Chemical investigation of Cedrela toona

doi:10.1016/S0031-9422(00)89902-1

Phytochemistry

Volume 10, Issue 10, October 1971, Pages 2533-2535

https://doi.org/10.1016/S0031-9422(00)89902-1 Get rights and content

Abstract

Two varieties of Cedrela toona Roxb. are available in West Bengal and the seeds of one variety produces cedrelone, 1,2-dihydrocedrelone, bergapten and β-sitosterol. Occurrence of 1,2-dihydrocedrelone, a new tetranortriterpenoid, provides further interesting evidence of the chemotaxonomic feature of Meliaceae.

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Cited by (20)

Chemical constituents of the pericarp of Toona sinensis and their chemotaxonomic significance
2022, Biochemical Systematics and Ecology
Citation Excerpt :
In our study, five sterols (10–14) were obtained from the pericarp of T. sinensis. β-sitosterol (10) is a commonly compound, which is widely distributed in the genus Toona and was reported from the timber, heartwood, stems, leaves, seeds, roots, and tress of T. ciliata (Chatterjee et al., 1971; Banerji and Mitra., 1975; Agostinho et al., 1994; Singh and Plant., 1995; Oiano Neto et al., 1998; Castro-Gamboa et al., 2004; Lu et al., 2009), the stems of T. ciliata var. australis (De Paula et al., 1997, 1998; Da Silva et al., 1999), the barks, roots, and fruits of T. sinensis (Li et al., 2006, 2013; Dong et al., 2013), and the stem barks of T. ciliata var.
Phytochemical investigation of the pericarp of Toona sinensis (A. Juss.) Roem (Meliaceae) led to the isolation and identification of 33 compounds, namely, 7 apotirucallane-type triterpenoids (1–7), 2 cycloartane-type triterpenoids (8–9), 5 sterols (10–14), 2 sesquiterpenes (15–16), 2 lignans (17–18), 3 flavonoids (19–21), and 12 phenols (22–33). The chemical structures of these compounds were elucidated based on spectroscopic data and comparison with previously reported data. This is the first report of compounds 11–12, 16, 18, 23, and 31 from the family Meliaceae, compounds 13–15, 26, and 30 within the genus Toona, and compound 33 from T. sinensis. The chemotaxonomic significance of the isolated compounds is also described in this study.
Leishmanicidal and cytotoxic activity from plants used in Tacana traditional medicine (Bolivia)
2018, Journal of Ethnopharmacology
Citation Excerpt :
The UV spectra of the two main peaks (Rt: 7.9 and 8.5 min) are identical and shows a very small molar extinction coefficient with a characteristic weak UV activity at λmax 262 nm. Triterpenoids from C. odorata (Campos et al., 1991), limonoids with antifeedant activity and triterpenoids from C. odorata (Kipassa et al., 2008), C. salvadorensis (Segura et al., 1994), Cedrela spp. (Céspedes et al., 2000), and C sinensis (Mitsui et al., 2004, 2005, 2006), tetranortriterpenoids, from C. angustifolia (Lavie et al., 1970), C. odorata (Veitch et al., 1999) and C. fissilis (Zelnik and Rosito, 1971), sesquiterpenoids from C. toona (Chatterjee et al., 1971) have been reported. Antiprotozoal activity was reported against L. infantum and Trypanosoma cruzi for C. odorata (González-Coloma et al., 2012), and against L. major for C. serrata (Takahashi et al., 2004).
Thirty-eight Tacana medicinal plant species used to treat skin problems, including leishmania ulcers, skin infections, inflammation and wound healing, were collected in the community of Buena Vista, Bolivia, with the Tacana people. Twenty two species are documented for the first time as medicinal plants for this ethnic group living in the northern area of the Department of La Paz.
To evaluate the leishmanicidal effect (IC₅₀) and cytotoxicity (LD₅₀) of the selected plants. To carry out bioguided studies on the active extracts. To assess the potential of Bolivian plant biodiversity associated with traditional knowledge in the discovery of alternative sources to fight leishmaniasis.
Seventy three ethanol extracts were prepared from 38 species by maceration and were evaluated in vitro against promastigotes of Leishmania amazonensis and L. braziliensis. Active extracts (IC₅₀ ≤ 50 μg/mL) were fractionated by chromatography on Silica gel column and the fractions were assessed against the two Leishmania strains. The most active fractions and the crude extracts were evaluated against reference strains of L. amazonensis, L. braziliensis, L. aethiopica, two native strains (L. Lainsoni and L. braziliensis) and for cytotoxicity against HeLa cells. The chromatographic profile of the active fractions was obtained by reverse phase chromatography using HPLC.
