Natural Compounds

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

13-[2′-(1′β(H)-Caryophyll-5-en-7-one)yloxy]-5β-hydroxy-1β(H)-caryophyll-2(15)-en-7-one (Pulidysenterin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_841

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

Biological sources: Pulicaria dysenterica Gaertn. [1]

C30H44O5: 484.3189

Mp: colorless gum (isolated as its 13-O-acetate) [1]

[α]24 (λ, nm) (5-OAc): −86° (589), −90° (578), −105° (546), −188° (436) (c 0.2, CHCl3) [1]

IR (CCl4) (5-OAc): 2070, 1740, 1687, 1625, 1240, 900 [1]

MS (5-OAc): 526.314 [M]+ (8) (C32H46O6), 464 (0.5), 275 (13), 274 (3), 250 (27), 233 (13), 232 (16), 215 (44), 201 (3), 147 (54), 119 (40), 95 (100), 93 (58) [1]

1H NMR (400 MHz, C6D6, TMS) (5-OAc): 0.86 (3H, s, H-13′), 0.90 (3H, s, H-12′), 0.99 (3H, s, H-12), 1.35 (1H, m, H-3′α), 1.56 (1H, dd, J = 9, H-10′β), 1.62 (1H, dd, J = 9.5; 11.5, H-10β), 1.72 (3H, s, OAc), 1.82 (1H, dd, J = 9, H-10′α), 1.82 (1H, dd, J = 9.5; 11.5, H-10α), 1.84 (1H, br ddd, J = ∼1; 10; 9, H-1′), 1.89 (1H, m, H-3α), 1.89 (1H, m, H-4), 1.91 (3H, br s, H-14′), 2.01 (1H, ddd,...

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References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 20(11), 2529 (1981)CrossRefGoogle Scholar

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