Alstiphyllanines I-O, ajmaline type alkaloids from Alstonia macrophylla showing vasorelaxant activity

Hiroko Arai; Kazumasa Zaima; Erika Mitsuta; Haruka Tamamoto; Aiko Saito; Yusuke Hirasawa; Abdul Rahman; Idha Kusumawati; Noor Cholies Zaini; Hiroshi Morita

doi:10.1016/j.bmc.2012.04.013

Alstiphyllanines I-O, ajmaline type alkaloids from Alstonia macrophylla showing vasorelaxant activity

Hiroko Arai, Kazumasa Zaima, Erika Mitsuta, Haruka Tamamoto, Aiko Saito, Yusuke Hirasawa, Abdul Rahman, Idha Kusumawati, Noor Cholies Zaini, Hiroshi Morita

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

Seven new ajmaline type alkaloids, alstiphyllanines I-O (1-7) were isolated from the leaves of Alstonia macrophylla together with six related alkaloids (8-13). Structures and stereochemistry of 1-7 were fully elucidated and characterized by 2D NMR analysis. A series of alstiphyllanines I-O (1-7) as well as the known ajmaline type alkaloids (8-13) showed that they relaxed phenylephrine (PE)-induced contractions against rat aortic ring. Among them, vincamedine (10) showed potent vasorelaxant activity, which may be mediated through inhibition of Ca ²⁺ influx through voltage-dependent Ca ²⁺ channels (VDCs) and/or receptor-operated Ca ²⁺ channels (ROCs) as well as partially mediated the NO release from endothelial cells. The presence of substituents at both N-1 and C-17 may be important to show vasorelaxation activity.

Original language	English
Pages (from-to)	3454-3459
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	20
Issue number	11
DOIs	https://doi.org/10.1016/j.bmc.2012.04.013
Publication status	Published - 1 Jun 2012

Keywords

Ajmaline type alkaloids
Alstiphyllanines I-O
Alstonia macrophylla
Indole alkaloids
Nitric oxide
ROCs
SAR
VDCs
Vasorelaxant activity

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10.1016/j.bmc.2012.04.013

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@article{f0a1f7967e174556929a4bd3e03333db,

title = "Alstiphyllanines I-O, ajmaline type alkaloids from Alstonia macrophylla showing vasorelaxant activity",

abstract = "Seven new ajmaline type alkaloids, alstiphyllanines I-O (1-7) were isolated from the leaves of Alstonia macrophylla together with six related alkaloids (8-13). Structures and stereochemistry of 1-7 were fully elucidated and characterized by 2D NMR analysis. A series of alstiphyllanines I-O (1-7) as well as the known ajmaline type alkaloids (8-13) showed that they relaxed phenylephrine (PE)-induced contractions against rat aortic ring. Among them, vincamedine (10) showed potent vasorelaxant activity, which may be mediated through inhibition of Ca 2+ influx through voltage-dependent Ca 2+ channels (VDCs) and/or receptor-operated Ca 2+ channels (ROCs) as well as partially mediated the NO release from endothelial cells. The presence of substituents at both N-1 and C-17 may be important to show vasorelaxation activity.",

keywords = "Ajmaline type alkaloids, Alstiphyllanines I-O, Alstonia macrophylla, Indole alkaloids, Nitric oxide, ROCs, SAR, VDCs, Vasorelaxant activity",

author = "Hiroko Arai and Kazumasa Zaima and Erika Mitsuta and Haruka Tamamoto and Aiko Saito and Yusuke Hirasawa and Abdul Rahman and Idha Kusumawati and Zaini, {Noor Cholies} and Hiroshi Morita",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and a Grant from The Open Research Center Project in Hoshi University.",

year = "2012",

month = jun,

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doi = "10.1016/j.bmc.2012.04.013",

language = "English",

volume = "20",

pages = "3454--3459",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Alstiphyllanines I-O, ajmaline type alkaloids from Alstonia macrophylla showing vasorelaxant activity

AU - Arai, Hiroko

AU - Zaima, Kazumasa

AU - Mitsuta, Erika

AU - Tamamoto, Haruka

AU - Saito, Aiko

AU - Hirasawa, Yusuke

AU - Rahman, Abdul

AU - Kusumawati, Idha

AU - Zaini, Noor Cholies

AU - Morita, Hiroshi

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and a Grant from The Open Research Center Project in Hoshi University.

PY - 2012/6/1

Y1 - 2012/6/1

N2 - Seven new ajmaline type alkaloids, alstiphyllanines I-O (1-7) were isolated from the leaves of Alstonia macrophylla together with six related alkaloids (8-13). Structures and stereochemistry of 1-7 were fully elucidated and characterized by 2D NMR analysis. A series of alstiphyllanines I-O (1-7) as well as the known ajmaline type alkaloids (8-13) showed that they relaxed phenylephrine (PE)-induced contractions against rat aortic ring. Among them, vincamedine (10) showed potent vasorelaxant activity, which may be mediated through inhibition of Ca 2+ influx through voltage-dependent Ca 2+ channels (VDCs) and/or receptor-operated Ca 2+ channels (ROCs) as well as partially mediated the NO release from endothelial cells. The presence of substituents at both N-1 and C-17 may be important to show vasorelaxation activity.

AB - Seven new ajmaline type alkaloids, alstiphyllanines I-O (1-7) were isolated from the leaves of Alstonia macrophylla together with six related alkaloids (8-13). Structures and stereochemistry of 1-7 were fully elucidated and characterized by 2D NMR analysis. A series of alstiphyllanines I-O (1-7) as well as the known ajmaline type alkaloids (8-13) showed that they relaxed phenylephrine (PE)-induced contractions against rat aortic ring. Among them, vincamedine (10) showed potent vasorelaxant activity, which may be mediated through inhibition of Ca 2+ influx through voltage-dependent Ca 2+ channels (VDCs) and/or receptor-operated Ca 2+ channels (ROCs) as well as partially mediated the NO release from endothelial cells. The presence of substituents at both N-1 and C-17 may be important to show vasorelaxation activity.

KW - Ajmaline type alkaloids

KW - Alstiphyllanines I-O

KW - Alstonia macrophylla

KW - Indole alkaloids

KW - Nitric oxide

KW - ROCs

KW - SAR

KW - VDCs

KW - Vasorelaxant activity

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U2 - 10.1016/j.bmc.2012.04.013

DO - 10.1016/j.bmc.2012.04.013

M3 - Article

C2 - 22560833

AN - SCOPUS:84861197474

SN - 0968-0896

VL - 20

SP - 3454

EP - 3459

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 11

ER -

Alstiphyllanines I-O, ajmaline type alkaloids from Alstonia macrophylla showing vasorelaxant activity

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Keywords

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