Structure of the Novel Insecticidal Sesquilignan, Haedoxan A

Taniguchi, Eiji; Imamura, Kensaburo; Ishibashi, Fumito; Matsui, Teppei; Nishio, Akira

doi:10.1080/00021369.1989.10869338

Cited by 11 publications

(9 citation statements)

References 7 publications

(8 reference statements)

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“…Previous phytochemical investigations showed that this plant is rich in lignans. Among them, (+)-haedoxan A (1, see Figure 1A), isolated in 1989 by Taniguchi, represents the major insecticidal ingredient (Taniguchi et al, 1989;Seo and Park, 2012). Structurally, this natural product is a sesquilignan, that is, a trimer of C6C3 units (n-propyl benzene).…”

Section: Introductionmentioning

confidence: 99%

“…Haedoxans exhibit excellent insecticidal activity against several insects, such as Musca domestica [Culex pipiens pallens (Xiao et al, 2012b)] and Mythimna separata (Xiao et al, 2012a). It is noteworthy that the insecticidal activity of Haedoxan A (1) is comparable to that of the commercial synthetic pyrethroids (Taniguchi et al, 1989;Hu et al, 2016). (+)-Phrymarolins I (4) and II (5) also show considerable synergistic activities with pyrethrin and carbamate pesticides (Park et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

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A Synthetic View on Haedoxans and Related Neolignans From Phryma leptostachya

et al. 2020

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Haedoxans are a series of sesquilignan natural products isolated from the traditional insecticidal plant Phryma leptostachya. Given their significant insecticidal activity, haedoxans and related analogs have been considered as potential agents for plant defense. Moreover, these compounds also exhibit promising antifungal, antibacterial, and anticancer activities. The present paper is a review of the structure, biological activity, and chemical synthesis of naturally occurring haedoxan-like molecules.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Synthetic View on Haedoxans and Related Neolignans From Phryma leptostachya

et al. 2020

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“…As natural insecticidal components, several lignans, such as phrymarolins I and II, and haedoxan A were isolated from P. leptostachya L. (Taniguchi and Oshima, 1972a; Taniguchi and Oshima, 1972b; Taniguchi et al ., 1989). The additional two lignans, such as leptostachyol acetate and 8’-acetoxy-2,2’,6-trimethoxy-3,4,4’,5’-dimethylenedioxyphenyl-7,7’-dioxabicyclo-[3.3.0]octane, were isolated from the roots of P. leptostachya var.…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory, Antioxidant, Anti-Angiogenic and Skin Whitening Activities of Phryma leptostachya var. asiatica Hara Extract

Jung

Cho

Lim³

et al. 2013

Biomolecules and Therapeutics

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This work aimed to assess some pharmacological activities of P. leptostachya var. asiatica Hara. The dried roots of P. leptostachya var. asiatica Hara were extracted with 70% ethanol to generate the powdered extract, named PLE. Anti-angiogenic activity was detected using chick chorioallantoic membrane (CAM) assay. In vitro anti-inflammatory activity was evaluated via analyzing nitric oxide (NO) content, inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. Antioxidant activity was determined by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay and reactive oxygen species (ROS) level in the stimulated macrophage cells. Matrix metalloproteinase-9 (MMP-9) and -2 (MMP-2) activities in the culture media were detected using zymography. PLE exhibits an anti-angiogenic activity in the CAM assay, and displays an inhibitory action on the generation of NO in the LPS-stimulated macrophage cells. In the stimulated macrophage cells, it is able to diminish the enhanced ROS level. It can potently scavenge the stable DPPH free radical. It suppresses the induction of iNOS and COX-2 and the enhanced MMP-9 activity in the stimulated macrophage cells. Both monooxygenase and oxidase activities of tyrosinase were strongly inhibited by PLE. Taken together, the dried roots of P. leptostachya var. asiatica Hara possess anti-angiogenic, anti-inflammatory, antioxidant and skin whitening activities, which might partly provide its therapeutic efficacy in traditional medicine.

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“…Investigation of natural products with insecticidal activities from plant may lead to find novel insecticides as the prominent examples of pyrethroids. The herbaceous perennial plant, Phryma leptostachya L., is widely distributed in the Himalayas, temperate Asia and northeast America, and has been traditionally used as a natural insecticide in East Asia [ 2 – 7 ]. As part of an ongoing effort to identify potential pesticide molecules derived from natural products it was shown that lignans including Haedoxane A, Phrymarolin B and Phrymarolins I are the main active components of P. leptostachya L. ( Figure 1 ) [ 8 – 10 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Larvicidal Activity against Culex pipiens pallens of New Triazole Derivatives of Phrymarolin from Phryma leptostachya L.

Zhang

Gao

et al. 2013

IJMS

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Twelve new triazole derivatives of Phrymarolin were prepared from Phrymarolin I and the structures of all the derivatives were fully characterized by 1H-NMR, 13C-NMR and MS spectral data analyses. Larvicidal activities against 4rd instar larvae of Culex pipiens pallens of these Phrymarolin analogues were assayed. Although the triazole derivatives of Phrymarolin showed certain larvicidal activity, they showed lower activity than Phrymarolin I. The typical non-natural groups triazole substituents reduced the larvicidal activity of Phrymarolin derivatives.

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Structure of the Novel Insecticidal Sesquilignan, Haedoxan A

Cited by 11 publications

References 7 publications

A Synthetic View on Haedoxans and Related Neolignans From Phryma leptostachya

A Synthetic View on Haedoxans and Related Neolignans From Phryma leptostachya

Anti-Inflammatory, Antioxidant, Anti-Angiogenic and Skin Whitening Activities of Phryma leptostachya var. asiatica Hara Extract

Synthesis and Larvicidal Activity against Culex pipiens pallens of New Triazole Derivatives of Phrymarolin from Phryma leptostachya L.

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