Khayanolides, rearranged phragmalin limonoid antifeedants from Khaya senegalensis

Abdelgaleil, Samir A. M.; Okamura, Hiroaki; Iwagawa, Tetsuo; Sato, Atsuko; Miyahara, Ikuko; Doe, Matsumi; Nakatani, Munehiro

doi:10.1016/s0040-4020(00)00994-7

Cited by 90 publications

(91 citation statements)

References 14 publications

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“…A literature survey revealed that iridoids, naphthoquinones, monoterpenoidnaphthoquinones, isocoumarins, lignans, sterols, and flavonoids have been identified from the genus Kigelia [12]. Herein we report the isolation and structural elucidation of two new limonoids, namely 1-O-deacetyl-2α-methoxykhayanolide (1) and kigelianolide (2), together with deacetylkhayanolide E (3) [13], 1-O-deacetyl-2α-hydroxykhayanolide E (4) [14], and khayanolide B (5) [15] ethyl acetate-soluble fraction of Kigelia africana (Fig. 1).…”

Section: Introductionmentioning

confidence: 94%

Isolation and Characterization of Limonoids from Kigelia africana

Jabeen

Riaz

2013

Zeitschrift Für Naturforschung B

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Two new limonoids, 1-O-deacetyl-2α-methoxykhayanolide (1) and kigelianolide (2), together with deacetylkhayanolide E (3), 1-O-deacetyl-2α-hydroxykhayanolide E (4) and khayanolide B (5) were isolated from the ethyl acetate-soluble fraction of the methanolic extract of Kigelia africana. The structures of these limonoids (1-5) were elucidated by the combination of 1D ( 1 H and 13 C NMR) and 2D (HMQC, HMBC and COSY) NMR spectroscopy and mass spectrometry (EIMS, HREIMS), and in comparison with literature data of related compounds. The structure of compound 1 was further confirmed by X-ray crystallography, and the absolute stereochemistry of compounds 1 and 2 was determined by electronic circular dichroism (ECD) spectroscopy. Limonoids 1-5 showed weak inhibitory activities against the enzymes acetylcholinesterase (AChE), butyrycholinesterase (BChE) and lipoxygenase (LOX) in a concentration-dependent manner with IC 50 values in the ranges 137.5 -225.2 µ M for AChE, 185.4 -241.5 µ M for BChE and 281.2 -189.6 µ M for LOX.

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Section: Introductionmentioning

confidence: 94%

Isolation and Characterization of Limonoids from Kigelia africana

Jabeen

Riaz

2013

Zeitschrift Für Naturforschung B

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“…The bark also contains substantial levels of khayanolides (Figure 1b) 20,21 and senagalene triterpenoids ( Figure 1d) 20 Angolensates have also been reported in the fruit. 8 Furthermore, the dimeric proanthocyanidins proanthocyanidin B3 (Figure 1e) and fisetinidol-(4α, 6)-catechin ( Figure 1f) were detected in K. senegalensis extracts [Kayser and Abreu, 2001], although that report does not state which part of the plant was investigated. Several similar compounds of these classes have been reported to have antimicrobial and anticancer therapeutic bioactivities.…”

Section: An Examination Of the Antimicrobial And Anticancer Propertiementioning

confidence: 94%

“…Bark extracts have been reported to have good anticancer 6,13,14 and anti-inflammatory properties 6 are good immunostimulants 11 and are insect deterrents. 8 K. senegalensis bark extracts have potential in the treatment of diabetes and have been reported to have anti-hyperglycemic activity comparable to glibenclamide. 12 Furthermore, K. senegalensis stem bark extracts have been shown to have high antioxidant content, 6 further indicating the therapeutic potential of this species.…”

Section: An Examination Of the Antimicrobial And Anticancer Propertiementioning

confidence: 99%

An examination of the Antimicrobial and Anticancer Properties of Khaya senegalensis (Desr.) A. Juss. Bark Extracts

Rabadeaux¹,

Vallette²,

Sirdaarta³

et al. 2017

Phcog J

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Background: Khaya senegalensis (Desr.) A. Juss. is a common component of the pharmacopeia's of multiple African groupings which inhabit the areas in which it grows. Amongst these groups there is a myriad of medicinal uses in the treatment of a wide variety of bacterial, fungal and protozoal infections, as well as in the treatment of cancers. This study was undertaken to test K. senegalensis bark extracts for the ability to inhibit microbial and cancer cell growth, and thus to validate traditional African medicinal usage of this plant in treating a variety of diseases. Materials and Methods: K. senegalensis bark powder was extracted by both solvent maceration and subcritical fluid extraction (SFE). The extracts were tested for the ability to inhibit bacterial and G. duodenalis growth. Inhibition of Caco-2 and HeLa cancer cells was evaluated using MTS-based colorimetric cell proliferation assays. Toxicity was evaluated using an Artemia franciscana nauplii bioassay and GC-MS headspace analysis was used to identify phytochemical components. Results: K. senegalensis bark extracts displayed strong inhibitory activity against bacterial triggers of several autoimmune inflammatory diseases. The growth inhibitory activity of the methanolic and subcritical extracts was particularly noteworthy against P. mirabilis (MIC values of 185 and 211µg/mL, respectively against the reference strains). These extracts were similarly potent growth inhibitors of K. pneumoniae and A. baylyi, and were moderate inhibitors (MIC >1000µg/mL) of P. aeruginosa and S. pyogenes growth. The methanolic and subcritical K. senegalensis extracts were also potent inhibitors of G. duodenalis (187 and 328µg/mL, respectively), as well as Caco-2 (268 and 470µg/mL, respectively) and HeLa carcinomas (155 and 174µg/mL, respectively). GC-MS analysis of the SFE extract revealed relative abundances of a variety of mono-and sesquiterpenoids. Furthermore, all K. senegalensis bark extracts were non-toxic in the Artemia franciscana toxicity assay, indicating their safety for therapeutic use. Conclusion: These studies validate traditional African therapeutic usage of K. senegalensis in the treatment of microbial infections, autoimmune inflammatory diseases and some cancers.