From the 73 extracts, 39 extracts (53.4%) were inactive and 34 showed activity. Thirteen species were sselected for bioguided studies. The crude extracts and their 36 fractions were evaluated against two Leishmania strains. The most active fraction were tested in a panel of five leishmania strains and for cytotoxicity. The Selective Index (SI = LD₅₀/IC₅₀) was calculated, and were generally low. Retention time and UV spectra were recorded for the active fractions by HPLC-DAD using a reverse phase column. Profiles were very different from each other, showing the presence of different compounds.
Bolivian traditional knowledge from the Tacanba was useful to identify plants with effect on Leishmania promastigotes. Chromatographic bioguided studies showed stronger leishmanicidal and cytotoxic activity for the medium polar fraction. HPLC analysis showed different chromatographic profiles of the active fractions.
Diverse tritepenoids from the fruits of Walsura robusta and their reversal of multidrug resistance phenotype in human breast cancer cells
2017, Phytochemistry
Citation Excerpt :
Therefore, the structures of 11–14 were as depicted. In addition, the 21 known compounds were characterized as walsuronoid B (15) (Yin et al., 2007), dysoxylumosins B-D and dysoxylumosin G (16–19) (Zhou et al., 2015), dihydrocedrelone (20) (Chatterjee et al., 1971), 11β-hydroxydihydrocedrelone (21), 11β-acetoxydihydrocedrelone (22), cedrelone (23), 11β-hydroxycedrelone (24) (Luo et al., 2000), 11β, 12α-diacetoxycedrelone (25) (Mulholland et al., 1998), anthothecol (26) (Adesogan et al., 1970), walsunoid H (27) (Wang et al., 2016), isowalsuranolide (28), walsurin (29) (Luo et al., 2000), spicatin (30) (Connolly et al., 1981), 7α-acetoxyl-17α-20S-21,24-epoxy-apotirucall-14-en-3-one-23R,24S,25-triol (31) (Luo et al., 2002), grandifoliolenone (32) (Mitsui et al., 2007), hispidol B (33) (Jolad et al., 1981), botulin (34) (Ragasa et al., 1997), betulinic acid (35) (Yili et al., 2009) by comparing the observed and reported spectroscopic data in the literature. As shown in Table 5, compounds 6, 7, 10, 21, 29 and 34 displayed potent reversal effects on MDR in MCF-7/DOX cells at non-toxic concentrations by possible inhibition of the P-glycoprotein (P-gp) function.
Four 18 (13 → 14)-abeo limonoids, five cedrelone limonoids, and five walsurin limonoids were isolated from the fruits of Walsura robusta together with 21 known compounds. Their structures were determined by extensive studies of their one- and two-dimensional NMR spectra and mass spectroscopy results. Among all the isolated compounds, the absolute configurations of 11-oxo-dihydrocedrelone, walsuronoid B, dysoxylumosin G, and walsunoid H were confirmed by single crystal X-ray diffraction. Selected compounds were evaluated for their reversal of multidrug resistance (MDR) phenotype in human breast cancer cells in vitro. Walsurin A showed significant effect in sensitization of these resistant cancer cells at non-toxic concentration to doxorubicin with the modulation factor of 62.76.
Traditional management of diabetes in Pakistan: Ethnobotanical investigation from Traditional Health Practitioners
2015, Journal of Ethnopharmacology
The uses of anti-diabetic plants are well anchored in the traditional health care system of Pakistan. To the best of our knowledge, this is the first ethno-botanical study about the uses of plants for the treatment of diabetes. The aim of the study is to record indigenous knowledge on anti-diabetic plants from Traditional Health Practitioners (THPs) and diabetic patients. In addition, it is aimed to ascertain and validate the traditional uses of anti-diabetic plants by citing pharmacological activities and phytochemical constitutes from previously published literature.
The ethno-medicinal data was documented during 14 field surveys, each comprising of 10 days, from 3 regions of Pakistan (Islamabad, Khyber Pukhtoonkhwa and Deserts of Sindh). In total, 113 THPs and 44 diabetic patients were interviewed using open-ended and semi-structured questionnaires. Quantitative indices, including Relative Frequency of Citation percentage (RFC %) and Disease Consensus Index (DCI) were calculated. The documented data is authenticated by comparing with 28 published articles on ethno-botanical aspects and many pharmacological studies.
