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tuberostemonine

$320

  • Brand : BIOFRON

  • Catalogue Number : BD-D0022

  • Specification : HPLC≥96%

  • CAS number : 6879-01-2

  • Formula : C22H33NO4 

  • Molecular Weight : 375.51

  • PUBCHEM ID : 100781

  • Volume : 20mg

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Catalogue Number

BD-D0022

Analysis Method

HPLC,NMR,MS

Specification

HPLC≥96%

Storage

-20℃

Molecular Weight

375.51

Appearance

White needle-shaped crystal

Botanical Source

StemonaceaeStemona japonica/Alkaloid from Stemona tuberosa, Stemona japonica and Stemona sessilifolia (Stemonaceae)

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CCC1C2CCCCN3C2C(CC3C4CC(C(=O)O4)C)C5C1OC(=O)C5C

Synonyms

(2S,7aR,8R,8aS,11S,11aS,11bR,11cR)-8-Ethyl-11-methyl-2-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]dodecahydroazepino[3,2,1-hi]furo[3,2-e]indol-10(2H)-one/TuberosteMonin/Tuberstemonine/Azepino[3,2,1-hi]furo[3,2-e]indol-10(2H)-one, 8-ethyldodecahydro-11-methyl-2-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-, (2S,7aR,8R,8aS,11S,11aS,11bR,11cR)-/(2S,7aR,8R,8aS,11S,11aS,11bR,11cR)-8-Ethyl-11-methyl-2-[(2S,4S)-4-methyl-5-oxotetrahydro-2-furanyl]dodecahydroazepino[3,2,1-hi]furo[3,2-e]indol-10(2H)-one

IUPAC Name

(1R,3S,9R,10R,11S,14S,15S,16R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.04,16.011,15]hexadecan-13-one

Applications

Density

1.2±0.1 g/cm3

Solubility

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

Flash Point

289.0±30.1 °C

Boiling Point

554.2±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C22H33NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h11-20H,4-10H2,1-3H3

InChl Key

GYOGHROCTSEKDY-UHFFFAOYSA-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#:6879-01-2) 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

28580601

Abstract

The occurrence of bioactive alkaloids and tocopherols was studied in 15 different provenances of Stemona tuberosa Lour. collected in southern China, to examine chemical variation of individuals that show notable differences in flower characteristics. Morphological variations stimulated examination of chemical characteristics of these individuals. Methanolic root extracts of 15 individuals of S. tuberosa were comparatively assessed with HPLC-UV-DAD/ELSD. Five of seven compounds were co-chromatographically identified. Two compounds were isolated and their structure elucidated using NMR and MS. Amounts of alkaloids and tocopherols were determined using HPLC-UV-DAD/ELSD with the external standard method. Five alkaloids, tuberostemonine (1), tuberostemonine A (2), neotuberostemonine (3), tuberostemonine N (4), stemoninine (5) and two 3,4-dehydrotocopherol derivatives were identified. Within S. tuberosa alkaloid accumulation tends either towards tuberostemonine (1) or stemoninine (5). All individuals show a notable co-occurrence of compounds 1 or 5 and 3,4-dehydro-δ-tocopherol (6). These results coincide with differences in flower morphology of S. tuberosa. Stemona tuberosa, as defined in the Flora of China, shows a remarkable variation in flower morphology and additionally in the accumulation of alkaloids. The obtained data show the need for future species delimitation to either species or subspecies level.

© 2017 German Botanical Society and The Royal Botanical Society of the Netherlands.

KEYWORDS

Bai Bu; Stemona alkaloids; Stemona tuberosa; chemotaxonomy; plant secondary metabolites

Title

Morphological and chemical variation of Stemona tuberosa from southern China - Evidence for heterogeneity of this medicinal plant species.

Author

Chen G1, Brecker L2, Felsinger S2, Cai XH3, Kongkiatpaiboon S4, Schinnerl J5.

