The
Malaysian Journal of Analytical Sciences Vol 11 No 1 (2007): 189 – 192
STYRYLDEHYDROPYRONE AND CLERODANE-TYPE DITERPENE
FROM CROTON ARGYRATUS
Norizan Ahmat A. H.1, Ikram M. Said 2,
Jalifah Latip 2, Laily B. Din 2, Yana Maolana Syah3
and Euis H. Hakim3
1Faculty of Applied S ciences, Universiti Teknologi
MARA,
40450 Shah Alam,
Selangor, Malaysia.
2Center of Chemical Sciences and Food Technology,
Faculty of Science and Technology,
Universiti
Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.
3Department of Chemistry, Institut Teknologi Bandung,
Jalan Ganesha 10,
Bandung 40132,
Indonesia
Abstract
Phytochemical
study on the roots of Croton argyratus (Euphorbiaceae) has been carried out .
Isolation and purification of the methanolic extract afforded a
styryldehydropyrone, (+)-goniothalamin and a clerodane-type diterpene,
(-)-junceic acid. The structures of these compounds were determined by spectroscopy methods such as mass spectrometry (MS), 1H and 13C NMR and by comparison with
those of previously reported data. This
paper report s the isolation and elucidat ion of the above compounds.
Keywords : Croton
argyratus, Euphorbiaceae, goniothalamin, junceic acid.
References
1. Ahmad, F. B., Tukol, W. A., Omar, S.
and Mohd. Sharif, A. 1991. 5-Acetyl goniothalamin, a styryl
dihydropyrone from Goniothalamus. Phytochemistry. 30(7):2430-2431.
2. Asakawa Y., Toyota, M. & Ueda, A.
1990. Sacculatane- and clerodane-type diterpenoids from the liverworts Porella
perottet iana and Heteroscyphus bescherellei.
Phytochemistry. 29(7) : 2165-2167.
3. Burkill, I. H. 1966. A Dictionary of
the Economic Product of the Malay Peninsular. Kuala Lumpur, 1 : 698-699.
4. Cavalheiro, A.
J. & Yoshida,
M. 2000. 6-[? -arylalkenyl]-5,6-dihydro-a-pyrones from
Cryptocarya moschata Lauraceae).
Phytochemistry. 53: 811-819.
5. Chan, K. M., Rajab, N. F., Ishak, M. H.
A., Ali, A. M., Yusoff, K., Din, L. B. & Inayat -Hussain, S. H. 2006. Goniothalamin induces apoptosis
in vascular smooth muscle cells. Chemico- Biological Interactions. 159:
129-140.
6. Corner, E. J. H. 1988. Wayside Trees of
Malaya. Jilid 1 & 2. United Press Kuala Lumpur.
7. De Fatima, A., Kohn, L. K., de Cavalho,
J. e. & Pilli, R. A. 2006. Cytotoxic activity of (S) -goniothalamin and
analogues against human cancer cells. Bioorganic & Medicinal Chemistry.
14(3): 622-631.
8. De
Heluani, C. S.,
Catalan, C. A.
N., Hernandez, L.
R. & Joseph-Nathan, P. 1998. 13C NMR
assignments and conformational evaluation of diterpenes from Croton
sarcopelatus Muell. Magnetic Resonance in Chemistry. 36 : 947- 950.
9. Habashy, R. R., Naim, A. A., Khalifa,
A. E. & Al-Azizi, M. 2005. Anti-inflammatory effects of jojoba liquid wax
in experimental models. Pharmacological Research. 51(2) : 95-105.
10. Hasan,
C. M., Mia, M. Y., Rashid, M. A. and
Connolly, J. D. 1994. 5-acetoxyisogoniothalamin oxide, an epoxystyryl lactone
from Goniothalamus sesquipedalis .
Phytochemistry. 37 (6):1763-1764.
11. Hisham,
A., Toubi, M., Shuaily, W., Ajitha Bai, M. D. & Fujimoto, Y. 2003.
Cardiobutanolide, a styryllactone from Goniothalamus cardiopelatus.
Phytochemistry. 62(4): 597-600.
