An oplopane from Senecio mexicanus

Joseph‐Nathan, Pedro; Villagómez, J.Roberto; Román, Luisa U.; Hernández, José Falcón

doi:10.1016/0031-9422(89)80210-9

Cited by 11 publications

(6 citation statements)

References 9 publications

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“…Therefore, the aforementioned data indicate an unprecedented 4,9‐ seco ‐oplopanane skeleton ( Figure 1). [14] …”

Section: Resultsmentioning

confidence: 99%

“…Therefore, the aforementioned data indicate an unprecedented 4,9-secooplopanane skeleton (Figure 1). [14] The relative configuration of levalide A was determined using the nuclear Overhauser effect spectroscopy (NOESY) signals of H-9/H-7α, H-7α/H-5, and H-14/H-5, which indicate the Z-double bond at C-3. The absolute configuration of 1 was ascertained by comparing the experimental electronic circular dichroism (ECD) curves of 1 and the calculated ECD spectra of the four stereoisomers 1a-d (Figure S31).…”

Section: Introductionmentioning

confidence: 99%

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Unprecedented 4,9‐Seco‐Oplopanane and Seven Drimane Sesquiterpenoids from the Chinese Liverwort Lejeunea flava (Sw.) Nees

Lou

Zhu

et al. 2022

Chemistry & Biodiversity

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An unprecedented 4,9-seco-oplopanane (1), two undescribed drimane epimers (2 and 3), and five known drimane sesquiterpenoids (4 -8) were isolated from the Chinese liverwort Lejeunea flava (Sw.) Nees. The structures of the new sesquiterpenoids were determined using nuclear magnetic resonance spectroscopy, electronic circular dichroism calculations, and single-crystal X-ray diffraction measurements. The inhibitory capacity of the new compounds against nitric oxide production in lipopolysaccharide-induced RAW 264.7 murine macrophages, along with the cytotoxicity of the new compounds against A549 and HepG-2 human cancer cell lines, were discussed.

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“…Therefore, the aforementioned data indicate an unprecedented 4,9‐ seco ‐oplopanane skeleton ( Figure 1). [14] …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Unprecedented 4,9‐Seco‐Oplopanane and Seven Drimane Sesquiterpenoids from the Chinese Liverwort Lejeunea flava (Sw.) Nees

Lou

Zhu

et al. 2022

Chemistry & Biodiversity

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“…β-oplopenone ( 3 ) [ 4 ]. GC: 99%; I Rtx-1 = 1596; I Rtx-Wax = 2050; EIMS (70 e/v): 220 (4), 177 (31.6), 107 (16), 91 (20), 79 (17), 67 (14), 55 (12), 43 (100), 41 (34); IR (KBr) υ max cm -1 (CCl 4 ): 3070, 2955, 2874, 1710, 1652, 1462, 1358, 887; 1 H-NMR: δ 0.65, 0.90 (3H, 2d, J = 6.8 Hz, Me-12 and Me-13), 1.97 (3H, s, Me-15), 2.34 (1H, ddd, J = 13.4 Hz; 2.6 Hz; 4.3 Hz, H-7 β ), 2.70 (1H, ddd, J = 5.1 Hz; 12.0 Hz; 10.5 Hz, H-3), 4.66 (1H, q, J = 1.6 Hz, H-10), 4.55 (1H, q, J = 1.6 Hz, H-10’) and 1.10 (1H, dq, 13.8 Hz; J = 4.3 Hz, H-6 β ); 13 C-NMR: 27.34 (C-1), 28.48 (C-2), 56.06 (C-3), 52.08 (C-4), 49.26 (C-5), 26.55 (C-6), 35.27 (C-7), 150.86 (C-8), 51.80 (C-9), 103.52 (C-10), 29.58 (C-11), 21.93 (C-12), 15.66 (C-13), 211.71 (C-14), 28.87 (C-15).…”

Section: Methodsmentioning

confidence: 99%

“…The oplopane derivatives were well represented from plants of the Senecioneae family [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. The sesquiterpenic ketone β -oplopenone was identified as a major component of the essential oil of Adenostyles briquetii , an endemic species from the island of Corsica [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

Spectral Data of Two New Asymmetric Sesquiterpene Alcohols: (14R)-β-Oplopenol and (14S)-β-Oplopenol

et al. 2008

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“…The presence of oplopanes in the genus Robinsonecio may have chemosystematic significance. Nevertheless, it is important to mention that this kind of compounds have been isolated from Roldana mexicana (Table 3) [60][61][62] and from several species of Senecio such as S. ovirensis (111a-b) [63] and S. kleinia (112a-b) [64].…”

Section: Genus Robinsoneciomentioning

confidence: 99%

Secondary Metabolites from Mexican Species of the Tribe Senecioneae (Asteraceae)

et al. 2020

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Abstract. A revision of the Mexican species belonging to the tribe Senecioneae chemically studied so far, shows that the genera Senecio and Packera (subtribe Senecioninae), and the genera Barkleyanthus, Pittocaulon, Psacalium, and Telanthophora (subtribe Tussilagininae) contain pyrrolizidine alkaloids (PAs) and eremophilane derivatives as their main secondary metabolites. However, from Roldana and Robinsonecio (subtribe Tussilagininae) no PAs have been isolated. A special case is the genus Pseudogynoxys in which neither PAs nor eremophilanes are reported. Resumen. Una revisión de las especies mexicanas de la tribu Senecioneae estudiadas químicamente hasta el momento, muestra que los géneros Senecio y Packera (subtribu Senecioninae), y los géneros Barkleyanthus, Pittocaulon, Psacalium y Telanthophora (subtribu Tussilagininae) contienen alcaloides pirrolizidínicos (APs) y derivados de eremofilano como sus metabolitos secundarios principales. Sin embargo, de Roldana y Robinsonecio (subtribu Tussilagininae) no se han aislado APs. Un caso especial es el género Pseudogynoxys para el cual no se han reportado ni APs ni eremofilanos.

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An oplopane from Senecio mexicanus

Cited by 11 publications

References 9 publications

Unprecedented 4,9‐Seco‐Oplopanane and Seven Drimane Sesquiterpenoids from the Chinese Liverwort Lejeunea flava (Sw.) Nees

Unprecedented 4,9‐Seco‐Oplopanane and Seven Drimane Sesquiterpenoids from the Chinese Liverwort Lejeunea flava (Sw.) Nees

Spectral Data of Two New Asymmetric Sesquiterpene Alcohols: (14R)-β-Oplopenol and (14S)-β-Oplopenol

Secondary Metabolites from Mexican Species of the Tribe Senecioneae (Asteraceae)

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