Macrolide diterpenes and other ent-labdanes from corymbium villosum

Zdero, C.; Bohlmann, Ferdinand

doi:10.1016/0031-9422(88)80620-4

Cited by 18 publications

(9 citation statements)

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“…The mass spectral fragmentation pattern of 2 was consistent with the presence of a carbomethoxy group by fragments at m/z = 314 [M ± MeOH] + and 286 [M ± MeOH ± CO, ] + . A negative Cotton effect pointed here to the presence of an ent-labdane diterpene skeleton [12]. Hence, compound 2 was determined as entlabda-8(17),13-dien-15,16-olid-19-oic acid methyl ester.…”

Section: Original Papermentioning

confidence: 85%

“…The configuration at C-12 could not be determined. A positive Cotton effect supported the presence of a labdane, and not an ent-labdane diterpene [12]. Thus, compound 1 was characterized as 15-acetoxy-12-hydroxy-16methyl labda-8(17),13E-diene.…”

Section: Original Papermentioning

confidence: 90%

“…The (E) stereochemistry of the double bond in the side chain was deduced from the chemical shift of the C-16 methyl group (d H = 1.65, d C = 10.7) [11], [12]. The configuration at C-12 could not be determined.…”

Section: Original Papermentioning

confidence: 99%

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Diterpenoids from Turraeanthus mannii

Vardamides¹,

Sielinou²,

Ndemangou³

et al. 2007

Planta Med

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Three new compounds, 15-acetoxy-12-hydroxy-16-methyl-labda-8(17),13E-diene (1), ent-labda-8(17),13-dien-15,16-olid-19-oic acid methyl ester (2), and 12-hydroxy-labda-8(17),13-dien-15,16-olide (3), together with two known compounds, 19-acetoxy-ent-labda-8(17),13-dien-15,16-olide (4), and 16-acetoxy-12,15-epoxy-15beta-hydroxy-labda-8(17),13(16)-diene (5) were isolated from the stem bark of Turraeanthus mannii (Meliaceae). The structures of compounds 1 - 3 were elucidated by analysis of the spectroscopic data. The crude methanol extract and compound 5 exhibited weak antibacterial and antifungal activity.

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Section: Original Papermentioning

confidence: 85%

Section: Original Papermentioning

confidence: 90%

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Diterpenoids from Turraeanthus mannii

Vardamides¹,

Sielinou²,

Ndemangou³

et al. 2007

Planta Med

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“…By the micromorphological character of particular cuticular striae on stylar hairs, we can support the isolated position of the genus. The traditional position within the tribe Vernonieae (e.g., Hoffmann 1894; Weitz 1989Weitz , 1990 was questioned because of deviating pollen characters (Bolick 1978) and chemical compounds (Zdero and Bohlmann 1988;Bohlmann and Jakupoviv 1990). Consequently, the genus was placed without tribal assignment in Cichorioideae (Bremer 1994).…”

Section: The Phylogenetic Applicability Of the Cuticular Patternsmentioning

confidence: 99%

Cuticular Patterns on Stylar Hairs in Asteraceae: a New Micromorphological Feature

Erbar

Leins

2015

International Journal of Plant Sciences

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JSTOR is a not-for-profit service that helps scholars, researchers, and students discover, use, and build upon a wide range of content in a trusted digital archive. We use information technology and tools to increase productivity and facilitate new forms of scholarship. For more information about JSTOR, please contact support@jstor.org.. The University of Chicago Press is collaborating with JSTOR to digitize, preserve and extend access to International Journal of Plant Sciences.Editor: Patrick S. Herendeen Premise of research. In the course of a detailed comparative study concerning style morphology (including 395 species of 258 genera covering all 44 tribes of the Asteraceae), we found a new microstructural feature, namely, often conspicuous cuticular patterns on the stylar hairs (involved in secondary pollen presentation) and stylar appendages. The observations raised questions as to whether the different striation patterns can be arranged in structural types and whether this new microcharacter could be of value in phylogenetic considerations.Methodology. Styles from liquid-preserved flowers or from herbarium material were studied by using scanning electron microscopy.Pivotal results. Five different patterns of cuticular striation can be discerned: crested pattern, triple pattern, double pattern, longitudinal pattern, and transverse pattern. By plotting the different cuticular patterns onto a generalized phylogenetic tree based on molecular data, it becomes obvious that there is considerable homoplasy in these features. Nevertheless, the cuticular patterns are still useful in characterizing some clades within the family. It is noteworthy that the small monogeneric subfamily Corymbioideae is characterized by a particular triple cuticular pattern on the stylar hairs that is otherwise found only rarely and isolated in some tribes (namely Mutisieae, Helenieae, Coreopsideae, and Heliantheae). The subfamily Mutisioideae is remarkable in the absence of simple patterns. A crested cuticular pattern is found only within the Mutisioideae (in Onoserideae and Mutisieae). Quite diverse in their cuticular patterns are the tribes Helenieae and Heliantheae within the Asteroideae.Conclusions. In comparison with the known influence of cuticular microstructures of petal cells on the wettability, we speculate that the cuticular striations of the stylar hairs increase the repellence of water drops in the flower, which would harm the viability of the pollen grains (due to osmosis, most pollen grains burst in pure water).

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“…The 13 C-NMR and DEPT spectra showed twenty-five carbon signals, including six quaternary carbons, six methyls, eight methylenes and five methines. The 1 H- and 13 C-NMR spectra (Table 1 and Table 2) revealed the presence of malonic acid monoethyl ester [14] and a labdane skeleton [13,15,16]. One oxygenated methylene [δ H 4.18 (2H, q, J = 7.2 Hz), δ C 62.3], one methyl [δ H 1.26 (3H, t, J = 7.2 Hz), δ C 14.1], one methylene [δ H 3.22 (2H, s), δ C 41.7], and two ester carbonyls [δ C 166.7, 166.6] were observed, suggesting the presence of malonic acid monoethyl ester [14].…”

Section: Resultsmentioning

confidence: 99%

Labdane Diterpenes from the Fruits of Sinopodophyllum emodi

et al. 2016

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Two new labdane diterpenes, sinoditerpene A (1) and B (2), were isolated from the fruits of Sinopodophyllum emodi, along with two known analogues 3 and 4. Their structures were established on the basis of extensive spectroscopic analysis. The isolation of compounds 1-4 represents the first report of diterpenes from the genus Sinopodophyllum. The cytotoxic activities of all isolated compounds were evaluated in comparison with 5-fluorouracil against the MCF-7 and HepG2 cell lines, towards which 3 showed more potent cytotoxicity.

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Macrolide diterpenes and other ent-labdanes from corymbium villosum

Cited by 18 publications

References 0 publications

Diterpenoids from Turraeanthus mannii

Diterpenoids from Turraeanthus mannii

Cuticular Patterns on Stylar Hairs in Asteraceae: a New Micromorphological Feature

Labdane Diterpenes from the Fruits of Sinopodophyllum emodi

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