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Oridonin, a Promising ent -Kaurane Diterpenoid Lead Compound

View Article: PubMed Central - PubMed

ABSTRACT

Oridonin belongs to ent-kaurane tetracyclic diterpenoid and was first isolated from Isodon species. It exhibits inhibitory activities against a variety of tumor cells, and pharmacological study shows that oridonin could inhibit cell proliferation, DNA, RNA and protein synthesis of cancer cells, induce apoptosis and exhibit an antimutagenic effect. In addition, the large amount of the commercially-available supply is also very important for the natural lead oridonin. Moreover, the good stability, suitable molecular weight and drug-like property guarantee its further generation of a natural-like compound library. Oridonin has become the hot molecule in recent years, and from the year 2010, more than 200 publications can be found. In this review, we summarize the synthetic medicinal chemistry work of oridonin from the first publication 40 years ago and share our research experience of oridonin for about 10 years, which may provide useful information to those who are interested in this research field.

No MeSH data available.


The dihydropyran-fused oridonin 30.
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ijms-17-01395-f014: The dihydropyran-fused oridonin 30.

Mentions: In the same year, a series of dihydropyran-fused oridonin derivatives was designed and synthesized as potential anticancer agents by Zhou’s group (Figure 14) [62]. 3,4-dihydro-2H-pyran moiety was introduced into the A-ring of oridonin by an optimized IED HDA (inverse electron demand hetero-Diels–Alder) reaction in a mild and concise approach. The inhibitory effects of these derivatives were evaluated against MCF-7, MDAMB-231, MDA-MB-468 and MCF-7/ADR cell lines. Among them, Compound 30 was the most potent one, which showed submicromolar IC50 values in MCF-7 (IC50 = 0.44 μM), MDA-MB-231 (IC50 = 0.54 μM) and MDA-MB-468 (IC50 = 0.52 μM) cells and an improved capability to overcome chemoresistance against the MCF-7/ADR cell line (IC50 = 1.6 μM).


Oridonin, a Promising ent -Kaurane Diterpenoid Lead Compound
The dihydropyran-fused oridonin 30.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5037675&req=5

ijms-17-01395-f014: The dihydropyran-fused oridonin 30.
Mentions: In the same year, a series of dihydropyran-fused oridonin derivatives was designed and synthesized as potential anticancer agents by Zhou’s group (Figure 14) [62]. 3,4-dihydro-2H-pyran moiety was introduced into the A-ring of oridonin by an optimized IED HDA (inverse electron demand hetero-Diels–Alder) reaction in a mild and concise approach. The inhibitory effects of these derivatives were evaluated against MCF-7, MDAMB-231, MDA-MB-468 and MCF-7/ADR cell lines. Among them, Compound 30 was the most potent one, which showed submicromolar IC50 values in MCF-7 (IC50 = 0.44 μM), MDA-MB-231 (IC50 = 0.54 μM) and MDA-MB-468 (IC50 = 0.52 μM) cells and an improved capability to overcome chemoresistance against the MCF-7/ADR cell line (IC50 = 1.6 μM).

View Article: PubMed Central - PubMed

ABSTRACT

Oridonin belongs to ent-kaurane tetracyclic diterpenoid and was first isolated from Isodon species. It exhibits inhibitory activities against a variety of tumor cells, and pharmacological study shows that oridonin could inhibit cell proliferation, DNA, RNA and protein synthesis of cancer cells, induce apoptosis and exhibit an antimutagenic effect. In addition, the large amount of the commercially-available supply is also very important for the natural lead oridonin. Moreover, the good stability, suitable molecular weight and drug-like property guarantee its further generation of a natural-like compound library. Oridonin has become the hot molecule in recent years, and from the year 2010, more than 200 publications can be found. In this review, we summarize the synthetic medicinal chemistry work of oridonin from the first publication 40 years ago and share our research experience of oridonin for about 10 years, which may provide useful information to those who are interested in this research field.

No MeSH data available.