Clerodane and 19-norclerodane diterpenoids from the tubers of Dioscorea antaly

Rakotobe, Lolona; Mambu, Lengo; Deville, Alexandre; Dubost, Lionel; Jeannoda, Victor; Rakoto, Danielle; Bodo, Bernard

doi:10.1016/j.phytochem.2010.03.014

Cited by 17 publications

(13 citation statements)

References 19 publications

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“…258 Compounds 650–653 are novel furano-clerodanes from Dioscorea antaly and D. bulbifera with a second δ-lactone ring bridging carbonyl C-19 to C-2. 259,260 …”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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“…258 Compounds 650–653 are novel furano-clerodanes from Dioscorea antaly and D. bulbifera with a second δ-lactone ring bridging carbonyl C-19 to C-2. 259,260 …”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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“…19) This conclusion was further confirmed by the NOESY correlations of H-1ax, H-5 and H-7ax with Me-19, H-3ax with H-5, which indicated that both of the A/B rings were adopted as the chair-like conformations. 10,19) The NOE cross peak from H-10 to H-12 indicated that the B/C (δ-lactone) rings were cis-fused.…”

Section: Resultsmentioning

confidence: 70%

“…Its molecular formula was established as C 19 13 C, and distortionless enhancement by polarization transfer (DEPT) NMR spectral data of 2 were similar to those of diosbulbin B (5) 10,12) with characteristic signals for a β-substituted furan ring and two γ-lactones, except for the lack of tetrahydrofuran ring of 5.…”

Section: Resultsmentioning

confidence: 89%

“…3) and by comparison to those of diosbulbin G 10) and 8-epidiosbulbin G. 19) The junction of the A-and B-rings was trans due to the trans-diaxial disposition of H-5 and H-10 (J H-5/H-10 =12.3 Hz). 19) This conclusion was further confirmed by the NOESY correlations of H-1ax, H-5 and H-7ax with Me-19, H-3ax with H-5, which indicated that both of the A/B rings were adopted as the chair-like conformations. 10,19) The NOE cross peak from H-10 to H-12 indicated that the B/C (δ-lactone) rings were cis-fused.…”

Section: Resultsmentioning

confidence: 93%

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New Norclerodane Diterpenoids from the Tubers of <i>Dioscorea bulbifera</i>

et al. 2014

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“…Meanwhile, phytochemical investigations of D. antaly were attempted, first from EtOAc extract leading to the isolation and identification of five diterpenoids and nine phenolics compounds. Among them, two new clerodane diterpenoids, antadiosbulbins A (1) and B (2) and two new 19‐norclerodane diterpenes, 8‐epidiosbulbin E (3) and 8‐epidiosbulbin G (4) were recently described (Rakotobe et al , 2010 b ). It is interesting to note that these compounds were isolated from the less polar sub‐fractions of water‐soluble extract demonstrating the effectiveness of detoxification in water to pull out bitter compounds.…”

Section: Discussionmentioning

confidence: 99%

Acute toxic effects of 8‐epidiosbulbin E, a 19‐norclerodane diterpene from yam Dioscorea antaly, on medaka Oryzias latipes embryos

Rakotobe

Mezhoud

Berkal

et al. 2010

Journal of Fish Biology

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The fractionation of an aqueous extract of yam Dioscorea antaly from Madagascar led to the isolation of terpenoids and flavonoids. Compounds were identified on the basis of modern mass spectrometry and two-dimensional nuclear magnetic resonance (2D-NMR). Toxicological effects of the most abundant isolated compound, 8-epidiosbulbin E were studied on medaka Oryzias latipes embryo-larval development. The lethal concentration (killing 50%; LC(50) ) to embryos treated 24 h before hatching and for 3 days after hatching was estimated to be 0·56 mg ml(-1) (P< 0·05). No mortality was observed with O. latipes larvae exposed after hatching until day 4. Anatomo-pathological studies of embryos exposed to 0·56 mg ml(-1) showed development anomalies of the central nervous system, liver, muscle and intestine. The present data thus extend the model of O. latipes embryos as a useful animal model to analyse the effects of food toxins.

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Clerodane and 19-norclerodane diterpenoids from the tubers of Dioscorea antaly

Cited by 17 publications

References 19 publications

Clerodane diterpenes: sources, structures, and biological activities

Clerodane diterpenes: sources, structures, and biological activities

New Norclerodane Diterpenoids from the Tubers of <i>Dioscorea bulbifera</i>

Acute toxic effects of 8‐epidiosbulbin E, a 19‐norclerodane diterpene from yam Dioscorea antaly, on medaka Oryzias latipes embryos

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