Synthesis of the Major Mammalian Metabolites of THCV
A simple synthesis of the major oxidized metabolites in mammalian tissues of (-)-Δ9-tetrahydrocannabivarin (THCV) (1) has been accomplished by kinetic studies of allylic oxidation using SeO2 on botanically derived THCV with the aim to yield primary and secondary allylic alcohols concurrently. This synthetic approach led to the preparation of numerous THCV derivatives, including two new compounds, 8α-hydroxy-Δ9-tetrahydrocannabivarin (2) and 8β-hydroxy-Δ9-tetrahydrocannabivarin (3), and the known compounds 11-hydroxy-Δ9-tetrahydrocannabivarin (4) and Δ9-tetrahydrocannabivarin-11-oic acid (5), without affecting the C-10a stereogenic center in the natural precursor and without formation of tricyclic dibenzopyran derivatives. This simple synthetic methodology could be useful to investigate the pharmacological role of THCV metabolites at, among others, the endocannabinoid CB1 and CB2 receptors for which THCV reportedly acts as respectively a neutral antagonist and partial agonist.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2020 |
|---|---|
| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:83 |
|---|---|
| Enthalten in: |
Journal of natural products - 83(2020), 7 vom: 24. Juli, Seite 2060-2065 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Tinto, Francesco [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
|---|
| Anmerkungen: |
Date Completed 18.08.2021 Date Revised 18.08.2021 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1021/acs.jnatprod.9b00831 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM312259824 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM312259824 | ||
| 003 | DE-627 | ||
| 005 | 20231225144028.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231225s2020 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.jnatprod.9b00831 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1040.xml |
| 035 | |a (DE-627)NLM312259824 | ||
| 035 | |a (NLM)32649196 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Tinto, Francesco |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of the Major Mammalian Metabolites of THCV |
| 264 | 1 | |c 2020 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 18.08.2021 | ||
| 500 | |a Date Revised 18.08.2021 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a A simple synthesis of the major oxidized metabolites in mammalian tissues of (-)-Δ9-tetrahydrocannabivarin (THCV) (1) has been accomplished by kinetic studies of allylic oxidation using SeO2 on botanically derived THCV with the aim to yield primary and secondary allylic alcohols concurrently. This synthetic approach led to the preparation of numerous THCV derivatives, including two new compounds, 8α-hydroxy-Δ9-tetrahydrocannabivarin (2) and 8β-hydroxy-Δ9-tetrahydrocannabivarin (3), and the known compounds 11-hydroxy-Δ9-tetrahydrocannabivarin (4) and Δ9-tetrahydrocannabivarin-11-oic acid (5), without affecting the C-10a stereogenic center in the natural precursor and without formation of tricyclic dibenzopyran derivatives. This simple synthetic methodology could be useful to investigate the pharmacological role of THCV metabolites at, among others, the endocannabinoid CB1 and CB2 receptors for which THCV reportedly acts as respectively a neutral antagonist and partial agonist | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Cannabinoids |2 NLM | |
| 700 | 1 | |a Villano, Rosaria |e verfasserin |4 aut | |
| 700 | 1 | |a Kostrzewa, Magdalena |e verfasserin |4 aut | |
| 700 | 1 | |a Ligresti, Alessia |e verfasserin |4 aut | |
| 700 | 1 | |a Straker, Hannah |e verfasserin |4 aut | |
| 700 | 1 | |a Manzo, Emiliano |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Journal of natural products |d 1979 |g 83(2020), 7 vom: 24. Juli, Seite 2060-2065 |w (DE-627)NLM000924377 |x 1520-6025 |7 nnns |
| 773 | 1 | 8 | |g volume:83 |g year:2020 |g number:7 |g day:24 |g month:07 |g pages:2060-2065 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.jnatprod.9b00831 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 83 |j 2020 |e 7 |b 24 |c 07 |h 2060-2065 | ||