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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

List of amino acids and amines isolated from sandal leaves
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Fig6: List of amino acids and amines isolated from sandal leaves

Mentions: The identification of the amino acids was done by Dr. T.F. Spande, National Institute of Diabetes and Digestive and kidney diseased, Bethesda, Maryland, U.S.A. The isatin positive material (Fraction II) was not found to be acelyted by acetic anhydride (2 h at room temperature) suggesting a tertiary amine. It was converted with CH3OH–BCL3 to a methyl ester (FTIR 1751 CM-1 Bohlmann) which chromatographed on GC–MS giving M/Z 169 (20, 154 (10), 14115, 138 (15), 110 (10), 108 (15), 83 (70), 82 (70) etc. A mass spectrum very similar to that reported for a diastereomeric ethyl ester isolated from an orchid. A 2D proton cosy spectrum established connectivities and indicated the above (or enantiomeric) structure unambiguously. This was further confirmed by 13C NMR and a proton carbon correlation spectrum (500 MHz). A sample was crystallized from CH3OH to EtOAc twice and had M.P. 213–5o (lit 215–6o) and a rotation of (α) D = 30.5o (H2O). These evidences indicated the structure of isatin-positive material is pyrrolizidine-1-carboxylic acid (Fig. 6).Fig. 6


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)

List of amino acids and amines isolated from sandal leaves
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Fig6: List of amino acids and amines isolated from sandal leaves
Mentions: The identification of the amino acids was done by Dr. T.F. Spande, National Institute of Diabetes and Digestive and kidney diseased, Bethesda, Maryland, U.S.A. The isatin positive material (Fraction II) was not found to be acelyted by acetic anhydride (2 h at room temperature) suggesting a tertiary amine. It was converted with CH3OH–BCL3 to a methyl ester (FTIR 1751 CM-1 Bohlmann) which chromatographed on GC–MS giving M/Z 169 (20, 154 (10), 14115, 138 (15), 110 (10), 108 (15), 83 (70), 82 (70) etc. A mass spectrum very similar to that reported for a diastereomeric ethyl ester isolated from an orchid. A 2D proton cosy spectrum established connectivities and indicated the above (or enantiomeric) structure unambiguously. This was further confirmed by 13C NMR and a proton carbon correlation spectrum (500 MHz). A sample was crystallized from CH3OH to EtOAc twice and had M.P. 213–5o (lit 215–6o) and a rotation of (α) D = 30.5o (H2O). These evidences indicated the structure of isatin-positive material is pyrrolizidine-1-carboxylic acid (Fig. 6).Fig. 6

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