Trichiliton A, a Novel Limonoid from <i>Trichilia connaroides</i>

Fang, Xin; Di, Ying‐Tong; Geng, Zhiqing; Tan, Carol; Guo, Jie; Ning, Jing; Hao, Xiao‐Jiang

doi:10.1002/ejoc.200901245

Cited by 29 publications

(19 citation statements)

References 37 publications

(9 reference statements)

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“…The phragmalin class limonoids reported by Najmuldeen et al . have a β ‐orientation for the 19‐methyl which might have arisen from the configurational ambiguity at C(10) . An α ‐orientation has been adopted for 19‐methyl in this review to comply with the conventional way.…”

Section: Chemistrymentioning

confidence: 99%

“… from CD spectral analysis which indicated it as a (3 R ,4 R ,5 S ,9 S ,10 R ,13 R ,17 R ) isomer while for chisomicine B ( 24 ), crystal structure was reported. Trichiliton A, a limonoid from the leaves of T. connaroides (Meliaceae) is the only other natural product reported so far with the same structural feature and differs from chisomicine A ( 53 ) by the presence of an O ‐acetyl group at C(3) instead of an O ‐2‐methylbut‐2‐enoyl moiety . In a previous report, a CD spectrum was used by Bordoloi et al .…”

Section: Chemistrymentioning

confidence: 99%

“…Plausible biogenetic pathway for the formation of mexicanolide, phragmalin, and mexicanolide‐derived A , B ‐ seco limonoids in Chisocheton .…”

Section: Chemistrymentioning

confidence: 99%

“…Phytochemical investigation of C. ceramicus bark afforded various classes of limonoids including highly modified structures of phragmalins and mexicanolides. Based on the published biogenetic pathways toward the formation of various limonoids, a plausible biogenetic pathway (Scheme 1) is proposed in this review toward the formation of mexicanolides and phragmalins of C. ceramicus from ring D-seco-limonoid gedunin (51) [37][38] [54]. The phragmalin class limonoids reported by Najmuldeen et al [49][55] have a b-orientation for the 19-methyl which might have arisen from the configurational ambiguity at C(10) [37].…”

Section: Limonoidsmentioning

confidence: 99%

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Advances in Chemistry and Bioactivity of the Genus Chisocheton Blume

Shilpi

Saha

Chong

et al. 2016

Chemistry & Biodiversity

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Chisocheton is one of the genera of the family Meliaceae and consists of ca. 53 species; the distribution of most of those are confined to the Indo-Malay region. Species of broader geographic distribution have undergone extensive phytochemical investigations. Previous phytochemical investigations of this genus resulted in the isolation of mainly limonoids, apotirucallane, tirucallane, and dammarane triterpenes. Reported bioactivities of the isolated compounds include cytotoxic, anti-inflammatory, antifungal, antimalarial, antimycobacterial, antifeedant, and lipid droplet inhibitory activities. Aside from chemistry and biological activities, this review also deals briefly with botany, distribution, and uses of various species of this genus.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

“…Plausible biogenetic pathway for the formation of mexicanolide, phragmalin, and mexicanolide‐derived A , B ‐ seco limonoids in Chisocheton .…”

Section: Chemistrymentioning

confidence: 99%

Section: Limonoidsmentioning

confidence: 99%

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Advances in Chemistry and Bioactivity of the Genus Chisocheton Blume

Shilpi

Saha

Chong

et al. 2016

Chemistry & Biodiversity

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“…3 Previous investigation on the chemical constituents of the genus Heynea has yielded a series of new limonoids, including trijugin-type, 30-nortrijugin-type, phragmalin-type, and mexicanolide-type. [4][5][6][7][8][9][10][11][12] In our continuing effort to search for novel limonoids from Meliaceae family, five new mexicanolide-type limonoids (1)(2)(3)(4)(5) were isolated from the branches and leaves of H. trijuga collected from Hainan province of China. Herein we describe the isolation, structural elucidation and bioactivity assays of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Five new mexicanolide type limonoids from Heynea trijuga

Yang

Kong

et al. 2012

Nat. Prod. Bioprospect.

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Senegalensions A–C, Three Limonoids from Khaya senegalensis

Yuan¹,

Li²,

Di³

et al. 2012

Chemistry An Asian Journal

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Limonoids, possessing highly complicated structures and broad range of bioactivities, have been becoming a hot topic in the field of natural products and synthetic chemistry. [1] In recent years, many new tetranortriterpenoids with unique skeletons and significant biological activities have been obtained. [2] The genus Khaya (Meliaceae) is distributed extensively in tropical regions of Africa and Madagascar, [3] and their barks were used as a traditional medicine for the treatment of fever and malaria in Africa. [4] Investigations on the genus have led to the isolation of a variety of rings B,D-seco limonoids such as mexicanolides, phragmalins, rearranged phragmalins, and angolensates. [5] Our previous studies on different genera of the Meliaceae family collected from several locations have resulted in a series of new limonoids. [6] In further study, senegalensions A (1; Figure 1) and B (2) with a unique C2-C4 linkage and senegalension C (3), pos-sessing a rare spiro ring system with an unprecedented tricyclo[3.3.1.0 1, 10 ]nonane moiety, were isolated from the leaves and twigs of K. senegalensis. Their structures were elucidated by extensive spectroscopic analysis and computational methods. A plausible biosynthetic pathway of them was also proposed.Senegalension A (1) was shown to have the molecular formula C 27 H 30 O 10 from high-resolution electron-spray ionization mass spectrometry (HR-ESI-MS) [m/z 537.1725 ([M+Na] + )], revealing 13 degrees of unsaturation. The 1 H and 13 C NMR spectroscopy data (Table 1), along with DEPT experiments, showed the presence of 27 carbon signals, including four methyl carbon atoms (one methoxy group), three methylenes, nine methines (four olefinic ones), and 11 quaternary carbons (two olefinic and three carbonyl ones). Apart from seven degrees of unsaturation consumed by a characteristic b-furan ring, three carbonyl groups, and a double bond, the remaining six degrees of unsaturation suggested compound 1 to be hexacyclic.Further analysis of the 13 C NMR and HMBC spectra (Figure 2 a) indicated that 1 was related to khayanolide C, [7] sharing the same A 1 , B, C, D, and E rings. The most striking characteristic of 1 was the formation of a five-membered A 2 ring with a "loose end" of C3 through the ring contraction of a six-membered A 2 ring as those in khayanolide C. [7] The HMBC correlations of a proton signal at d = 6.27 ppm (s, OH) with C2, C3, C4, and C30 indicated a unique linkage of C3, C4, and C30 to C2. Moreover, a five-membered ring (A 2 ) was assigned by HMBC correlations of a proton resonance at d = 5.42 ppm (s, OH) with C1, C29, and C30, along with HMBC correlations of H 3 C28 with C2, C4, and C29. The "loose end" of ester carbonyl C3 and the severely downfield-shifted signal at d = 88.9 ppm (C8), [8] coupled with the remaining one degree of unsaturation, revealed that an unusual 3,8-g-lactone ring (A 3 ) was formed between C3 and C8 through an ester bond. Thus, the above evidence assigned the planar structure of 1.The relative configuration of 1 was deduced by the ...

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Trichiliton A, a Novel Limonoid from Trichilia connaroides

Cited by 29 publications

References 37 publications

Advances in Chemistry and Bioactivity of the Genus Chisocheton Blume

Advances in Chemistry and Bioactivity of the Genus Chisocheton Blume

Five new mexicanolide type limonoids from Heynea trijuga

Senegalensions A–C, Three Limonoids from Khaya senegalensis

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