Skip to main content
SpringerLink
Log in

Spectroscopic characterizations, X-ray studies, and electronic circular dichroism calculations of two alkaloid triterpenoids

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

Two alkaloid triterpenoids formulated as C26H35NO3 (1) and C30H45NO2 (2) were isolated from the timer tree Aphanamixis grandifolia. The structure of 1 and 2 was determined by IR, HRESIMS, 1D, and 2D-NMR. Compound 1 was confirmed by X-ray single crystal diffraction. Compound 1 crystallizes in the monoclinic, space group C2 with unit cell parameters a = 53.195(4) Å, b = 7.6339(8) Å, c = 11.202(2) Å, β = 94.6520(2)°. Intermolecular hydrogen bonding and π–π stacking were presented in the molecular packing of 1. The absolute configurations of 1 and 2 were established by comparison of experimental circular dichroism properties with their electronic circular dichroism predicted by molecular modeling DFT calculations.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Wang XN, Yin S, Fan CQ, Wang FD, Lin LP, Ding J, Yue JM (2006) Org Lett 8:3845–3848

    Article  CAS  Google Scholar 

  2. He XF, Wang XN, Gan LS, Yin S, Dong L, Yue JM (2008) Org Lett 10:4327–4330

    Article  CAS  Google Scholar 

  3. Luo J, Wang JS, Wang XB, Luo JG, Kong LY (2009) Org Lett 11:2281–2284

    Article  CAS  Google Scholar 

  4. Yuan T, Zhu RX, Zhang H, Odecu OA, Yang SP, Liao SG, Yue JM (2010) Org Lett 12:252–255

    Article  CAS  Google Scholar 

  5. Nishizawa M, Inoue A, Hayashi Y, Sastrapradja S, Kosela S, Iwashita T (1984) J Org Chem 49:3660–3664

    Article  CAS  Google Scholar 

  6. Polonsky J, Varon Z, Arnoux B, Pettit GR, Schmidt JH, Lange LM (1978) J Am Chem Soc 100:2575–2576

    Article  CAS  Google Scholar 

  7. Polonsky J, Varon Z, Arnoux B, Pettit GR, Schmidt JH (1978) J Am Chem Soc 100:7731–7733

    Article  CAS  Google Scholar 

  8. Zhang XY, Li Y, Wang YY, Cai XH, Feng T, Luo XD (2010) J Nat Prod 73:1385–1388

    Article  CAS  Google Scholar 

  9. Sheldrick GM (2008) Acta Cryst A64:112–122

    CAS  Google Scholar 

  10. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 09, Revision B.01. Gaussian, Inc., Wallingford

    Google Scholar 

  11. Mora AJ, Delgado G, de Delgado GD, Usubillaga A, Khourib N, Bahsasc A (2001) Acta Cryst c57:638–640

    CAS  Google Scholar 

  12. Chen HD, Yang SP, Wu Y, Dong L, Yue JM (2009) J Nat Prod 72:685–689

    Article  CAS  Google Scholar 

  13. Sang YS, Zhou CY, Lu AJ, Min ZD, Tan RX (2009) J Nat Prod 72:917–920

    Article  CAS  Google Scholar 

  14. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354–1358

    Article  CAS  Google Scholar 

  15. Rao ST, Westhof E, Sundaralingam M (1981) Acta Cryst a37:421–425

    CAS  Google Scholar 

  16. Etter MC (1990) Acc Chem Res 23:120–126

    Article  CAS  Google Scholar 

  17. Bernstein J, Davis RE, Shimoni L, Chang NL (1995) Angew Chem Int Ed 34:1555–1573

    Article  CAS  Google Scholar 

  18. Desiraju GR (1995) Angew Chem Int Ed 34:2311–2327

    Article  CAS  Google Scholar 

  19. Ren YL, Lantvit DD, de Blanco C, Kardono LBS, Riswan S, Chai H, Cottrell CE, Farnsworth NR, Swanson SM, Ding YQ, Li XC, Marais JPJ, Ferreira D, Kinghorn AD (2010) Tetrahedron 66:5311–5320

    Article  CAS  Google Scholar 

  20. Stephens PJ, Harada N (2010) Chirality 22:229–233

    CAS  Google Scholar 

  21. Lunazzi L, Mancinelli M, Mazzanti A, Pierini M (2010) J Org Chem 75:5927–5933

    Article  CAS  Google Scholar 

  22. McChesney JD, Dou JH, Sindelar RD, Goins DK, Walker LA, Rogers RD (1997) J Chem Crystallogr 27:283–290

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The research work was partially supported by National Key Scientific and Technological Special Project (Grant No. 2009ZX09502-011).

Author information

Authors and Affiliations

  1. Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People’s Republic of China

    Xiao-Bing Wang, Yao Zhang, Jun-Song Wang & Ling-Yi Kong

  2. Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210009, People’s Republic of China

    He-Quan Yao & Hong-Bin Sun

Authors
  1. Xiao-Bing Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yao Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jun-Song Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. He-Quan Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hong-Bin Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ling-Yi Kong
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ling-Yi Kong.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, XB., Zhang, Y., Wang, JS. et al. Spectroscopic characterizations, X-ray studies, and electronic circular dichroism calculations of two alkaloid triterpenoids. Struct Chem 22, 1241–1248 (2011). https://doi.org/10.1007/s11224-011-9818-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-011-9818-8

Keywords

Search

Navigation