New Clerodane and Halimane Diterpenes from the Leaves and Woody Stems of Casearia grayi (Flacourtiaceae/Salicaceae)

Abstract

The leaves and woody stems of Casearia grayi (Flacourtiaceae/Salicaceae) have yielded several known flavone glycosides and a number of clerodane and halimane diterpenes, which were characterized mainly by analysis of NMR spectra. New compounds were identified as (rel)-2(R)-hydroxy-18(S),19(R)-diacetoxy-18,19-epoxy-4(S),5(S),8(S),9(S),10(R)-clerodan-13(16),14-dien-6-one (1), (rel)-2(R),18(S),19(R)-triacetoxy-18,19-epoxy-4(S),5(S),8(S),9(S),10(R)-clerodan-13(16),14-dien-6-one (4), (rel)-2(R)-hydroxy-18(S),19(R)-diacetoxy-18,19-epoxy-4(S),5(S),8(S),9(S),10(R)-clerodan-12(E),14-dien-6-one (7), (rel)-18(S),19(R)-diacetoxy-18,19-epoxy-2(R)-hydroxy-4(S),5(R),8(S),9(S),10(R)-clerodan-12(E),14-diene (8), and 16-hydroxy-halima-5(10),13(E)-dien-15-oic acid (9).

Keywords

Casearia grayi Flacourtiaceae Salicaceae clerodane diterpenes halimane diterpenes

References

Jessup

. (1984) Celastraceae. In: George

(Ed). Flora of Australia 22, ABRS: Canberra, 150–184.

Chase

, Zmaezty

, Lledo

, Wurdack

, Swensen

, Fay

. (2002) When in doubt, put it in Flacourtiaceae: a molecular phylogenetic analysis based on plastid rbcl DNA sequences. Kew Bulletin, 57, 141–181.

Mosaddik

, Banbury

, Forster

, Booth

, Leach

, Waterman

. (2004) Screeniing of some Australian Flacourtiaceae species for in vitro antioxidant, cytotoxic and antimicrobial activity. Phytomedicine, 11, 461–466.

Khan

, Gray

, Reed

, Sadler

, Waterman

. (1990) Diterpenes from Zuelania guidonia. Phytochemistry, 29, 1609–1614.

Khan

, Gray

, Sadler

, Waterman

. (1990) Clerodane diterpenes from Casearia corymbosa stem bark. Phytochemistry, 29, 3591–3595.

Chen

T-B

, Wiemer

. (1991) Corymbotins A-I: Highly oxidized kolovane derivatives from Casearia corymbosa. Journal of Natural Products, 54, 1612–1618.

Gibbons

, Gray

, Waterman

. (1996) Clerodane diterpenes from the leaves of Laetia procera. Phytochemistry, 43, 635–638.

Hunter

, Corley

, Carron

, Rowold

, Kilpatrick

, Durley

. (1997) Four new clerodane diterpenes from the leaves of Casearia guianensis which inhibit the interaction of leukocyte function antigen 1 with intercellular adhesion molecule 1. Journal of Natural Products, 60, 894–899.

Beutler

, McCall

, Herbert

, Herald

, Pettit

, Johnson

, Shoemaker

, Boyd

. (2000) Novel cytotoxic diterpenes from Casearia arborea. Journal of Natural Products, 63, 657–661.

10.

Prakash

CVS

, Hoch

, Kingston

DGI

. (2002) Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascan rainforest. Journal of Natural Products, 65, 100–107.

11.

Hara

, Asaki

, Fujimoto

, Gupta

, Singh

, Sahai

(1995) Clerodane and ent-halimane diterpenes from Polyalthia longifolia. Phytochemistry, 38, 189–194.

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