Phragmalin-type limonoids from the roots of Trichilia sinensis

Liu, Shou-Bai; Chen, Huiqin; Guo, Zhi‐Kai; Dong, Wei; Wang, Jun; Mei, Wen‐Li; Dai, Hao‐Fu

doi:10.1039/c7ra01785e

“…The absolute configuration of Turrapubin H (421) was assigned by comparing the CD spectrum of previously isolated Turrapubesin D 225 . The hydroxyl group at γ-lactone ring in compound ( 421) is absent in Toonaciliatavarin H (422). The structure of Tooniliatone A (423) was confirmed by Cu Kα X-ray crystallographic analysis.…”

Section: Vilasininmentioning

confidence: 89%

“…Compounds (1105, 1106) were tested for their inhibitory activities towards several enzymes, such as hPTP1B (human protein tyrosine phosphatase 1B), CDC25B dual specificity phosphatase and pancreatic lipase, but they showed no inhibition 404 . Compound (114) exhibited in vitro inhibitory activity against PTP1B with IC 50 value of 3.93 µg/mL compared to positive control oleanolic acid with IC 50 value of 1.05 µg/mL 114 422 . Protein tyrosine phosphatase 1B (PTP1B) which has significant role in cell regulation, growth, and the onset of human diseases was inhibited in vitro by compound (1395) with IC 50 value of 16.7 µM compared to positive control oleanolic acid with IC 50 value of 2.3 µM, while compounds (1396, 1397, 1398) were inactive 455 .…”

Section: Antineoplastic Activitymentioning

confidence: 99%

Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

¹

,

Nandikol

²

,

Thulasiram

³

2022

Preprint

0

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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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“…Evaluation of the inhibitory effects on acetylcholinesterase was performed by the spectrophotometric method developed by Ellman with slight modifications as reported [ 40 ], and on c-Met and PTP1B by using the enzyme-linked immunosorbent assay (ELISA) methodology [ 41 ].…”

Section: Methodsmentioning

confidence: 99%

Terpenoids from the Soft Coral Sinularia sp. Collected in Yongxing Island

Qin

¹

,

Tang

²

,

Sun

³

et al. 2018

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Three new sesquiterpenoids (sinuketal (1), sinulins A and B (2 and 3)) and two new cembranoids (sinulins C and D (4 and 5)), as well as eight known sesquiterpenoids (6–13) and eight known cembranoids (14–21), were isolated from the Xisha soft coral Sinularia sp. Their structures were elucidated by extensive spectroscopic analysis. Compound 1 possesses an unprecedented isopropyl-branched bicyclo [6.3.0] undecane carbon skeleton with unique endoperoxide moiety, and a plausible biosynthetic pathway of it was postulated. According to the reported biological properties of endoperoxide, the antimalarial, cytotoxic, antiviral, and target inhibitory activities of 1 were tested. Compound 1 showed mild in vitro antimalarial activity against Plasmodium falciparum 3D7, weak cytotoxic activities toward Jurkat, MDA-MB-231, and U2OS cell lines, inhibitory effects against influenza A viruses H1N1 and PR8, as well as mild target inhibitory activity against acetylcholinesterase. The other compounds were evaluated for cytotoxicities against HeLa, HCT-116, and A549 tumor cell lines and target inhibitory activities against protein tyrosine phosphatase 1B (PTP1B). Compound 20 exhibited cytotoxicities against HeLa and HCT-116, and compounds 5, 11, and 15 showed mild target inhibitory activities against PTP1B.

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“…Compound (114) exhibited in vitro inhibitory activity against PTP1B with IC 50 value of 3.93 µg/mL compared to positive control oleanolic acid with IC 50 value of 1.05 µg/mL 114 . At 50 mg/mL, compounds (1209, 1210, 1211, 1212, 1213, 1214, 1215, 1216, 1273, 1274, 1275, 1276) showed in vitro acetylcholinesterase inhibitory activity with inhibition rate of <10, 24.4, 19.7, <10, <10, 17.2, 19.4, 16.9, <10, 10.6, 34.9 and 19.5 % respectively 422 . Protein tyrosine phosphatase 1B (PTP1B) which has significant role in cell regulation, growth, and the onset of human diseases was inhibited in vitro by compound (1395) with IC 50 value of 16.7 µM compared to positive control oleanolic acid with IC 50 value of 2.3 µM, while compounds (1396, 1397, 1398) were inactive 455 .…”

Section: Antineoplastic Activitymentioning

confidence: 99%

Chemistry and Biology of Novel Meliaceae Limonoids

Mulani

¹

,

Nandikol

²

,

Thulasiram

³

2022

Preprint

View full text Add to dashboard Cite

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.

show abstract

Phragmalin-type limonoids from the roots of Trichilia sinensis

Abstract: Twelve new limonoids were isolated from Trichilia sinensis. Some compounds exhibited cytotoxicity and acetylcholinesterase-inhibiting activity.

Cited by 14 publications

References 28 publications

Chemistry and Biology of Novel Meliaceae Limonoids

Chemistry and Biology of Novel Meliaceae Limonoids

Terpenoids from the Soft Coral Sinularia sp. Collected in Yongxing Island

Chemistry and Biology of Novel Meliaceae Limonoids

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