Triterpenoids and Sterones from the Stem Bark of Ailanthus altissima

Zhou, Xianmin; Xu, Min; Li, Xuesong; Wang, Yue‐Hu; Ye, Gao; Cai, Rui; Cheng, Yong‐Xian

doi:10.5012/bkcs.2011.32.1.127

Cited by 19 publications

(6 citation statements)

References 22 publications

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“…Compound (67) is trinor protolimonoid differing at side chain in additional methylene group in comparison with previously reported (4,4,14-trimethyl-3-oxo-24-nor-5α,13α,14β,17α,20S-chol-7-en-23-oic acid) 83 . The shift in double bond at ∆ 6,7 to ∆ 7,8 with peroxide bridge formation between C5-C8 and additional olefinic bond at ∆ 9,11 in Compound (68) are the structural differences when compared to previously reported (4,4,14-trimethyl-3oxo-24-nor-5α,13α,14β,17α,20S-chol-7-en-23-oic acid) 83 . Dysolenticin C (69) is the trinor analog of compound (48).…”

Section: Nor Protolimonoidsupporting

confidence: 79%

“…Toosendine I (82), Chisopanin F (84), Chisopanin H (86) and Xylogranatumine A (106) are C21 epimer of compounds (81), (83), (85) and Protoxylogranatin A reported previously 88 respectively. Chisopanin E (83) is C3 acetyl, C7 deacetyl analog of compound (80). Chisopanin I (87) is a C25 methoxy analog of compound (85).…”

Section: Apoprotolimonoid/apotirucallanetriterpenoidmentioning

confidence: 90%

“…Toosendine H (81) and Chisopanin G (85) are C21 ethoxy C25 hydroxy analaogs of compounds (79) and (83) respectively. Toosendine I (82), Chisopanin F (84), Chisopanin H (86) and Xylogranatumine A (106) are C21 epimer of compounds (81), (83), (85) and Protoxylogranatin A reported previously 88 respectively. Chisopanin E (83) is C3 acetyl, C7 deacetyl analog of compound (80).…”

Section: Apoprotolimonoid/apotirucallanetriterpenoidmentioning

confidence: 99%

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Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

Nandikol

Thulasiram

2022

Preprint

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Nature has bestowed us with abundant bioactive/drug molecules for various uses in our everyday life. One such group of plant specialized molecules is limonoids, which are structurally characterized as 4,4,8-trimethyl-17-furanyl steroidal skeleton. Limonoids are well known for their various biological activities such as potent anti-feedent, anti-cancer, anti-inflammatory, insecticidal, anti-diabetic, anti-viral, anti-microbial etc. These tetranortriterpenes are highly oxygenated and structurally diversified molecules majorly found in Meliaceae and Rutaceae and less frequently in the Cneoraceae families in the plant kingdom. Many of these plants have been used in traditional medicine from ages. One of the well-known limonoid, azadirachtin A is highly valued and widely popular for its outstanding insecticidal properties. Till date, nearly 2500 limonoids with over 35 unique carbon frameworks have been observed. In recent times, these molecules have dig a great interest among researchers due to their myriad biological properties. With the advancement of analytical techniques, the limonoid research is aced to explore more different molecules from their sources. In our review we cover all the Meliaceous limonoids isolated during July 2010 to Dec 2020. We found over 1502 new limonoids, which are reported from various Meliaceae plants after Jun 2010. We have classified them based on their skeletal structure rearrangements and functional groups into various classes such as protolimonoids, Apoprotolionoid, Azadirone, Vilasinin, Cedrelone, Havanensin, Trichilin, Nimbin, Salannin, Azadirachtin, Nimbolidin, Nimbolinin, Obacunol, Evodulone, Trijugin, Cipadesin, Andirobin, Mexicanolide, Phragmalin, Khayanolide, Preieurianin, Aphanamixoid, Nor Limonoid and N-containing derivatives. Further we have discussed their biological activities in detail.

