Perisesaccharides A–E, New Oligosaccharides from the Root Barks of Periploca sepium

Abstract

Five new oligosaccharides, named perisesaccharides A–E (1–5), were isolated from the root barks of Periploca sepium. Their structures were elucidated by NMR and HRESIMS data. The absolute configurations of these compounds were determined by a combination of X‐ray diffraction analysis, modified Mosher's method, circular dichroism spectroscopy, and acid hydrolysis. The boat conformation of oleandronic acid δ-lactone was reported for the first time.

Key words

Asclepiadaceae - Periploca sepium - oligosaccharid - perisesaccharides A–E - oleandronic acid δ‐lactone

References

• 1 New Medical College of Jiangsu .Dictionary of Chinese Materia Medica. Shanghai; Shanghai People's Publishing House 1977: 1683-1684
• 2 Zhang Y H, Wang F P. Recent advances of chemical constituents of Periploca plants.  Nat Prod Res Dev. 2003;  15 157-161
• 3 Feng J Q, Zhang R J, Zhou Y, Chen Z H, Tang W, Liu Q F, Zuo J P, Zhao W M. Immunosuppressive pregnane glycosides from Periploca sepium and Periploca forrestii.  Phytochemistry. 2008;  69 2716-2723
• 4 Feng J Q, Zhao W M. Five new pregnane glycosides from the root barks of Periploca sepium.  Helv Chim Acta. 2008;  91 1798-1805
• 5 Wang L, Yin Z Q, Shen W B, Zhang Q W, Ye W C. A new pregnane and a new diphenylmethane from the root barks of Periploca sepium.  Helv Chim Acta. 2007;  90 1581-1585
• 6 Wang L, Yin Z Q, Zhang L H, Ye W C, Zhang X Q, Shen W B, Zhao S X. Chemical constituents from root barks of Periploca sepium.  Zhong Guo Zhong Yao Za Zhi. 2007;  32 1300-1302
• 7 Yin Z Q, Wang L, Zhang X Q, Ye W C, Zhang J. Steroids from the roots of Periploca sepium.  Chin Pharm J. 2009;  44 968-971
• 8 Flack H D. On enantiomorph-polarity estimation.  Acta Crystallogr. 1983;  A39 876-881
• 9 Hooft R W W, Straver L H, Spek A L. Determination of absolute structure using Bayesian statistics on Bijvoet differences.  J Appl Crystalllogr. 2008;  41 96-103
• 10 Liu Y B, Tang W Z, Yu S S, Qu J, Liu J, Liu Y. Eight new C-21 steroidal glycosides from Dregea sinensis var. corrugata.  Steroids. 2007;  72 514-523
• 11 Bai H, Koike W K, Satou T, Chen Y J, Nikaidoa T. Cynanosides A–J, ten novel pregnane glycosides from Cynanchum atratum.  Tetrahedron. 2005;  61 5797-5811
• 12 Sigler P, Saksena R, Deepak D, Khare A. C₂₁ steroidal glycosides from Hemidesmus indicus.  Phytochemistry. 2000;  54 983-987
• 13 Abe F, Yamauchi T. Pregnane glycosides from the roots of Asclepias tuberose.  Chem Pharm Bull. 2000;  48 1017-1022
• 14 Xu J P, Takeya K, Itokawa H. Pregnanes and cardenolides from Periploca sepium.  Phytochemistry. 1990;  29 344-346
• 15 Yoshikawa K, Nishino H, Arihara S, Chang H C, Wang J D. Oligosaccharides from Hoya carnosa.  J Nat Prod. 2000;  63 146-148
• 16 Itokawa H, Xu J P, Takeya K. Studies on chemical constituents of antitumor fraction from Periploca sepium. V.: Structures of new pregnane glycosides, periplocosides J, K, F and O.  Chem Pharm Bull. 1988;  36 4441-4446
• 17 Fontana A, González M C, Gavagnin M, Templado J, Cimino G. Structure and absolute stereochemistry of stolonoxide A, a novel cyclic peroxide from the marine tunicate Stolonica socialis.  Tetrahedron Lett. 2000;  41 429-432
• 18 Korver O. Optical rotatory dispersion and circular dichroism of δ-lactones: determination of the absolute configuration of (+)5-decanolide and (+)5-dodecanolide.  Tetrahedron. 1970;  26 2391-2396