Isolation of New Rotenoids from Boerhaavia diffusa and Evaluation of their Effect on Intestinal Motility

Abstract

A bioassay-guided separation of a methanolic extract obtained from the roots of Boerhaavia diffusa L. (Nyctaginaceae) allowed us to isolate five compounds belonging to the class of rotenoids: the known boeravinone D (1), boeravinone E (2), compound 5 and two novel compounds that we have named boeravinone G (3) and boeravinone H (4). The structures of the new molecules have been determined on the basis of their HR-EI-MS, ¹H- and ¹³C-NMR and 2D-NMR (HMQC, HMBC) data. All the isolated rotenoids have been evaluated for their effect on intestinal motility in vitro. Three of them (boeravinone G, boeravinone E and compound 5) exhibited spasmolytic activity. Preliminary structure-activity relationships have been established highlighting the effect of substitutions on rings B and D.

Key words

Nyctaginaceae - Boerhaavia diffusa - rotenoids - boeravinones - spasmolytic activity

References

• 1 Lad V. The Complete Book of Ayurvedic Home Remedies. New York; Three Rivers Press 1999
• 2 Rawat A K, Mehrotra S, Tripathi S C, Shome U. Hepatoprotective activity of Boerhaavia diffusa L. roots - a popular Indian ethnomedicine.  J Ethnopharmacol. 1997;  56 61-6
• 3 Mehrotra S, Mishra K P, Maurya R, Srimal R C, Singh V K. Immunomodulation by ethanolic extract of Boerhaavia diffusa roots.  Intern Immunopharmacol. 2002;  2 987-96
• 4 Pari L ., Amarnath Satheesh M. Antidiabetic activity of Boerhaavia diffusa L.: effect on hepatic key enzymes in experimental diabetes.  J Ethnopharmacol. 2004;  91 109-13
• 5 Hiruma-Lima C A, Gracioso J S, Bighetti E J, Germonsen Robineou L, Souza Brito A R. The juice of fresh leaves of Boerhaavia diffusa L. (Nyctaginaceae) markedly reduces pain in mice.  J Ethnopharmacol. 2000;  71 267-74
• 6 Singh A, Singh R G, Singh R H, Mishra N, Singh N. An experimental evaluation of possible teratogenic potential in Boerhaavia diffusa in Albino rats.  Planta Med. 1991;  57 315-6
• 7 Nandi R P, Chatterjee S K. Occurrence of punarnavines in Boerhaavia repens .  Indian J Exp Biol. 1974;  12 509-11
• 8 Kadota S, Lami N, Tezuka Y, Kikuchi T. Constituents of the roots of Boerhaavia diffusa L. Examination of sterols and structure of new rotenoids, boeravinones A and B.  Chem Pharm Bull. 1989;  37 3214-20
• 9 Kadota S, Lami N, Tezuka Y, Kikuchi T. Structure and NMR spectra of boeravinone C, a new rotenoid analog from Boerhaavia diffusa Linn.  Chem Pharm Bull. 1988;  36 2289-92
• 10 Lami N. Kadota S. Kikuchi T. Constituents of the roots of Boerhaavia diffusa L. IV. Isolation and structure determination of boeravinones D, E, and F.  Chem Pharm Bull. 1991;  39 1863-5
• 11 Fattorusso E, Lanzotti V, Tagliatatela-Scafati O, Tron G C, Appendino G. Bisnorsesquiterpenoids from Euphorbia resinifera Berg. and an expeditious procedure to obtain resiniferatoxin from its fresh latex. Eur J Org Chem 2002: 71-8
• 12 Corea G, Fattorusso E, Lanzotti V, Taglialatela-Scafati O, Appendino G, Ballero M. et al . Jatrophane diterpenes as P-glycoprotein inhibitors. First insights of structure-activity relationships and discovery of a new, powerful lead.  J Med Chem. 2003;  46 3395-402
• 13 Appendino G, Borrelli F, Capasso R, Campagnuolo C, Fattorusso E, Petrucci F. et al . Minor diterpenoids from cascarilla (Croton eluteria Bennet) and evaluation of the cascarilla extract and cascarillin effect on gastric acid secretion.  J Agric Food Chem. 2003;  51 6970-4
• 14 Appendino G, Bianchi F, Bader A, Campagnuolo C, Fattorusso E, Taglialatela-Scafati O. et al . Coumarins from Opopanax chironium. New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and heraclenin.  J Nat Prod. 2004;  67 532-6
• 15 Kupchan S M, Britton R W, Ziegler M F, Sigel C W. Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica .  J Org Chem. 1973;  38 178-9
• 16 Tallarida R J, Murray R B. Manual of pharmacological calculation with computer programs. Berlin; Springer-Verlag 1986
• 17 Yang S -W, Ubillas R, McAlpine J, Stafford A, Ecker D M, Talbot M K. et al . Three new phenolic compounds from a manipulated plant cell culture, Mirabilis jalapa .  J Nat Prod. 2001;  64 313-7