Publish date

2017 Sep

PMID

28448890

Abstract

Neotuberostemonine (NS) and tuberostemonine (TS), a pair of stereoisomers, are the active components contained in Stemona tuberosa, an antitussive herbal medicine in China. Two isomers have different pharmacological efficacies, which will be related with their in vivo disposition. However, the metabolic fates of NS and TS remain unknown. A method of high performance liquid chromatography/quadrupole time-of-flight mass spectrometry coupled with mass detect filter technique was established to investigate the metabolites in rat plasma, bile, urine, and feces after oral administration of the equal doses of NS and TS. The results showed that NS produced 48 phase I metabolites, including NS, 3 hydrolyzed, 14 hydroxylated, 20 monohydrolyzed+hydroxylated and 10 dihydrolyzed+hydroxylated metabolites. The number of detected NS metabolites was 11, 39, 22 and 30 in plasma, bile, urine and feces. TS yielded 23 phase I metabolites, including TS, 3 hydrolyzed, 7 hydroxylated, 9 monohydrolyzed+hydroxylated and 3 dihydrolyzed+hydroxylated metabolites. Besides, TS yielded 9 phase II metabolites, including 1 glucuronic acid and 2 glutathione conjugates, and the later further degraded and modified into cysteine-glycine, cysteine and N-acetylcysteine conjugates. The number of detected TS metabolites was 9, 24, 24 and 15 in plasma, bile, urine and feces. Different metabolic patterns may be one of the main reasons leading to different pharmacological effects of NS and TS.

Copyright © 2017 Elsevier B.V. All rights reserved.

KEYWORDS

Metabolic pathway; Metabolites; Neotuberostemonine; Stemona alkaloids; Stereoisomers; Tuberostemonine

Title

Metabolic profiles of neotuberostemonine and tuberostemonine in rats by high performance liquid chromatography/quadrupole time-of-flight mass spectrometry.

Author

Tong Y1, Xu W1, Wu Y1, Ou L1, Zhang M2, Xu X1, Zhang C3.

Publish date

2017 Jul 15

PMID

26902410

Abstract

OBJECTIVE:
Our previous study demonstrated that a Stemona tuberosa extract had significant effects on cigarette smoking (CS)-induced lung inflammation in mice. The present study evaluated the potential of tuberostemonine N (T.N) to prevent airway inflammation and suppress airway responses in a CS-induced in vivo COPD model.

METHODS:
T.N was isolated from the root of ST and analyzed using 1D and 2D NMR. The purity of T.N was accessed using HPLC-ELSD analysis. C57BL/6 mice in this study were whole-body exposed to mainstream CS or room air for 4 weeks, and T.N (1, 5 and 10 mg/kg body wt.) was administered to mice via intraperitoneal (i.p.) injection before CS exposure. The number of inflammatory cells, including neutrophils, macrophages and lymphocytes, and the amount of proinflammatory cytokines and chemokines were accessed from bronchoalveolar lavage fluid (BALF) to investigate the anti-inflammatory effects of T.N. Average alveoli size was also measured using histological analyses.

RESULTS:
Cellular profiles and histopathological analyses revealed that the infiltration of peribronchial and perivascular inflammatory cells decreased significantly in the T.N-treated groups compared to the CS-exposed control group. T.N significantly inhibited the secretion of proinflammatory cytokines and chemokines in BALF and decreased alveoli size in lung tissue.

CONCLUSIONS:
These data suggest that T.N exerts anti-inflammatory effects against airway inflammation, and T.N may be a novel therapeutic agent for lung diseases, such as COPD.

Copyright © 2015 Elsevier GmbH. All rights reserved.

KEYWORDS

COPD; Cigarette smoke; Stemona tuberosa; Tuberostemonine N

Title

Tuberostemonine N, an active compound isolated from Stemona tuberosa, suppresses cigarette smoke-induced sub-acute lung inflammation in mice.

Author

Jung KH1, Kil YS2, Jung J1, Park S1, Shin D1, Lee K1, Seo EK3, Bae H4.

Publish date

2016 Jan 15