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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.


Selective acylated products of oridonin at 6-O (4) or 14-O (5).
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ijms-17-01395-f003: Selective acylated products of oridonin at 6-O (4) or 14-O (5).

Mentions: Five years later (in 1981), Fujita et al. selectively synthesized the first series of derivatives of 1 by acylation at 6-O (4) or/and 14-O (5, Figure 3) [47]. The antitumor activity of synthetic derivatives against Ehrlich ascites carcinoma cells in mouse were evaluated, and the structure activity relationship (SAR) showed that the activity increased with the increase of the acyl carbon chain length. The importance of the hydrogen bond and the ester side chain for the antitumor activity was also demonstrated in the derivatives of oridonin; while the 1,14-diacetate derivative of oridonin could be obtained by the treatment of oridonin with acetic anhydride in pyridine [48].


Oridonin, a Promising ent -Kaurane Diterpenoid Lead Compound
Selective acylated products of oridonin at 6-O (4) or 14-O (5).
© Copyright Policy
Related In: Results  -  Collection

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

ijms-17-01395-f003: Selective acylated products of oridonin at 6-O (4) or 14-O (5).
Mentions: Five years later (in 1981), Fujita et al. selectively synthesized the first series of derivatives of 1 by acylation at 6-O (4) or/and 14-O (5, Figure 3) [47]. The antitumor activity of synthetic derivatives against Ehrlich ascites carcinoma cells in mouse were evaluated, and the structure activity relationship (SAR) showed that the activity increased with the increase of the acyl carbon chain length. The importance of the hydrogen bond and the ester side chain for the antitumor activity was also demonstrated in the derivatives of oridonin; while the 1,14-diacetate derivative of oridonin could be obtained by the treatment of oridonin with acetic anhydride in pyridine [48].

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.