Two Antimicrobial Alkaloids from Heartwood of Liriodendron tulipifera L

Hufford, Charles D.; Funderburk, Mary Jo; Morgan, Jody; Robertson, Larry W.

doi:10.1002/jps.2600640512

Cited by 135 publications

(68 citation statements)

References 18 publications

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“…The assay was carried out according to the method of Hufford et al 15) with some modifications. The media used was Sabouraud Dextrose agar (Difco).…”

Section: Larvicidal Antimycobacterial and Antifungal Compounds From mentioning

confidence: 99%

Larvicidal, Antimycobacterial and Antifungal Compounds from the Bark of the Peruvian Plant Swartzia polyphylla DC

Rojas

Bustamante

Ventosilla

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Perú is a country with a large number of medicinal plants, many of which are used for the treatment of infectious diseases, 1) although only few studies have been conducted to prove their efficacy and safety. 2,3) Due to the emergence of micro-organism resistance to the common antibiotics 4) and its worldwide impact on health, our research aims to identify new natural products that may lead to the discovery of new antibacterial agents with higher efficiency and lower toxicity.As part of our continuing work on bioactive compounds from Peruvian medicinal plants, [5][6][7] the in vitro antimycobacterial activity of 102 ethanol extracts from 84 plants-used traditionally in Perú for the treatment of inflammatory or infectious disorders-was screened using a tetrazolium microplate assay (TEMA).8) In a separate screening, the antifungal and larvicidal activities of over 100 plants, including those previously tested for antimycobacterial activity, were bio-assayed.As a result of these screenings, Swartzia polyphylla DC (Fabaceae) was found to exhibit powerful antimycobacterial action against the sensitive H 37 Rv and multidrug-resistant Mycobacterium tuberculosis. It also inhibited the in vitro growth of the dermatophyte Trichophyton mentagrophytes, and was active against the larvae of the mosquito Culex quinquefasciatus. We are now pleased to report the isolation of the larvicidal, antimycobacterial and antifungal principles present in the crude extract of S. polyphylla.A solvent-partition of the 95% ethanol extract showed that the larvicidal and antimycobacterial activities were concentrated in the hexane fraction, while the 90% methanol fraction was active only in the antifungal assay. The hexane fraction (28 g) was chromatographed on a silica gel column using a hexane-chloroform-methanol gradient. Each fraction (F1-F7) was evaluated for larvicidal and antimycobacterial activity in vitro. The most active fraction (F6, 8.7 g) was purified by column chromatography using a hexanedichloromethane-ethanol gradient and then by MPLC (Lobar Lichroprep silica gel RP-8, 40-63 mm, 310ϫ25 mm, Merck) with acetonitrile-methanol-water (3 : 2 : 2) yielding the most active fraction F-6-4-2 (51.4 mg). This fraction was finally purified by HPLC (Waters Nova-pak H R silica 6 mm, 3.9ϫ300 mm, Waters Model 600E with Waters 2996 PDA detector) using hexane-chloroform gradient (0 to 70%) to obtain T-cadinol (1, 9 mg) (Fig. 1). 9,10) The 90% methanol fraction (25.5 g) was subjected to column chromatography (silica gel, 0.063-0.200 mm) using a hexane-chloroform-methanol gradient. Each fraction (F1-F9) was tested for antifungal activity in vitro. The most active fraction (F3) yielded fraction F3-7-5 (756 mg) after repeated column chromatography using hexane-ethylacetatemethanol as eluent. This fraction was finally purified by MPLC with methanol-water (6 : 4) to afford biochanin A (2, 15 mg) and dihydrobiochanin A (3, 59 mg) (Fig. 1). 11)The bark of S. polyphylla contains various flavonoids and isoflavones, some of them with strong activity against...

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“…The assay was carried out according to the method of Hufford et al 15) with some modifications. The media used was Sabouraud Dextrose agar (Difco).…”

Section: Larvicidal Antimycobacterial and Antifungal Compounds From mentioning

confidence: 99%

Larvicidal, Antimycobacterial and Antifungal Compounds from the Bark of the Peruvian Plant Swartzia polyphylla DC

Rojas

Bustamante

Ventosilla

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The major advantage of this approach over chemical synthesis or modification of existing agents is the probability of identifying new prototype drugs with quite different chemical structures and, hence, dissimilar toxicities and cross-resistances with present drug therapies. Although microorganisms have traditionally served as the primary source for new antibiotics, it has recently been shown that higher plants also serve as sources for a number of diverse antimicrobial agents (2)(3)(4)(5)(6)(7)(8).…”

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3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens

Liu

Oguntimein

Hufford

et al. 1990

Antimicrob Agents Chemother

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Further examination of the active ethanolic extract of the root bark of Cleistopholis patens by using bioassay-directed fractionation resulted in the isolation of a new alkaloid, 3-methoxysampangine (compound I), together with three known alkaloids, eupolauridine (compound II), liriodenine (compound III), and eupolauridine N-oxide (compound IV). The proposed structure of compound I was based on its physicochemical properties and spectral data. 3-Methoxysampangine exhibited significant antifungal activity against Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans. This is the first report of the isolation of liriodenine (compound III) from the root bark of C. patens.

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“…Sesquiterpenes and aporphine alkaloids have been isolated from this plant as bioactive constituents with anticancer, antiplasmodial and antimicrobial activities. [4][5][6][7][8] However, there has been no report related to the antifibrotic activity of this plant. Thus, we have attempted to isolate the antifibrotic constituents from the leaves and twigs of L. tulipifera through bioactivity-guided fractionation.…”

Section: )mentioning

confidence: 99%

Antifibrotic Compounds from <i>Liriodendron tulipifera</i> Attenuating HSC-T6 Proliferation and TNF-α Production in RAW264.7 Cells

Jeong

Kim

Heo

et al. 2015

Biological & Pharmaceutical Bulletin

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Two Antimicrobial Alkaloids from Heartwood of Liriodendron tulipifera L

Cited by 135 publications

References 18 publications

Larvicidal, Antimycobacterial and Antifungal Compounds from the Bark of the Peruvian Plant Swartzia polyphylla DC

Larvicidal, Antimycobacterial and Antifungal Compounds from the Bark of the Peruvian Plant Swartzia polyphylla DC

3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens

Antifibrotic Compounds from <i>Liriodendron tulipifera</i> Attenuating HSC-T6 Proliferation and TNF-α Production in RAW264.7 Cells

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