A monoterpene alkaloid from Incarvillea sinensis

Chi, Yu‐Ming; Yan, Wen‐Mei; Chen, Dechang; Noguchi, Hiroshi; Iitaka, Yōichi; Sankawa, Ushio

doi:10.1016/0031-9422(92)83672-l

Phytochemistry

1992

DOI: 10.1016/0031-9422(92)83672-l

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A monoterpene alkaloid from Incarvillea sinensis

Yu‐Ming Chi

Wen‐Mei Yan

Dechang Chen

et al.

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Cited by 42 publications

(26 citation statements)

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“…Plants of this genus are used in Chinese folk medicine to treat rheumatism and to relieve pain (1). Previous chemical investigation of this genus led to the isolation of alkaloids with antinociceptive activity from I. sinensis and I. delavayi (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13), iridoids and their glycosides (14,15) from I. olgae, and a novel monoterpene glycoside (dissectol A) from I. dissectifoliola (16,17). A bacteriostatic compound, argutone, together with ursolic acid and hentriacontane, was isolated from I. arguta, which is used to treat hepatitis and infectious diseases (18,19).…”

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Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Luo

et al. 2004

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Novel ceramides, rel-(3S,4S,5S)-3-[(2R)-2-hydroxy- (2) were isolated from the aqueous ethanolic extract of the roots of Incarvillea arguta, together with eight known compounds: β-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), β-sitosterol 6′-O-acyl-β-D-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10). Their structures were elucidated on the basis of spectral data including IR, MS, NMR [ 1 H NMR, 13 C NMR (distortionless enhancement by polarization transfer), 1 H-1 H COSY, heteronuclear multiplequantum coherence, and heteronuclear multiple-bond coherence correlations]. The relative configurations were established by nuclear Overhauser effect spectroscopy experiments and by comparison of the NMR spectral data and coupling constants with those already reported in the literature.

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Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Luo

et al. 2004

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“…1) In the course of our investigations of its antinociceptive substances, a number of novel monoterpene alkaloids and macrocyclic spermine alkaloids have been characterized. [2][3][4][5][6][7][8][9] One of the monoterpene alkaloids, incarvillateine (INCA, Fig. 1), demonstrated a significant antinociceptive effect against the mouse pain model induced by formalin.…”

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Pharmacological Study on the Novel Antinociceptive Agent, a Novel Monoterpene Alkaloid from Incarvillea sinensis

Chi¹,

Nakamura²,

Yoshizawa³

et al. 2005

Biological & Pharmaceutical Bulletin

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Incarvillea sinensis LAM. (Bignoniaceae) is a wild plant distributed in the northern area of China, and dried whole plants have traditionally been used in treating rheumatism and relieving pain as an ancient Chinese crude drug designated "Tougucao". 1) In the course of our investigations of its antinociceptive substances, a number of novel monoterpene alkaloids and macrocyclic spermine alkaloids have been characterized. [2][3][4][5][6][7][8][9] One of the monoterpene alkaloids, incarvillateine (INCA, Fig. 1), demonstrated a significant antinociceptive effect against the mouse pain model induced by formalin. We also reported the antinociceptive effect of INCA and comparison of its action with morphine (MOR). In comparison with antinociceptive effects of different doses of INCA and MOR, the ED 50 values of INCA were about 1.06 (early phase) and 1.33 (late phase) times lower than those of MOR. In addition, the antinociceptive effect of INCA in early phase was partially antagonized by pretreatment with naloxone (a narcotic antagonist, 5 mg/kg, s.c), while the effect of morphine was completely reversed. These results suggested the possibility that the action of INCA was partially related to its influence on the central opioid pathways.10) However, details on the pharmacological aspect of the mechanism have not, to our knowledge, been undertaken.In order to examine the antinociceptive mechanism, some opiate antagonists and adenosine receptor antagonist were administered to mice prior to incarvillateine injection in a formalin test, and the licking time of their pain reaction (paw licking) was measured. MATERIALS AND METHODSChemicals INCA was prepared according to the previous report.2) Nor-binaltorphimine (nor-BNI) and b-funaltrexamine (b-FNA) were purchased from Tocris Cookson (Bristol, U.K.). Naltrindole (NTI) was obtained from Sigma (St. Louis, U.S.A.). Theophylline (THEO) and Tween 80 (polyoxyethylene sorbitan monooleate) were obtained from Nacalai Tesque (Kyoto, Japan). Ringer solution was purchased from Fuso Pharmaceutical (Osaka, Japan).Formalin Test This method represented a modification of that described by Dubuisson and Dennis.11) Male ddy mice (25Ϯ5 g) were used. The tested drugs were prepared as suspensions with 0.5% Tween 80/saline. Since the test has a biphasic pain response with two peaks, from 0 to 10 min (early phase) and from 10 to 30 min (late phase), the time spent licking the injected paw was recorded and the data were expressed as total licking time in the early phase and late phase. Treatments of AntagonistsThe experiments were performed according to a modified method described by Kamei et al. 12) and Santos et al. 13) In measurement of the early phase, b-FNA (40 mg/kg, s.c) and nor-BNI (20 mg/kg, s.c) were administered 24 h before the inducer treatment, while NTI (0.5 mg/kg, s.c) and THEO (5 mg/kg, s.c.) were treated 10 min prior to the inducer injection.In measurement of the late phase, b-FNA and nor-BNI were administered 24 h before the inducer treatment. NTI and THEO were administered at ...

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“…In the studies on its pharmacological active substances, seventeen novel alkaloids including incarvilline, 1,2) incarvine A (2),3) incarvine C (3) 4) and incarvillateine (4) 5) were isolated and their structures were characterized. [1][2][3][4][5][6][7][8] Incarvillateine (4) was found to show a more potent antinociceptive effect than morphine in the formalin test, and the mechanism of antinociception was regarded to be different from that of morphine.…”

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“…In the studies on its pharmacological active substances, seventeen novel alkaloids including incarvilline, 1,2) incarvine A (2),…”

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confidence: 99%

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A Monoterpene Alkaloid from Incarvillea sinensis

Ming¹,

Nakamura²,

Zhao³

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Incarvillea sinensis LAM., a well-known traditional Chinese crude drug, has been used to treat rheumatism and to relieve pain. In the studies on its pharmacological active substances, seventeen novel alkaloids including incarvilline, 1,2) incarvine A (2),3) incarvine C (3) 4) and incarvillateine (4) 5) were isolated and their structures were characterized. [1][2][3][4][5][6][7][8] Incarvillateine (4) was found to show a more potent antinociceptive effect than morphine in the formalin test, and the mechanism of antinociception was regarded to be different from that of morphine. 9) In this paper, we describe the isolation and structure elucidation of a new monoterpene alkaloid, incarvillateine E (1).The aerial parts (3.0 kg) of I. sinensis were extracted with EtOH, and the extract was subsequently treated with weak acid and alkali in order to attain a facile separation of alkaloids, followed by Al 2 O 3 and silica gel column chromatography to yield compound 1 (14.9 mg).Incarvillateine A novel monoterpene alkaloid, named incarvillateine E, possessing three moles of incarvilline moieties, has been obtained from the aerial parts of Incarvillea sinensis LAM. (Bignoniaceae). On the basis of spectroscopic evidence, the structure of incarvillateine E has been characterized.

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A monoterpene alkaloid from Incarvillea sinensis

Cited by 42 publications

References 1 publication

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Pharmacological Study on the Novel Antinociceptive Agent, a Novel Monoterpene Alkaloid from Incarvillea sinensis

A Monoterpene Alkaloid from Incarvillea sinensis

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