Biologically active constituents from the fruiting body of Taiwanofungus camphoratus

Shi, Liu; Chao, Chih‐Hua; Shen, De Yang; Chan, Hsiu Hui; Chen, Chou Hsiung; Liao, Yu-Hsien; Wu, Shwu Jen; Leu, Yann Lii; Shen, Yuh Chiang; Kuo, Yao Haur; Lee, E-Jian; Qian, Keduo; Wu, Tong; Lee, Kuo Hsiung̀

doi:10.1016/j.bmc.2010.10.032

Cited by 36 publications

(27 citation statements)

References 23 publications

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“…After protection with bromochloromethane in the presence Cs 2 CO 3 at 110 °C [11], the 1,3-benzodioxole 3 was obtained in 70% yield. Iodination of 3 with N-iodosuccinimide [12] produced 5-iodo-4,7-dimethoxy-6-methylbenzo[d] [1,3]dioxole 6. The Sonogashira reaction [13] was utilized to couple iodide 6 with 2-methyl-1-buten-3-yne, using the catalysts Pd(PPh 3 ) 4 and CuI.…”

Section: Synthesis and Structural Characterization Of Antrocamphin O (1)mentioning

confidence: 99%

“…The product, 6, was obtained as a light-orange oil (248 mg, yield: 88%). [1,3]dioxole (1). N,N-Dimethylacetamide (DMA, 1.0 mL) was placed in a 10 mL flask and heated to 60 °C for 20 min while purging with argon gas.…”

Section: Synthesis Of 47-dimethoxy-5-methyl-13-benzodioxole (3)mentioning

confidence: 99%

“…Designated an endangered species in Taiwan, the fungus is a rare and unique mushroom used in folk medicine and as a health food. To date, over 200 constituent compounds, consisting of small molecules (terpenoids, benzenoids, lignans, benzoquinone derivatives, and succinic and maleic derivatives) and macromolecules (polysaccharides, nucleic acids, and proteins), have been reported [1][2][3]. Preparations from the fruiting bodies have been used for the prevention or treatment of numerous maladies, including liver diseases, food and drug intoxication, diarrhea, abdominal pain, hypertension, itchy skin, and tumorigenic diseases [4].…”

Section: Introductionmentioning

confidence: 99%

“…Preparations from the fruiting bodies have been used for the prevention or treatment of numerous maladies, including liver diseases, food and drug intoxication, diarrhea, abdominal pain, hypertension, itchy skin, and tumorigenic diseases [4]. Previous research has shown the anti-cancer and anti-inflammatory effects of the triterpenoids derived from A. camphorate [3,5]. The major chemical constituents, the enynyl-benzenoids, are the key components responsible for anti-inflammatory activity [6,7].…”

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata

Chen

Tang³

et al. 2013

Molecules

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Abstract:A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3′-methylbut-3-en-1-ynyl)benzo [d] [1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including 1D and 2D NMR, high-resolution MS, IR, and UV) and total synthesis. Compound 1 was prepared through the Sonogashira reaction of 5-iodo-4,7-dimethoxy-6-methylbenzene and 2-methylbut-1-en-3-yne as the key step. The benzenoids were tested for cytotoxicity against the HT29, HTC15, DLD-1, and COLO 205 colon cancer cell lines, and activities are reported herein.

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Section: Synthesis and Structural Characterization Of Antrocamphin O (1)mentioning

confidence: 99%

Section: Synthesis Of 47-dimethoxy-5-methyl-13-benzodioxole (3)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…

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mentioning

confidence: 99%

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Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata

Chen

Tang³

et al. 2013

Molecules

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Resolution of the nomenclature for niu‐chang‐chih (Taiwanofungus camphoratus), an important medicinal polypore

