SMB01000
Grandiflorenic acid
≥90% (LC/MS-ELSD)
Synonym(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
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
UNSPSC Code:
12352205
NACRES:
NA.25
MDL number:
biological source
plant
assay
≥90% (LC/MS-ELSD)
form
solid
mol wt
300.44
solubility
water: slightly soluble
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
−20°C
SMILES string
OC(=O)[C@]1([C@@H]2[C@@](CCC1)(C3=CCC4CC3(CC2)CC4=C)C)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
InChI key
RJIPNPHMQGDUBW-MZWQVCBVSA-N
General description
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.
Biochem/physiol Actions
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.
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 shows moderate cytotoxic (IC50 15μM in RAW264.7 cells) and antiplasmodial activities (IC50 23μM against P. falciparum).
Features and Benefits
- High quality compound suitable for multiple research applications
- Compatible with HPLC and mass spectrometry techniques
Other Notes
For additional information on our range of Biochemicals, please complete this form.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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)
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