Macrocyclic Diterpenoids from the Latex of Euphorbia helioscopia

Abstract

One new jatrophane diterpenoid, 7α,9β,15β-triacetoxy-3β-benzoyloxy-14β-hydroxyjatropha-5E,11 E-diene (3), together with four known macrocyclic diterpenoids, euphoheliosnoid A (1), epieuphoscopin B (2), euphohelioscopin A (4) and euphoscopin C (5), were isolated from the stem latex of Euphorbia helioscopia. Their structures were established by spectroscopic analyses. In the anti-inflammatory assay, euphohelioscopin A (4) exhibited moderate inhibitory activity on the release of cytokine TNF-α (IC₅₀ = 23.7 ± 1.7 μM), IL-6 (IC₅₀ = 46.1 ± 1.1 μM) and chemokine MCP-1 (IC₅₀ = 33.7 ± 3.8 μM) in lipopolysaccharide (LPS) induced RAW 264.7 macrophages without notable cytotoxicity (IC₅₀ > 80 μM).

Keywords

Euphorbia helioscopia Latex Jatrophane diterpenoid Lathyrane diterpenoid Anti-inflammatory activity

References

Konno

(2011) Plant latex and other exudates as plant defense systems: Roles of various defense chemicals and proteins contained therein. Phytochemistry, 72, 1510–1530.

Agrawal

, Konno

(2009) Latex: a model for understanding mechanisms, ecology, and evolution of plant defense against herbivory. Annual Review of Ecology and Systematics, 40, 311–331.

Wang

, Wang

, Liu

, Qin

, Kang

. (2015) Tigliane diterpenoids from the Euphorbiaceae and Thymelaeaceae families. Chemical Reviews, 115, 2975–3011.

Feng

, Liu

, Chen

, Guo

, You

. (2007) Five novel prenylated xanthones from Resina Garciniae. Journal of Asian Natural Products Research, 9, 735–741.

Shi

, Su

, Kiyota

(2008) Chemical and pharmacological research of the plants in genus Euphorbia. Chemical Reviews, 108, 4295–4327.

Vasas

, Hohmann

(2014) Euphorbia diterpenes: isolation, structure, biological activity, and synthesis (2008–2012). Chemical Reviews, 114, 8579–8612.

Fernandez-Arche

, Saenz

, Arroyo

, de la Puerta

, Garcia

. (2010) Topical anti-inflammatory effect of tirucallol, a triterpene isolated from Euphorbia lactea latex. Phytomedicine, 17, 146–148.

Fatope

, Zeng

, Ohayaga

, Shi

, McLaughlin

. (1996) Selectively cytotoxic diterpenes from Euphorbia poisonii. Journal of Medicinal Chemistry, 39, 1005–1008.

Chen

, Wang

, Yang

, Jin

, Yang

, Wang

, Xu

, Ohizumi

, Guo

. (2014) Diterpenes inhibiting NO production from Euphorbia helioscopia. Fitoterapia, 95, 133–138.

10.

Cateni

, Zilic

, Altieri

, Zacchigna

, Procida

, Gaggeri

, Rossi

, Collina

(2014) Lipid metabolites with free-radical scavenging activity from Euphorbia helioscopia L. Chemistry and Physics of Lipids, 181, 90–98.

11.

, Guan

, Li

, Chen

, Zhang

, Huang

, Liu

, Guo

. (2008) Cytotoxic diterpenoids from Euphorbia helioscopia. Journal of Natural Products, 71, 873–876.

12.

Zhang

, Guo

. (2006) Chemical studies on the constituents of the Chinese medicinal herb Euphorbia helioscopia L. Chemical & Pharmaceutical Bulletin, 54, 1037–1039.

13.

Zhang

, Guo

. (2005) Three new jatrophone-type diterpenoids from Euphorbia helioscopia. Planta Medica, 71, 283–286.

14.

Tao

, Hao

, Liu

, Zhu

. (2008) Cytotoxic macrocyclic diterpenoids from Euphorbia helioscopia. Archives of Pharmacal Research, 31, 1547–1551.

15.

Yamamura

, Shizuri

, Kosemura

, Ohtsuka

, Tayama

, Ohba

, Ito

, Saito

, Terada

(1989) Diterpenes from Euphorbia helioscopia. Phytochemistry, 28, 3421–3436.

16.

Chen

, Tong

, Feng

, Wu

, Zhao

, Ruan

, Pi

, Zhang

(2015) Ursane-type nortriterpenes with a five-membered A-ring from Rubus innominatus. Phytochemistry, 116, 329–336.

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