Kirk

Redhead

et al. 2012

TAXON

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Niu‐chang‐chih, a medicinal polypore restricted to Taiwan on the endemic tree species Cinnamomum kanehirae, currently goes by the names Antrodia cinnamomea T.T. Chang & W.N. Chou, A. camphorata (M. Zang & C.H. Su) Sheng H. Wu & al., and Taiwanofungus camphoratus (M. Zang & C.H. Su) Sheng H. Wu & al., the latter two based on Ganoderma camphoratum M. Zang & C.H. Su. The basidiocarps on the holotypes for the two basionyms Antrodia cinnamomea and Ganoderma camphoratum are of niu‐chang‐chih. The first validly published name that was applied to this species was G. camphoratum M. Zang & C.H. Su published in 1990. However, the original type of G. camphoratum consisted of mixed material, consisting chiefly of a basidiocarp of niu‐chang‐chih but also of the spores of another unrelated fungus. The two elements are represented in the original description and accompanying illustrations. Later Chang & Chou (2004) lectotypifed G. camphoratum limiting it to the spores described and illustrated by Zang and Su, the only portion of the original type that Chang and Chou believed to belong in Ganoderma, and applied the name Antrodia cinnamomea Chang & Chou (1995) to niu‐chang‐chih. Many, however, reject Chang and Chou's conclusions and continue to apply the name Ganoderma camphoratum, and combinations based on it (i.e., Antrodia camphoratum, Taiwanofungus camphoratus), to niu‐chang‐chih, relegating Antrodia cinnamomea to synonymy. Based on careful examination of the type of G. camphoratum, it is concluded that the spores upon which Chang and Chou's lectotype is based are a minor admixture with the original gathering of the niu‐chang‐chih specimen and thus cannot serve as the lectotype for the name Ganoderma camphoratum. Ganoderma camphoratum is lectotypified here so as to exclude the spores present in the original holotype that are not from niu‐chang‐chih. Furthermore, since this conclusion could be subject to challenge and the species is exceptionally important medicinally and economically, we also propose to conserve the name with a conserved type that is consistent with the lectotype effected herein. An overview of the taxonomy of niu‐chang‐chih is also provided and a new combination, Taiwanofungus salmoneus, for a related species is effected.

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Secondary Metabolites from Higher Fungi

Chen

Liu

2017

Progress in the Chemistry of Organic Natural Products

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Secondary metabolites of higher fungi (mushrooms) are an underexplored resource compared to plant-derived secondary metabolites. An increasing interest in mushroom natural products has been noted in recent years. This chapter gives a comprehensive overview of the secondary metabolites from higher fungi, with 765 references highlighting the isolation, structure elucidation, biological activities, chemical syntheses, and biosynthesis of pigments, nitrogen-containing compounds, and terpenoids from mushrooms. Mushroom toxins are also included in each section.In a section on pigments of higher fungi, pigments are classified into four categories, namely, those from the shikimate-chorismate, acetate-malonate, and mevalonate biosynthetic pathways, and pigments containing nitrogen, with 145 references covering the years 2010-2016.In a section on other nitrogen-containing compounds of higher fungi, compounds are categorized primarily into nitrogen heterocycles, nucleosides, non-protein amino acids, cyclic peptides, and sphingolipids, with 65 references covering the years 2010-2016. In turn, in a section describing terpenoids of higher fungi, the sesquiterpenoids and diterpenoids are thoroughly elaborated, spanning the years 2001-2016, and 2009-2016, respectively. The divergent biosynthetic pathways from farnesyl pyrophosphate to sesquiterpenoids are also described. Selected triterpenoids with novel structures and promising biological activities, including lanostanes and ergostanes, are reported from the genus Ganoderma, and the fungi Antrodia cinnamomea and Poria cocos. In addition, cucurbitanes and saponaceolides are also compiled in this section.

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Biologically active constituents from the fruiting body of Taiwanofungus camphoratus

Cited by 36 publications

References 23 publications

Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata

Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata

Resolution of the nomenclature for niu‐chang‐chih (Taiwanofungus camphoratus), an important medicinal polypore

Secondary Metabolites from Higher Fungi

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