Detailed characterization of saponins isolated from Zygophyllum Propinqueem Decne

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Detailed characterization of saponins isolated from Zygophyllum Propinqueem Decne

Muhammad Qaisar, Farina Kanwal, Muhammad Siddique, Muhammad Akram, Yousaf Ali Khan, Humaira Inayat, Farah Gul, Yaqoob ur Rehman, Shazma Anwar, Rifat Naz, Syed Murtaza Hussain, Mushtaq Ahmad
Int. J. Biosci.22( 1), 70-76, January 2023.
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Abstract

Zygophyllum propinquum Decne (syn. Z. coccineum, family: Zygophyllaceae) is a low shrub, perennial herb, or desert succulent undershrub and has several important biological activities. The major secondary metabolites of this plant are a class of ursane-type triterpene saponins. Saponins derive their name from stable foam formation in water. These saponins have peculiar properties like, bitterness, fish poisoning, haemolysis, complex formation with cholesterol. Saponins are consisting of two main parts, one is the aglycone part while the other one is the glycone part. The glycone part is further consisting of sugar moieties. Current studies were conducted to isolate specifically biologically important saponins. Saponins were isolated successfully using standard procedures and characterized successfully using different spectroscopic techniques including Fourier Transform-Infrared Spectroscopy, Mass Spectrometry and Nuclear Magnetic Resonance Spectroscopy. Two saponins were isolated from the whole plant of Zygophyllum propinquum Decne with the help of repeated column chromatography and HPLC. The purified saponins were hydrolyzed with H2SO4-dioxane resulting in lactone formation. All the compounds (saponins and lactone) were characterized with the help of FAB-MS and 1D and 2D-NMR techniques. Their structures were confirmed to be 3-Oβ-D-glucopyranosyl-(1→6)- β-D-2-O-sulfo-glucuronopyranosylurs-20(21)-en28 oic acid 28-O-[β-D-glucuronopyranosyl] ester (1), (3βO-2-O-sulfo-β-D-glucuronopyranosylurs-20(21)-en28 oic acid 28-O-[β-D-2-O-sulfonylglucuronopyranosyl] ester (2), and 3β-Hydroxy urs-28,20 β-olide (3).

VIEWS 127

Amin E, El-Hawary SS, Fathy MM, Mohammad R, Ali Z, Tabanca N, Wadge DE, Becnel JJ, Khan IA. 2011. Triterpenoidal saponins: bioactive secondary metabolites from Zygophyllum coccineum. Planta Medica 77, 488-491. https://doi.org/10.1055/s-0030-1250463

Ahmad VU, Ghazala, Uddin S. 1992. A triterpenoid saponin from Zygophyllum propinquum. Phytochemistry 31, 1051-1054. https://doi.org/10.1016/0031-9422(92)80073-N

Ahmad VU, Ghazala, Uddin S, Ali MS. 1993. Saponins from Zygophyllum propinquum. Phytochemistry 33, 453-455. https://doi.org/10.1016/0031-9422(93)85538-3.

Ahmad VU, Ghazala, Uddin S, Bano S. 1990. Saponins from Zygophyllum propinquum, Journal of Natural Products 53, 1193-1197. https://doi.org/10.1021/np50071a010.

Ahmad VU, Iqbal S, Kousar F, Badar S, Arshad S, Tareen RB. 2005. Two new saponins from Zygophyllum atriplicoides, Chemical and Pharmaceutical Bulletin 53, 1126-1130. https://doi.org/10.1248/cpb.53.1126.

Chludil HD, Seldes AM, Maier MS. 2002. Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: structure-activity correlations, Journal of Natural Products 65, 153-157. https://doi.org/10.1021/np010332x.

Cui M, Sun W, Song F, Liu Z, Liu S. 1999. Multi-stage mass spectrometric studies of triterpenoid saponins in crude extracts from Acanthopanax senticosus harms, Rapid Communication in Mass Spectrometry 13, 873-879.https://doi.org/10.1002/(SICI)1097-0231(19990530)13:10<873::AID-RCM571>3.0.CO;2-2

Errington SG, Jefferies PR. 1988. Triterpenoid sapogenins of Pittosporum phillyraeoides, Phytochemistry 27, 543-545. https://doi.org/10.1016/0031-9422(88)83138-8.

Elgamal MHA, Shaker KH, Pöllmann K, Seifert K. 1995. Triterpenoid saponins from Zygophyllum species, Phytochemistry 40, 1233-1236. https://doi.org/10.1016/0031-9422(95)00436-B.

Eskander EF, Won JH. 1995. Hypoglycaemic and hyperinsulinemic effects of some Egyptian herbs used for treatment of diabetes mellitus (Type II) in rats, Egyptian Journal of Pharmaceutical Sciences 36, 331-342.

Fenwick GR, Price KR, Tsukamoto C, Okubo K. 1991. Toxic Substances in Crop Plants, eds. J.P.F. D’Mello, C. M. Duffus, H. Duffus, The Royal Society of Chemistry, Cambridge.

Ghafoor A. Zygophyllaceae. 1974. In: Nasir E, Ali SI, editors. Flora of West Pakistan. Karachi: University of Karachi, p 1-35.

Ghazala. 1992. Studies on chemical constituents of Zygophyllum propinquum (Z. coccineum). PhD thesis, HEJ Research Institute of Chemistry, University of Karachi, Pakistan.

Gibbons S, Oriowo MA. 2001. Antihypertensive effect of an aqueous extract of Zygophyllum coccineum L. in rats, Phytotherapy Research 15, 452-455.  https://doi.org/10.1002/ptr.836.

Hostettmann K, Marston A. 1995. Saponins. Cambridge University Press, Cambridge.

Kofler L. 1927. Die Saponine, Julius Springer Verlag, Vienna. 7-40 p. https://doi.org/10.1007/978-3-7091-9826-1_3.

Nasir E, Ali S. (Eds.). 1970-1979. Flora of West Pakistan. No. 1-131. Islamabad, Karachi.

Pöllmann K, Gagel S, Elgamal MHA, Shaker CH, Seifert K. 1997. Triterpenoid saponins from the roots of Zygophyllum species, Phytochemistry 44, 485-489. https://doi.org/10.1016/s0031-9422(96)00552-3.

Qaisar M, Uddin G, Ahmad VU, Rauf A. 2011. Mass Fragmentation Pattern of New Zygophyllosides from Zygophyllum propinquum Decne, Middle-East Journal of Scientific Research 8, 526-529.

Reed JD. 1997. Ecological biochemistry of secondary plant compounds in herbivore nutrition. Session 11- Constraints on Animal Production from forages and grasslands. http://www.internationalgrasslands.org/files/igc/publications/1997/iii-221.pdf.

Saber AH, El-Moghazy Shoaib AM. 1960. Zygophyllum coccineum. V. Chemistry of leaf and Stem. Journal of Pharmaceutical Science of the U.A.R., 1, 1-6.

Soliman G. 1939. Quinovic acid from Zygophyllum coccineum L., Journal of Chemical Society 1760-1761. https://doi.org/10.1039/JR9390001760.

Van Setten DC, ten Hove GJ, Wiertz EJHJ, Kamerling JP, Van de Werken G. 1998. Multiple stage tendom mass spectrometry for structural characterization of saponins, Analytical Chemistry 70, 4401-4409. https://doi.org/10.1021/ac980365q.