Vitexlactam A, a novel labdane diterpene lactam from the fruits of Vitex agnus-castus

Sheng Hong Li; Hongjie Zhang; Sheng Xiang Qiu; Xue Mei Niu; Bernard D. Santarsiero; Andrew D. Mesecar; Harry H.S. Fong; Norman R. Farnsworth; Han Dong Sun

doi:10.1016/S0040-4039(02)00981-4

Vitexlactam A, a novel labdane diterpene lactam from the fruits of Vitex agnus-castus

Sheng Hong Li
, Hongjie Zhang
, Sheng Xiang Qiu^*
, Xue Mei Niu
, Bernard D. Santarsiero
, Andrew D. Mesecar
, Harry H.S. Fong
, Norman R. Farnsworth
, Han Dong Sun

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

60 Citations (Scopus)

Abstract

A novel labdane diterpene alkaloid, vitexlactam A (1) was isolated as a prism from the n-hexane extract of the fruits of Vitex agnus-castus through normal and reverse phase column chromatography. Its structure was elucidated to be 6β-acetoxy-9α-hydroxy-13(14)-labden-16,15-amide, based on chemical and spectral evidences including 1D and 2D NMR spectra. The structure was confirmed by X-ray crystallographic analysis. Compound 1 is the first naturally occurring labdane diterpenoid containing an α,β-unsaturated γ-lactam moiety.

Original language	English
Pages (from-to)	5131-5134
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4039(02)00981-4
Publication status	Published - 15 Jul 2002

User-Defined Keywords

Labdane diterpene
Lactam
NMR
Verbenaceae
Vitex agnus-castus
Vitexlactam A
X-ray

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10.1016/S0040-4039(02)00981-4

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title = "Vitexlactam A, a novel labdane diterpene lactam from the fruits of Vitex agnus-castus",

abstract = "A novel labdane diterpene alkaloid, vitexlactam A (1) was isolated as a prism from the n-hexane extract of the fruits of Vitex agnus-castus through normal and reverse phase column chromatography. Its structure was elucidated to be 6β-acetoxy-9α-hydroxy-13(14)-labden-16,15-amide, based on chemical and spectral evidences including 1D and 2D NMR spectra. The structure was confirmed by X-ray crystallographic analysis. Compound 1 is the first naturally occurring labdane diterpenoid containing an α,β-unsaturated γ-lactam moiety.",

keywords = "Labdane diterpene, Lactam, NMR, Verbenaceae, Vitex agnus-castus, Vitexlactam A, X-ray",

author = "Li, \{Sheng Hong\} and Hongjie Zhang and Qiu, \{Sheng Xiang\} and Niu, \{Xue Mei\} and Santarsiero, \{Bernard D.\} and Mesecar, \{Andrew D.\} and Fong, \{Harry H.S.\} and Farnsworth, \{Norman R.\} and Sun, \{Han Dong\}",

note = "Funding Information: The authors wish to thank the members of the analytical group of Phytochemistry Laboratory of Kunming Institute of Botany, Academic Sinica, for measurements of the NMR, MS, IR, UV and ORD spectral data, and Dr. Phillip E. Fanwick from the Department of Chemistry, Purdue University, for collecting the X-ray diffraction data. X-Ray analysis was made possible through partial funding by grant P50 AT00155 through the National Center for Complementary and Alternative Medicine (NCCAM), the Office of Dietary Supplements (ODS), the National Institute of General Medicine (NIGMS), and the Office for Research on Women's Health (ORWH). Contents are solely the responsibility of the authors and do not necessarily represent the official views of NCCAM, ODS, NIGMS, or ORWH.",

year = "2002",

month = jul,

day = "15",

doi = "10.1016/S0040-4039(02)00981-4",

language = "English",

volume = "43",

pages = "5131--5134",

journal = "Tetrahedron Letters",

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T1 - Vitexlactam A, a novel labdane diterpene lactam from the fruits of Vitex agnus-castus

AU - Li, Sheng Hong

AU - Zhang, Hongjie

AU - Qiu, Sheng Xiang

AU - Niu, Xue Mei

AU - Santarsiero, Bernard D.

AU - Mesecar, Andrew D.

AU - Fong, Harry H.S.

AU - Farnsworth, Norman R.

AU - Sun, Han Dong

N1 - Funding Information: The authors wish to thank the members of the analytical group of Phytochemistry Laboratory of Kunming Institute of Botany, Academic Sinica, for measurements of the NMR, MS, IR, UV and ORD spectral data, and Dr. Phillip E. Fanwick from the Department of Chemistry, Purdue University, for collecting the X-ray diffraction data. X-Ray analysis was made possible through partial funding by grant P50 AT00155 through the National Center for Complementary and Alternative Medicine (NCCAM), the Office of Dietary Supplements (ODS), the National Institute of General Medicine (NIGMS), and the Office for Research on Women's Health (ORWH). Contents are solely the responsibility of the authors and do not necessarily represent the official views of NCCAM, ODS, NIGMS, or ORWH.

PY - 2002/7/15

Y1 - 2002/7/15

N2 - A novel labdane diterpene alkaloid, vitexlactam A (1) was isolated as a prism from the n-hexane extract of the fruits of Vitex agnus-castus through normal and reverse phase column chromatography. Its structure was elucidated to be 6β-acetoxy-9α-hydroxy-13(14)-labden-16,15-amide, based on chemical and spectral evidences including 1D and 2D NMR spectra. The structure was confirmed by X-ray crystallographic analysis. Compound 1 is the first naturally occurring labdane diterpenoid containing an α,β-unsaturated γ-lactam moiety.

AB - A novel labdane diterpene alkaloid, vitexlactam A (1) was isolated as a prism from the n-hexane extract of the fruits of Vitex agnus-castus through normal and reverse phase column chromatography. Its structure was elucidated to be 6β-acetoxy-9α-hydroxy-13(14)-labden-16,15-amide, based on chemical and spectral evidences including 1D and 2D NMR spectra. The structure was confirmed by X-ray crystallographic analysis. Compound 1 is the first naturally occurring labdane diterpenoid containing an α,β-unsaturated γ-lactam moiety.

KW - Labdane diterpene

KW - Lactam

KW - NMR

KW - Verbenaceae

KW - Vitex agnus-castus

KW - Vitexlactam A

KW - X-ray

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U2 - 10.1016/S0040-4039(02)00981-4

DO - 10.1016/S0040-4039(02)00981-4

M3 - Journal article

AN - SCOPUS:0037100013

SN - 0040-4039

VL - 43

SP - 5131

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Vitexlactam A, a novel labdane diterpene lactam from the fruits of Vitex agnus-castus

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