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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:
22338-67-6
Molecular Weight:
300.44
UNSPSC Code:
12352205
NACRES:
NA.25
MDL number:
MFCD23103740

Key Documents

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Product Name

Grandiflorenic acid, ≥90% (LC/MS-ELSD)

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

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

Related Categories

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 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.

Features and Benefits

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

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.

Other Notes

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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)
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
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
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)

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