Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities

Jia Han Xia; Shou De Zhang; Yong Li Li; Liang Wu; Zhi Jun Zhu; Xian Wen Yang; Hua Wu Zeng; Hong Lin Li; Ning Wang; Andre Steinmetz; Wei Dong Zhang

doi:10.1016/j.phytochem.2011.11.011

Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities

Jia Han Xia, Shou De Zhang, Yong Li Li, Liang Wu, Zhi Jun Zhu, Xian Wen Yang^*, Hua Wu Zeng, Hong Lin Li, Ning Wang, Andre Steinmetz, Wei Dong Zhang

^*Corresponding author for this work

Department of Cancer Research

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

49 Citations (Scopus)

Abstract

Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC ₅₀ value of 113.1 μM. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC ₅₀ values of 0.9, 4.2, and 2.0 μM, respectively. (23R,25R)-3,4-seco-9βH-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC ₅₀ = 14.7 μM).

Original language	English
Pages (from-to)	178-184
Number of pages	7
Journal	Phytochemistry
Volume	74
DOIs	https://doi.org/10.1016/j.phytochem.2011.11.011
Publication status	Published - Feb 2012

Keywords

Abies holophylla
Cytotoxicity
Electronic circular dichroism (ECD)
Nitric oxide (NO)
Pinaceae
Sesquiterpenoids
Triterpenoids

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10.1016/j.phytochem.2011.11.011

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title = "Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities",

abstract = "Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC 50 value of 113.1 μM. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC 50 values of 0.9, 4.2, and 2.0 μM, respectively. (23R,25R)-3,4-seco-9βH-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC 50 = 14.7 μM).",

keywords = "Abies holophylla, Cytotoxicity, Electronic circular dichroism (ECD), Nitric oxide (NO), Pinaceae, Sesquiterpenoids, Triterpenoids",

author = "Xia, {Jia Han} and Zhang, {Shou De} and Li, {Yong Li} and Liang Wu and Zhu, {Zhi Jun} and Yang, {Xian Wen} and Zeng, {Hua Wu} and Li, {Hong Lin} and Ning Wang and Andre Steinmetz and Zhang, {Wei Dong}",

note = "Funding Information: This work was supported by the Shanghai Leading Academic Discipline Project (B906), the Special Program for New Drug Innovation of the Ministry of Science and Technology, China ( 2009ZX09308-005 ), the National Natural Science Foundation of China ( 41176148 , 21002110 , 30725045 ), and the FP7 People Work Program (FP7-People-IRSES-2008, No. 230232). ",

year = "2012",

month = feb,

doi = "10.1016/j.phytochem.2011.11.011",

language = "English",

volume = "74",

pages = "178--184",

journal = "Phytochemistry",

issn = "0031-9422",

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T1 - Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities

AU - Xia, Jia Han

AU - Zhang, Shou De

AU - Li, Yong Li

AU - Wu, Liang

AU - Zhu, Zhi Jun

AU - Yang, Xian Wen

AU - Zeng, Hua Wu

AU - Li, Hong Lin

AU - Wang, Ning

AU - Steinmetz, Andre

AU - Zhang, Wei Dong

N1 - Funding Information: This work was supported by the Shanghai Leading Academic Discipline Project (B906), the Special Program for New Drug Innovation of the Ministry of Science and Technology, China ( 2009ZX09308-005 ), the National Natural Science Foundation of China ( 41176148 , 21002110 , 30725045 ), and the FP7 People Work Program (FP7-People-IRSES-2008, No. 230232).

PY - 2012/2

Y1 - 2012/2

N2 - Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC 50 value of 113.1 μM. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC 50 values of 0.9, 4.2, and 2.0 μM, respectively. (23R,25R)-3,4-seco-9βH-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC 50 = 14.7 μM).

AB - Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC 50 value of 113.1 μM. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC 50 values of 0.9, 4.2, and 2.0 μM, respectively. (23R,25R)-3,4-seco-9βH-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC 50 = 14.7 μM).

KW - Abies holophylla

KW - Cytotoxicity

KW - Electronic circular dichroism (ECD)

KW - Nitric oxide (NO)

KW - Pinaceae

KW - Sesquiterpenoids

KW - Triterpenoids

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U2 - 10.1016/j.phytochem.2011.11.011

DO - 10.1016/j.phytochem.2011.11.011

M3 - Article

C2 - 22169016

AN - SCOPUS:84855939760

SN - 0031-9422

VL - 74

SP - 178

EP - 184

JO - Phytochemistry

JF - Phytochemistry

ER -

Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities

Abstract

Keywords

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