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Guajadial

$1,280

  • Brand : BIOFRON

  • Catalogue Number : BN-O1008

  • Specification : 95%(HPLC)

  • CAS number : 959860-49-2

  • Formula : C30H34O5

  • Molecular Weight : 474.59

  • PUBCHEM ID : 46197930

  • Volume : 5mg

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Catalogue Number

BN-O1008

Analysis Method

HPLC,NMR,MS

Specification

95%(HPLC)

Storage

-20℃

Molecular Weight

474.59

Appearance

Powder

Botanical Source

This product is isolated and purified from the leaves Psidium guajava

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CC2C1CCC3(C(CCC2=C)C(C4=C(C(=C(C(=C4O3)C=O)O)C=O)O)C5=CC=CC=C5)C)C

Synonyms

(2aR,4aR,10R,10aS,13aS)-7,9-Dihydroxy-2,2,4a-trimethyl-13-methylene-10-phenyl-1,2,2a,3,4,4a,10,10a,11,12,13,13a-dodecahydrocyclobuta[6,7]cyclonona[1,2-b]chromene-6,8-dicarbaldehyde Benzo[b]cyclobuta[5,6]cyclonona[1,2-e]pyran-6,8-dicarboxaldehyde, 1,2,2a,3,4,4a,10,10a,11,12,13,13a-dodecahydro-7,9-dihydroxy-2,2,4a-trimethyl-13-methylene-10-phenyl-,/(2aR,4aR,10R,10aS,13aS)-/guajadial

IUPAC Name

(1R,4R,7S,11S,12R)-14,16-dihydroxy-1,5,5-trimethyl-8-methylidene-12-phenyl-19-oxatetracyclo[9.8.0.04,7.013,18]nonadeca-13,15,17-triene-15,17-dicarbaldehyde

Density

1.3±0.1 g/cm3

Solubility

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

Flash Point

160.7±23.6 °C

Boiling Point

518.7±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H

InChl Key

NSFVENNIBGTQJE-XRXODSDBSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:959860-49-2) 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

29928966

Abstract

Guajadial, one of natural dialdehyde meroterpenoids, demonstrated significant antineoplasmic activity. The present research was to investigate the inhibitory effects of guajadial by using two NSCLC cells (A549 and H1650) proliferation and migration. Western blotting was employed to explore the underlying mechanisms of VEGF receptor (VEGFR)2-mediated. This research indicated that guajadial not only inhibited endothelial cell proliferation and migration but also suppress tumor growth in human NSCLC xenograft mouse models. It is also suggested that guajadial inhibited A549 proliferation via blocking the Ras/MAPK pathway.

KEYWORDS

Cell proliferation; Guajadial; Tumor migration; VEGFR2-mediated.

Title

Guajadial Inhibits NSCLC Growth and Migration Following Activation of the VEGF receptor-2

Author

Yongfeng Wang 1, Meiling Duan 2, Lijiang Zhao 2, Ping Ma 2

Publish date

2018 Sep;

PMID

32230839

Abstract

The research of natural products has allowed for the discovery of biologically relevant compounds inspired by plant secondary metabolites, which contributes to the development of many chemotherapeutic drugs used in cancer treatment. Psidium guajava leaves present a diverse phytochemical composition including flavonoids, phenolics, meroterpenoids, and triterpenes as the major bioactive constituents. Guajadial, a caryophyllene-based meroterpenoid, has been studied for potential anticancer effects tested in tumor cells and animal experimental models. Moreover, guajadial has been reported to have a mechanism of action similar to tamoxifen, suggesting this compound as a promisor phytoestrogen-based therapeutic agent. Herein, the anti-estrogenic action and anti-proliferative activity of guajadial is reported. The enriched guajadial fraction was obtained by sequential chromatographic techniques from the crude P. guajava dichloromethane extract showing promising anti-proliferative activity in vitro with selectivity for human breast cancer cell lines MCF-7 and MCF-7 BUS (Total Growth Inhibition = 5.59 and 2.27 µg·mL-1, respectively). Furthermore, evaluation of anti-estrogenic activity in vivo was performed demonstrating that guajadial enriched fraction inhibited the proliferative effect of estradiol on the uterus of pre-pubescent rats. These results suggest a relationship between anti-proliferative and anti-estrogenic activity of guajadial, which possibly acts in tumor inhibition through estrogen receptors due to the compounds structural similarity to tamoxifen.

KEYWORDS

Psidium guajava L.; anti-proliferative activity in vitro; estrogenic/anti-estrogenic activity.

Title

Anti-Estrogenic Activity of Guajadial Fraction, From Guava Leaves ( Psidium guajava L.)

Author

Jaqueline Moraes Bazioli 1 2, Jonas Henrique Costa 2, Larissa Shiozawa 1 3, Ana Lúcia Tasca Gois Ruiz 1, Mary Ann Foglio 1, João Ernesto de Carvalho 1

Publish date

2020 Mar 27

PMID

30929998

Abstract

Multidrug resistance remains a major challenge in the chemotherapy of breast cancer. Guajadial, a natural meroterpenoid, has been found to possess anti-tumor activity. However, the role of guajadial in drug resistance has not been investigated. The aim of this study was to evaluate the effect of guajadial on drug resistance in drug-resistant breast cancer cells. Cell viability was measured by MTT assay, and the IC50 values were calculated. The expression of ATP-binding cassette (ABC) transporters including P-glycoprotein (P-gp) and the breast cancer resistance protein (BCRP) was detected by qRT-PCR and western blot. The expression of Akt, p-Akt, p70S6K, and p-p70S6K was determined by western blot. We found that guajadial significantly inhibited cell viability of parental non-resistant cell line MCF-7, adriamycin (ADR)-resistant cell line MCF-7/ADR, and paclitaxel (PTX)-resistant cell line MCF-7/PTX in a dose-dependent manner. Guajadial enhanced ADR and PTX sensitivity of MCF-7/ADR and MCF-7/PTX cells, and inhibited the expression of P-gp and BCRP. Guajadial treatment resulted in an inactivation of PI3K/Akt pathway in drug-resistant MCF-7 cells. In conclusion, guajadial acted as an inhibitor of drug resistance, which might be mediated by the inhibition of ABC transporter expression and PI3K/Akt pathway in drug-resistant breast cancer cells. These findings suggested that guajadial treatment might be a new approach to overcome the drug resistance in the chemotherapy of breast cancer.

KEYWORDS

ATP-Binding cassette (ABC) transporters; Breast cancer; Drug resistance; Guajadial; PI3K/Akt pathway.

Title

Guajadial Reverses Multidrug Resistance by Inhibiting ABC Transporter Expression and Suppressing the PI3K/Akt Pathway in Drug-Resistant Breast Cancer Cells

Author

Yaxun Li 1, Zhenhua Zhai 2, Hao Li 3, Xudong Wang 2, Yinpeng Huang 2, Xin Su 2

Publish date

2019 May 25


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