The structures of ferocin and ferocinin

Golovina, L. A.; Saidkhodzhaev, Ashraf I.

doi:10.1007/bf00565515

Cited by 7 publications

(4 citation statements)

References 3 publications

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“…167 Ferula pachyphylla 168 contains ferocidin 179, which is a new ester of the known humulane derivative fecerol 180. 169 The structure of ferocin, another humulene ester, has now been determined by Xray analysis. 170 Buddlindeterpene A 181 and buddlindeterpene B 182 are two new humulane derivatives, which have been isolated from Buddeleia lindleyana.…”

Section: Himachalane Longifolane and Longipinanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2006

Nat. Prod. Rep.

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Section: Himachalane Longifolane and Longipinanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2006

Nat. Prod. Rep.

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“…It was identical to previously isolated fecerol [4]. Isovanillic acid C 8 H 8 O 5 (III), mp 250-251°C, was isolated from the acid part of the hydrolysate.…”

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confidence: 65%

Structure of ferocidin

Omiraliev

Komilov

2004

Chem Nat Compd

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Plants of the Ferula L. genus (celery, Apiaceae) are rich sources of terpenoids such as coumarins, terpenoid esters, and sesquiterpene lactones [1][2][3]. Preparations with physiological properties are based on terpenoids.We isolated a new terpenoid ester from roots of Ferula pachyphylla Korov. and called it ferocidin. The UV spectrum of this compound exhibits maxima at 262 and 295 nm (log ε 4.16 and 4.05), which are typical of 3,4-dihydroxybenzoic acid derivatives.The IR spectrum of the compound contains absorption bands at 3450-3540, 1715, 1615, 1530, 1270, and 1245 cm -1 , which are due to the presence of hydroxyl, ester carbonyl, and an aromatic ring.Basic hydrolysis of ferocidin by aqueous alcoholic NaOH (20%) isolated a sesquiterpene alcohol C 15 H 24 O (II) from the neutral part of the hydrolysate. It was identical to previously isolated fecerol [4]. Isovanillic acid C 8 H 8 O 5 (III), mp 250-251°C, was isolated from the acid part of the hydrolysate.The PMR spectrum of the compound confirmed the above data. The following proton signals were observed (C 5 D 5 N, δ, ppm, J/Hz): 1.10 and 1.17 (3H, both s, 2CH 3 -1), 1.65 (3H, br.s, CH 3 -8), 4.90 (1H, m, H-10), 5.44 (1H, t, J = 7.5, H-7), 4.96 and 5.06 (1H each, d, J = 2.0, C 4 =CH 2 ), 5.44 and 5.91 (1H each, d, J = 16.0, H-2, H-3), 6.85 (1H, d, J = 9.5, H-3′), 7.70 (1H, dd, J 1 = 9.5, J 2 = 2.5, H-2′), 7.60 (1H, d, J = 2.5, H-6′).

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“…int.) [M -C3H7]+ 359 (7), 235 (26), 217 (9), 191 (23), 168 (36), 163 (10). Hydrolysis of 6.-Compound 6 (100 mg), dissolved in MeOH (2 ml), was treated with a 3% solution of KOH in MeOH (3 ml), at room temperature for 10 h. Usual workup afforded lapidol (6 mg) and vanillic acid (12 mg).…”

Section: Experimental General Experimentalmentioning

confidence: 99%

“…species: 10ß-hydroxy-5 -/>-hydroxybenzoyloxy-l -angeloyloxydauc-2-ene [3], 10ßhydroxy-5a-/>-anisoyloxy-la-angeloyloxydauc-2-ene [4} (14), lapidin [5] (15), lapiferin [7], lapiferol [8] (16), felikiol 3-angelare [9], and webiol 3-angelare [11] (17). Felikiol [10] was found for the first time as a natural product. Compounds 1 and 6 have not hitherto been reported.…”

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confidence: 99%