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BRYONOLIC ACID
Bryononic acid is an organic hydroxy compound.
Bryonolic acid is a natural product found in Benincasa hispida, Macaranga conifera, and other organisms.
CAS: 24480-44-2
IUPAC Name: (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-2-carboxylic acid
Molecular Formula: C30H48O3
Molecular Weight: 456.7 g/mol
Bryonolic acid (3β-hydroxy-D:C-friedoolean-8-en-29-oic acid, BA) is a naturally occurring triterpenoid that has been identified in multiple species of the Cucurbitaceae family and in dispersed species of other reported plant families (Meliaceae, Tetramelaceae, and Anisophylleaceae).
Bryonolic acid (BA) is a triterpenoid found in the Cucurbitaceae family of plants.
Bryonolic acid is an active triterpenoid compound with immunomodulatory, anti-inflammatory, antioxidant and anticancer activities.
Bryonolic acid exerts anti-allergic activity by inhibiting homologous passive cutaneous anaphylaxis and delayed hypersensitivity.
Bryonolic acid reduces nitric oxide by suppressing inducible nitric oxide synthase expression, indicating anti-inflammatory activity
Bryonolic acid isolated from the herbs of Sandoricum indicum.
Bryononic acid induces a obviously increase in the expression of a phase 2 response enzyme and heme oxygenase 1 (HO-1) in a dose-dependent manner.
Bryonolic acid, 3β-hydroxy-D:C-friedoolean-8en-29-oic acid belongs to pentacyclic triterpenoids.
Unlike other pentacyclic triterpenoids, such as betulinic acid and ursolic acid3, bryonolic acid and its derivatives have not yet been widely studied on their pharmacological activities due to non-commercial availability.
Therefore, bryonolic acid is an interesting compound which can be used as lead compound for structural modication in structure-activity relationship studies to develop new bioactive substances.
Based on bryonolic acid structure, there are some functional groups that can be derivatized, including C-3 hydroxyl and C-20 carboxyl groups.
There are several routes to modify bryonolic acid structure. For examples, both functional groups are available for either esterification or amide formation. Moreover, carboxyl group can be subjected to reduction reaction to yield aldehyde or alcohol derivatives.
While hydroxyl group can be oxidized to ketone. Also, bryonolic acid glycosides, obtained by glycosylation reaction, should be other interesting derivatives since attached sugar compounds will provide hydrophilic groups and can improve pharmacokinetic properties of bryonolic acid.
Based on these results, bryonolic acid with its unique properties may be considered as a promising natural lead compound for derivatization in order to obtain new semi-synthetic compounds which can be used as promising drug candidates in the future.
Bryonolic acid, also known as bryonolate, belongs to the class of organic compounds known as cyclic alcohols and derivatives.
These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.
Bryonolic acid has been detected, but not quantified in, several different foods, such as calabashes (Lagenaria siceraria), fruits, olives (Olea europaea), towel gourds (Luffa aegyptiaca), and watermelons (Citrullus lanatus).
This could make bryonolic acid a potential biomarker for the consumption of these foods.
Bryonolic acid (BA) is a triterpenoid found in the Cucurbitaceae family of plants, has anti-inflammatory and antioxidant activities.
A pentacyclic triterpenoid C-friedooleanane-type triterpenoids extracted from the stems of Lagenaria siceraria and roots of Coriaria intermedia and has been found to exhibit antineoplastic activity.
Substituents:
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Aliphatic homopolycyclic compound
Bryonolic acid is an analytical reference material that is naturally found in plants.
Bryononic acid has been shown to have antifungal and antibacterial properties, as well as the ability to reduce inflammation.
Bryonolic acid is used in research and development for quality control purposes, as a screening tool for plant-derived products, and as a reference material for HPLC standards.
General tips
For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.
Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day.
However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃.
In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
1. Bryonolic acid has anti-allergic activity.
2. Bryonolic acid exhibits cytotoxic activity to various tumor cells in vitro, independent of cell type.
3. Bryonolic acid can induce a marked increase in the expression of a phase 2 response enzyme, heme oxygenase 1 (HO-1), in a dose-dependent manner.
4. Bryonolic acid can protect PC12 cells against NMDA-induced apoptosis by inhibiting Ca2+ influx and regulating gene expression in the Ca2+-CaMKII-CREB signal pathway, supports that it may be a promising neuroprotective agent for the treatment of cerebral ischemia disease.
5. Bryonolic acid has anti-inflammatory and antioxidant activities, it can reduce the inflammatory mediator NO by suppressing the expression of the inflammatory enzyme inducible nitric oxide synthase (iNOS) in LPS-activated RAW 264.7 macrophage cells.
SYNONYMS:
Bryononic acid
Bryonolic acid
24480-44-2
(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-Hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-eicosahydro-picene-2-carboxylic acid
(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-2-carboxylic acid
24480-45-3
D:C-Friedoolean-8-en-29-oic acid, 3-oxo-
CHEMBL482596
DTXSID30947378
CHEBI:172017
FS-9647
(20R)-3-Oxo-D:C-friedoolean-8-en-29-oic acid
(2R, 4aS, 6aS, 8aR, 10S, 12aS, 14aS, 14bR)-10-hydroxy-2, 4a, 6a, 9, 9, 12a, 14a-heptamethyl-1, 3, 4, 5, 6, 7, 8, 8a, 10, 11, 12, 13, 14, 14b-tetradecahydropicene-2-carboxylic acid
(2R-alpha,4abeta,6abeta,8aalpha,12abeta,14aalpha,14bbeta))- 1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-Eicosahydro-2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-2-picenecarboxylic acid
10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylic acid
D:C-Friedoolean-8-en-29-oic acid, 3-hydroxy-, (3,20)-; D:C-Friedoolean-8-en-29-oic acid, 3-hydroxy-
