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Key Documents

SMB01000

Sigma-Aldrich

Grandiflorenic acid

≥90% (LC/MS-ELSD)

Synonyme(s) :

(4S,5R,9R)-5,9-Dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadec-10-ene-5-carboxylic acid, Kaura-9(11),16-dien-18-oic acid

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About This Item

Formule empirique (notation de Hill):
C20H28O2
Numéro CAS:
Poids moléculaire :
300.44
Numéro MDL:
Code UNSPSC :
12352205
Nomenclature NACRES :
NA.25

Source biologique

plant

Pureté

≥90% (LC/MS-ELSD)

Forme

solid

Poids mol.

300.44

Solubilité

water: slightly soluble

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

InChI

1S/C20H28O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h6,14-15H,1,4-5,7-12H2,2-3H3,(H,21,22)/t14?,15-,18+,19+,20?/m0/s1

Clé InChI

RJIPNPHMQGDUBW-MZWQVCBVSA-N

Description générale

Grandiflorenic acid, a diterpenoid, is a natural product commonly derived from Wedelia trilobata, Sphagneticola trilobata and Siegesbeckia orientalis L. It exhibits various biological activities such as anti-inflammatory, anti-depressant, anti-fertility, and anti-microbial properties.

Application

It is a natural product derived from plant source that finds application in compound screening libraries, metabolomics, phytochemical, and pharmaceutical research.

Actions biochimiques/physiologiques

Grandiflorenic acid exhibits antibacterial, anti-inflammatory, antileishmanial and wound-healing properties.
Grandiflorenic acid shows moderate cytotoxic (IC50 15μM in RAW264.7 cells) and antiplasmodial activities (IC50 23μM against P. falciparum).
Grandiflorenic acid (GFA) shows promise as an anticancer agent by inhibiting cell proliferation and reducing cell size in breast (MCF7), lung (A549), and liver (HuH7.5) tumor cell lines. Further, it also shows effects on uterine motility throughout the estrus cycle suggesting it may have antifertility properties, possibly by affecting hormones and adrenergic pathways in the uterus.

Caractéristiques et avantages

  • High quality compound suitable for multiple research applications
  • Compatible with HPLC and mass spectrometry techniques

Autres remarques

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Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

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Grandiflorenic acid from Wedelia trilobata plant induces apoptosis and autophagy cell death in breast adenocarcinoma (MCF7), lung carcinoma (A549), and hepatocellular carcinoma (HuH7.5) cells lines
Fagundes TR, et al.
Toxicon, 217, 112-120 (2022)
Bruna Taciane da Silva Bortoleti et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 46, 11-20 (2018-08-12)
American tegumentary leishmaniasis (ATL) is a zoonotic disease caused by protozoa of the genus Leishmania. The high toxicity, high costs and resistance of some strains to current drugs has prompted the search for therapeutic alternatives for the management of this
The in vitro effect of grandiflorenic acid and zoapatle aqueous crude extract upon spontaneous contractility of the rat uterus during oestrus cycle
Bejar E. et al.
Journal of Ethnopharmacology, 11, 87-97 (1984)
Amira Arciniegas et al.
Chemistry & biodiversity, 15(3), e1700529-e1700529 (2018-02-11)
The chemical study of Ageratina deltoidea afforded grandiflorenic acid (1), ent-kaurenoic acid (2), and eight benzylbenzoates (3 - 10), two of them, 3,5-dimethoxybenzyl 2,3,6-trimethoxybenzoate (5) and 4-(β-d-glucopyranosyloxy)-3-hydroxybenzyl 2,6-dimethoxybenzoate (9), described for the first time. In addition, the new sesquiterpene lactone deltoidin C

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