Skin irritant diterpene orthoesters of the daphnane type from Peddiea africana and P. Volkensii

Adolf, W.; Dossaji, S. F.; Seip, E. H.; Hecker, Erich

doi:10.1016/s0031-9422(00)83119-2

Cited by 16 publications

(23 citation statements)

References 5 publications

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“…This interpretation is supported by the chemical shifts of 8-H and 14-H appearing downfield as compared to the corresponding signals in the spectrum of Fl . This was already demonstrated for two factors from Peddiea uolkensii (Thymelaeaceae) (Adolf et al, 1985). Multiple of ten protons at 6 7.96-7.33 are indicative of the presence of two phenyl moieties, one of them forming the 9,13,14-orthobenzoate, the other the 12benzoate.…”

Section: Isolation Procedures and Structures Of The Daphne Factorsmentioning

confidence: 64%

“…The 9,13,14-orthobenzoate, 12-benzoate factor F2 (genkwadaphnin) is comparably active as the structurally related daphnetoxin (I), reflecting the weak influence of a 12-acyloxy group on irritancy in this specific case. More pronounced effects of a 12-acyloxy group were demonstrated for some Peddiea (Adolf et al, 1985) and Synaptolepis (Adolf et al, 1988) factors.…”

Section: Bioactivities Of the Daphne Factors Fmentioning

confidence: 95%

“…Esters of this type can 1). easily be transformed to the corresponding 9,13,14orthoesters Adolf et al, 1985). Therefore factor F3 is called 'prohuratoxin' (Fig.…”

Section: Isolation Procedures and Structures Of The Daphne Factorsmentioning

confidence: 99%

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Oligo‐ and macrocyclic diterpenes in thymelaeaceae and euphorbiaceae occurring and utilized in Yunnan (Southwest China) 1. Daphnane type diterpene esters from Daphne feddei

Sorg

Adolf

et al. 1991

Phytotherapy Research

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From roots of the Chinese folk medical plant Daphnefeddei Levl. three Daphne factors FI , F2 and F3 have been isolated. They proved identical with the known daphnane type 9,13,14-orthoesters huratoxin (F,), genkwadaphnin (F3 and with the known daphnane type 14-ester prohuratoxin (F3). From stem bark of the plant a new factor F4 was obtained and identified as the 1,Zdihydro derivative of the known daphnane type 9,13,14-orthoester daphnetoxin. The factors FI-F4 exhibit moderate to strong irritant activity on the mouse ear. F4 assayed in the standard protocol 16 for tumor promoting activity on the back skin of mice was nearly inactive. Certain structure/activity relationships are pointed out along the conceptual idea to develop diterpene structures with diminished or abolished irritant and tumor promoting activities but retained immune stimulating, differentiating or otherwise antineoplastic activities.

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Section: Isolation Procedures and Structures Of The Daphne Factorsmentioning

confidence: 64%

Section: Bioactivities Of the Daphne Factors Fmentioning

confidence: 95%

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Oligo‐ and macrocyclic diterpenes in thymelaeaceae and euphorbiaceae occurring and utilized in Yunnan (Southwest China) 1. Daphnane type diterpene esters from Daphne feddei

Sorg

Adolf

et al. 1991

Phytotherapy Research

Self Cite

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“…Compounds extracted from Daphne species are known to exhibit toxic effects evaluated by toxicity tests using goldfish (2), (11), (16) and by irritant effects in rat skin (8), (14). However, some of them may also exhibit antileukemic activity as shown by tests performed according to the standard protocols Fig.…”

Section: Discussionmentioning

confidence: 99%

Differential Activation by Daphnetoxin and Mezerein of PKC-Isotypes α, βI, δ and ζ

Fresco¹,

Pinto²,

Portugal³

et al. 2001

Planta med

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Daphnetoxin, a mezerein derivative, was isolated from the stem bark of Daphne gnidium. Mezerein is a PKC activator that exhibits antileukemic properties. However, daphnetoxin and its analogue 12-hydroxydaphnetoxin were described as being devoid of this effect. In the present study daphnetoxin and mezerein were compared as PKC activators on classical (alpha and beta I), novel (delta) and atypical (zeta) isoforms, using an alternative in vivo yeast phenotypic assay. The aim was to clarify if daphnetoxin is a PKC activator and if the differences between the antiproliferative effect of mezerein and of its analogue daphnetoxin may be ascribed to differences on their potency or selectivity as PKC activators. Yeast samples expressing each of the mammalian PKC isoforms tested were incubated with daphnetoxin or mezerein. Growth inhibition caused by these drugs was assumed to be due to PKC activation since it did not occur when expression was not induced. Mezerein inhibited the growth of yeast expressing PKC alpha (IC(50) = 1190 +/- 237 nM; n = 20), PKC beta I (IC(50) = 908 +/- 46 nM; n = 20), and PKC delta (IC(50) = 141 +/- 25 nM; n = 20) but not of yeast expressing PKC zeta. Daphnetoxin also inhibited the growth of yeast expressing isoforms alpha, beta I and delta, being more potent than mezerein on PKC alpha (IC(50) = 536 +/- 183 nM; n = 20; P < 0.05), as potent as mezerein on PKC beta I (IC(50) = 902 +/- 129 nM; n = 20) and less potent than mezerein upon PKC delta (IC(50) = 3370 +/- 492 nM; n = 20; P < 0.05). These results show that daphnetoxin is a potent PKC activator but with a selectivity different from that of mezerein. It is suggested that the lack of antileukemic and antiproliferative effects of daphnetoxin may be due to its lower potency to activate PKC delta.

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“…Further daphnetoxin-analogues were isolated from various plants belonging to the Excoecaria, Wikstroemia and Synaptolepsis species [22][23][24]26,29,[38][39][40][41][42][43]80]. The strong irritant and tumor promoting activity of synaptolepsis factor K7 (23) is worth mention [26].…”

Section: Daphnetoxin and Analoguesmentioning

confidence: 99%

Daphnane-Type Diterpene Orthoesters and their Biological Activities

Cik²,

Appendino³

et al. 2002

MRMC

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Skin irritant diterpene orthoesters of the daphnane type from Peddiea africana and P. Volkensii

Cited by 16 publications

References 5 publications

Oligo‐ and macrocyclic diterpenes in thymelaeaceae and euphorbiaceae occurring and utilized in Yunnan (Southwest China) 1. Daphnane type diterpene esters from Daphne feddei

Oligo‐ and macrocyclic diterpenes in thymelaeaceae and euphorbiaceae occurring and utilized in Yunnan (Southwest China) 1. Daphnane type diterpene esters from Daphne feddei

Differential Activation by Daphnetoxin and Mezerein of PKC-Isotypes α, βI, δ and ζ

Daphnane-Type Diterpene Orthoesters and their Biological Activities

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