12. Horgen, F. D., Edrada, R. A., Reyes G.,
Agcaoili, F., Madulid, D. A., Wongpanich, V., Angerhofer, C. K., Pezzuto, J. M.,
Soejarto, D. D. & Farnsworth, N. R. 2001. Biological screening of rain forest plot trees from Palawan Island (Philippines). Phytomedicine.
8(1) : 71-81.
13. Maciel,
M. A. M., Pinto, A. C., Arruda, A. C., Pamplona, S., Vanderlinde F. A., Lapa,
A. J., Echevarria, A., Grynberg, N. F., Colus, I. M. S., Farias, R. A. F., Luna
Costa, A. M. & Rao, V. S. N. 2000. Ethnopharmacology, phytochemistry and
pharmacology: a successful combination in the study of Croton cajucara. Journal
of Ethnopharmacology. 70: 41-55.
14. Melo,
P. S., Duran, N., Lima, C. A. H., Brito, A. R. M. S. & Haun, M. 2003.
Comparison of a gastroprotective effect of a diterpene lactone isolated from
Croton cajucara with its synthetic derivatives. Journal of Ethnopharmacology.
87(2-3) : 169-174.
15. Morales,
A., Perez, P., Mendoza, R., Compagnone, R. Suarez, A. I., Arvelo, F., Ramirez,
J. L. & Castro, I. G. 2005. Cytotoxic and proapoptotic activity of ent
-16ß-17a -dihydroxykaurane on human mammary carcinoma cell line MCF-7. Cancer
Letters. 218 (1) : 109-116.
16. Mosaddik, M.
A., Haque, M. E. &
Rashid, M. A.
2000. Goniothalamin fro m
Bryonopsis laciniosa Linn (Cucurbitaceae). Biochemical Systematics
and Ecology. 28(10): 1039-1040.
17. Roengsumran, S., Petsom, A., Sommit, D.
& Vilaivan, T. 1999. Labdane diterpenoids from Croton
oblongifolius. Phytochemistry. 50: 449-453.
18. Sam,
T. W., Sew -Yeu, C., Matsjeh, S.,
Gan, E. K., Razak, D. & Mohamed, A.
L. 1987. Goniothalamin oxide: An
embryotoxic compound from Goniothalamus macrophyllus (annonaceae). Tetrahedron Letters. 28(22):
2541-2544.
19. Silva,
R. M., Oliveira, F. A., Cunha, K. M. A., Maia, J. L., Maciel, M. A. M., Pinto,
A. C., Nascimento, N. R. F., Santos, F. A. & Rao, V. S. N. 2005.
Cardiovascular of
trans-dehydrocrotonin, a diterpene from Croton cajucara in rats. Bioorganic
& Medicinal Chemistry. 13: 4238-4242.
20. Suárez,
A. I, Blanco, Z., Compagnone, R. S., Salazar-Bookaman, M. M., Zapata, V &
and Alvarado, C.
2006. Anti- inflammatory activity of Croton cuneatus aqueoous extract.
Journal of Ethnopharmacology. 105 (1-2) : 99-101.
21. Sundby,
E., Perk, L., Anthonsen, T., Aasen, A. J. & Hansen, T. V. 2004. Synthesis
of (+)-goniothalamin and its enantiomer
by combination of lipase catalyzed resolution and alkene metathesis .
Tetrahedron. 60: 521-524.
22. Sutthivaiyakit,
S., Nareeboon, P., Ruangrangsi, N., Ruchirawat, S., Pisutjaroenpong, S.
& Chulaborn, M. 2001. Labdane and primarane diterpenes
from Croton cajucara. Phytochemistry. 56 : 811-814.
23. Sylvestre,
M., Pichette, A., Longtin, A., Nagau, F. & Lagault, J. 2006. Essential oil
analysis and anticancer activity of leaf essential oil of Croton flavens L.
from Guadeloupe. Journal of Ethnopharmacology. 103(1) : 99-102.
24. Umar-Tsafe,
N., Mohamed- Said, M. S., Rosli, R., Din, l. B. & Lai, L. C. 2004.
Genotoxicity of goniothalamin in CHO cell lines. Genetic Toxicology and
Environment Mutagenesis. 562: 91-102.
25. Whitmore,
T. C. 1972. Tree Flora of Malaya. Longman. 2 : 84-85.