Record Information |
---|
Version | 1.0 |
---|
Created at | 2021-06-21 00:42:22 UTC |
---|
Updated at | 2021-06-30 00:18:49 UTC |
---|
NP-MRD ID | NP0043240 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | tenuifolin D |
---|
Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
---|
Description | Tenuifolin D belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. tenuifolin D is found in Isodon tenuifolius. It was first documented in 2002 (PMID: 33651529). Based on a literature review a small amount of articles have been published on Tenuifolin D (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454) (PMID: 33851450) (PMID: 24702811). |
---|
Structure | [H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])[C@@]11[C@@]([H])(O[H])C([H])([H])[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])C2([H])[H] InChI=1S/C24H36O7/c1-11-14-7-15(30-12(2)25)20-23(6)16(8-18(28)24(20,10-14)21(11)29)22(4,5)17(27)9-19(23)31-13(3)26/h14-21,27-29H,1,7-10H2,2-6H3/t14-,15+,16-,17+,18+,19+,20+,21-,23+,24+/m1/s1 |
---|
Synonyms | Not Available |
---|
Chemical Formula | C24H36O7 |
---|
Average Mass | 436.5450 Da |
---|
Monoisotopic Mass | 436.24610 Da |
---|
IUPAC Name | (1R,2S,4R,6S,8S,9R,10S,11S,13S,15R)-8-(acetyloxy)-2,6,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate |
---|
Traditional Name | (1R,2S,4R,6S,8S,9R,10S,11S,13S,15R)-8-(acetyloxy)-2,6,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])[C@@]11[C@@]([H])(O[H])C([H])([H])[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])C2([H])[H] |
---|
InChI Identifier | InChI=1S/C24H36O7/c1-11-14-7-15(30-12(2)25)20-23(6)16(8-18(28)24(20,10-14)21(11)29)22(4,5)17(27)9-19(23)31-13(3)26/h14-21,27-29H,1,7-10H2,2-6H3/t14-,15+,16-,17+,18+,19+,20+,21-,23+,24+/m1/s1 |
---|
InChI Key | OTPQVCJGZXJUEW-KNGCFTRFSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 600 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, C5D5N, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | Species Name | Source | Reference |
---|
Isodon tenuifolius | JEOL database | - Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013)
|
|
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Prenol lipids |
---|
Sub Class | Diterpenoids |
---|
Direct Parent | Kaurane diterpenoids |
---|
Alternative Parents | |
---|
Substituents | - Kaurane diterpenoid
- Dicarboxylic acid or derivatives
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid ester
- Polyol
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homopolycyclic compound
|
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
- Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
- Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
- Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
- Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
- Koganezawa N, Sekino Y, Kawakami H, Fuchino H, Kawahara N, Shirao T: NMDA receptor-dependent and -independent effects of natural compounds and crude drugs on synaptic states as revealed by drebrin imaging analysis. Eur J Neurosci. 2021 Jun;53(11):3548-3560. doi: 10.1111/ejn.15231. Epub 2021 Apr 27. [PubMed:33851450 ]
- Zhou YH, Zhang SY, Guo Q, Chai XY, Jiang Y, Tu PF: Chemical investigation of the roots of Polygala sibirica L. Chin J Nat Med. 2014 Mar;12(3):225-8. doi: 10.1016/S1875-5364(14)60038-8. [PubMed:24702811 ]
- Ma B, Li X, Li J, Zhang Q, Liu Y, Yang X, Sun J, Yao D, Liu L, Liu X, Ying H: Quantitative analysis of tenuifolin concentrations in rat plasma and tissue using LCMS/MS: application to pharmacokinetic and tissue distribution study. J Pharm Biomed Anal. 2014 Jan;88:191-200. doi: 10.1016/j.jpba.2013.07.012. Epub 2013 Jul 23. [PubMed:24055855 ]
- Zhang H, Han T, Zhang L, Yu CH, Wan DG, Rahman K, Qin LP, Peng C: Effects of tenuifolin extracted from radix polygalae on learning and memory: a behavioral and biochemical study on aged and amnesic mice. Phytomedicine. 2008 Aug;15(8):587-94. doi: 10.1016/j.phymed.2007.12.004. Epub 2008 Mar 4. [PubMed:18289838 ]
- Diome C, Mitaine-Offer AC, Miyamoto T, Delaude C, Mirjolet JF, Duchamp O, Lacaille-Dubois MA: Saponins from the roots of Nylandtia spinosa. J Nat Prod. 2007 Oct;70(10):1680-2. doi: 10.1021/np0703186. Epub 2007 Oct 11. [PubMed:17927264 ]
- Yang, J. -H., et al. (2013). Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013). J. Nat. Prod..
|
---|