Chemical Constituents of Two Chinese Magnoliaceae Plants, Tsoongiodendron odorum and Manglietiastrum sinicum, and their Inhibition of Platelet Aggregation

Abstract

Phytochemical investigations of Tsoongiodendron odorum and Manglietiastrum sinicum, both Magnoliaceae, led to the isolation of twenty compounds in total. Among them, one was a new sesquiterpene, 11-O-oleoyl-β-eudesmol (2), and another, 1-(3,4-dimethoxypheny)-4-(3,4-methylenedioxyphenyl)-2,3-dimethylbutane (12) was isolated as a natural product for the first time. Moreover, ¹³C-NMR spectral data of isoguaiacin (16) are reported here for the first time. Structure elucidations for compounds reported here were mainly based on their spectral data. The ethanolic extracts of T. odorum and M. sinicum, and six pure compounds, 4(15)-eudesmen-11-ol (β-eudesmol) (1), 1β-hydroxy-4(15),11(13)-eudesmadien-12,6α-olide (reynosin) (3), 3,11(13)-eudesmadien-12,6α-olide (α-cyclocostunolide) (5), erythro-1-(4-hydroxy-3-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-2,3-dimethylbutane (11), nectandrin-B (18), and syringaresinol (19), displayed considerable inhibition against platelet aggregation induced by AA, by ADP, or by PAF.

Key words

Tsoongiodendron odorum - Manglietiastrum sinicum - Magnoliaceae - chemical constituents - inhibition - platelet aggregation

References

• 1 Law  Y W.. A preliminary study on the taxonomy of the family Magnoliaceae.  Zhiwu Fenlei Xuebao (Acta Phytotoaxonomica Sinica). 1984;;  22 89-109
• 2 Born  G VR.. Aggregation of blood platelets by adenosine diphosphate and its reversal.  Nature. 1962;;  194 927-9
• 3 Zhao  Q,, Hao  X J,, Chen  Y Z,, Zou  C.. Sesquiterpenoids from Hedychium yunnanense. .  Yunnan Zhiwu Yanjiu (Acta Botanic Yunnanica). 1995;;  17 201-3, and references cited therein
• 4 Batchelor  J G,, Cushley  R J,, Prestegard  J H.. Carbon-13 fourier transform nuclear magnetic resonance VIII, role of steric and electric field effects in fatty acid spectra.  Journal of Organic Chemistry. 1974;;  39 1698-705
• 5 Nakatani  N,, Ikeda  K,, Kikuzaki  H,, Kido  M,, Yamaguchi  Y.. Diaryldimethylbutane lignans from Myristica argentea and their antimicrobial action against Streptococcus mutans. .  Phytochemistry. 1988;;  27 3127-9
• 6 Martinez  V JC,, Yoshida  M,, Gottlieb  O R.. Arylnaphthalene neolignans from Virola calophylla. .  Phytochemistry. 1990;;  29 2655-2657
• 7 Kato  M J,, Yoshida  M,, Gottlieb  O R.. Lignoids and arylalkanones from fruits of Virola elongata. .  Phytochemistry. 1990;;  29 1799-810
• 8 Wu  T S,, Leu  Y L,, Chan  Y Y,, Yu  S M,, Teng  C M,, Su  J D.. Lignans and an aromatic acid from Cinnamomum philippinense. .  Phytochemistry. 1994;;  36 785-8
• 9 Konno  C,, Lu  Z Z,, Xue  H Z,, Erdelmeier  C AJ,, Meksuriyen  D,, Che  C T,, Cordell  G A,, Soejarto  D D,, Waller  D P,, Fong  H S.. Furanoid lignans from Larrea tridentata. .  Journal of Natural Products. 1990;;  53 396-406, and references cited therein
• 10 Yoshioka  H,, Renold  W,, Fischer  N H,, Higo  A,, Mabry  T J.. Sesquiterpene lactones from Ambrosia confertiflora (Compositae).  Phytochemistry. 1970;;  9 823-32
• 11 Govindan  S V,, Bhattacharyya  S C.. Alantolides and cyclocostunolides from Saussurea lappa Clarke (costus root).  Indian Journal of Chemistry. 1977;;  15B 956-7
• 12 Pascual  T JD,, Bellido  I S,, Gonzalez  M S.. Chenopodiaceae components: polyoxygenated sesquiterpenes from Chenopodium botrys. .  Tetrahedron. 1980;;  36 371-6
• 13 Ruangrungsi  N,, Rivepiboon  A,, Lange  G,, Lee  M,, Decicco  C P,, Picha  P,, Preechanukool  K.. Constituents of Paramichelia baillonii:.  A new antitumor germacranolide alkaloid.. Journal of Natural Products  1987;;  50 891-6
• 14 Shimomura  H,, Sashida  Y,, Oohara  M.. Lignans from Machilus thunberghii. .  Phytochemistry. 1987;;  26 1513-5
• 15 Gnabre  J N,, Ito  Y,, Ma  Y,, Huang  R C.. Isolation of anti-HIV-1 lignans from Larrea tridentata by counter-current chromatography.  Journal of Chromatography A. 1996;;  719 353-64
• 16 Caffrey  P B,, Christen  R D,, Sachdev  O P,, Khandwala  A,, Howell  S B.. Modulation of vinblastine pharmacology in human tumor cells by meso-nordihydroguaiaretic acid.  Cell Pharmacol.. 1995;;  2 75-80. CA 122: 255750z
• 17 Liu  J S,, Huang  M F.. Studies on the constituents of Schisandra sphenanthera Rehd. et Wils.  Huaxue Xuebao (Acta Chimica Sinica). 1984;;  42 264-70
• 18 Shimomura  H,, Sashida  Y,, Oohara  M.. Lignans from Machilus thunbergii. .  Phytochemistry. 1988;;  7 634-6
• 19 Chang  F R,, Chao  Y C,, Teng  C M,, Wu  Y C.. Chemical constituents from Cassytha filiformis II.  Journal of Natural Products. 1998;;  61 863-6
• 20 Braquet  P,, Touqui  L,, Shen  T Y,, Vargaftig  B B.. Perspectives in platelet-activating factor research.  Pharmacol. Rev.. 1987;;  39 97-145