Widespread occurrence of syn-alkane-6,8-diols in the flowers of the compositae

Akihisa, Toshihiro; Inoue, Youhei; Yasukawa, Ken; Kasahara, Yoshiyuki; Yamanouchi, Sakae; Kumaki, Kunio; Tamura, Toshitake

doi:10.1016/s0031-9422(98)00273-8

Cited by 10 publications

(9 citation statements)

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“…Noteworthy exceptions are detailed analyses of petal waxes for Crataegus monogyna and three cultivars of Rubus idaeus (Griffiths et al, 2000), Antirrhinum majus (Goodwin et al, 2003), Vicia faba (Griffiths et al, 1999), Cistus albidus (Hennig et al, 1988), Petunia hybrida (King et al, 2007), Arabidopsis (Arabidopsis thaliana; Shi et al, 2011), and Rosa damascena (Stoianova-Ivanova et al, 1971). Selected compound classes have been investigated for some more species, including selected Ericaceae (Salasoo, 1989), Rosaceae (Wollrab, 1969a(Wollrab, , 1969b, and Asteraceae (Akihisa et al, 1998) species. Some major plant families, such as the Asteraceae, have not been investigated in much detail.…”

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confidence: 99%

Wax Layers onCosmos bipinnatusPetals Contribute Unequally to Total Petal Water Resistance

2014

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V6T 1Z1 (R.J.) Cuticular waxes coat all primary aboveground plant organs as a crucial adaptation to life on land. Accordingly, the properties of waxes have been studied in much detail, albeit with a strong focus on leaf and fruit waxes. Flowers have life histories and functions largely different from those of other organs, and it remains to be seen whether flower waxes have compositions and physiological properties differing from those on other organs. This work provides a detailed characterization of the petal waxes, using Cosmos bipinnatus as a model, and compares them with leaf and stem waxes. The abaxial petal surface is relatively flat, whereas the adaxial side consists of conical epidermis cells, rendering it approximately 3.8 times larger than the projected petal area. The petal wax was found to contain unusually high concentrations of C 22 and C 24 fatty acids and primary alcohols, much shorter than those in leaf and stem waxes. Detailed analyses revealed distinct differences between waxes on the adaxial and abaxial petal sides and between epicuticular and intracuticular waxes. Transpiration resistances equaled 3 3 10 4 and 1.5 3 10 4 s m 21 for the adaxial and abaxial surfaces, respectively. Petal surfaces of C. bipinnatus thus impose relatively weak water transport barriers compared with typical leaf cuticles. Approximately two-thirds of the abaxial surface water barrier was found to reside in the epicuticular wax layer of the petal and only one-third in the intracuticular wax. Altogether, the flower waxes of this species had properties greatly differing from those on vegetative organs.

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confidence: 99%

Wax Layers onCosmos bipinnatusPetals Contribute Unequally to Total Petal Water Resistance

2014

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“…[4][5][6] In the course of our search for potential bioactive compounds from natural sources, 7,8 we have demonstrated that various mono-, di-, and trihydroxylated triterpenoids and syn-alkane-6,8-diols isolated from extracts of Asteraceae flowers, including the flowers of marigold (Calendula officinalis L.), exhibited marked antiinflammatory and anti-tumor-promoting effects. [9][10][11][12][13][14] We now report the isolation and characterization of four new (2, 3, 5, and 8) and six known oleanane-type triterpene glycosides (1, 4, 6, 7, 9, and 10), along with five known flavonol glycosides (11)(12)(13)(14)(15), from an n-butanol (n-BuOH)-soluble fraction of the methanol (MeOH) extract of C. officinalis flowers. Inhibitory effects on 12-Otetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice for nine triterpene glycosides, 1-9, and on Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA for all compounds 1-15 were evaluated as a preliminary screen for their potential cancer chemopreventive activities.…”

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Anti-Inflammatory, Anti-Tumor-Promoting, and Cytotoxic Activities of Constituents of Marigold (Calendula officinalis) Flowers

et al. 2006

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Ten oleanane-type triterpene glycosides, 1-10, including four new compounds, calendulaglycoside A 6'-O-methyl ester (2), calendulaglycoside A 6'-O-n-butyl ester (3), calendulaglycoside B 6'-O-n-butyl ester (5), and calendulaglycoside C 6'-O-n-butyl ester (8), along with five known flavonol glycosides, 11-15, were isolated from the flowers of marigold (Calendula officinalis). Upon evaluation of compounds 1-9 for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, all of the compounds, except for 1, exhibited marked anti-inflammatory activity, with ID50 values of 0.05-0.20 mg per ear. In addition, when 1-15 were evaluated against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA, compounds 1-10 exhibited moderate inhibitory effects (IC50 values of 471-487 mol ratio/32 pmol TPA). Furthermore, upon evaluation of the cytotoxic activity against human cancer cell lines in vitro in the NCI Developmental Therapeutics Program, two triterpene glycosides, 9 and 10, exhibited their most potent cytotoxic effects against colon cancer, leukemia, and melanoma cells.

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“…In Japan the traditionally edible flower is used in the liquor 'Kikuka-shu' and in the tea 'Kikubana-cha,' although airborne and contact dermatitis can result from contact with various parts of the plant. C. morifolium has antiallergic, antiaphid, antibacterial, antifungal, antiviral, antispirochetal, anti-inflammatory, and anticarcinogenic activity due to triterpene triols and diols, constituents also probably responsible for reported inhibition of tumor growth and lens aldose reductase and for antioxidant activities 36 JOURNAL OF HERBS, SPICES & MEDICINAL PLANTS (6,67,89,101). C. morifolium has been used to maintain liver health and for the treatment of AIDS, HIV, boils, coughs, digestive problems, dizziness, eyesight disorders, fevers, headaches, and respiratory and vascular disorders (15).…”

Section: Chrysanthemum Morifoliummentioning

confidence: 99%

Important Secondary Metabolites and Essential Oils of Species Within the Anthemideae (Asteraceae)

Silva

Yonekura

Kaganda

et al. 2005

Journal of Herbs, Spices & Medicinal Plants

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Widespread occurrence of syn-alkane-6,8-diols in the flowers of the compositae

Cited by 10 publications

References 4 publications

Wax Layers onCosmos bipinnatusPetals Contribute Unequally to Total Petal Water Resistance

Wax Layers onCosmos bipinnatusPetals Contribute Unequally to Total Petal Water Resistance

Anti-Inflammatory, Anti-Tumor-Promoting, and Cytotoxic Activities of Constituents of Marigold (Calendula officinalis) Flowers

Important Secondary Metabolites and Essential Oils of Species Within the Anthemideae (Asteraceae)

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