Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2015 Sep 24:4:546.
doi: 10.1186/s40064-015-1303-1. eCollection 2015.

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

Ramadasan Kuttan  1 , Beena Panikkar  1 , Ponnamparambil Purushothaman Binitha  1
Affiliations
Review

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

Ramadasan Kuttan et al. Springerplus. .

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.

Keywords: Biosynthetic pathways; Hydroxy prolines; Lachrymatory precursor; Sandal (Santalum album); sym. Homospermidine.

PubMed Disclaimer

Figures

Fig. 1
Fig. 1
Structure of hydroxyproline
Fig. 2
Fig. 2
Demonstration of presence of 3, 4 dehydroproline in sandal leaf extract using paper chromatographic procedure
Fig. 3
Fig. 3
Two dimensional paper chromatography of Ehrlich positive material. 1 cis-4-hydroxy proline. 2 Proline. 3, 4, 5 Ehrlich positive material
Fig. 4
Fig. 4
Biosynthesis of cis-4-hydroxyproline
Fig. 5
Fig. 5
Paper chromatogram of isatin positive material in phenol–KCl: HCl Buffer (1) Isatin positive material, (2) proline, (3) hydroxyproline
Fig. 6
Fig. 6
List of amino acids and amines isolated from sandal leaves
Fig. 7
Fig. 7
Biosynthesis of sym. homospermidine
Fig. 8
Fig. 8
Production of lachrymatory factor from γ-glutamyl-s-propenyl-l-cysteine Sulfoxide
See this image and copyright information in PMC

References

    1. Fischer E. Über eine neue Aminosäure aus Leim. Chem Ber. 1902;35:2660–2665. doi: 10.1002/cber.19020350324. - DOI
    1. Kuttan R, Radhakrishnan AN. The biosynthesis of cis-4-hydroxy-l-proline in sandal (Santalum album L.) Biochem J. 1970;117:1015–1017. doi: 10.1042/bj1171015. - DOI - PMC - PubMed
    1. Kuttan R, Radhakrishnan AN, Spande T, Witkop B. sym-Homospermidine, a naturally occurring polyamine. Biochemistry. 1971;10:361–365. doi: 10.1021/bi00779a001. - DOI - PubMed
    1. Kuttan R, Nair GN, Radhakrishnan AN, Spande T, Yeh HJ, Witkop B. The isolation and characterization of γ-l-Glutamyl-S-(trans-1-propenyl)-l-cysteine sulfoxide from sandal (Santalum album L) an interesting occurrence of sulfoxide diasterioisomers in nature. Biochemistry. 1974;113:4394. doi: 10.1021/bi00718a024. - DOI - PubMed
    1. Kuttan R, Pattabhiaman KSV, Radhakrishnan AN. Possible chemotaxonomic significance of the occurrence of cis-4-hydroxy-l-proline in Santalaceae. Phytochemistry. 1974;13:453–454. doi: 10.1016/S0031-9422(00)91231-7. - DOI

LinkOut - more resources