In total, 120 plant species belonging to 50 families were reported. The ethno-botanical results indicated that Moraceae (11 species); herb (56 reports) is dominant life form; the leaves (56 reports) are the most used plant part and decoction (24%) is the preferred mode of preparation. The quantitative analysis shows that RFC% ranges from 14 to 42 and DCI varies from 0.15 to 0.74. By comparing to previous studies, 64 species are reported new in traditional treatment of DM; 40 species are new to pharmacological evidence and 3 species are new to phytochemical studies.
This study recoded the significant indigenous knowledge about anti-diabetic plants among the THPs and diabetic patients in Pakistan. This type of ethno-botanical knowledge on traditional use of anti-diabetic plants is an important step in designing detailed pharmacological and clinical trials for Diabetes Miletus treatment. It is recommended that further pharmacological and phytochemical analysis should be conducted on those species which lack previous references in literature and have highest Frequency of Citation (FC), Disease Consensus Index (DCI) and Relative Frequency of Citation percentage (RFC%).
Limonoids from the leaves of Toona ciliata var. yunnanensis
2012, Phytochemistry
Citation Excerpt :
So far no phytochemical study has been done on this plant. In order to clarify its chemical constituents, our first research on the title plant resulted in isolation of 12 new limonoids, toonayunnanins A–L (1–12) and 11 known compounds, cedrelone (13) (Chatterjee et al., 1971), epoxyazadiradione (14) (Lavie et al., 1971), toonafolin (15) (Kraus and Grimminger, 1981), toonaciliatin E (16) (Liao et al., 2007), toonaciliatin H (17) (Kraus et al., 1982), dysobinin (18) (Singh et al., 1976), 12-deacetoxytoonacilin (19) (Neto et al., 1995), 17-hydroxyazadiradione (20) (Siddiqui et al., 1978), dihydroniloticin (21) (Luo et al., 2000), dehydroodoratol (22) (Neto et al., 1998), and 21-α-methylmelianodiol (23) (Zhou et al., 2007; Xu et al., 2008). In addition, all the isolates were established for their cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 human cell lines.
Twelve limonoids, toonayunnanins A–L (1–12) and eleven known compounds (13–23) were isolated from the leaves of Toona ciliata var. yunnanensis, and their structures were elucidated by means of extensive spectroscopic analyses, particularly 1D and 2D NMR techniques. The inhibitory effects of all the isolated compounds were evaluated on human tumor cell lines, such as HL-60, SMMC-7721, A-549, MCF-7 and SW480. Cedrelone (13) and dysobinin (18) showed significant cytotoxicity, and toonayunnanin B (2) and epoxyazadiradione (14), were found to be slightly cytotoxic against the above cell lines. Furthermore, this study provides valuable information for the chemotaxonomy of T. ciliata varieties.
Chemical constituents of Toona microcarpa (C. DC.) Harms in Engl. (Meliaceae)
2010, Biochemical Systematics and Ecology
Citation Excerpt :
Previous phytochemical investigations on the genus Toona were confined to two species, T. ciliate and T. sinensis. The investigations of T. ciliate have shown that it contains limonoids especially B-seco type (Aghoramurthy et al., 1962; Agostinho et al., 1994; Banerji and Mitra, 1975; Chatterjee et al., 1971; Chen et al., 2009; Hodges et al., 1963; Kraus et al., 1978, 1982; Kraus and Kypke, 1979; Kraus and Grimminger, 1980, 1981; Liao et al., 2007; Mulholland and Taylor, 1992; Neto et al., 1995, 1998), steroids (Chowdhury et al., 2002, 2003), and phenylpropanoids (Bhatia et al., 1969; Chowdhury, 2004; Singh and Plant, 1995). Investigations of T. sinensis have found B, D-seco obacunone-type limonoids (Luo et al., 2000; Mitsui et al., 2004) and D-seco gedunin-type limonoids (Mitsui et al., 2006), triterpenoids (Mitsui et al., 2005, 2007), and flavonoids (Hsieh et al., 2006; Wang et al., 2006), which are quite different from those reported from T. ciliate.

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Short communicationChemical investigation of Cedrela toona

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Tetrahedron Letters

Proc. Chem. Soc.

Proc. Chem. Soc.

J. Chem. Soc.

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Chemical investigation of Cedrela toona