## 16beta,17-dihydroxy-ent-kaurane-19-oic acid: A Key Molecule in Research
**16beta,17-dihydroxy-ent-kaurane-19-oic acid**, also known as **ent-kaurenoic acid**, is a diterpenoid compound naturally occurring in various plants, particularly in the genus *Salvia*. It holds significant research interest due to its diverse biological activities and potential therapeutic applications.
**Chemical Structure and Properties:**
* **Diterpenoid:** It belongs to the diterpenoid family, meaning it is derived from a 20-carbon isoprene unit.
* **Ent-kaurane:** The ent prefix refers to the enantiomeric form, meaning its molecular structure is a mirror image of the normal kaurane molecule.
* **16beta, 17-dihydroxy:** It has hydroxyl groups attached to the 16th and 17th carbon positions in a specific spatial arrangement.
* **-19-oic acid:** It has a carboxylic acid group attached to the 19th carbon.
**Biological Activities and Potential Therapeutic Applications:**
**1. Anti-inflammatory Activity:**
Studies suggest that 16beta,17-dihydroxy-ent-kaurane-19-oic acid exhibits anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines, such as TNF-α and IL-6. This makes it a promising candidate for treating conditions like rheumatoid arthritis, inflammatory bowel disease, and asthma.
**2. Antioxidant Activity:**
Its ability to scavenge free radicals and protect cells from oxidative damage contributes to its antioxidant properties. This could be beneficial for preventing and treating conditions related to oxidative stress, such as cancer and cardiovascular disease.
**3. Anti-tumor Activity:**
Research has demonstrated its potential to inhibit the growth and proliferation of various cancer cell lines, including leukemia, lung cancer, and breast cancer. Further studies are needed to explore its therapeutic potential in cancer treatment.
**4. Neuroprotective Activity:**
Some studies suggest that it might protect neurons from damage and improve cognitive function. Its potential in treating neurodegenerative diseases like Alzheimer's and Parkinson's disease is under investigation.
**5. Other Potential Applications:**
Beyond the mentioned activities, 16beta,17-dihydroxy-ent-kaurane-19-oic acid is being investigated for its potential in treating:
* **Diabetes:** By regulating blood sugar levels.
* **Cardiovascular diseases:** By improving blood flow and reducing blood pressure.
* **Infectious diseases:** By inhibiting the growth of bacteria and viruses.
**Research Significance:**
The diverse biological activities and potential therapeutic applications of 16beta,17-dihydroxy-ent-kaurane-19-oic acid have made it a subject of intense research interest. Scientists are actively investigating its mechanisms of action, its therapeutic efficacy, and its safety profile to pave the way for the development of novel drugs for various human diseases.
**Note:** It's important to remember that research is ongoing, and more studies are needed to confirm the efficacy and safety of this compound for therapeutic purposes.
