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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.


Installation of azides and 1,2,3-triazole at the C-1, -2, or -3 position derivatives (19–21) of oridonin.
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ijms-17-01395-f010: Installation of azides and 1,2,3-triazole at the C-1, -2, or -3 position derivatives (19–21) of oridonin.

Mentions: In 2013, Zhou’s group developed an efficient and concise synthetic approach to install the azide functional group at the C-1, C-2 or C-3 positions of the A-ring of oridonin rapidly and diversely with highly-controlled regio- and stereo-selectivity (Figure 10) [53]. These azides were further functionalized through click chemistry to yield triazole derivatives. The antiproliferative activity of representative 1,2,3-triazolesubstituted derivatives (19 and 20) against breast cancer cell lines MCF-7 and MDA-MB-231 was tested. These derivatives with 1,2,3-triazole installed in the A-ring exhibited significantly improved antiproliferative activity compared to oridonin. Among them, Compound 21 showed the strongest potency with IC50 of 0.38 and 0.48 μM, respectively. This work provided access to an expanded potential anticancer natural scaffold-based compound library from the lead oridonin.


Oridonin, a Promising ent -Kaurane Diterpenoid Lead Compound
Installation of azides and 1,2,3-triazole at the C-1, -2, or -3 position derivatives (19–21) of oridonin.
© Copyright Policy
Related In: Results  -  Collection

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

ijms-17-01395-f010: Installation of azides and 1,2,3-triazole at the C-1, -2, or -3 position derivatives (19–21) of oridonin.
Mentions: In 2013, Zhou’s group developed an efficient and concise synthetic approach to install the azide functional group at the C-1, C-2 or C-3 positions of the A-ring of oridonin rapidly and diversely with highly-controlled regio- and stereo-selectivity (Figure 10) [53]. These azides were further functionalized through click chemistry to yield triazole derivatives. The antiproliferative activity of representative 1,2,3-triazolesubstituted derivatives (19 and 20) against breast cancer cell lines MCF-7 and MDA-MB-231 was tested. These derivatives with 1,2,3-triazole installed in the A-ring exhibited significantly improved antiproliferative activity compared to oridonin. Among them, Compound 21 showed the strongest potency with IC50 of 0.38 and 0.48 μM, respectively. This work provided access to an expanded potential anticancer natural scaffold-based compound library from the lead oridonin.

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.