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Section: Nor Protolimonoidsupporting

confidence: 79%

Section: Apoprotolimonoid/apotirucallanetriterpenoidmentioning

confidence: 90%

Section: Apoprotolimonoid/apotirucallanetriterpenoidmentioning

confidence: 99%

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Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

Nandikol

Thulasiram

2022

Preprint

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“…[ 9‐10 ] Phytochemical investigations of the species have afforded numerous compounds with various structural patterns, and quassinoids are considered as chemotaxonomic indicators and principal active constituents of the A. altissima . [ 11‐13 ]…”

Section: Background and Originality Contentmentioning

confidence: 99%

Quassinoids from the Root Barks of Ailanthus altissima: Isolation, Configurational Assignment, and Cytotoxic Activities

Bai

et al. 2021

Chin. J. Chem.

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Ailanthus altissima | Simaroubaceae | Quassinoids | Cytotoxicity | Apoptosis Quassinoids, a class of highly oxygenated triterpenes, have been isolated as bitter principles from the plants of Simaroubaceae family. Five new quassinoids, chouchunlactone A-E (1-5), and two known ones were identified from the root barks of Ailanthus altissima Swingle (Simaroubaceae). The chemical structures of the new compounds were deduced by spectroscopic data analyses, NMR calculations and DP4+ probability analysis. The absolute configurations were defined by comparison of their experimental and calculated electronic circular dichroism (ECD) spectra data, and compounds 1-2 were further confirmed by single-crystal X-ray diffraction. Biologically, compound 5 showed potencies equivalent to sorafenib (IC 50 value, 9.70 μmol•L-1) against HepG2 cells. The Hoechst 33342 staining, JC-1 fluorescent dye and Annexin V/PI analysis studies demonstrated that 5 can induce apoptosis and attenuate mitochondrial membrane potential (MMP) in HepG2 cells.

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“…The stem and root bark have been used as traditional Chinese medicines for the treatment of colds, bleeding, and gastric diseases [ 3 , 4 ]. Phytochemical studies, especially on the stem and root bark of A. altissima , have led to the characterization of quassinoids [ 5 , 6 ], alkaloids [ 7 , 8 ], triterpenoids [ 9 , 10 ], coumarins [ 9 ], lignans [ 11 ], as well as sterols, lipids, and other phenolic derivatives [ 12 ]. However, little is known concerning the constituents of the fruit of A. altissima , which was also used as traditional Chinese medicine for bleeding and antibacterial.…”

Section: Introductionmentioning

confidence: 99%

Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus altissima

Shi

Tan

et al. 2017

Molecules

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Four novel compounds—two phenylpropionamides, one piperidine, and one phenolic derivatives—were isolated and identified from the fruit of a medicinal plant, Ailanthus altissima (Mill.) Swingle (Simaroubaceae), together with one known phenylpropionamide, 13 known phenols, and 10 flavonoids. The structures of the new compounds were elucidated as 2-hydroxy-N-[(2-O-β-d-glucopyranosyl)phenyl]propionamide (1), 2-hydroxy-N-[(2-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl)phenyl]propionamide (2), 2β-carboxyl-piperidine-4β-acetic acid methyl ester (4), and 4-hydroxyphenyl-1-O-[6-(hydrogen-3-hydroxy-3-methylpentanedioate)]-β-d-glucopyranoside (5) based on spectroscopic analysis. All the isolated compounds were evaluated for their inhibitory activity against Tobacco mosaic virus (TMV) using the leaf-disc method. Among the compounds isolated, arbutin (6), β-d-glucopyranosyl-(1→6)-arbutin (7), 4-methoxyphenylacetic acid (10), and corilagin (18) showed moderate inhibition against TMV with IC50 values of 0.49, 0.51, 0.27, and 0.45 mM, respectively.

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Triterpenoids and Sterones from the Stem Bark of Ailanthus altissima

Cited by 19 publications

References 22 publications

Chemistry and Biology of Novel Meliaceae Limonoids

Chemistry and Biology of Novel Meliaceae Limonoids

Quassinoids from the Root Barks of Ailanthus altissima: Isolation, Configurational Assignment, and Cytotoxic Activities

Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus altissima

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