New Diarylheptanoids from the Rhizomes of Dioscorea spongiosa and Their Antiosteoporotic Activity

Abstract

Bioassay-guided fractionation of the water extract of the rhizomes of Dioscorea spongiosa led to the isolation and identification of new diarylheptanoids, diospongins A - C, together with three known lignans. Their structures, including absolute stereochemistry, were determined by analyses of NMR data, chemical conversions and CD spectrum. The isolated compounds, except for diospongin A, exerted potent inhibitory activities on bone resorption induced by parathyroid hormone in a bone organ culture system.

Key words

Dioscorea spongiosa - Dioscoreaceae - MTPA ester - bone resorption.

References

• 1 Zhao W, He J, Xi J. New species of Mian Bixie.  China J Chin Materia Med. 1994;  19 199-200
• 2 Yin J, Kouda K, Tezuka Y, Tran Q L, Miyahara T, Kadota S. Steroidal glycosides from the rhizomes of Dioscorea spongiosa.  J Nat Prod. 2003;  66 646-50
• 3 Abe F, Yamauchi T. 9α-Hydroxypinoresinol, 9α-hydroxymedioresinol and related lignans from Allamanda neriifolia .  Phytochemistry. 1988;  27 575-7
• 4 Abe F, Yahara S, Kubo K, Nonaka G, Okabe H, Nishioka I. Studies on Xanthoxylum spp. II. Constituents of the bark of Xanthoxylum piperitum DC.  Chem Pharm Bull. 1974;  22 2650-5
• 5 Chiung Y M, Hayashi H, Matsumoto H, Otani T, Yoshida K, Huang M Y. et al . New metabolites, tetrahydrofuran lignans, produced by Streptomyces sp. IT-44.  J Antibiot. 1994;  47 487-91
• 6 Ohtani I, Kusumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids.  J Am Chem Soc. 1991;  113 4092-6
• 7 Rychnovsky S D, Richardson T I, Rogers B N. Two-dimensional NMR analysis of acetonide derivatives in the stereochemical assignments of polyol chains: The absolute configurations of dermostatins A and B.  J Org Chem. 1997;  62 2925-34
• 8 Wiesler W T, Nakanishi K. Relative and absolute configurational assignments of acyclic polyols by circular dichroism.1. Rationale for a simple procedure based on the exciton chirality method.  J Am Chem Soc. 1989;  111 9205-13
• 9 Shigeno C, Yamamoto I, Dokoh S, Hino M, Aoki J, Yamada K ,. et al . Identification of 1,24(R)-dihydroxyvitamin D₃-like bone-resorbing lipid in a patient with cancer-associated hypercalcemia.  J Clin Endocrin Metab. 1985;  61 761-8
• 10 Li H, Li J, Prasain J K, Tezuka Y, Namba T, Miyahara T. et al . Antiosteoporatic activity of the stems of Sambucus sieboldiana .  Biol Pharm Bull. 1998;  21 594-8
• 11 Rychnovsky S D, Skalitzky D J. Stereochemistry of alternating polyol chains: ¹³C NMR analysis of 1,3-diol acetonides.  Tetrahedron Lett. 1990;  31 945-8
• 12 Harada N, Sato A, Ono H, Gawronski J, Gawronska K, Sugioka T. et al . A CD method for determination of the absolute stereochemistry of acyclic glycols. 1. Application of CD exciton chirality method to acyclic 1, 3-dibenzoate systems.  J Am Chem Soc. 1991;  113 3842-50
• 13 Suzuki H, Nakamura I, Takahashi N, Ikuhara T, Matsuzaki K, Isogai Y. et al . Calcitonin-induced changes in the cytoskeleton are mediated by signal pathway associated with protein kinase A in osteoclasts.  Endocrinology. 1996;  137 4685-90