Clerodane and labdane diterpenoids from Nuxia sphaerocephala

Mambu, Lengo; Grellier, Philippe; Florent, Loic; Joyeau, Roger; Ramanitrahasimbola, David; Rasoanaivo, Philippe; Frappier, François

doi:10.1016/j.phytochem.2005.11.024

Cited by 23 publications

(22 citation statements)

References 22 publications

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“…The leaves of this tree contain flavonoids, saponins, tannins (Forgacs et al, 1981). Results obtained by recent research on an other representative of this genus against Plasmodium are heartening: triterpenoids have been isolated from an ethyl acetate extract of the leaves of Nuxia sphaerocephala, these compounds exhibited in vitro inhibitory activity against FcB1, the best IC 50 values being 1.55 g/ml (Mambu et al, 2006).…”

Section: Discussionmentioning

confidence: 99%

Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity

Jonville¹,

Kodja²,

Humeau³

et al. 2008

Journal of Ethnopharmacology

115

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Section: Discussionmentioning

confidence: 99%

Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity

Jonville¹,

Kodja²,

Humeau³

et al. 2008

Journal of Ethnopharmacology

115

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“…78 In addition to having a free carboxylic acid rather than ethyl ester at the side chain terminus, compounds 231 and 232 have a formyloxy group and an acetyloxy group, respectively, on C-2 compared with the hydrogen in 233 . 79 All three compounds were isolated from Clausena dunniana .…”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

“…31 Clerodane diterpenoids 227–230 also inhibited the growth of the chloroquine-resistant strain FeB1, with IC 50 values between 4.3 and 14.6 μg mL −1 . 78 Penianthic acid ( 1295 ) and epicordatine ( 1296 ) exhibited weak activity against chloroquine-resistant strain K1. 503 Casearlucine A ( 1297 ), caseamembrol A ( 119 , see structure in Section 3.5), and laetiaprocerines A–D ( 101–103, 274, see structures in Section 3.5) displayed activity against P. falciparum with IC 50 values as low as 0.5 μM against FeB1 and F-32 strains.…”

Section: Biological Activitiesmentioning

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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“…isolated the clerodanes (13 S )-ent-7β-hydroxy-3-cleroden-15-oic acid ( 64 ), ent-7β-hydroxy- 2-oxo-3-cleroden-15-oic acid ( 65 ), ent-2,7-dioxo-3-clero-den-15-oic acid ( 66 ) and ent-18-( E )-caffeoyloxy-7β-hydroxy-3-cleroden-15- oic acid ( 67 ) and the labdanes (13 S )-ent-18-( E )-coumaroyloxy-8(17)-labden-15-oic acid ( 68 ), ent-18-( E )-caffeoyloxy-8(17)-labden-15-oic acid ( 69 ) and ent-15- E -caffeoyloxy-8(17)-labden-18-oic acid ( 70 ) from Nuxia sphaerocephala , growing in Ankazobe, 100 km from Antananarivo, Madagascar [83]. The compounds showed in vitro anti-plasmodial activities against the FcB1 P. falciparum strain, with respective IC 50 values 14.6, 4.3, 8.0, 7.3, 11.4, 21.0, 16.0 μg mL -1 .…”

Section: Introductionmentioning

confidence: 99%

“…The in vitro anti-plasmodial activity of the isolated compound against chloroquine-resistant strain (Dd2) of P. falciparum was IC 50 = 0.5 μg mL -1 , while the cytotoxicity on lymphocyte proliferation model was detected at IC 50 = 6.8 μg mL -1 . The lupane-type triterpenoids 3-oxolupenal (3-oxolup-20(29)-en-30-al) ( 156 ), 3β-hydroxylupenal (3β-hydroxylup-20(29)-en-30-al) ( 157 ) and 3-oxolupenol (30-hydroxylup-20(29)-en-3-one) ( 158 ) were obtained from the leaves of Nuxia sphaerocephala (Loganiaceae), along with oleanolic acid ( 160 ), its acetylated ester ( 159 ), lupeol, uvaol, ursolic acid, and 3β-acetylursolic acid [83]. Among the compounds isolated from this study, 156 and 157 showed the best inhibitory activity against P. falciparum with the IC 50 values between 1.55 and 4.67 μg mL -1 in vitro , respectively.…”

Section: Introductionmentioning

confidence: 99%

The potential of anti-malarial compounds derived from African medicinal plants. Part I: A pharmacological evaluation of alkaloids and terpenoids

Ntie‐Kang

Onguéné

Lifongo

et al. 2013

Malar J

159

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Traditional medicine caters for about 80% of the health care needs of many rural populations around the world, especially in developing countries. In addition, plant-derived compounds have played key roles in drug discovery. Malaria is currently a public health concern in many countries in the world due to factors such as chemotherapy faced by resistance, poor hygienic conditions, poorly managed vector control programmes and no approved vaccines. In this review, an attempt has been made to assess the value of African medicinal plants for drug discovery by discussing the anti-malarial virtue of the derived phytochemicals that have been tested by in vitro and in vivo assays. This survey was focused on pure compounds derived from African flora which have exhibited anti-malarial properties with activities ranging from “very active” to “weakly active”. However, only the compounds which showed anti-malarial activities from “very active” to “moderately active” are discussed in this review. The activity of 278 compounds, mainly alkaloids, terpenoids, flavonoids, coumarines, phenolics, polyacetylenes, xanthones, quinones, steroids, and lignans have been discussed. The first part of this review series covers the activity of 171 compounds belonging to the alkaloid and terpenoid classes. Data available in the literature indicated that African flora hold an enormous potential for the development of phytomedicines for malaria.

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Clerodane and labdane diterpenoids from Nuxia sphaerocephala

Cited by 23 publications

References 22 publications

Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity

Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity

Clerodane diterpenes: sources, structures, and biological activities

The potential of anti-malarial compounds derived from African medicinal plants. Part I: A pharmacological evaluation of alkaloids and terpenoids

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