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Amino acids in sandal (Santalum album L) with special reference to cis-4-hydroxy-l-proline and sym. homospermidine.

Kuttan R, Panikkar B, Binitha PP - Springerplus (2015)

Bottom Line: Sandal also contains sym. homospermidine which is not present in any other plants till today.Moreover sandal leaves contain γ-glutamyl derivative of the lachrymatory precursor of onion, γ-glutamyl-S-propenyl cysteine superoxide.This review summarizes the studies on the amino acids in sandal.

View Article: PubMed Central - PubMed

Affiliation: Amala Cancer Research Centre, Amala Nagar, Thrissur, Kerala 680555 India.

ABSTRACT
Sandal (Santalum album L) contains several interesting amino acids and amines which are not seen in other plants. This includes cis-4-hydroxy-l-proline in free form in leaves, flowers and seeds while trans-4-hydroxy-l-proline in bound form. Traces of 3, 4 dehydroproline is also detected in sandal leaves. Biosynthesis of cis-4-hydroxy proline indicates that hydroxylation taken place at proline present in peptidyl form especially bound to glutamic acid and aspartic acid. Pyrrolizidine-2-carboxylic acid an interesting isatin positive heterocyclic compound is also present in sandal leaves. Sandal also contains sym. homospermidine which is not present in any other plants till today. Biosynthesis of sym. homospermidine goes by a unique pathway of putrescine oxidation, Schiff base formation, condensation and reduction. Moreover sandal leaves contain γ-glutamyl derivative of the lachrymatory precursor of onion, γ-glutamyl-S-propenyl cysteine superoxide. This review summarizes the studies on the amino acids in sandal.

No MeSH data available.


Related in: MedlinePlus

Biosynthesis of sym. homospermidine
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Fig7: Biosynthesis of sym. homospermidine

Mentions: Two dimensional chromatography of an alcoholic extract of sandal leaves showed prominent ninhydrin positive malene near the origin in butanol acetic acid water (4:1:1). During Dowex 50 × 8H+ column chromatography this material was not eluted with 1 N ammonium hydroxide in which most of the amino acids eluted. When the column was further eluted a stronger base piperidine (1 M) this ninhydrin positive material was found to be eluted as a single spot. Operation of this procedure using longer column led to the purification of this compound which was further characterized by NMR IR spectrum and mass spectrum analysis as sym. homospermidine, a new polyamine, not reported earlier from any other system. (yield was 1.5 g). Structure of the sym. homospermidine was seen in Fig. 7. Moreover synthetic homospermide hydrochloride was prepared which superimposed on that of natural homospermidine. Chromatographic behavior of both was identical.Fig. 7


Amino acids in sandal (Santalum album L) with special reference to cis-4-hydroxy-l-proline and sym. homospermidine.

Kuttan R, Panikkar B, Binitha PP - Springerplus (2015)

Biosynthesis of sym. homospermidine
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4582034&req=5

Fig7: Biosynthesis of sym. homospermidine
Mentions: Two dimensional chromatography of an alcoholic extract of sandal leaves showed prominent ninhydrin positive malene near the origin in butanol acetic acid water (4:1:1). During Dowex 50 × 8H+ column chromatography this material was not eluted with 1 N ammonium hydroxide in which most of the amino acids eluted. When the column was further eluted a stronger base piperidine (1 M) this ninhydrin positive material was found to be eluted as a single spot. Operation of this procedure using longer column led to the purification of this compound which was further characterized by NMR IR spectrum and mass spectrum analysis as sym. homospermidine, a new polyamine, not reported earlier from any other system. (yield was 1.5 g). Structure of the sym. homospermidine was seen in Fig. 7. Moreover synthetic homospermide hydrochloride was prepared which superimposed on that of natural homospermidine. Chromatographic behavior of both was identical.Fig. 7

Bottom Line: Sandal also contains sym. homospermidine which is not present in any other plants till today.Moreover sandal leaves contain γ-glutamyl derivative of the lachrymatory precursor of onion, γ-glutamyl-S-propenyl cysteine superoxide.This review summarizes the studies on the amino acids in sandal.

View Article: PubMed Central - PubMed

Affiliation: Amala Cancer Research Centre, Amala Nagar, Thrissur, Kerala 680555 India.

ABSTRACT
Sandal (Santalum album L) contains several interesting amino acids and amines which are not seen in other plants. This includes cis-4-hydroxy-l-proline in free form in leaves, flowers and seeds while trans-4-hydroxy-l-proline in bound form. Traces of 3, 4 dehydroproline is also detected in sandal leaves. Biosynthesis of cis-4-hydroxy proline indicates that hydroxylation taken place at proline present in peptidyl form especially bound to glutamic acid and aspartic acid. Pyrrolizidine-2-carboxylic acid an interesting isatin positive heterocyclic compound is also present in sandal leaves. Sandal also contains sym. homospermidine which is not present in any other plants till today. Biosynthesis of sym. homospermidine goes by a unique pathway of putrescine oxidation, Schiff base formation, condensation and reduction. Moreover sandal leaves contain γ-glutamyl derivative of the lachrymatory precursor of onion, γ-glutamyl-S-propenyl cysteine superoxide. This review summarizes the studies on the amino acids in sandal.

No MeSH data available.


Related in: MedlinePlus