16beta,17-dihydroxy-ent-kaurane-19-oic acid : A ent-kaurane diterpenoid that is ent-kaurane-19-oic acid substituted by hydroxy groups at positions 16 and 17 (the 16beta stereoisomer). It is isolated from Helianthus sp. and Annona squamosa and exhibits anti-HIV activity. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Annona | genus | A plant genus of the family ANNONACEAE. It has edible fruit and seeds which contain acetogenins and benzoquinazoline and other alkaloids.[MeSH] | Annonaceae | The custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH] |
| Helianthus | genus | A genus herbs of the Asteraceae family. The SEEDS yield oil and are used as food and animal feed; the roots of Helianthus tuberosum (Jerusalem artichoke) are edible.[MeSH] | Asteraceae | A large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH] |
| Annona squamosa | species | [no description available] | Annonaceae | The custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 469209 |
| CHEMBL ID | 482613 |
| CHEBI ID | 65778 |
| Synonym |
|---|
| 16.beta.,17-dihydroxy-ent-kauran-19-oic acid |
| 16b,17-dihydroxykaruran-18-oic acid |
| CHEMBL482613 |
| chebi:65778 , |
| 16beta,17-dihydroxy-ent-kaurane-19-oic acid |
| (5beta,8alpha,9beta,10alpha)-16,17-dihydroxykauran-18-oic acid |
| LMPR0104130006 |
| Q27134265 |
| (1s,4s,5r,9s,10r,13r,14s)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid |
| 16alpha,17-dihydroxy-ent-kauran-19-oic acid |
| Role | Description |
|---|---|
| metabolite | Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| anti-HIV agent | An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| ent-kaurane diterpenoid | A diterpenoid compound having an ent-kaurane skeleton. |
| hydroxy monocarboxylic acid | Any monocarboxylic acid which also contains a separate (alcoholic or phenolic) hydroxy substituent. |
| diol | A compound that contains two hydroxy groups, generally assumed to be, but not necessarily, alcoholic. Aliphatic diols are also called glycols. |
| tertiary alcohol | A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it. |
| primary alcohol | A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it. |
| bridged compound | A polycyclic compound in which two rings have two or more atoms in common. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID355091 | Antiviral activity against HIV1 3B replication in human H9 cells after 3 days by p24 antigen capture assay | 1996 | Journal of natural products, Jun, Volume: 59, Issue:6 | Identification of ent-16 beta, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa. |
| AID1416503 | Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay | 2017 | MedChemComm, Aug-01, Volume: 8, Issue:8 | Extraction of antioxidant and antiproliferative ingredients from fruits of |
| AID336447 | Antiplatelet activity against washed rabbit platelet assessed as inhibition of arachidonic acid-induced platelet aggregation at 200 uM | 2002 | Journal of natural products, Oct, Volume: 65, Issue:10 | New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa. |
| AID336450 | Antiplatelet activity against washed rabbit platelet assessed as inhibition of thrombin-induced platelet aggregation at 200 uM | 2002 | Journal of natural products, Oct, Volume: 65, Issue:10 | New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa. |
| AID1354615 | Neuroprotective activity against H2O2-induced cell death in human SH-SY5Y cells assessed as increase in cell viability up to 100 uM | |||
| AID336448 | Antiplatelet activity against washed rabbit platelet assessed as inhibition of collagen-induced platelet aggregation at 200 uM | 2002 | Journal of natural products, Oct, Volume: 65, Issue:10 | New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa. |
| AID1416505 | Cytotoxicity against human A549 cells after 24 hrs by MTT assay | 2017 | MedChemComm, Aug-01, Volume: 8, Issue:8 | Extraction of antioxidant and antiproliferative ingredients from fruits of |
| AID1176269 | Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells after 24 hrs by Griess assay relative to vehicle-treated control | 2015 | Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2 | New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages. |
| AID1176267 | Cytotoxicity against mouse RAW264.7 cells at 30 uM by MTT assay relative to control | 2015 | Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2 | New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages. |
| AID1416504 | Cytotoxicity against human Bel7402 cells after 24 hrs by MTT assay | 2017 | MedChemComm, Aug-01, Volume: 8, Issue:8 | Extraction of antioxidant and antiproliferative ingredients from fruits of |
| AID1416506 | Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay | 2017 | MedChemComm, Aug-01, Volume: 8, Issue:8 | Extraction of antioxidant and antiproliferative ingredients from fruits of |
| AID1176268 | Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells at 30 uM after 24 hrs by Griess assay relative to vehicle-treated control | 2015 | Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2 | New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages. |
| AID355093 | Therapeutic index, ratio of inhibition of human H9 cells to EC50 for HIV1 3B | 1996 | Journal of natural products, Jun, Volume: 59, Issue:6 | Identification of ent-16 beta, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa. |
| AID336449 | Antiplatelet activity against washed rabbit platelet assessed as inhibition of platelet activating factor-induced platelet aggregation at 200 uM | 2002 | Journal of natural products, Oct, Volume: 65, Issue:10 | New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 1 (20.00) | 18.2507 |
| 2000's | 1 (20.00) | 29.6817 |
| 2010's | 3 (60.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.94) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||