Natural Compounds

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

3α-Angeloyloxy-7αH-eremophila-9(10),11(12)-dien-9-one (Angeloyloxy-neopetasol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1010

CAS Registry Number: 70387-53-0 Open image in new window

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

Biological sources: Petasites hybridus (= P. officinalis Moench) [1, 2, 3]; P. fragrans (Vill.) C. Presl [4]; P. japonicus (Siebold et Zucc.) Maxim. [5]; Senecio cathcartensis O. Hoffm. [6], S. greyi Hook f. [7]; S. ovirensis (Koch) DC. [8]; S. polyodon DC. [9]; S. speciosus Willd. [10]

C20H28O3: 316.2038

Mp: viscous oil (mix. with isopetasin and petasin) [4]

[α]D22 −87.6° (c 1.35, CHCl3) [5]

CD [θ]322 +1404 (EtOH) [5]

UV (cyclohexan) 224 [1]

IR (CCl4): 1711, 1679, 1646, 1628 [1]; (neat): 1710, 1675, 1650sh, 1630, 890 [4]

MS: 316.2040 [M]+ (calc. for C20H28O3: 316.2038) [1]

CI-MS: 317 [M + 1]+ (base), 245, 217, 201, 189, 161, 148, 135 [5]

HPLC: [2, 3]

1H NMR (360 MHz, CDCl3, TMS): 1.01 (3H, d, J = 7, H-15), 1.17 (3H, s, H-14), 1.45 (1H, q, J = 5; 11, H-2ax), 1.78 (3H,...

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