Biosynthesis of grayanotoxins in Leucothoe grayana max. Incorporation of mevalonic acid and ( - )-kaurene into grayanotoxin-III.

Masutani, Tetsuya; HAMADA, Masayuki; KAWANO, Eiko; Iwasa, Junkichi; Kumazawa, Zenzaburo; Ueda, Hiroo

doi:10.1271/bbb1961.45.1281

Cited by 10 publications

(15 citation statements)

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“…To investigate this possibility, we employed a path analysis framework to assess the direction and magnitude of phenotypic selection on leaf, flower and nectar GTXs in native and non-native R. ponticum populations. This approach allowed us to devise a realistic path model—reflecting foliar biogenesis of GTXs [18,19] leading to linked expression in flowers and nectar—to quantify the extent to which phenotypic selection on a certain plant part was imposed directly, and indirectly (i.e. arising from phenotypic linkage with other plant parts).…”

Section: Introductionmentioning

confidence: 99%

Pollinator selection against toxic nectar as a key facilitator of a plant invasion

Egan

Stevenson

2022

Phil. Trans. R. Soc. B

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Plant compounds associated with herbivore defence occur widely in floral nectar and can impact pollinator health. We showed previously that Rhododendron ponticum nectar contains grayanotoxin I (GTX I) at concentrations that are lethal or sublethal to honeybees and a solitary bee in the plant's non-native range in Ireland. Here we further examined this conflict and tested the hypotheses that nectar GTX I is subject to negative pollinator-mediated selection in the non-native range, but that phenotypic linkage between GTX I levels in nectar and leaves acts as a constraint on independent evolution. We found that nectar GTX I experienced negative directional selection in the non-native range, in contrast to the native Iberian range, and that the magnitude and frequency of pollinator limitation indicated that selection was pollinator-mediated. Surprisingly, nectar GTX I levels were decoupled from those of leaves in the non-native range, which may have assisted post-invasion evolution of nectar without compromising the anti-herbivore function of GTX I (here demonstrated in bioassays with an ecologically relevant herbivore). Our study emphasizes the centrality of pollinator health as a concept linked to the invasion process, and how post-invasion evolution can be targeted toward minimizing lethal or sub-lethal effects on pollinators. This article is part of the theme issue ‘Natural processes influencing pollinator health: from chemistry to landscapes’.

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Section: Introductionmentioning

confidence: 99%

Pollinator selection against toxic nectar as a key facilitator of a plant invasion

Egan

Stevenson

2022

Phil. Trans. R. Soc. B

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“…19 These grayanane diterpenoids originate from ent-kaurane skeleton and are thus biosynthetically related to each other (Figure 1). 3,20 Grayanoids exhibit a wide spectrum of biological properties such as neuroprotective effects, cAMP regulation, antifeedant, insecticidal, analgesic, and sedative properties, and sodium channelmodulating activity. 21,22 Although the genus Pieris is a relatively small group belonging to the large family Ericaceae, its exclusive metabolites, particularly the unique grayanoids, together with their extensive bioactivities, have aroused the attention of chemists and biologists.…”

Section: ■ Introductionmentioning

confidence: 99%

Structural Diversity and Biological Activity of the Genus Pieris Terpenoids

Yan

Zhang

et al. 2017

J. Agric. Food Chem.

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Secondary metabolites, particularly the grayanane diterpenoids produced by the members of genus Pieris, have been investigated in past decades for their remarkable antifeedant and insecticidal activities and toxicity. Grayanoids exhibit diverse biological properties such as antifeedant, insecticidal, cAMP regulatory, and sodium-channel-modulating activities. Structural complexity and diverse bioactivity of grayanoids have made them attractive targets for chemical, biological, and synthetic purposes. The current review synthesized findings published from 1966 to 2017, which include 135 reports that describe 130 terpenoids, including 103 grayanoids. The distribution, structure, skeleton, as well as the antifeedant and insecticidal activity of terpenoids, particularly the grayanane diterpenoids, are discussed in detail in this review. In cases where sufficient information is available, the structure-activity relationships of their antifeedant activity are also presented. We hope that this contribution will prompt more scientists to pay attention to these diterpenoids, which may be potentially applied in the agricultural field.

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“…Some grayanoids exhibited potent sodium-channel-modulating, analgesic, sedative, and insect antifeedant activities, which have attracted great interest from both synthetic and biological perspectives . The biogenetic precursor for grayanane is assumed to be ent -kaurene . To date, nine types of grayanane-related carbon skeletons have been reported, including grayanane (A-nor-B-homo- ent -kaurane), 1,5-secograyanane, 3,4-secograyanane, 9,10-secograyanane, 1,10:2,3-disecograyanane, leucothane (A-homo-B-norgrayanane), kalmane (B-homo-C-norgrayanane), 1,5-secokalmane and micranthane (C-homograyanane) .…”

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confidence: 99%

“…4 The biogenetic precursor for grayanane is assumed to be entkaurene. 5 To date, nine types of grayanane-related carbon skeletons have been reported, including grayanane (A-nor-Bhomo-ent-kaurane), 6 1,5-secograyanane, 7 3,4-secograyanane, 8 9,10-secograyanane, 9 1,10:2,3-disecograyanane, 10 leucothane (A-homo-B-norgrayanane), 11 kalmane (B-homo-C-norgrayanane), 12 1,5-secokalmane 13 and micranthane (C-homograyanane). 14 Seven types of skeletons have been found in plants of the Rhododendron genera, the largest genera of the Ericaceae family.…”

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confidence: 99%

Mollanol A, a Diterpenoid with a New C-Nor-D-homograyanane Skeleton from the Fruits of Rhododendron molle

Liu

et al. 2014

Org. Lett.

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Two new grayanoids, mollanol A (1) and rhodomollein XXV (2), were isolated from the fruits of Rhododendron molle. Their structures were elucidated by spectroscopic methods and X-ray diffraction analyses. Mollanol A (1) possesses a new C-nor-D-homograyanane carbon skeleton, while rhodomollein XXV (2) is the first example of an 11,16-epoxygrayanane and features a caged oxa-tricyclo[3.3.1.0(3.7)]nonane ring system. Plausible biogenetic pathways for 1 were proposed. Compound 1 exhibited transcriptional activation effects on the xbp1 upstream promoter in IEC-6, 293T, and RAW264.7 cells.

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Biosynthesis of grayanotoxins in Leucothoe grayana max. Incorporation of mevalonic acid and ( - )-kaurene into grayanotoxin-III.

Cited by 10 publications

References 0 publications

Pollinator selection against toxic nectar as a key facilitator of a plant invasion

Pollinator selection against toxic nectar as a key facilitator of a plant invasion

Structural Diversity and Biological Activity of the Genus Pieris Terpenoids

Mollanol A, a Diterpenoid with a New C-Nor-D-homograyanane Skeleton from the Fruits of Rhododendron molle

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