Furanosesquiterpenoids of Commiphora myrrha

N. Zhu; H. Kikuzaki; S. Sheng; S. Sang; M. M. Rafi; M. Wang; N. Nakatani; R. S. DiPaola; R. T. Rosen; C. T. Ho

doi:10.1021/np010072j

Furanosesquiterpenoids of Commiphora myrrha

N. Zhu, H. Kikuzaki, S. Sheng, S. Sang, M. M. Rafi, M. Wang, N. Nakatani, R. S. DiPaola, R. T. Rosen, C. T. Ho

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

56 Scopus citations

Abstract

An investigation on the gum exudates of Commiphora myrrha has led to the isolation of six sesquiterpenoids. On the basis of spectroscopic data interpretation, they were determined as two new furanosesquiterpenoids, rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one (1) and rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (2), and four known furanosesquiterpenoids, rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one(3),rel-2R-methoxy-4R- furanogermacr-1(10)E-en-6-one(4),furanogermacra-1(10)Z,4Z-dien-6-one, 1(10)Z,4Z-dien-6-one, and curzerenone [6,7-dihydro-5β-isopropenyl-3,6β-dimethyl-6-vinylbenzofuran- 4(5H)-one]. This is the first report of the relative stereochemistry for the known compounds 3 and 4. Compound 1 exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a clonogenic assay, while the other five compounds were inactive in this assay.

Original language	English
Pages (from-to)	1460-1462
Number of pages	3
Journal	Journal of Natural Products
Volume	64
Issue number	11
DOIs	https://doi.org/10.1021/np010072j
State	Published - 2001

ASJC Scopus subject areas

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

Access to Document

10.1021/np010072j

Cite this

@article{3cf789323f1e4f7b9ec1a7fddfd4daae,

title = "Furanosesquiterpenoids of Commiphora myrrha",

abstract = "An investigation on the gum exudates of Commiphora myrrha has led to the isolation of six sesquiterpenoids. On the basis of spectroscopic data interpretation, they were determined as two new furanosesquiterpenoids, rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one (1) and rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (2), and four known furanosesquiterpenoids, rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one(3),rel-2R-methoxy-4R- furanogermacr-1(10)E-en-6-one(4),furanogermacra-1(10)Z,4Z-dien-6-one, 1(10)Z,4Z-dien-6-one, and curzerenone [6,7-dihydro-5β-isopropenyl-3,6β-dimethyl-6-vinylbenzofuran- 4(5H)-one]. This is the first report of the relative stereochemistry for the known compounds 3 and 4. Compound 1 exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a clonogenic assay, while the other five compounds were inactive in this assay.",

author = "N. Zhu and H. Kikuzaki and S. Sheng and S. Sang and Rafi, {M. M.} and M. Wang and N. Nakatani and DiPaola, {R. S.} and Rosen, {R. T.} and Ho, {C. T.}",

year = "2001",

doi = "10.1021/np010072j",

language = "English",

volume = "64",

pages = "1460--1462",

number = "11",

}

TY - JOUR

T1 - Furanosesquiterpenoids of Commiphora myrrha

AU - Zhu, N.

AU - Kikuzaki, H.

AU - Sheng, S.

AU - Sang, S.

AU - Rafi, M. M.

AU - Wang, M.

AU - Nakatani, N.

AU - DiPaola, R. S.

AU - Rosen, R. T.

AU - Ho, C. T.

PY - 2001

Y1 - 2001

N2 - An investigation on the gum exudates of Commiphora myrrha has led to the isolation of six sesquiterpenoids. On the basis of spectroscopic data interpretation, they were determined as two new furanosesquiterpenoids, rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one (1) and rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (2), and four known furanosesquiterpenoids, rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one(3),rel-2R-methoxy-4R- furanogermacr-1(10)E-en-6-one(4),furanogermacra-1(10)Z,4Z-dien-6-one, 1(10)Z,4Z-dien-6-one, and curzerenone [6,7-dihydro-5β-isopropenyl-3,6β-dimethyl-6-vinylbenzofuran- 4(5H)-one]. This is the first report of the relative stereochemistry for the known compounds 3 and 4. Compound 1 exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a clonogenic assay, while the other five compounds were inactive in this assay.

AB - An investigation on the gum exudates of Commiphora myrrha has led to the isolation of six sesquiterpenoids. On the basis of spectroscopic data interpretation, they were determined as two new furanosesquiterpenoids, rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one (1) and rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (2), and four known furanosesquiterpenoids, rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one(3),rel-2R-methoxy-4R- furanogermacr-1(10)E-en-6-one(4),furanogermacra-1(10)Z,4Z-dien-6-one, 1(10)Z,4Z-dien-6-one, and curzerenone [6,7-dihydro-5β-isopropenyl-3,6β-dimethyl-6-vinylbenzofuran- 4(5H)-one]. This is the first report of the relative stereochemistry for the known compounds 3 and 4. Compound 1 exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a clonogenic assay, while the other five compounds were inactive in this assay.

UR - http://www.scopus.com/inward/record.url?scp=0035195802&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035195802&partnerID=8YFLogxK

U2 - 10.1021/np010072j

DO - 10.1021/np010072j

M3 - Article

C2 - 11720534

AN - SCOPUS:0035195802

SN - 0163-3864

VL - 64

SP - 1460

EP - 1462

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 11

ER -

Furanosesquiterpenoids of Commiphora myrrha

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this