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Oridonin, a Promising ent -Kaurane Diterpenoid Lead Compound

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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.


Synthesis routine of lasiokaurin (11). (a) 2,2-Dimethoxypropane, acetone, TsOH, 56 °C; (b) Ac2O, TEA (triethylamine), DMAP (4-dimethylaminopyridine), rt (room temperature); (c) 10% HCl, THF (tetrahydrofuran), rt.
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ijms-17-01395-f006: Synthesis routine of lasiokaurin (11). (a) 2,2-Dimethoxypropane, acetone, TsOH, 56 °C; (b) Ac2O, TEA (triethylamine), DMAP (4-dimethylaminopyridine), rt (room temperature); (c) 10% HCl, THF (tetrahydrofuran), rt.

Mentions: 1-OAc oridonin was also a natural product, which was called lasiokaurin (11). In 2006, Liu’s group synthesized 11 from 1 in a 69% overall yield via three steps by selective acetonide protection (9), acetylation (10) and deprotection (Figure 6). The antiprotozoan activity of lasiokaurin and oridonin was tested, and the median lethal concentration was 25 and 50 μM, respectively, which indicated that 1-hydroxyl had some benefits on the antiprotozoan activity [51]. These reactions were used extensively in the further modification of oridonin.


Oridonin, a Promising ent -Kaurane Diterpenoid Lead Compound
Synthesis routine of lasiokaurin (11). (a) 2,2-Dimethoxypropane, acetone, TsOH, 56 °C; (b) Ac2O, TEA (triethylamine), DMAP (4-dimethylaminopyridine), rt (room temperature); (c) 10% HCl, THF (tetrahydrofuran), rt.
© Copyright Policy
Related In: Results  -  Collection

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

ijms-17-01395-f006: Synthesis routine of lasiokaurin (11). (a) 2,2-Dimethoxypropane, acetone, TsOH, 56 °C; (b) Ac2O, TEA (triethylamine), DMAP (4-dimethylaminopyridine), rt (room temperature); (c) 10% HCl, THF (tetrahydrofuran), rt.
Mentions: 1-OAc oridonin was also a natural product, which was called lasiokaurin (11). In 2006, Liu’s group synthesized 11 from 1 in a 69% overall yield via three steps by selective acetonide protection (9), acetylation (10) and deprotection (Figure 6). The antiprotozoan activity of lasiokaurin and oridonin was tested, and the median lethal concentration was 25 and 50 μM, respectively, which indicated that 1-hydroxyl had some benefits on the antiprotozoan activity [51]. These reactions were used extensively in the further modification of 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.