Chemical Constituents from Alnus formosana Burk. II. Polar Constituents from the Leaves

Abstract

This study was aimed to explore the n-BuOH soluble constituents of the leaves of Alnus formosana Burk. A total of 13 compounds were isolated and characterized. Of these, 2″'-cinnamoyloregonin is a new diaryl heptanoid glycoside. Ten of the remaining twelve known compounds, i.e. platyphylloside, aceroside VII, myzodendrone, quercetin, kaempferol-3-O-rhamnoside, quercetin-3-O-rhamnoside, quercetin-3-O-glucoside, rhamnetin-3-O-rhamnoside, inositol, and shikimic acid, are reported for the first time for an Alnus species. The structures were characterized by spectral analysis.

Keywords

Alnus formosana Betulaceae leaves diarylheptanoid 2″'-cinnamoyloregonin flavonoid

References

Aoki

, Ohta

, Suga

(1990) Triterpenoids, diarylheptanoids and their glycosides in the flowers of Alnus species. Phytochemistry, 29, 3611–3614.

Hirata

, Murai

, Suga

(1977) Structure of alnuserol, the first reported naturally occurring 11-hydroxylated C₃₁-dammarane-type triterpene. Chemistry Letters, 50, 95–98.

Suga

, Ohta

, Hirata

, Aoki

(1982) The absolute configuration of diarylheptanoid xyloside, oregonin, isolated from the female flowers of Alnus serrulatoides. Chemistry Letters, 55, 895–898.

Lee

, Kim

, Jeong

, Ahn

, Toh

, Surh

. (2000) Inhibition of cyclooxygenase-2 expression by diarylheptanoids from the bark of Alnus hirsuta var. sibirica. Biological and Pharmaceutical Bulletin, 23, 517–518.

Liao

. (1996) Betulaceae. In Flora of Taiwan. 2^nd Ed. Vol. 2, Huang

. (Editor-in Chief). Editorial Committee of the Flora of Taiwan, Taipei, Taiwan. 44–45.

Chen

, Tuh

, Chen

, Kuo

, Lee

. (2006) Triterpenoids and sterols from the stems of Alnus formosana Burk. Natural Product Communications, 1, 291–293.

Ohta

, Koyama

, Aoki

, Suga

(1985) Absolute configuration of platyphylloside and (-)-centrolobol. Bulletin of the Chemical Society of Japan, 58, 2423–2424.

Smite

, Lundgren

, Anderson

(1993) Arylbutanoid and diarylheptanoid glycosides from inner bark of Betula pendula. Phytochemistry, 32, 365–369.

Fuchino

, Konishi

, Tanaka

(1996) Chemical evaluation of Betula species in Japan. II. Constituents of Betula patyphlla var. Japonica. Chemical and Pharmaceutical Bulletin, 44, 1033–1038.

10.

Nagai

, Kenmochi

, Fujita

, Furukawa , Inoue

(1986) Studies on the constituents of Aceraceae plants. VI. Revised stereochemistry of (-)-centrolobol, and new glycosides from Acer nikoense. Chemical and Pharmaceutical Bulletin, 34, 1056–1060.

11.

Pabst

, Barron

, Schreier

(1990) Phenylbutan-2-one β-D-glucosides from raspberry fruit. Phytochemistry, 29, 3853–3858.

12.

Reyrs

, Munoz

, Cox

(1986) Chemistry of Myzodendraceae, I. Myzodendrone, a new phenylbutanone of Myzodendron punctulatum. Journal of Natural Products, 49, 318–320.

13.

Lee

, Wang

, Chen

KCS

. (1995) Chemical constituents from the roots of Zizyphus jujube Mill. var. spinosa (I). Journal of the Chinese Chemical Society, 42, 77–82 and references cited therein.

14.

Fossen

, Larsen

, Kirenire

. (1999) Flavonoids from blue flowers of Nymphaea caerulea. Phytochemistry, 51, 1133–1137.

15.

Zhong

, Otsuka

, Takeda

(1997) Three flavonol glycosides from leaves of Myrsine seguinii. Phytochemistry, 46, 943–946.

16.

Fukunaga

, Nishiya

, Watanabe

(1988) Chemical studies on the constituents of Hyphear tanakae hosokawa from different host trees. Chemical and Pharmaceutical Bulletin, 36, 1180–1184.

17.

Breitmaier

, Voelter

(1990) Carbon-13 NMR spectroscopy. 3^rd Ed. VCH, Weinheim Germany. 401.

18.

Seidel

, Bailleul

, Waterman

. (1999) Partially acetylated tri- and tetrarhamnoside dodecanyl ether derivatives from Cleistopholis patens. Phytochemistry, 52, 465–472.

19.

Dictionary of Natural Product on CD-ROM, (2005) Version 14:1, Chapman and Hall/ CRC, London UK.

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