Neo-clerodane diterpenoids from Scutellaria altissima and S. albida

Bruno, Maurizio; Piozzi, Franco; Rodrı́guez, Benjamı́n; Torre, Marı́a C. de la; Vassallo, Nadia; Servettaz, Orietta

doi:10.1016/0031-9422(96)00081-7

Cited by 31 publications

(28 citation statements)

References 16 publications

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“…Scupolin K ( 811 ) from S. polyodon was found as a mixture of the C-15 epimers of the 14,15-dihydro- 15-hydroxy derivative of scupolin J, 310 and scutalsin ( 818 ) from S. altissima was also a 1 : 1 epimeric mixture of the C-15 hemiacetal function. 312 Compounds 812–814 and 832–833 , which have ethoxy acetal groups, are considered to be artifacts from Scutellaria discolor formed in the course of extraction or separation using ethanol. 311 Compounds 824 and 825 from Ajuga salicifolia are the C-15 epimers of the 14,15-dihydro-15-hydroxy derivative of 826 .…”

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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Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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“…Due to this diversion, the infrageneric classification is not well understood, although the position of the genus in the Lamiaceae family remains established (Beardsley et al, 2006). Previous investigations in the S. albida group (Çalis et al, 1993, Bruno et al, 1996, Skaltsa et al, 1996, Shang et al, 2010 revealed the presence of iridoid glucosides. Iridoids have been used as chemical markers for the Lamiiflorae superorder, and, in chemosystematics, the iridoid character is important in plant classification, phylogeny and evolution (SampaioSantos and Kaplan, 2001).…”

Section: Previous Workmentioning

confidence: 99%

Iridoids from Scutellaria goulimyi Rech. f., Lamiaceae. Morphological and chemical relations with Scutellaria albida L. ssp albida

Gousiadou

Gotfredsen

Jensen

et al. 2012

Biochemical Systematics and Ecology

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“…The molecular formula was established as C 30 H 41 NO 8 by HR-FAB mass spectrum, which gave a quasi-molecular ion at m/z 544.2919 [MϩH] ϩ . The IR spectrum displayed absorption bands at 1726, 1710, 1590, 1478, 1440, 1251, 888 4,5) Based on the above data and comprehensive 2D NMR experiments ( 1 H-1 H COSY, HMQC, HMBC), the structure of 1 was established as shown in Fig. 1.…”

mentioning

confidence: 96%

“…4,5) Based on the above data and comprehensive 2D NMR experiments ( 1 H-1 H COSY, HMQC, HMBC), the structure of 1 was established as shown in Fig. 1.…”

mentioning

confidence: 99%

New neo-Clerodane Diterpenoid Alkaloids from Scutellaria barbata with Cytotoxic Activities

et al. 2008

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In our previous phytochemical studies on Scutellaria barbata D. DON, we reported the isolation of ten neo-clerodane diterpenoid alkaloids, which showed significant cytotoxic activities.1-3) As a continuous search for more novel neo-clerodane diterpenoids, we have further investigated the aerial parts of this species and isolated four new neo-clerodane diterpenoid alkaloids, named scutebarbatines I-L (1-4). By means of detailed spectroscopic methods, the structures of four new compounds, 1-4, were elucidated. In addition, the four new compounds were screened for cytotoxity against three tumor cell lines (HONE-1 nasopharyngeal, KB oral epidermoid carcinoma, and HT29 colorectal carcinoma cells), with IC 50 values being in the range 3.2-8.3 mM. Herein we report on the isolation, structure elucidation, as well as evaluation of the cytotoxic effects of these four new compounds. Results and DiscussionCompound 1 was isolated as white needles, and showed a positive response to many alkaloid reagents. The molecular formula was established as C 30 H 41 NO 8 by HR-FAB mass spectrum, which gave a quasi-molecular ion at m/z 544.2919 [MϩH] ϩ . The IR spectrum displayed absorption bands at 1726, 1710, 1590, 1478, 1440, 1251, 888 4,5) Based on the above data and comprehensive 2D NMR experiments ( 1 H-1 H COSY, HMQC, HMBC), the structure of 1 was established as shown in Fig. 1. The relative stereochemistry of the chiral centers in 1 was resolved by 2D ROESY data. In the ROESY experiment (Fig. 1), the cross peaks were observed from H-10 to H 2 -18 and H-6, and from H 3 -20 to H-11, H 3 -17 and H 2 -19. Thus, H 3 -17, H 2 -19, H 3 -20 and H-11 were on the same molecular plane (a-configuration) while H-6, H-10 and H 2 -18 were on the opposite side of the molecular plane (b-configuration). Four new neo-clerodane diterpenoid alkaloids, named scutebarbatines I-L (1-4), were isolated from the whole plant of Scutellaria barbata D. DON. Their structures were established on the basis of detailed spectral analyses. In vitro, the four new compounds showed significant cytotoxic activities against three human cancer lines (HONE-1 nasopharyngeal, KB oral epidermoid carcinoma, and HT29 colorectal carcinoma cells), and gave IC 50 values in the range 3.2-8.3 m mM.

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Neo-clerodane diterpenoids from Scutellaria altissima and S. albida

Cited by 31 publications

References 16 publications

Clerodane diterpenes: sources, structures, and biological activities

Clerodane diterpenes: sources, structures, and biological activities

Iridoids from Scutellaria goulimyi Rech. f., Lamiaceae. Morphological and chemical relations with Scutellaria albida L. ssp albida

New neo-Clerodane Diterpenoid Alkaloids from Scutellaria barbata with Cytotoxic Activities

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