Lanopropic Acid, A Novel Natural 2,3-Secolanostane Triterpenoid from Schisandra propinqua var. propinqua

 

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Abstract

A triterpenetricarboxylic acid with a novel 2,3-secolanostane-type framework named lanopropic acid (1) was isolated from the aerial parts of Schisandra propinqua var. propinqua. The structure of 1 was elucidated as 2,3-secolanost-9(11),24(Z)-diene-2,3,26-trioic acid on the basis of spectroscopic techniques and X-ray diffraction studies. This is the first report of natural occurrence of 2,3-secolanostane type triterpenoid.

References

• 1 Sun H D, Qiu S X, Lin L Z, Wang Z Y, Lin Z W, Pengsuparp T. et al . Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.  J Nat Prod. 1996;  59 525-7
  CrossrefPubMedGoogle Scholar
• 2 Li R T, Han Q B, Zhao A H, Sun H D. Micranoic acids A and B: two new octanortriterpenoids from Schisandra micrantha.  Chem Pharm Bull. 2003;  51 1174-6
  CrossrefPubMedGoogle Scholar
• 3 Li R T, Xiao W L, Shen Y H, Zhao Q S, Sun H D. Structure characterization and possible biogenesis of three new families of nortriterpenoids: schisanartane, schiartane, and 18-norschiartane.  Chem Eur J. 2005;  11 2989-96
  CrossrefPubMedGoogle Scholar
• 4 Xiao W L, Huang S X, Zhang L, Tian R R, Li X L, Pu J X. et al . Triterpenoids from Schisandra lancifolia with anti-HIV-1 activity.  J Nat Prod. 2006;  69 277-9
  CrossrefPubMedGoogle Scholar
• 5 Huang S X, Yang L B, Xiao W L, Lei C, Liu J P, Lu Y. et al . Wuweizidilactones A - F: novel highly oxygenated nortriterpenoids with unusual skeletons from Schisandra chinensis.  Chem Eur J. 2007;  13 4816-22
  CrossrefPubMedGoogle Scholar
• 6 Huang S X, Li R T, Liu J P, Lu Y, Chang Y, Lei C. et al . Isolation and characterization of biogenetically related highly oxygenated nortriterpenoids from Schisandra chinensis.  Org Lett. 2007;  9 2079-82
  CrossrefPubMedGoogle Scholar
• 7 Liu J S, Huang M F, Yong T. Anwuweizonic acid and manwuweizic acid, the putative anticancer active principle of Schisandra propinqua.  Can J Chem. 1988;  66 414-5
  CrossrefPubMedGoogle Scholar
• 8 Dai P, Han G Q, Arison B H. A new triterpenoid from Kadsura heteroclita (Roxb) Craib.  Chem J Chin Univ. 1990;  11 423-4
  PubMedGoogle Scholar
• 9 Kotaro T, Masako T. Studies on constituents of medicinal plants. Constituents of Schisandra nigra .1.  Chem Pharm Bull. 1975;  23 538-42
  PubMedGoogle Scholar
• 10 Li L N, Xue H. Triterpenoids from roots and atems of Kadsura coccinea.  Planta Med. 1986;  52 492-3
  Article in Thieme ConnectPubMedGoogle Scholar
• 11 Yue J M, Xu J, Chen Y Z. Triterpenoids of Schisandra sphenanthera.  Phytochemistry. 1994;  35 1068-9
  CrossrefPubMedGoogle Scholar
• 12 Li L N, Xue H, Ge D L, Kunio K, Toshio M, Sadafumi O. Isolation and structure elucidation of seco-neokadsuranic acid A and 3,4-seco-(24Z)-lanosta-4(30),8,24-triene-3,26-dioic acid.  Planta Med. 1989;  55 300-2
  Article in Thieme ConnectPubMedGoogle Scholar
• 13 Chen Y G, Qin G W, Cao L, Leng Y, Xie Y Y. Triterpenoid acids from Schisandra propinqua with cytotoxic effect on rat luteal cells and human decidual cells in vitro.  Fitoterapia. 2001;  72 435-7
  CrossrefPubMedGoogle Scholar
• 14 Ovindachari T R, Viswanathan G N, Sidhaye A R. Reaction of terpenoid hydroxymethylene ketones with hydrogen peroxide.  Indian J Chem. 1972;  10 786-8
  PubMedGoogle Scholar
• 15 Ikeda M, Sato Y, Izawa M, Sassa T, Miura Y. Isolation and structure of fasciculol A, a new plant growth inhibitor from Neamatoloma fasciculare.  Agric Biol Chem. 1977;  41 1539-41
  PubMedGoogle Scholar
• 16 Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D. et al . Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines.  J Natl Cancer Inst. 1991;  83 757-66
  CrossrefPubMedGoogle Scholar

Prof. Dr. Han-Dong Sun

State Key Laboratory of Phytochemistry and Plant Resources in West China

Kunming Institute of Botany

Chinese Academy of Sciences

Heilongtan

Kunming 650204

People’s Republic of China

Fax: +86-871-521-6343

Email: hdsun@mail.kib.ac.cn