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SML2345

Sigma-Aldrich

Rhynchophylline

≥95% (HPLC)

Synonym(s):

(αE,1′R,6′R,7′S,8′aS)-6′-Ethyl-1,2,2′,3′,6′,7′,8′,8′a-octahydro-α-(methoxymethylene)-2-oxo- Spiro[3H-indole-3,1′(5′H)-indolizine]-7′-acetic acid methyl ester, (7β,16E,20α)-16,17-Didehydro-17-methoxy-2-oxo-corynoxan-16-carboxylic acid methyl ester, Mitrinermin, NSC 21731, Rhynchophyllin, Rhyncophylline, Mitrinermine

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About This Item

Empirical Formula (Hill Notation):
C22H28N2O4
CAS Number:
76-66-4
Molecular Weight:
384.47
MDL number:
MFCD00221748
UNSPSC Code:
12352200
NACRES:
NA.77

biological source

Uncaria rhynchophylla

Assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

shipped in

wet ice

storage temp.

−20°C

InChI

1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1

InChI key

DAXYUDFNWXHGBE-KAXDATADSA-N

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Biochem/physiol Actions

Rhynchophylline is a spirocyclic alkaloid isolated from Uncaria species that exibits numerous pharmacological activities including hypotensive, neuroprotective, anticonvulsive, antiepileptic, antiarrhythmic, anticoagulant, antispasmodic, and sedative. Rhynchophylline modulates voltage-gated K+ (Kv) channel slow inactivation in mouse neuroblastoma N2A cells. Also it acts as noncompetitive antagonists of NMDA receptor channels in Xenopus oocytes.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chun-Hsiao Chou et al.
Journal of natural products, 72(5), 830-834 (2009-04-01)
Rhynchophylline (1), a neuroprotective agent isolated from the traditional Chinese medicinal herb Uncaria rhynchophylla, was shown to affect voltage-gated K(+) (Kv) channel slow inactivation in mouse neuroblastoma N2A cells. Extracellular 1 (30 microM) accelerated the slow decay of Kv currents
Hou-Cai Huang et al.
Evidence-based complementary and alternative medicine : eCAM, 2017, 7593027-7593027 (2017-03-30)
Goutengsan, a Chinese herbal formula, potential protection on Alzheimer's disease (AD) has been less reported. In current study, we investigated the protection of Goutengsan on Aβ1-42-induced pheochromocytoma-derived cells (PC12). Furthermore, the components from Goutengsan in rat plasma were identified by
Bao-Yuan Huang et al.
International journal of oncology, 51(1), 257-268 (2017-05-24)
The overexpression of ATP-binding cassette (ABC) transporters is the main cause of cancer multidrug resistance (MDR), which leads to chemotherapy failure. Uncaria alkaloids are the major active components isolated from uncaria, which is a common Chinese herbal medicine. In this

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