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“…They are classified by the type of foursusually highly oxidizedsrings (designated as A, B, C, and D) in the intact triterpene. Phragmalins, such as pseudrelones A 1 and A 2 1 isolated from Pseudocedrela kotschyii and khayanolides A-C 2 from Khaya senegalensis, have characteristic tricyclo[3.3.1 2,10 .1 1,4 ]decane or tricyclo[4.2.1 10,30 .1 1,4 ]decane ring systems. The family Meliaceae has proved to produce a variety of antifeedant limonoids, such as azadirachtin 3 from the neem tree, Azadiracha indica, and harrisonin 4 from Harrisonnia abyssinica.…”

mentioning

confidence: 99%

“…In the current paper, we present the isolation and characterization of five additional phragmalins (1)(2)(3)(4)(5), each with a C-30 carbonyl group, and a unique ring-D-opened 16-norphragmalin (6), from seeds of the same Indian mangrove, X. moluccensis (Lam.) M Roem.…”

mentioning

confidence: 99%

Limonoids and Tirucallane Derivatives from the Seeds of a Krishna Mangrove, Xylocarpus moluccensis

Yang

et al. 2010

J. Nat. Prod.

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Six new phragmalins, moluccensins H-M (1-6), two new andirobin-type limonoids, moluccensins N and O (7, 8), and two new tirucallane derivatives, moluccensins P and Q (9, 10), were isolated from seeds of an Indian mangrove, Xylocarpus moluccensis, together with the known compound 3 ,22S-dihydroxytirucalla-7,24-dien-23-one. The structures of these compounds were established on the basis of spectroscopic data. Moluccensins H-L were phragmalins with a C-30 carbonyl group, and moluccensin M was a unique ring-D-opened 16-norphragmalin. Moluccensins H-J possess conjugated ∆ 8,9 and ∆ 14,15 double bonds, moluccensins K and L contain a ∆ 8,14 double bond, and moluccensin M has a characteristic C 15 -C 30 linked five-membered lactone ring. Moluccensins H and I showed moderate insecticidal activity against the fifth instar larvae of Brontispa longissima (Gestro) at a concentration of 100 mg/L. ]decane ring systems. The family Meliaceae has proved to produce a variety of antifeedant limonoids, such as azadirachtin 3 from the neem tree, Azadiracha indica, and harrisonin 4 from Harrisonnia abyssinica. Two meliaceous mangroves, Xylocarpus granatum and X. moluccensis, are known for producing antifeedant limonoids, especially phragmalins and mexicanolides. Previous investigations on seeds of these two species yielded an andirobin, two phragmalins, three gedunins, and 14 mexicanolides, including xyloccensins A-K. 5-9Previously we have reported the isolation and identification of eight unique 8,9,30-phragmalin ortho esters and 13 limonoids with a new carbon skeleton from the bark and seeds of a Chinese mangrove, X. granatum. [10][11][12] To date, 42 mexicanolides and 23 phragmalins, including three 1,8,9-phragmalin ortho esters, eight 8,9,30-phragmalin ortho esters, and 12 polyhydroxylated phragmalins, have been isolated from the wood, seeds, and fruits of X. granatum and X. moluccensis. 13 We recently identified seven phragmalins, moluccensins A-G, 14 from seeds of an Indian mangrove, X. moluccensis, collected in the mangrove wetlands of Krishna estuary, AndhraPradesh. In the current paper, we present the isolation and characterization of five additional phragmalins (1-5), each with a C-30 carbonyl group, and a unique ring-D-opened 16-norphragmalin (6), from seeds of the same Indian mangrove, X. moluccensis (Lam.) M Roem. (Meliaceae), together with two new andirobin-type limonoids (7, 8), two new tirucallane derivatives (9, 10), and the known compound 3 , 22S-dihydroxytirucalla-7,24-dien-23-one. 15 The structures of these compounds were established on the basis of spectroscopic data or comparison with data in the literature. The new compounds were tested for insecticidal activity against the fifth instar larvae of Brontispa longissima (Gestro) at a concentration of 100 mg/L. (Tables 1 and 2) indicated that nine of the 15 elements of unsaturation came from a conjugated ketone group, four carbon-carbon double bonds, and four ester functionalities. Therefore, the molecule Results and Discussion

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Khayanolides, rearranged phragmalin limonoid antifeedants from Khaya senegalensis

Cited by 90 publications

References 14 publications

Isolation and Characterization of Limonoids from Kigelia africana

Isolation and Characterization of Limonoids from Kigelia africana

An examination of the Antimicrobial and Anticancer Properties of Khaya senegalensis (Desr.) A. Juss. Bark Extracts

Limonoids and Tirucallane Derivatives from the Seeds of a Krishna Mangrove, Xylocarpus moluccensis

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