Phytotoxic clerodane diterpenes from Salvia miniata Fernald (Lamiaceae)

Bisio, Angela; Damonte, Gianluca; Fraternale, Daniele; Giacomelli, Emanuela; Salis, Annalisa; Romussi, Giovanni; Cafaggi, Sergio; Ricci, Donata; Tommasi, Nunziatina De

doi:10.1016/j.phytochem.2010.11.011

Cited by 34 publications

(29 citation statements)

References 40 publications

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“…The most active diterpenoids, 149, 150 and 151 inhibited the germination of the seeds of P. rhoeas when applied at concentration of 10-60 mg/ml (Table 4). Moreover, in addition to 149 that was the strongest phytotoxic compound, also 152, 153, and 154 inhibited the seeds of A. sativa from germination, an effect which was comparable to that for pendimethalin, an herbicidal positive control (Bisio et al 2011).…”

Section: Allelopathic Interactionmentioning

confidence: 82%

“…Dichloromethane extract of the leaves' surface exudates of S. miniata showed antigerminative activity against the seeds of Papaver rhoeas L. and Avena sativa L. which was then subjected to bioassay guided purification. Using different chromatography separations, several bioactive clerodane related diterpenoid were isolated and then identified by IR and different NMR spectral data (Bisio et al 2009b(Bisio et al , 2011. The most active diterpenoids, 149, 150 and 151 inhibited the germination of the seeds of P. rhoeas when applied at concentration of 10-60 mg/ml (Table 4).…”

Section: Allelopathic Interactionmentioning

confidence: 99%

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Bioactive phytochemicals from shoots and roots of Salvia species

et al. 2015

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The plants of the genus Salvia L. are important medicinal herbs of the Lamiaceae family and some of them such as S. officinalis (sage), S. miltiorrhiza (red sage, Danshen) and S. sclarea (clary sage) have been used as medicinal plants in the folk medicine of several countries. In this review, we discuss the reports that have examined Salvia species with the aim of isolation of pure compounds with different biological activities. The phytochemical analyses of various sage plants have reported 10 monoterpenoids (1-10), 1 sesquiterpenoid (11), 8 labdane (13-20), 15 ent-kaurane (21-35), 82 abietane, rearranged abietane and tanshinone (36-117), 3 icetexane (118-120), 43 clerodane (121-163), and 3 pimarane (164-166) diterpenoids with cytotoxic and antimicrobial, antiprotozoal, antioxidant, phytotoxic and insecticide effects. The other heavier terpenoids, including 3 sesterterpenes (167-169), 10 triterpenoids and b-sitosterol (170-180) have been introduced as minor bioactive compounds in the sage plants. Sahandinone (107), 6,7-dehydroroyleanone, 7-a-acetoxyroyleanone (40), and tanshinone like diterpenoids have been isolated from the roots' extracts of different Salvia species. On the other hand, several radical scavenger phenolic compounds like simple phenolics and caffeic acid derivatives (181-201) including rosmarinic acid, flavonoids (202-217) as well as phenolic diterpenoids, such as carnosol and carnosic acid have been isolated from the aerial parts of these plants. One pyrrole (218) and 3 antimicrobial oxylipins (219-221) are among the other less detected constituents in the members of Salvias. Furthermore, sages also synthesize antifungal, antileishmanial and antimalarial phytochemicals in their roots and shoots, which are reviewed in this paper. We also examine the allelopathic phenomena and the ecologically important phytochemicals identified in different parts of the sage plants. Finally, antifeedant and insecticide phenomena, which are due to the presence of volatile monoterpenes and clerodane diterpenes in these plants, are discussed. Considering the presence of diverse biologically active phytochemicals in the sage plants, they can be suggested as suitable candidates for the formulation of valuable natural medicines.

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Section: Allelopathic Interactionmentioning

confidence: 82%

Section: Allelopathic Interactionmentioning

confidence: 99%

Bioactive phytochemicals from shoots and roots of Salvia species

et al. 2015

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“…Compound 319 from Salvia miniata has an oxygenated structure containing C-19/C-20 and C-7/C-20 acetalic bridges. 108 The C-20/C-19 δ-lactone in 321 (ref. 116) from Teucrium oxylepis and the C-20/C-6 δ-lactol ring in 323 (ref.…”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

“…84,274 Remarkably, the structures of orcadensin ( 690 ) also from A. lindenbergianus , as well as salvianduline D ( 691 ) from Salvia miniata , contain cyclic ketal functions with two oxygen bridges from C-12 to different positions of the decalin moiety. 84,108 …”

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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“…其次, 异海松酸对结核病毒具有显著的疗效 [6] , 并对爱博斯坦巴尔病毒也显示出抑制效果 [7] . 此外, 异海松酸对 12-O-佛波酯- [8] 、 5-脂氧酶(5-LOX, 一种催化产生炎症的媒介) [9] 、鼠尾草种子发芽 [10] 、棉红铃虫幼虫生长 [11] 及多种细菌、真菌 [12,13] 等具有明显的抑制作用, 并对舞毒蛾觅食表现出阻碍作用 [14] . 因异海松酸本身具有广泛的生物活性, 且异海松酸的化学结构中含有可反应的官能团羧基及双键, 因此可将其作为化工中间体或以其骨架结构作为药理活性中心, 开发具有生物活性的新型异海松酸类衍生物.…”

Section: 酰基-N′-(3-甲基苯基)硫脲(3c)和 N-异海松酰胺基-n'-(4-氟苯基)硫脲(6b)对癌细胞的抑制率达到unclassified