Gambogic acid and epigambogic acid, C-2 epimers with novel anticancer effects from Garcinia hanburyi

Planta medica
Quan-Bin HanHong-Xi Xu

Abstract

Gambogic acid, usually isolated as an inseparable stereomeric mixture of C-2 epimers, was newly separated into two epimers (1 and 2) from the gamboges of Garcinia hanburyi. The stereochemistry at C-2 was clearly defined by extensive spectroscopic analysis and direct comparison of NMR and HPLC data with those of the known R-epimer. Both epimers were examined for their cytotoxicities against human leukemia K562 (K562/S) and doxorubicin-resistant K562 (K562/R) cell lines. Different from doxorubicin (IC (50) = 10.78 microM for K562/R and 0.66 microM for K562/S), epimers 1 and 2 exhibited similar activities against both cell lines (IC(50) = 1.32 and 0.89 microM for 1, IC(50) = 1.11 and 0.86 microM for 2). These results suggested that both epimers were not multidrug resistance (MDR) substrates. Furthermore, epimers 1 and 2 were tested for their inhibitory effects against six human cytochrome P-450 enzymes. Epimers 1 and 2 showed little inhibitory effects toward five of the enzymes except CYP2C9. Interestingly, when tested against CYP2C9, S-epimer 2 had an inhibitory effect 20-fold stronger than that of R-epimer 1.

Citations

Nov 12, 2010·Journal of Natural Products·Yulin RenA Douglas Kinghorn
May 24, 2008·Natural Product Reports·Otto Sticher
Jul 1, 2008·Chinese Medicine·Songlin LiHongxi Xu
Jun 2, 2007·Chemical & Pharmaceutical Bulletin·Nian-Yun YangHong-Xi Xu
Sep 18, 2012·Fitoterapia·Yun-Xia DengZhi-Yu Shao
Dec 27, 2011·Pharmaceutical Biology·Natthinee AnantachokeVichai Reutrakul
Dec 22, 2015·Fitoterapia·Yu ChenGuangzhong Yang
Jul 15, 2015·AAPS PharmSciTech·Buyun JiaWeidong Chen
Jan 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·João RibeiroMadalena M M Pinto
Apr 3, 2007·Journal of Separation Science·Jing-Zheng SongHong-Xi Xu
May 19, 2007·Chemistry & Biodiversity·Quan-Bin HanHong-Xi Xu
Mar 6, 2012·Phytotherapy Research : PTR·Shuli ManChangxiao Liu
Jan 19, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joana AraújoMaria Elizabeth Tiritan
Jul 22, 2010·Chemistry : a European Journal·Oraphin ChantarasriwongEmmanuel A Theodorakis
Aug 1, 2008·Journal of Natural Products·Guido F PauliJ Brent Friesen
Dec 17, 2008·Journal of Natural Products·Si-Jia TaoDe-An Guo

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.