Current Science

Open Access Open Access  Restricted Access Subscription Access

X-ray crystal structure of a new triterpene, 3,23-cycloglutin-5(10)-ene from Euphorbia vajravelui


Affiliations
1 Phytochemistry and Phytopharmacology Division, KSCSTE-Jawaharlal Nehru Tropical Botanic Garden and Research Institute, Pacha-Palode, Thiruvananthapuram 695 562, India
 

Euphorbia species are known for their diversity of terpenoid constituents. Euphorbia vajravelui is an endemic plant species distributed in the southern Western Ghats of India. Though conventional spectroscopic techniques are common in structure elucidation of secondary metabolites from plants, X-ray crystal structure analysis of a compound offers valuable information with minimum sample requirement. The present study reports the characterization of a new triterpene, 3,23-cycloglutin-5(10)-ene isolated from E. vajravelui, using single-crystal X-ray diffraction studies. Triclinic crystalline system was obtained for the compound, having P1 space group with unit cell parameters; a = 6.2907(8) Å, b = 7.4458(10) Å, c = 14.5802(18) Å, α = 94.899(6)°, β = 95.365(6)°, γ = 114.392(6)°, V = 613.43(14) Å3 and Z = 1. The triterpene has a glutinane skeletal structure containing a cyclopropane ring with a methyl group.

Keywords

Euphorbia vajravelui, glutinane skeleton, terpenoid constituents, triterpene, X-ray crystal structure.
User
Notifications
Font Size

  • Balakrishnan, N. P. and Chakrabarty, T., The Family Euphorbiaceae in India: A Synopsis of its Profile, Taxonomy and Bibliography, Bishen Singh Mahendra Pal Singh, Dehra Dun, 2007.

  • Shi, Q. W., Su, X. H. and Kiyota, H., Chemical and pharmacological research of the plants in genus Euphorbia. Chem. Rev., 2008, 108, 4295–4327.

  • Rizk, A. F. M., The chemical constituents and economic plants of the Euphorbiaceae. Bot. J. Linn. Soc., 1987, 94, 293–326.

  • Starratt, A. N., Triterpenoid constituents of Euphorbia cyparissias. Phytochemistry, 1966, 5, 1341–1344.

  • Madureira, A. M., Ascenso, J. R., Valdeira, L., Duarte, A., Frade, J. P., Freitas, G. and Ferreira, M. J. U., Evaluation of the antiviral and antimicrobial activities of triterpenes isolated from Euphorbia segetalis. Nat. Prod. Res., 2003, 17, 375–380.

  • Hsu, C. L., Fang, S. C., Huang, H. W. and Yen, G. C., Antiinflammatory effects of triterpenes and steroid compounds isolated from the stem bark of Hiptage benghalensis. J. Funct. Foods, 2015, 12, 420–427.

  • Lee, S. S., Kishore, P. H. and Chen, C. H., Three novel triterpenoiddienolides from Phyllanthus myrtifolius. Helv. Chim. Acta, 2002, 85, 2403–2408.

  • Courtney, J. L., Gascoigne, R. M. and Szumer, A. Z., Triterpenes of the friedelane series. Part III. The course of the friedelene– oleanene rearrangement. J. Chem. Soc. (Resumed), 1958, 881–886.

  • Akiyama, E., Moriyama, Y., Murae, T., Tsuyuki, T. and Takahashi, T., Preparation of D:B-Friedoolean-5(10)-en-1-one and related compounds. A comment on the structure of glut-5(10)-en1-one from Euphorbia nerifolia. Bull. Chem. Soc. Jpn., 1978, 51, 2702–2704.

  • Alberman, K. B. and Kipping, F. B., Phyllanthol. A new alcohol from the ischolar_main bark of Phyllanthus engleri (Pax). J. Chem. Soc. (Resumed), 1951, 2296–2297.

  • Ndlebe, V. J., Crouch, N. R. and Mulholland, D. A., Triterpenoids from the African tree Phyllanthus polyanthus. Phytochem. Lett., 2008, 1, 11–17.

