Triterpenoid saponins with antifeedant activities from stem bark of Catunaregam spinosa (Rubiaceae) against Plutella xylostella (Plutellidae)

Gao, Guangchun; Lü, Zhongxian; Tao, Shu-Hong; Zhang, Si; Wang, Fa‐Zuo

doi:10.1016/j.carres.2011.07.022

Cited by 23 publications

(14 citation statements)

References 15 publications

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“…Triterpene glycosides: [194] Catunaregam spinosa Triterpene glycosides: catunarosides A-D; swartziatrioside; aralia-saponin V-IV [195] Coptosapelta Iridoids: 8-epi-apodantheroside; 7β,8β-epoxy-8α-dihydrogeniposide …”

Section: Catunaregam Niloticamentioning

confidence: 99%

Secondary Metabolites from Rubiaceae Species

2015

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This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, anthraquinones, triterpenes, indole alkaloids as well as other varying alkaloid subclasses, have shown to be the most common. These compounds have been mostly isolated from the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. The occurrence and distribution of iridoids, alkaloids and anthraquinones point out their chemotaxonomic correlation among tribes and subfamilies. From an evolutionary point of view, Rubioideae is the most ancient subfamily, followed by Ixoroideae and finally Cinchonoideae. The chemical biosynthetic pathway, which is not so specific in Rubioideae, can explain this and large amounts of both iridoids and indole alkaloids are produced. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it produces indole alkaloids together with other alkaloids. The chemical biosynthetic pathway now supports this botanical conclusion.

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Section: Catunaregam Niloticamentioning

confidence: 99%

Secondary Metabolites from Rubiaceae Species

2015

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“…senegalensis, C. zeyheri, T. stenostachya and C. spinosa (anti-tumoral) (Ahmed et al, 2010;Fyhrquist et al, 2006;Gao et al, 2010;Nibret et al, 2010); Burkea africana (glaucoma) (Dzoyem and Eloff, 2015). Attention should also be given to potentially new eco-friendly pesticides providers such as Annona senegalensis (Lame et al, 2015) and Catunaregam spinosa (Gao et al, 2011). The safety and efficacy of traditional medicine has been demonstrated by its long historical use.…”

Section: Discussionmentioning

confidence: 99%

“…C. spinosa extracts mainly contains glycosides, triterpenoid glycoside and saponins (Prakash, 2015). Triterpenoid saponins were isolated from stem bark extracts (Gao et al, 2010(Gao et al, , 2011 and two of the compounds isolated (catunaregin and epicatunaregin) exhibited moderate inhibition against the mammary cancer F10 cell line (Gao et al, 2010). Leaf extracts showed antioxidant and anti-inflammatory activities, human cyclooxygenase (COX)-2 inhibitory effects and a prominent protection of DNA (Shailasree et al, 2014).…”

Section: Rubiaceaementioning

confidence: 99%

“…Leaf extracts showed antioxidant and anti-inflammatory activities, human cyclooxygenase (COX)-2 inhibitory effects and a prominent protection of DNA (Shailasree et al, 2014). Antifeedant activity against the pest Plutella xylostella was detected in components (triterpenoid saponins) of the stem bark (Gao et al, 2011). C. spinosa use should be treated with caution, as studies have shown that it can cause damage to genetic material (Fennell et al, 2004).…”

Section: Rubiaceaementioning

confidence: 99%

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Woody species from the Mozambican Miombo woodlands: A review on their ethnomedicinal uses and pharmacological potential

Moura¹,

Duvane²,

Silva³

et al. 2018

J. Med. Plants Res.

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Miombo woodlands cover about two thirds of Mozambique national territory. They provide a wide collection of goods and services to the formal and informal economies. A review on the traditional uses of 15 Miombo tree species in human and animal health, as well as the status of research towards the identification of bioactive compounds is presented. Among the 15 species selected, 12 have been screened for their biological activity and/or pharmacological properties and/or toxicity. The information gathered in this work is a key to further exploit potential new uses and future opportunities for research and valorization of the selected species.

