Brassicasterol

Brassicasterol

Brassicasterol Brassicasterol
Ball-and-stick model of brassicasterol
Names
IUPAC name Ergosta-5,22-dien-3β-ol
Systematic IUPAC name (1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,3E,4R)-5,6-Dimethylhept-3-en-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Other names brassicasterol (3β,22E)-ergosta-5,22-dien-3-ol 24β-methylcholesta-5,22-dien-3 beta-ol 24-methyl cholest-5,22-dien-3β-ol
Identifiers
CAS Number	474-67-9 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3168
ChemSpider	4444704 checkY
ECHA InfoCard
E number
PubChem CID	6432458
UNII	2B0KG2XFOF checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1 checkY Key: OILXMJHPFNGGTO-ZAUYPBDWSA-N checkY InChI=1/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1 Key: OILXMJHPFNGGTO-ZAUYPBDWBS
SMILES O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@@]2([C@H](CC[C@@H]12)[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@@]3(C)CC4
Properties
Chemical formula	C28H46O
Molar mass	398.675 g·mol−1
Appearance	White solid
Melting point	150 to 151 °C (302 to 304 °F; 423 to 424 K)
Hazards
Flash point	Non-flammable
Related compounds
Related Sterols	cholesterol β-sitosterol campesterol stigmasterol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is checkY☒N ?) Infobox references

Brassicasterol (24-methyl cholest-5,22-dien-3β-ol) is a 28-carbon sterol synthesised by several unicellular algae (phytoplankton) and some terrestrial plants, like rape. This compound has frequently been used as a biomarker for the presence of (marine) algal matter in the environment, and is one of the ingredients in stigmasterol-rich plant sterols (Number E499 in the European numbering system). There is some evidence to suggest that it may also be a relevant additional biomarker in Alzheimer's disease.

Chemical properties

Solubility

Brassicasterol has a low water solubility and, as a consequence, a high octanol-water partition coefficient. This means that, in most environmental systems, brassicasterol will be associated with the solid phase.

Degradation

In anaerobic sediments and soils, brassicasterol is stable for many hundreds of years, enabling it to be used as an indicator of past algal production (see below).

Chemical analysis

Since the molecule has a hydroxyl (-OH) group, it is frequently bound to other lipids including glycerols; most analytical methods, therefore, utilise a strong alkali (KOH or NaOH) to saponify the ester linkages. Typical extraction solvents include 6% KOH in methanol. The free sterols are then separated from the polar lipids by partitioning into a less polar solvent such as hexane. Prior to analysis, the hydroxyl group is frequently derivatised with BSTFA (bis-trimethyl silyl trifluoroacetamide) to replace the hydrogen with the less exchangeable trimethylsilyl (TMS) group. Instrumental analysis is frequently conducted on gas chromatograph (GC) with either a flame ionisation detector (FID) or mass spectrometer (MS). The mass spectrum for the TMS ether of brassicasterol can be seen in the figure.
Mass fragmentation pattern for brassicasterol at 70eV on a Fisons MD800 mass spectrometer

Formation and occurrences

It can be found in Mirabilis jalapa.

Algal sources

Brassicasterol is formed in plants from the isoprenoid squalene through campesterol as an intermediate. A list of the algae in which brassicasterol has been identified is shown below together with approximate composition.

Sterol content of selected dinoflagellates (as percentage). Data from Volkman, 1986

Species	A	B	C	D	E	F	G	H	others
Gonyaulax spp	100	0	0	0	0	0	0	0	0
Peridinium foliaceum	100	0	0	0	0	0	0	0	0
Peridinium foliaceum	80	20	0	0	0	0	0	0	0
Gonyaulax diegensis	39	0	0	0	0	0	0	29	32
Pyrocystis lunula	76	6	0	2	1	0	0	0	15
Gonyaulax polygramma	36	1	0	9	7	0	0	0	47
Gymnodinium wilczeki	26	39	0	35	1	0	0	0	0
Glenodinium hallii	8	50	0	0	0	42	0	0	0
Noctiluca milaris	0	1	1	5	73	0	6	0	14
Gymnodinium simplex	0	0	0	0	53	0	0	0	47
Prorocentrum cordatum	7	0	0	0	5	0	63	0	25

A = cholesterol

B = campesterol

C = sitosterol

D = 22-dehydrocholesterol ((22E)-cholesta-5,22-dien-3β-ol)

E = brassicasterol

F = stigmasterol

G = 24-methylene cholesterol

H = fucosterol

Use as a tracer for marine algae

The principal source of brassicasterol in the environment is from marine algae. Its relatively high concentration and stability allows it to be used in the assessment of the origin of organic matter in samples, especially sediments.

Brassicasterol / cholesterol ratio

The concentration of brassicasterol down a sediment core from Loch Striven, Scotland together with it ratio to cholesterol

The concentration of brassicasterol in a core sample from Loch Striven, Scotland. Highest values may be seen in the top sections of the sediment, which decrease with depth. However, the cholesterol behaves in a similar manner, and the ratio brassicasterol/cholesterol is fairly uniform at all depths, indicating either a comparable degradation rate with no change in source or different degradation rates and a change in source.

Multivariate analysis

Multivariate statistical analyses such as principal component analysis of a range of lipid biomarkers (e.g., other sterols, fatty acids, and fatty alcohols) enable identification of compounds that have similar origins or behaviour. An example can be seen in the loadings plot for sediment samples from the Mawddach Estuary, Wales.

Principal Component Analysis of several lipid biomarkers from the Mawddach Esturay - brassicasterol is highlighted in red
The location of brassicasterol in this figure (shown in red) indicates that the distribution of this compound is similar to that of the short-chain fatty acids and alcohols, which are of marine origin. The terrestrially derived biomarkers such as β-sitosterol are on the opposite side of the figure and are mutually exclusive.