersensitivity in Chronic Pain Through Stimulation of Spinal Dynorphin A Expression

Author

Ming-Li Sun 1 , Jun-Ping Ao 2 , Yi-Rui Wang 1 , Qian Huang 1 , Teng-Fei Li 1 , Xin-Yan Li 1 , Yong-Xiang Wang 3 4

Publish date

2018 Sep

PMID

30723741

Abstract

Lappaconitine is extracted from Aconitum sinomontanum Nakai, which belongs to the Ranunculaceae. Lappaconitine is as a diterpenoid alkaloid used as a nonaddictive analgesic. To assure the rational use of the drug, ultrahigh-pressure liquid chromatography tandem mass spectrometry (UPLC-MS/MS) was conducted to determine lappaconitine in mouse blood and its application to pharmacokinetics. In this study, khasianine was used as internet standard (IS). A UPLC BEH C18 column was used for chromatographic separation and the mobile phase consisted of acetonitrile and 10 mmol/L ammonium acetate (0.1% formic acid). The flow rate of was 0.4 mL/min. Quantitative detection was performed in a multiple reaction monitoring (MRM) mode using an electrospray ionization source in positive mode. Twenty-four mice were randomly divided into four groups, three of which received 2, 4, and 8 mg/kg lappaconitine by intragastric administration, while the other group received 1 mg/kg lappaconitine by intravenous administration. After 0.0833, 0.5, 1, 1.5, 2, 3, 4, and 8 h, blood samples were collected and acetonitrile was used for protein precipitation. A linear calibration relationship (R2 = 0.9979) in the range of 0.1-500 ng/mL in mouse blood indicated good results. The lower limit of quantitation was 0.1 ng/mL and the limit of detection was 0.04 ng/mL. The intra-day and inter-day precision were below 13% and 14%, respectively. The accuracy was 90.1-107.2%, and the recovery exceeded 81.1%. The matrix effect ranged between 102.1 and 108.8%. The absolute bioavailability of lappaconitine was 2.0%. UPLC-MS/MS achieved high sensitivity, speed, and selectivity. Methodological verification indicated this method as suitable for determination of lappaconitine in mouse blood.

KEYWORDS

Bone cancer pain; Dynorphin a; Lappaconitine; Neuropathic pain; Spinal microglia.

Title

Quantification of Lappaconitine in Mouse Blood by UPLC-MS/MS and Its Application to a Pharmacokinetic Study

Author

Fan Chen 1 , Xiuwei Shen 1 , Peng Huang 1 , Huiyan Fu 2 , Yue Jin 2 , Congcong Wen 2

Publish date

2019 Jan 6

PMID

26019998

Abstract

Bone pain is a common and severe symptom in cancer patients. The present study employed a mouse model of leukemia bone pain by injection K562 cells into tibia of mouse to evaluate the analgesic effects of lappacontine. Our results showed that the lappaconitine treatment at day 15, 17 and 19 could effectively reduce the spontaneous pain scoring values, restore reduced degree in the inclined-plate test induced by injection of K562 cells, as well as restore paw mechanical withdrawal threshold and paw withdrawal thermal latency induced by injection of K562 cells to the normal levels. Additionally, the molecular mechanisms of lappaconitine’s analgesic effects may be related to affect the expression levels of endogenous opioid system genes (POMC, PENK and MOR), as well as apoptosis-related genes (Xiap, Smac, Bim, NF-κB and p53). Our present results indicated that lappaconitine may become a new analgesic agent for leukemia bone pain management.

KEYWORDS

Analgesia; Bone pain; Lappaconitine; Leukemia.

Title

Analgesic Effects of Lappaconitine in Leukemia Bone Pain in a Mouse Model

Author

Xiao-Cui Zhu 1 , Chen-Tao Ge 1 , Pan Wang 1 , Jia-Li Zhang 1 , Yuan-Yang Yu 1 , Cai-Yun Fu 1

Publish date

2015 May 7


Description :

Lappaconitine, isolated from Aconitum sinomontanum Nakai, was characterized as analgesic principle.IC50 value:Target:In vitro: In vivo: Lappaconitine was characterized as analgesic principle by our laboratory. The results suggest that lappaconitine can produce analgesia, possibly through a decrease in cellular calcium availability and PAG may be involved in the Ca2+ antagonistic effect on lappaconitine analgesia [1]. Changes in lappaconitine levels in blood, brain and spinal cord following subcutaneous (s.c.) injection were correlated with the analgesic activity at intervals up to 90 minutes after injection. The equianalgesic doses of lappaconitine (ED50 by the s.c. route and additive ED50 by the i.c.v. plus i.t. route) gave closely similar concentrations of the drug in brain and spinal cord. These results indicate that a simultaneous action of lappaconitine on supraspinal and spinal sites is likely to be important for the analgesia produced by systemically administered lappaconitine [2].