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“…Our previous investigations on this plant had led to the isolation of iridioid, 8) norneolignans, 9) triterpenoid saponins. 10,11) In continuation of our studies on the plants, four new triterpenoid saponins, Catunarosides I-L, together with Arjunetoside and Randiasaponin VII, were isolated from the n-BuOH extract of its stem bark by preparative HPLC. The isolation and structure determination of those triterpenoid saponins were elucidated in this paper.…”

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confidence: 97%

Catunarosides I–L, Four New Triterpenoid Saponins from the Stem Bark of <i>Catunaregam spinosa</i>

Huang

Jiang

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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Catunaregam spinosa T. (Rubiaceae), distributed in tropical and semitropical areas, was known as a folk medicine in India and Brazil for its antispasmodic, antidysenteric, anti-inflammatory, immunomodulatory and antifertility properties. [1][2][3][4] Many phytochemical research has been done on this plant, and coumarin glucosides, 5) iridoid glucosides, 1) and triterpenoid saponins 4,6,7) were found. Our previous investigations on this plant had led to the isolation of iridioid, 8) norneolignans, 9) triterpenoid saponins. 10,11) In continuation of our studies on the plants, four new triterpenoid saponins, Catunarosides I-L, together with Arjunetoside and Randiasaponin VII, were isolated from the n-BuOH extract of its stem bark by preparative HPLC. The isolation and structure determination of those triterpenoid saponins were elucidated in this paper. Results and DiscussionCompound 1 was obtained as a colorless amorphous powder. The molecular formula C 48 H 78 O 20 was determined by a combination of NMR spectra and high resolution-electrospray ionization (HR-ESI)-MS which exhibited a molecular ion peak at m/z: 997.4980 [M+Na] + (Calcd for C 48 H 78 O 20 Na:977.4984). On acid hydrolysis, 1 afforded only glucose as sugar moiety that was identical to an authentic sample by Silica gel TLC. The IR spectrum showed absorption bands at 3417 cm −1 (OH), 1726 cm −1 (C=O), 1643 cm −1 (C=C). The 13 C-NMR spectrum exhibited 48 signals, of which 30 were assigned to the aglycone moiety and 18 to the sugars. In the 1 H-NMR spectrum, seven methyl protons (δ 1.37, 1.05, 0.96, 1.14, 1.63, 1.14 and 0.98 ppm; each 3H, s), one olefinic methine proton (δ 5.49, br s), and three anomeric protons (δ 4.91, d, 8.0 Hz; 5.29, d, 7.5 Hz; 6.38, d,8.0 Hz) were observed. The 13 C-NMR spectrum also showed seven methyl carbons at δ 28.4, 18.0, 16.6, 17.6, 24.9, 28.7 and 24.6 ppm, two olefinic carbons at δ 122.9 and 144.3 ppm, three oxygenated methine carbons at δ 66.6, 95.7 and 81.0 ppm, and three anomeric carbons at δ 106.0, 105.9 and 95.9. Based on the above data, it was deduced that 1 was an olean-12-ene type triterpenoid glycoside with three units of glucose. The comparison of 1 H-and 13 C-NMR spectrum data of aglycone part of 1 with that of arjunic acid 12) indicated that compound 1 possessed a 2α,3β,19α-trihydroxyolean-12-ene-28-oic acidic aglycone. The chemical shifts of C-3 (δ 95.7) and C-28 (δ 177.2) 13) implied that 1 was a 3,28-bisdesmosidic glycoside. This hypothesis was also in agreement with the relatively downfield shifts of anomeric protons (δ 4.91, 6.38 ppm) and the corresponding upfield shifts of anomeric carbons (δ 106.0, 95.9 ppm). In the heteronuclear multiple bond connectivity (HMBC) spectrum, significant correlations between signals at δ 4.91(H-1′) and δ 95.7 (C-3), δ 5.29 (H-1″) and δ 88.9 (C-3′), and δ 6.37 (H-1⁗) and δ 177.2 (C-28) were observed. The β-anomeric configurations of glucose units were determined by the relatively large 3 J H1, H2 coupling constants (7.5-8.0 Hz). Considering above information compound 1 was e...

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Triterpenoid saponins with antifeedant activities from stem bark of Catunaregam spinosa (Rubiaceae) against Plutella xylostella (Plutellidae)

Cited by 23 publications

References 15 publications

Secondary Metabolites from Rubiaceae Species

Secondary Metabolites from Rubiaceae Species

Woody species from the Mozambican Miombo woodlands: A review on their ethnomedicinal uses and pharmacological potential

Catunarosides I–L, Four New Triterpenoid Saponins from the Stem Bark of <i>Catunaregam spinosa</i>

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