Diterpenoids from <i>Croton laui</i> and Their Cytotoxic and Antimicrobial Activities

Liu, Cuiping; Xu, Jin‐Biao; Zhao, Jin‐Xin; Xu, Cheng-Hui; Dong, Lei; Ding, Jian; Yue, Jian‐Min

doi:10.1021/np500042c

Cited by 66 publications

(52 citation statements)

References 30 publications

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“…Crotonolide G ( 404 , Croton laui ), with a unique 2,5-dihydrofuran rather than furan in the C-9 side chain, displayed significant antibacterial activity with an MIC value of 43.4 μM against four strains of Gram-positive bacteria, including Staphylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228, Micrococcus luteus ATCC 9341, and Bacillus subtilis CMCC 63501. 165 Crotomembranafuran ( 414 , Croton membranaceus ), which has a less common ethanone rather than ethyl or ethylene linkage between the decalin and furan ring systems, had an IC 50 value of 10.6 μM against PC-3 cells. 168 …”

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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“…Their absolute configurations were determined by circular dichroism (CD) spectrum and biogenetic considerations. Crotonolides B-D and isocrotonolides B-D (25-30) were isolated from Croton laui, which compose of a cage structure through the ether bonds between C-20 and C-12 and C-19 (Liu et al 2014a). Multiple substitutions with different groups and formation of ether rings cause their great structural diversity.…”

Section: Type Iamentioning

confidence: 99%

Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

et al. 2016

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Furanoditerpenoids are a special group of diterpenoids composing of one or more furan rings, which are rarely found in nature. This review aims to survey the various naturally occurring furanoditerpenoids and their pharmacological activities. A fairly large number of furanoditerpenoids have been reported from the families Euphorbiaceae, Fabaceae and Lamiaceae, and a few ones from the families Asteraceae, Codoniaceae, Dioscoreaceae, Fossombroniaceae, Jamesoniellaceae, Meliaceae, Menispermaceae, Olacaceae, Psathyrellaceae, Sapindaceae and Scapaniaceae. Their distribution correlates strongly with the taxonomic divisions. Most of these plants are widely used in traditional medicines, and furanoditerpenoids have therefore been disclosed with a wide range of bioactivities including anti-cancer, antiinflammation and anti-microorganism. To structure this review, the furanoditerpenoids were classified into seven types, including clerodane-type (Type I), labdane-type (Type II), cassane-type (Type III), abietane-type (Type IV), spongian-type (Type V), prenylbisabolane-type (Type VI) and miscellaneous type (Type VII). On the basis of 170 references, this review covers the distribution, phytochemistry, synthesis and pharmacological activities of furanoditerpenoids, describing 444 compounds. The information provided in this review might shed light on further research and development of furanoditerpenoids as potential therapeutic agents.

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“…6 The genus Croton (Euphorbiaceae) has been reported to be another rich source of clerodane diterpenoids, 1 which is still of interest to natural product scientists. 7,8 Croton euryphyllus W. W. Smith is a shrub widely distributed in southwest China especially in the Karst region of Guangxi Province, 9 and its roots have been used as a traditional medicine for the treatment of rheumatism, traumatic injury, and related diseases. 10 The phytochemical constituents of Croton euryphyllus had never been investigated unless our recent report on the volatile constituents of this plant.…”

Section: Introductionmentioning

confidence: 99%

“…11 Our continuous phytochemical investigation of this plant has led to the isolation of three new norclerodane diterpenoids, crotoeurins A-C (1-3) (Fig. 1), and four known ones, teucvin (4), 12 teucvidin (5), 13 isoteucvin (6), 14 and isocrotocaudin (7). 15 Crotoeurin A (1) is the first nor-clerodane type diterpenoid dimer with a cyclobutane ring formed through [2+2] cycloaddition.…”

Section: Introductionmentioning

confidence: 99%