  • Anju, V., Priya, S., Sabulal, B. and Rameshkumar, K. B., Chemical constituents and cytotoxicity of Euphorbia vajravelui. Lett. Org. Chem., 2019, 16, 643–646.

  • Bruker, APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA, 2004.

  • Sheldrick, G. M., Crystal structure refinement with SHELXL. Acta Crystallogr. Sect. C, 2015, 71, 3–8.

  • Farrugia, L. J., ORTEP-3 for Windows – a version of ORTEP-III with a graphical user interface (GUI). J. Appl. Crystallogr., 1997, 30, 565.

  • Bruno, I. J. et al., New software for searching the Cambridge Structural Database and visualizing crystal structures. Acta Crystallogr. Sect. B, 2002, 58, 389–397.

  • Ohki, M., Tachibana, K., Kuroda, T., Takenaka, A. and Sasada, Y., Structure of alnusenone (D:B‐friedoolean‐5‐en‐3‐one). Acta Crystallogr. Sect. B, 1981, 37, 2092–2094.

  • Connolly, J. D., Freer, A. A., Anjaneyulu, V., Ravi, K. and Sambasivarao, G., Structure of 5,24‐cyclofriedelan‐3‐one, a novel hexacyclic triterpenoid in space group P1. Acta Crystallogr. Sect. C, 1986, 42, 1352–1354.

  • Masaki, N., Niwa, M. and Kikuchi, T., Studies on the neutral constituents of Pachysandra terminalis Sieb. etZucc. Part IV. X-ray structure of 3-O-acetyl-16-O-p-bromobenzoylpachysandiol B: new conformation of a friedelin-type triterpene. J. Chem. Soc. Perkin Trans. 2, 1975, 610–614.

  • Rogers, D., Phillips, F. L., Joshi, B. S. and Viswanathan, N., Revised structures of the triterpenes Q, T, and U from Salacia prinoides DC; X-ray crystal structure of triterpene T. J. Chem. Soc. Chem. Commun., 1980, 22, 1048–1049.


Abstract Views: 200

PDF Views: 79




  • X-ray crystal structure of a new triterpene, 3,23-cycloglutin-5(10)-ene from Euphorbia vajravelui

Abstract Views: 200  |  PDF Views: 79

Authors

Vijayalekshmi Anju
Phytochemistry and Phytopharmacology Division, KSCSTE-Jawaharlal Nehru Tropical Botanic Garden and Research Institute, Pacha-Palode, Thiruvananthapuram 695 562, India
Koranappallil Bahuleyan Rameshkumar
Phytochemistry and Phytopharmacology Division, KSCSTE-Jawaharlal Nehru Tropical Botanic Garden and Research Institute, Pacha-Palode, Thiruvananthapuram 695 562, India

Abstract


Euphorbia species are known for their diversity of terpenoid constituents. Euphorbia vajravelui is an endemic plant species distributed in the southern Western Ghats of India. Though conventional spectroscopic techniques are common in structure elucidation of secondary metabolites from plants, X-ray crystal structure analysis of a compound offers valuable information with minimum sample requirement. The present study reports the characterization of a new triterpene, 3,23-cycloglutin-5(10)-ene isolated from E. vajravelui, using single-crystal X-ray diffraction studies. Triclinic crystalline system was obtained for the compound, having P1 space group with unit cell parameters; a = 6.2907(8) Å, b = 7.4458(10) Å, c = 14.5802(18) Å, α = 94.899(6)°, β = 95.365(6)°, γ = 114.392(6)°, V = 613.43(14) Å3 and Z = 1. The triterpene has a glutinane skeletal structure containing a cyclopropane ring with a methyl group.

Keywords


Euphorbia vajravelui, glutinane skeleton, terpenoid constituents, triterpene, X-ray crystal structure.

References





DOI: https://doi.org/10.18520/cs%2Fv120%2Fi10%2F1623-1626