solacasine

2. a New Steroidal Alkaloid from Solanum pseudocapsicum
Possessing Antimicrobial Activity

3. Index
Introduction
Historical Background
Techniques Used
Isolation
Experiment

4. Introduction[1]
 In 1975, L. A. Mitscher, J. V. Juvarkar and J. L. Beal
observed additional antimicrobially active agents instead of
previously reported alkaloid “Solanocapsine”.
 Based on physiochemical studies, a structure is proposed.

6. Historical Background[1][5]
 Solacasine was derived from Solanum pseudocapsicum.
 Solanum pseudocapsicum is a posionous plant.
 Native to Peru and Ecuador.
 Commonly known as Jerusalem Cherry.
 Various forms are kept as ornamentals.
 Has great chemical and biological value.

7. Family Chain[4]
Kingdom
Division
Clade
Clade
Order
Family
Genus
Specie

8. Techniques
Used
Mass
Spectrometry
(EI,CI)
Infrared
Spectroscopy
Chromatography
(Column,Thin-Layer)

9. Mass Spectrometry
 Mass spectrometry is the study of matter through the
formation of ions that are characterized by their mass and
charge.[6]
 Different techniques of MS use now a days.
 EIMS and CIMS used in this experiment.

10. MS Scheme Diagram

11. EIMS[7] CIMS[7]
 Electron Ionization Mass
Spectrometry.
Electrons interact with gas
phase atoms or molecules to
produce ions.
‘Harder’ technique, high levels
of fragmentaion observed .
Chemical Ionization Mass
Spectrometry.
Ions are produced through the
collision of the analyte with
ions of a reagent gas.
‘Softer’ technique, less
fragmentation observed.

12. Infrared Spectrosopy[9]
It is the spectroscopy that deals with the infrared region of
the electromagnetic spectrum.
It is use to identify the functional groups.
A molecule absorbs only selected frequencies of IR radiation.
Only those bonds which have dipole moment are capable of
absorbing in IR region.
Amplitude of vibrational motion of bond increases with absorbance.
Different modes of vibrations.

13. Symmetrical
stretching
Antisymmetrical
stretching Scissoring
Rocking Wagging Twisting
Vibrational
Modes

14. Chromatoghraphy[8]
Derived from Greek words chroma “color” and graphine
“to write”.
It is used to purify individual chemical
compounds from mixture.
The various constituents of the mixture travel at
different speeds, causing them to separate.
CC and TLC used in isolation.

15. Column Chromatography
Glass tube is used as column.
Stationary phase is solid, usually silica gel.
The mobile phase is either a pure solvent or a
mixture of different solvents.
Can be used on large and small scale.
Simple and low cost.

16. Thin-Layer Chromatography
Used for identifying substances and testing the purity.
Performed on a sheet of glass, plastic, or aluminium foil.
Coated with thin layer of stationary phase.
Mobile phase is drawn up the plate via capillary action.
Very quick.

18. Isolation[3]
18 hrs

19. Isolation[3]

21. Solacasine[1]
 Steroidal alkaloid
 Main antibacterial costituent of S.pseudocapsicum
 Yield 0.006%
 Molecular Formula: C28H46N2O2
 Molecular Mass: 442.68 u
 Melting Point: 215-220o
 Specific Rotation [α]: +29 (methanol)

22. Structure[1]

23. IR Spectrum of Solacasine
3400 cm-1 (-NH2)
1660 cm-1 (C=N)

24. EIMS Spectrum
M+ 442 (38%)
427 (22%)
410 (M+ -MeOH, 10%)
130 (14%)
189 (8%)
169 (10%)
115 (100%)
95 (10%)
93 (10%)
83 (10%)
82 (16%)
73 (22%)
69 (12%)
57 (10%)
56 (28%)
55 (23%)

25. CIMS Spectrum of Solacasine
MH+ 443 (100%)
411 (MH+ -MeOH ,30%)
No other peaks of significant intensity.

28. EIMS (1) (2) (3) (4)
M+ 430 (7%) 444 (9%) 442 (38%) 486 (5%)
M+-H2O 412 (100%)
M+-CH3OH 412 (64%) 410 (10%) 454 (53%)
Same peaks
82 (20%) 82 (16%)
56 (25%) 56 (28%)
Mass Spectra Comparison

30. In Vitro Antimicrobial Activity[1]
Microorganism 1* 2* 3* 4*
Staphylococcus
aureus
100 100 12.5 100
Mycobacterium
smegmatis
100 100 5.0 100
Candida
albicans
100 50 2.5 50
*µg/ml

31. References
1. Mitscher, L. A.; Juvarkar, J. V.; Beal, J. L. , Experientia, Volume: 32, Issue: 4, Pages: 415-16, Journal,
1976.
2. Barger, L. G.; Fraenkel-Conrat, H. L. , Journal of the Chemical Society, Pages: 1537-42, Journal, 1936.
3. Vijayan, P.; Vinod Kumar, S.; Dhanaraj, S. A.; Badami, Shrishailappa; Suresh, Pharmaceutical Biology
(Lisse, Netherlands), Volume: 40, Issue: 6, Pages: 456-460, Journal, 2002.
4. http://en.wikipedia.org/wiki/Solanum_pseudocapsicum
5. Posionous Plants by Dietrich Frohne Hans Jürgen Pfänder, 2nd edition.
6. http://www.iupac.org/fileadmin/user_upload/publications/recommendations/murray_prs.pdf
7. http://www.chm.bris.ac.uk/ms/theory/eici-ionisation.html
8. https://en.wikipedia.org/wiki/Chromatography
9. Introduction to spectroscopy by D.l. Pavia, G.M. Lampman, G.S. Kriz

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