Natural Compounds

2013 Edition
| Editors: Shakhnoza S. Azimova, Ashraf I. Saidkhodzhaev

2β-Angeloyloxy-10βH-furanoeremophilane (Furanojaponin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1110

CAS Registry Number: 34335-98-3 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Eremophilanes – Furanoeremophilanes – Monoesters

Biological sources: Petasites japonicus (Siebold et Zucc.) Maxim. [1]; P. niveus Baumg. [2]; Senecio alatus Wall. [3]

C20H28O3: 316.2038

Bp.: 110–130° (bath temp)/5 × 10−4 mmHg [1]

Mp: colorless oil [2]

IR: 1708, 1230, 1148 [1]

[α]D22 −33.5° (c 1.17, CHCl3) [2]

[α]24 (λ, nm): −26.9° (589), −27.4° (578), −31.0° (546) (c 1.4, CHCl3) [3]

UV (cyclohexane) 219 (4.00) [2]

IR (film): 1710, 1650, 1571 [2]

MS: 316 [M]+ (3), 233 (3), 216 (10), 108 (100), 55 (30) [2]

HPLC: [2]

1H NMR (CCl4): 5.05 (m, W1/2 = ca. 15, H-2); OAng: 1.89 (3H, s, H-5′), 1.96 (3H, d, J = 7, H-4′), 5.94 (1H, q, J = 7, 1, H-3′) [1]

1H NMR (CCl4, CDCl3, C6D6): 0.96, 0.96, 0.81 (3H, d, J = 7.0, H-15), 0.99, 1.00, 0.79 (3H, s, H-14), 1.85, 1.90, 1.89 (3H, m, =CMe-C(O)O-), 1.87, 1.90, 1.79 (3H, d, J =...

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References

  1. 1.
    K. Naya, M. Nakagawa, M. Hayashi, K. Tsuji, M. Naito, Tetrahedron Lett. 31, 2961 (1971)CrossRefGoogle Scholar
  2. 2.
    A. Guerriero, F. Pietra, Phytochemistry 21(12), 2887 (1982)CrossRefGoogle Scholar
  3. 3.
    F. Bohlmann, J. Ziesche, Phytochemistry 19(12), 2681 (1980)CrossRefGoogle Scholar

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