Cytotoxic Alkaloids from the Flowers of Senna spectabilis

Lawan Sriphong; Uthai Sotanaphun; Siripan Limsirichaikul; Penpan Wetwitayaklung; Chaiyo Chaichantipyuth; Sunibhond Pummangura

doi:10.1055/s-2003-45156

Cytotoxic Alkaloids from the Flowers of Senna spectabilis

Lawan Sriphong, Uthai Sotanaphun, Siripan Limsirichaikul, Penpan Wetwitayaklung, Chaiyo Chaichantipyuth, Sunibhond Pummangura

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

24 Citations (Scopus)

Abstract

Three new alkaloids, 3(R)-benzoyloxy-2(R)-methyl-6(R)-(11′- oxododecyl)-piperidine (3), 5-hydroxy-2-methyl-6-(11′-oxododecyl) -pyridine (4) and 5-hydroxy-2-methyl-6-(11′-oxododecyl)-pyridine N-oxide (5), together with a known alkaloid, (-)-cassine (1), were isolated from the flowers of Senna spectabilis. A derivative, N,O-diacetylcassine (2), was semisynthesized. Their structures and stereochemistry were established on the basis of spectroscopic analysis. Cytotoxic activity and brine shrimp lethality of these compounds were evaluated. Compounds 2, 3 and 5 exhibited cytoxicity against KB cell lines with IC₅₀ values of 5.2, 3.7 and 2.0 μg/mL, respectively.

Original language	English
Pages (from-to)	1054-1056
Number of pages	3
Journal	Planta Medica
Volume	69
Issue number	11
DOIs	https://doi.org/10.1055/s-2003-45156
Publication status	Published - 11-2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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title = "Cytotoxic Alkaloids from the Flowers of Senna spectabilis",

abstract = "Three new alkaloids, 3(R)-benzoyloxy-2(R)-methyl-6(R)-(11′- oxododecyl)-piperidine (3), 5-hydroxy-2-methyl-6-(11′-oxododecyl) -pyridine (4) and 5-hydroxy-2-methyl-6-(11′-oxododecyl)-pyridine N-oxide (5), together with a known alkaloid, (-)-cassine (1), were isolated from the flowers of Senna spectabilis. A derivative, N,O-diacetylcassine (2), was semisynthesized. Their structures and stereochemistry were established on the basis of spectroscopic analysis. Cytotoxic activity and brine shrimp lethality of these compounds were evaluated. Compounds 2, 3 and 5 exhibited cytoxicity against KB cell lines with IC50 values of 5.2, 3.7 and 2.0 μg/mL, respectively.",

author = "Lawan Sriphong and Uthai Sotanaphun and Siripan Limsirichaikul and Penpan Wetwitayaklung and Chaiyo Chaichantipyuth and Sunibhond Pummangura",

year = "2003",

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doi = "10.1055/s-2003-45156",

language = "English",

volume = "69",

pages = "1054--1056",

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AU - Sriphong, Lawan

AU - Sotanaphun, Uthai

AU - Limsirichaikul, Siripan

AU - Wetwitayaklung, Penpan

AU - Chaichantipyuth, Chaiyo

AU - Pummangura, Sunibhond

PY - 2003/11

Y1 - 2003/11

N2 - Three new alkaloids, 3(R)-benzoyloxy-2(R)-methyl-6(R)-(11′- oxododecyl)-piperidine (3), 5-hydroxy-2-methyl-6-(11′-oxododecyl) -pyridine (4) and 5-hydroxy-2-methyl-6-(11′-oxododecyl)-pyridine N-oxide (5), together with a known alkaloid, (-)-cassine (1), were isolated from the flowers of Senna spectabilis. A derivative, N,O-diacetylcassine (2), was semisynthesized. Their structures and stereochemistry were established on the basis of spectroscopic analysis. Cytotoxic activity and brine shrimp lethality of these compounds were evaluated. Compounds 2, 3 and 5 exhibited cytoxicity against KB cell lines with IC50 values of 5.2, 3.7 and 2.0 μg/mL, respectively.

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JO - Planta Medica

JF - Planta Medica

IS - 11

ER -

Cytotoxic Alkaloids from the Flowers of Senna spectabilis

Abstract

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