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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.


ent-Kaurane diterpenoid dimer 45.
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ijms-17-01395-f023: ent-Kaurane diterpenoid dimer 45.

Mentions: Many ent-kaurane diterpenoid dimers with diverse structures were isolated from natural sources [80,81,82]. It was found that oridonin could be a good lead to semi-synthesize ent-kaurane diterpenoid dimer derivatives to achieve the final drug candidate. A 3,4-dihydro-2H-pyran ring was firstly constructed in the A-ring of oridonin using an optimized IED HDA (inverse electron demand hetero-Diels–Alder) reaction. ent-Kaurane diterpenoid dimers were synthesized through a homo-HDA reaction by a self-dimerization of the exocyclic enone in the A-ring (Figure 23) [62]. The antiproliferative effects were evaluated against four breast cancer cell lines, MCF-7, MDA-MB-468, MDAMB-231 and MCF-7/ADR, by the MTT method, and the IC50 values were in the submicromolar range with a significantly improved capability to overcome chemoresistance.


Oridonin, a Promising ent -Kaurane Diterpenoid Lead Compound
ent-Kaurane diterpenoid dimer 45.
© Copyright Policy
Related In: Results  -  Collection

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

ijms-17-01395-f023: ent-Kaurane diterpenoid dimer 45.
Mentions: Many ent-kaurane diterpenoid dimers with diverse structures were isolated from natural sources [80,81,82]. It was found that oridonin could be a good lead to semi-synthesize ent-kaurane diterpenoid dimer derivatives to achieve the final drug candidate. A 3,4-dihydro-2H-pyran ring was firstly constructed in the A-ring of oridonin using an optimized IED HDA (inverse electron demand hetero-Diels–Alder) reaction. ent-Kaurane diterpenoid dimers were synthesized through a homo-HDA reaction by a self-dimerization of the exocyclic enone in the A-ring (Figure 23) [62]. The antiproliferative effects were evaluated against four breast cancer cell lines, MCF-7, MDA-MB-468, MDAMB-231 and MCF-7/ADR, by the MTT method, and the IC50 values were in the submicromolar range with a significantly improved capability to overcome chemoresistance.

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.