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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 dienone derivatives (25–28) of oridonin with the α,β-unsaturated ketone system in the A-ring.
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ijms-17-01395-f012: The dienone derivatives (25–28) of oridonin with the α,β-unsaturated ketone system in the A-ring.

Mentions: In late 2013, a series of dienone derivatives of oridonin with an additional α,β-unsaturated ketone system installed in the A-ring was synthesized by Zhou’s group (Figure 12) [56]. Regioselective enone construction strategies were established. These derivatives significantly induced apoptosis and exhibited superior antitumor effects to oridonin against drug-resistant and aggressive breast cancer cells in vitro and in vivo (26 suppressed MDA-MB-231 xenograft tumor growth at 5.0 mg/kg) and also exhibited low toxicity to normal human mammary epithelial cells. The preliminary mechanism studies revealed that selected dienone analogues (25, 26) were found to induce the apoptosis of MDA-MB-231 cells in a concentration-dependent manner through regulation of a series of apoptotic-related proteins.


Oridonin, a Promising ent -Kaurane Diterpenoid Lead Compound
The dienone derivatives (25–28) of oridonin with the α,β-unsaturated ketone system in the A-ring.
© Copyright Policy
Related In: Results  -  Collection

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

ijms-17-01395-f012: The dienone derivatives (25–28) of oridonin with the α,β-unsaturated ketone system in the A-ring.
Mentions: In late 2013, a series of dienone derivatives of oridonin with an additional α,β-unsaturated ketone system installed in the A-ring was synthesized by Zhou’s group (Figure 12) [56]. Regioselective enone construction strategies were established. These derivatives significantly induced apoptosis and exhibited superior antitumor effects to oridonin against drug-resistant and aggressive breast cancer cells in vitro and in vivo (26 suppressed MDA-MB-231 xenograft tumor growth at 5.0 mg/kg) and also exhibited low toxicity to normal human mammary epithelial cells. The preliminary mechanism studies revealed that selected dienone analogues (25, 26) were found to induce the apoptosis of MDA-MB-231 cells in a concentration-dependent manner through regulation of a series of apoptotic-related proteins.

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.