Allelopathic Prenylflavanones from the Fallen Leaves of Macaranga tanarius

Tseng, Mei-Huims; Chou, Chang‐Hung; Chen, Yih-Ming; Kuo, Yueh‐Hsiung

doi:10.1021/np0100338

Cited by 43 publications

(31 citation statements)

References 11 publications

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“…Cyclization of chalcone 13 by treatment with NaOAc in EtOH gave the final compounds 2 and 14 in a ratio of 2:1 in 80% yield. The spectroscopic data of synthetic product was agreement with those of the natural products [9].…”

Section: Resultssupporting

confidence: 78%

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First total synthesis of (±)-malaysianone A and (±)-tanariflavanones B

Yang

Chen

Xie

et al. 2013

Chinese Chemical Letters

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Section: Resultssupporting

confidence: 78%

“…M. triloba are widely distributed in tropical and subtropical regions and used as folk medicines [8]. Tanariflavanones B was isolated from the fallen leaves of Macaranga tanarius and showed inhibition of radicle growth of lettuce seedlings at 200 ppm [9]. As far as we know, the total synthesis of 1 and 2 has not been reported.…”

Section: Introductionmentioning

confidence: 99%

First total synthesis of (±)-malaysianone A and (±)-tanariflavanones B

Yang

Chen

Xie

et al. 2013

Chinese Chemical Letters

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“…This extract was found to be active in the A2780 ovarian cancer cytotoxicity assay, with an IC 50 value of 3.5 µg/mL. Bioassay-guided fractionation led to the isolation of the five new compounds; the four new prenylated stilbenes schweinfurthins E-H (1-4), and the new geranylated dihydroflavonol, alnifoliol (5). Five known compounds were also isolated: the prenylated stilbene, vedelianin (6), the two geranylated dihydroflavonols, bonanniol A (7) and diplacol (8), and the two geranylated flavanones, bonannione A (9) and diplacone (or nymphaeol A) (10).…”

Section: Resultsmentioning

confidence: 99%

“…Its 1 H NMR spectrum indicated the presence of an asymmetrical stilbene core (δ 6.87 ppm, 1H, d, J = 16 Hz, H-1′; δ 6.77 ppm, 1H, d, J = 16. 5 Hz, H-2′) with both an AA′ benzene ring system (δ 6.46 ppm, 2H, s, H-4′ and -8′) and an AB benzene ring system (δ 6.91 ppm, 1H, d, H-6; δ 6.84 ppm, 1H, d, H-8). Proton signals at δ 5.23 (1H, tq, J = 7, 1.5 Hz, H-2″), 3.27 (H-1″, partially obscured by solvent), 1.76 (3H, s, H-4″), and 1.65 ppm (3H, s, H-5″) indicated the presence of an isoprenyl group.…”

Section: Resultsmentioning

confidence: 99%

Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest^,1

et al. 2007

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Bioassay-guided fractionation of an extract of the fruit of Macaranga alnifolia from Madagascar led to the isolation of four new prenylated stilbenes, schweinfurthins E-H (1-4), and one new geranylated dihydroflavonol, alnifoliol (5). The known prenylated stilbene, vedelianin (6), and the known geranylated flavonoids, bonanniol A (7), diplacol (8), bonannione A (9) and diplacone (10), were also isolated. All ten compounds were tested for antiproliferative activity in the A2780 human ovarian cancer cell line assay. Vedelianin (IC 50 = 0.13 µM) exhibited the greatest activity among all isolates, while schweinfurthin E (IC 50 = 0.26 µM) was the most potent of the new compounds.The genus Macaranga is a large genus of the Euphorbiaceae family. Observation of Macaranga plants in their natural environment has revealed that they produce thread-like wax crystals on their ste ms, which make the slippery surfaces impassable for all insects except a species of ants known as "wax runners". Chemical analysis has indicated that terpenoids make up a majority of the wax bloom content that helps maintain this symbiotic relationship between plant and insect. 2 One of the more commonly studied species of this genus is M. tanarius, noted for its diterpenoid 3,4 and flavonoid 5-7 content. Work has also been performed on the isolation and characterization of terpenes from M. carolinensis ,8 flavonoids from M. conifera 9 and M. denticulate ,10 chromenoflavones from M. indica , 11 clerodane diterpenes from M. monandra , 12 bergenin derivatives and polyphenols from M. peltata , 13 , 14 prenylflavones from M. pleiostemona , 15 a geranyl flavanone from M. schweinfurthii ,16 tannins from M. sinensis ,17 a rotenoid and other compounds from M. triloba , 18 and a geranylflavonol from M. vedeliana. 19 No phytochemical studies have been previously reported for M. alnifolia.

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“…Thus, it is possible that Yakushijin et al (1980) There are several reports that the leaves of M. tanarius contain prenylflavonoids. Tseng et al (2001Tseng et al ( , 2003, Phommart et al (2005), and Guhling et al (2005) isolated the prenylflavonoids nymphaeols-A (3), -B (1), and -C (5) from the leaves of M. tanarius. M. tanarius is known as a pioneer tree and also as an ant plant.…”

Section: Discussionmentioning

confidence: 99%

Plant origin of Okinawan propolis: honeybee behavior observation and phytochemical analysis

Kumazawa

Nakamura

Murase

et al. 2008

Naturwissenschaften

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Propolis is a natural resinous product collected by honeybees from certain plants. It has gained popularity as a food and alternative medicine. Poplar and Baccharis are well known as the source plants of European and Brazilian propolis, respectively. However, the propolis from Okinawa, Japan, contains some prenylflavonoids not seen in other regions such as Europe and Brazil, suggesting that the plant origin of Okinawan propolis is a particular plant that grows in Okinawa. To identify the plant origin of Okinawan propolis, we observed the behavior of honeybees as they collected material from plants and caulked it inside the hive. Honeybees scraped resinous material from the surface of plant fruits of Macaranga tanarius and brought it back to their hive to use it as propolis. We collected samples of the plant and propolis, and compared their constituents by high-performance liquid chromatography with a photo-diode array detector. We also compared their 1,1-diphenyl-2-picryl-hydrazyl radical scavenging activity. The chemical constituents and biological activity of the ethanol extracts of the plant did not differ from those of propolis. This indicates directly that the plant origin of Okinawan propolis is M. tanarius.

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Allelopathic Prenylflavanones from the Fallen Leaves of Macaranga tanarius

Cited by 43 publications

References 11 publications

First total synthesis of (±)-malaysianone A and (±)-tanariflavanones B

First total synthesis of (±)-malaysianone A and (±)-tanariflavanones B

Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest^,1

Plant origin of Okinawan propolis: honeybee behavior observation and phytochemical analysis

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Allelopathic Prenylflavanones from the Fallen Leaves of Macaranga tanarius

Cited by 43 publications

References 11 publications

First total synthesis of (±)-malaysianone A and (±)-tanariflavanones B

First total synthesis of (±)-malaysianone A and (±)-tanariflavanones B

Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest,1

Plant origin of Okinawan propolis: honeybee behavior observation and phytochemical analysis

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Antiproliferative Prenylated Stilbenes and Flavonoids from Macaranga alnifolia from the Madagascar Rainforest^,1