New clerodane diterpenoids from Croton crassifolius

Qiu, Maosong; Cao, Di; Youheng, Gao; Li, Shuhua; Jin-ping, Zhu; Yang, Bao; Zhou, Lian; Zhou, Yuan; Jin, Jing; Zhao, Zhongxiang

doi:10.1016/j.fitote.2015.11.016

Cited by 37 publications

(24 citation statements)

References 21 publications

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“…In order to isolate bioactive compounds, this fraction was submitted to fractionation on a chromatographic column and the subfractions were also assayed in the DPPH. From that results, the most active subfractions were purified by chromatographic methods affording indolinone and N-substituted tryptamine alkaloid type compounds (1)(2)(3)(4)(5) which chemical structures are shown in Figure 1. In addition, were isolated flavonoids derived from kaempferol and quercetin (6-9), as well was benzoic acid derivatives (10)(11)(12).…”

Section: Resultsmentioning

confidence: 99%

Bioactive Indole Alkaloids fromCroton echioides

Novello

Marques

Pires

et al. 2016

Journal of the Brazilian Chemical Society

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Bioguided fractionation of a hydroethanolic extract from the stem bark of Croton echioides Baill. led to isolation of the new indole alkaloid N-trans-feruloyl-3,5-dihydroxyindolin-2-one as a stereoisomeric mixture and the known alkaloids N-trans-p-coumaroyl-tryptamine, N-trans-pcoumaroyl-5-hydroxytryptamine, N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine, N-transferuloyl-5-hydroxytryptamine (moschamine), from the ethyl acetate fraction. The flavonoids 3-o-methyl kaempferol, 3-o-methyl quercetin, 3,7-di-o-methyl quercetin and 3,3'-di-o-methyl quercetin, together with the benzoic acid derivatives 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid and 4-hydroxy-3,5-dimethoxybenzoic acid were also isolated. Alkaloids and the flavonoids showed strong antioxidant properties in vitro radical scavenging assay (2,2-diphenyl-1-picrylhydrazyl, DPPH), with IC 50 values ranging from 9.2 to 17.5 µmol L

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Section: Resultsmentioning

confidence: 99%

Bioactive Indole Alkaloids fromCroton echioides

Novello

Marques

Pires

et al. 2016

Journal of the Brazilian Chemical Society

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“…Compounds of this kind functionalized at C6 in ring B are not frequent, only crassifolin D (114), crassifolin E (115), crassifolin I (117), 143,144 118, 138 cracroson G (122), 151 crassifolin M (123), 44 and mallotucin B (127) 136 show this functionalization. Functionalization at C7 is seen in compounds 128, 134 and 140 and at C8 only on compound 140.…”

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

“…8, Table S2 †). Compounds of this type have been isolated from plants of the families Euphorbiaceae, 44,78,105,107,109,[111][112][113][114][136][137][138][139][140][141][142][143][144][145][146][147][148][149][150][151] Compositae, 45 Annonaceae, 122 Lamiaceae, 91 Jungermanniaceae, 152,153 Asteraceae, 76 and Meliaceae, 154 and in sponges of genus Agelas. 79,135 Among them, chettaphanin II (102) 111 is found.…”

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

“…A series of ent-halim-5(10)-enes known as crassifolins 112-117, 119-121, 123-124 and crassin C (125) has been isolated from Croton crassifolius. 44,78,144 The absolute conguration of several of them was conrmed by CD. The structure of crassifolin D (114) was corroborated by X-ray; however, its absolute conguration was not determined.…”

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

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Halimane diterpenoids: sources, structures, nomenclature and biological activities

et al. 2018

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Covering: 1970 to 2017 Diterpenes with a halimane skeleton constitute a small group of natural products that can be biogenetically considered as being between labdane and clerodane diterpenoids. Some of these compounds show biological activities, such as antitumour, mosquito repellency, germination inhibition and antimicrobial, as well as being biomarkers for tuberculosis. To the best of our knowledge, there are no reviews on these compounds. In this review, halimane skeleton diterpenoids are classified according to their biogenetic origin, characterization and/or the enzymes involved in their biosynthesis. Herein, a review of their synthesis or synthetic approaches is communicated.

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“…5 The norclerodane trans-dehydrocrotonin (t-DCTN, Figure 1) is the main diterpene present in Croton cajucara. In vitro studies have shown that t-DCTN presents potential effects as antigenotoxic, 6 antileishmanial, 7 antiulcerogenic, 8 antitumor, [9][10][11] and hypoglycemic. 12 Recent publication from our group 13 on the interaction between t-DCTN and bovine serum albumin (BSA) demonstrated that there is a spontaneous, weak and entropy-driven association between BSA and t-DCTN in the ground state, typical of hydrophobic interactions.…”

Section: Introductionmentioning

confidence: 99%

In vitro Analysis of the Interaction between Human Serum Albumin and Semi‑Synthetic Clerodanes

Chaves¹,

Echevarrı́a²,

Esteves-Souza³

et al. 2018

J. Braz. Chem. Soc.

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The interaction between HSA and two semi-synthetic potential anti-cancer agents derived from trans-dehydrocrotonin-methyl-hydrazone (MHDCTN) and phenyl-hydrazone (PHDCTN) was evaluated under physiological conditions at 296, 303 and 310 K by multi-spectroscopic techniques and molecular docking calculations. Steady state fluorescence quenching indicated a ground state association (static quenching) for both samples; however, the quenching induced by PHDCTN was not essentially static and can be accompanied by a dynamic quenching mechanism. The binding is strong (modified Stern-Volmer binding constant (K a ) ca. 10 5 M -1 ), causing a very weak perturbation on the secondary structure of the protein and there is just one main binding site for both samples (Sudlow's site I). Molecular docking results suggested hydrogen bonding and hydrophobic interactions as the main binding forces for both samples.

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New clerodane diterpenoids from Croton crassifolius

Cited by 37 publications

References 21 publications

Bioactive Indole Alkaloids fromCroton echioides

Bioactive Indole Alkaloids fromCroton echioides

Halimane diterpenoids: sources, structures, nomenclature and biological activities

In vitro Analysis of the Interaction between Human Serum Albumin and Semi‑Synthetic Clerodanes

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