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Merck

SMB01000

Sigma-Aldrich

Grandiflorenic acid

≥90% (LC/MS-ELSD)

Synonym(e):

(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

Empirische Formel (Hill-System):
C20H28O2
CAS-Nummer:
Molekulargewicht:
300.44
MDL-Nummer:
UNSPSC-Code:
12352205
NACRES:
NA.25

Biologische Quelle

plant

Assay

≥90% (LC/MS-ELSD)

Form

solid

Mol-Gew.

300.44

Löslichkeit

water: slightly soluble

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

−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

InChIKey

RJIPNPHMQGDUBW-MZWQVCBVSA-N

Allgemeine Beschreibung

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.

Anwendung

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

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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

Sonstige Hinweise

For additional information on our range of Biochemicals, please complete this form.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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)
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
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

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