Merrilactone A, a novel neurotrophic sesquiterpene dilactone from Illicium merrillianum

Huang, Jianmei; Yokoyama, Ritsuko; Yang, Chunshu; Fukuyama, Yoshiyasu

doi:10.1016/s0040-4039(00)01023-6

Cited by 186 publications

(108 citation statements)

References 14 publications

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“…Fractions A-E were purified by various types of chromatography to afford new compounds, as described in our previous papers. [7][8][9][10][11][12][13][14] Our further studies of the residual fractions E, D, and C led to the isolation of seven new sesquiterpenes 1-7. This paper deals with the isolation and structural elucidation of these new sesquiterpenes.…”

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confidence: 94%

“…We have continued chemical studies on the pericarps of Illicium merrillianum since 1999. As results, about 36 structurally novel sesquiterpenes have been isolated from this species [7][8][9][10][11][12][13][14] and classified into the seco-prezizaane, anislactone, and allo-cedrane types. It is worthy of note that an anislactone-type compound, merrilactone A, isolated from this plant shows interesting neurotrophic activity.…”

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confidence: 97%

“…It is worthy of note that an anislactone-type compound, merrilactone A, isolated from this plant shows interesting neurotrophic activity. 14) Thus it has attracted synthetic organic chemists due to its structural complexity and outstanding biological activity. 15) Those results inspired us to undertake the systematic studies on I. merrillianum.…”

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Seven Novel seco-Prezizaane-Type Sesquiterpenes from the Pericarps of Illicium merrillianum

Huang¹,

Yang

Zhao³

et al. 2004

Chem. Pharm. Bull.

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The genus Illicium is a rich source of prenylated C 6 -C 3 compounds, 1-3) neolignans 4) and seco-prezizaane-type sesquiterpenes. 5,6) These compounds belong to unique structural types and occur exclusively in Illicium species and are considered to be characteristic chemical markers of Illicium species. The former two types are usually accumulated in the stem bark, root bark, and leaves. However, most sesquiterpenes tend to be biosynthesized in the fruit. We have continued chemical studies on the pericarps of Illicium merrillianum since 1999. As results, about 36 structurally novel sesquiterpenes have been isolated from this species [7][8][9][10][11][12][13][14] and classified into the seco-prezizaane, anislactone, and allo-cedrane types. It is worthy of note that an anislactone-type compound, merrilactone A, isolated from this plant shows interesting neurotrophic activity.14) Thus it has attracted synthetic organic chemists due to its structural complexity and outstanding biological activity. 15) Those results inspired us to undertake the systematic studies on I. merrillianum. The methanol extract of I. merrillianum was first separated into fractions A-G (see Experimental). The main chemical constituent of fractions F and G was shikimic acid. Fractions A-E were purified by various types of chromatography to afford new compounds, as described in our previous papers. [7][8][9][10][11][12][13][14] Our further studies of the residual fractions E, D, and C led to the isolation of seven new sesquiterpenes 1-7. This paper deals with the isolation and structural elucidation of these new sesquiterpenes.Compound 1 had the molecular formula C 15 H 22 O 5 , as established by high-resolution (HR) FAB-MS at m/z 305.1352 [MϩNa] ϩ . In its IR spectrum, the absorptions at 3389 and 1728 cm Ϫ1 showed the presence of a hydroxyl and a carbonyl group, respectively. The 1 H-NMR spectral data of 1 (Table 1) contained signals characteristic of pseudoanisatin (8), 16) except for the absence of an oxygenated proton signal at d H 4.80 (1H, m) due to H-3a in 8 and the presence of signals for a methylene group at d H 1.70 (ddd, Jϭ13.5, 9.5, 3.3 Hz) and d H 2.60 (ddd, Jϭ13.5, 11.8, 5.5 Hz), which were assignable to H-3b and H-3a. These structural data showed that 1 is pseudoanisatin (8) without a hydroxyl group at the C-3 position. The 1 H-1 H correlation spectroscopy (H-detected heteronuclear multiple-quantum coherence (HMQC), and 1 H-detected heteronuclear multiple-bond connectivity (HMBC) data confirmed the planar structure of 1. The relative configurations for chiral centers C-1 and C-6 were determined to be the same 1R* and 6R* as those of 8 by nuclear Overhauser effect spectroscopy (NOESY), in which CH 3 -15 showed cross-peaks to H-10a and H-8b, and CH 3 -12 showed a cross-peak to H-14a. Thus 1 was assigned to be 3-deoxypseudoanisatin. Ϫ1. The 1 H-and 13 C-NMR spectral data (Table 1) suggested that 2 is 6-deoxypseudoanisatin (11) 16) bearing a hydroxyl group at the C-2 position. The H-2 signal at d Yamashiro-cho, Tokushima 770-8...

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Seven Novel seco-Prezizaane-Type Sesquiterpenes from the Pericarps of Illicium merrillianum

Huang¹,

Yang

Zhao³

et al. 2004

Chem. Pharm. Bull.

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“…[2][3][4][5][6][7] In many cases, these compounds were found to stimulate the outgrowth of neurites in undiŠerentiated neural cells, including rat pheochromocytoma PC12 cells, 8) in the absence or presence of NGF. It is very important to search for a variety of compounds that may contribute to the development of medical drugs for treating various neurodegenerative diseases, including dementia.…”

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Potentiation of Nerve Growth Factor-Induced Neurite Outgrowth in PC12 Cells by a Coptidis Rhizoma Extract and Protoberberine Alkaloids

Shigeta

Ootaki

Tatemoto

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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“…Previously, we reported that the Illicium plants such as I. merrillianum and I. jiadifengpi produce interesting sesquiterpenoids with neurotrophic properties, 3) which are represented by merrilactone A, 4) jiadifenin, 5) and jiadifenolide. 6) Therefore, we have focused on the Illicium plants in our search for neurotrophin-like natural products.…”

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New Prenylated C6-C3 Compounds from the Twigs of Illicium anisatum

et al. 2011

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Merrilactone A, a novel neurotrophic sesquiterpene dilactone from Illicium merrillianum

Cited by 186 publications

References 14 publications

Seven Novel seco-Prezizaane-Type Sesquiterpenes from the Pericarps of Illicium merrillianum

Seven Novel seco-Prezizaane-Type Sesquiterpenes from the Pericarps of Illicium merrillianum

Potentiation of Nerve Growth Factor-Induced Neurite Outgrowth in PC12 Cells by a Coptidis Rhizoma Extract and Protoberberine Alkaloids

New Prenylated C6-C3 Compounds from the Twigs of Illicium anisatum

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