1979
DOI: 10.1021/jf60222a027
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Diterpenoid acids, (-)-cis- and (-)-trans-ozic acid, in wild sunflower, Helianthus occidentalis

Abstract: Communicationsservation possibly related to the fact that the high incidence of stomach cancer in Japan may be related to dietary factors (Marquardt et al., 1977).

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Cited by 30 publications
(17 citation statements)
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“…The communic acids have been characterized for resin from C. columellaris [21]. Ozic acid (XVII, 4- epi -communic acid, assumed 12E-isomer) was a dominant component in two samples, and its mass spectra (Figure 2i and Figure S1ii) were interpreted by comparison with literature data [37,38] and the GC retention indices versus those of the communic acids. Lambertianic acid (XXII) is a major component in most samples and its mass spectra (Figure 2k and Figure S1nn) were interpreted by comparison with a surrogate standard from resin of Pinus lambertiana [39].…”
Section: Resultsmentioning
confidence: 99%
“…The communic acids have been characterized for resin from C. columellaris [21]. Ozic acid (XVII, 4- epi -communic acid, assumed 12E-isomer) was a dominant component in two samples, and its mass spectra (Figure 2i and Figure S1ii) were interpreted by comparison with literature data [37,38] and the GC retention indices versus those of the communic acids. Lambertianic acid (XXII) is a major component in most samples and its mass spectra (Figure 2k and Figure S1nn) were interpreted by comparison with a surrogate standard from resin of Pinus lambertiana [39].…”
Section: Resultsmentioning
confidence: 99%
“…Estes dados foram comparados com os dados da literatura de cada um dos compostos identificando o óxido de cariofileno (1), 6 1β-metoxicariolan-9β-ol (2), 14,15 ácido kaur-16-en-19-oico (3), 16 ácido cis-ozoico (4), 17,18 espatulenol (5), [19][20][21] lupeol (6), 22 7δ-metoxi-opposit-4(15)-en-1β-ol (7), 23,24 germacra-4(15),5,10(14)-trien-1β-ol (8), 25,26 β-sitosterol (9), 27 ent-kaur-16-en-18-ol (10), 16 ácido 15-metoxi-neo--clerodan-3,13-dien-16,15-olid-18-oico (11), [28][29][30] 6α-metoxieudesm--4(15)-en-1β-ol (12), 31 sacarose (13) 32 e a N-metil-trans-4-hidroxi-Lprolina (14) (Figura 1). 33 Estudos prévios sobre a Croton gratissimus focaram-se sobre as folhas.…”
Section: Resultsunclassified
“…Finalmente, a fração E, frações 43-59, foi cromatografada sob sílica gel (Hex-AcOEt, 1:0 → 0:1; ±100 mL; 103 frações) e as frações 29-30 foram purificadas por CF com sílica gel (Hex-AcOEt 1:0→0:1; ±100 mL; 60 frações), obtendo-se o composto 11 (12 mg; Hex-AcOEt 9:1; frações [17][18][19].…”
Section: Extração E Isolamentounclassified
“…The 1 H– 1 H COSY spectrum, heteronuclear multiple bond correlations (HMBCs) and other spectral data of 3 revealed the presence of 12( Z )‐labda‐8(17),12,14‐trien‐18‐ol17, 18 and α‐arabinose19 (Figure 6). The configuration of the C12C13 double bond ( Z ) was determined by comparison of the signal pattern in the 13 C NMR spectra with those reported for cis ‐ and trans ‐methyl ozate 20. Acid hydrolysis of 3 was carried out to determine the absolute stereochemistry of the aglycone and sugar moieties of the compound.…”
Section: Resultsmentioning
confidence: 99%