芸香科九里香属及美栌木属的化学分类

摘要/Abstract

摘要：

通过化学分析证明，美栌木与九里香属内的九里香组植物较为接近，两者均含月橘烯碱

及8-戊烯化香豆精，而棕茎组植物则与黄皮属植物亲缘关系较近。据此肯定了Tanaka的观

点，认为棕茎组比九里香组原始。黄皮族内的亲缘关系亦可作如下推断：小芸木属→山小桔

属→黄皮属→九里香属棕茎组→九里香属九里香组→美栌木属。

关键词: 化学分类, 月橘烯碱, 8-戊烯化香豆精, 黄皮族, 九里香属, 九里香组, 棕茎组, 美栌木属

Abstract:

Swingle^[14-15] divided Aurantioideac into two tribes, one of which, Clausereae was

further divided into three subtribes, namely, Micromelinae, Clauseninae and Merrilliinae. Mic-

romelinae and Merrilliinae each have one genus, whereas Clauseninae has three genera. Mor-

phologically, the Clauseneae is a natural tribe, the five genera are related in a linear sequence,

starting with Micromelum as the most primitive and progressing in sequence to Glycosmis,

Clausena, Murraya and Merrillia. Chemical studies also support this linear relationship, as

revealed by the degree of oxygenation and complexity of the 3-methyl carbazole alkaloids,

from CH₃ and C1₃ in Glycosmis to CHO and C₁₈ in Clausena and COOH and C₂₃ in Mur-

raya^[20-21]. Distribution of flavonoids also indicates the progression from Clauseninae to

Merrilliinae^[18-19].

Extensive work has been conducted on the chemistry and taxonomy of the genus Mur-

raya ^{[1,5,7-13,16]}, and the data from these studies clearly indicate the presence of two distinct

groups. Based on a combination of morphological and chemical differences, we agreed with

Tanaka^[16-17] in dividing Murraya into two sections, i.e. section Murraya and section Ber-

gera^[1].

However, our previous study^[1] has not touched on the relationship between the two sections.

Tanaka^[16-17] placed section Bergera before section Murraya, and indicated that the former is

close to Micromelum and the latter to Merrillia. Swingle^[14-15], on the other hand, put taxa of

section Murraya ahead of those of section Bergera, presumably suggesting that plants of sec-

tion Murraya are more primitive than those of section Bergera, this arrangement was followed

by Huang^[2-3]. The two conflicting viewpoints would have direct bearings on the interpreta-

tion of the trends of biogenesis of prenylated indole and carbazole alkaloids, as well as on the

weighing of the relative advancement of the morphological characters within the genus, such

as in the assignment of indices of divergence and in the construction of Wagner Divergence

Diagrams. Without more objective criteria, we find it difficult to select one of the two systems.

In order to determine the relationship between the two sections of Murraya, we decided

to study plants of related genera, with the hope that the chemical data may shed light on the

problem. A plant that attracted our attention is Merrillia caloxylon (Ridley) Swingle. So far,

only eupatorin and a few other flavonoids have been reported from the fruit of this species^[4,6].

Although Me. caloxylon belongs to Merrilliinae, a subtribe next to Clauseninae, Tanaka^[16-17]

believes that it is close to Murraya section Murraya. Swingle^[15], also suggested that this species

might have developed from the same stock that gave rise to Mu. paniculata. If their inter-

pretations were accurate, we would expect that Me. caloxylon would also contain yuehchukene

and 8-prenylated coumarins. The presence of the antiimplantation agent would not only open

up a new source of the compound but also help us judge the relationship between the two sec-

tions of Murraya. It is in this context that we studied the chemical composition of Me. calo-

xylon.

Indeed, root and stem bark of Me. caloxylon were found to contain the antiimplanta-

tion indole alkaloid yuehchukene (1), and the 8-prenylated coumarins sibiricin (II) and phe-

balosin (III), as well as 3-(3-methy1-buta-1,3-diene) indole (IV) and eupatorin (V.) Details

on the chemical profiles are reported in another paper.

Through this exercise, we have confirmed the close relationship between Merrilliinae and

Murraya section Murraya, plants of both taxa contain yuehchukene and 8-prenylated coumarins,

but no carbazole alkaloid. Root and stem bark of Me. caloxylon, like those of plants of section

Murraya, are strawcolored to pale whitish. Its leaves also bear wings along the rachis an in

Mu. alata, and the seeds are also villous. However, Me. caloxylon has long trumpetshaped flo-

wers 55-60 mm long, much larger than those found in other rutaceous plants. Its fruit is ob-

long, up to 11 cm long and 8 cm across, bearing a thick and warty pericarp, exuding a very stick

mucilage when cut, and containing numerous seeds (>30). The plant was known to exist in

the Malay Peninsula and north Sumatra^[15], but, according to David Jones (per. comm.) of

the University of Malaya, is now only available in cultivation in Malaysia and Singapore, a li-

mitation to any further exploitation as an additional source of yuehchukene.

Besides confirming the close relationship between Merrillia and section Murraya, we may

also conclude that section Bergera is close to Glycosmis and Clausena, since they are known

to contain carbazole alkaloids but no yuehchukene. Accordingly, we find Tanaka’s arrange-

ment more acceptable: plants of section Bergera are more primitive than those of section Mur-

raya, the former is close to Clausena whereas the latter (notably Mu. alata) to Merrillia. The

relationship among the gonera with in Clauseneae may be illustrated as follow: Micromelum→

Glycosmis→Clausena→Murraya sect. Bergera→Murraya sect. Murraya→Marrillia.

Accordingly, we may decide that the following character states are more primitive am-

ong plants of Murraya and Merrillia: root and stem bark dark brown, leaf rachis wingless,

flower small, fruit purple-black with few seeds, and seed coat glabrous. In contrast, straw-

colored or pale whitish bark, winged leaf rachis, large flower, red or yellow fruit with many

seeds and villous seed coat can be regarded as more advanced characters.

Acknowledgments Partial support was received from the World Health Organiz-

ation Special Programme on Human Reproduction and the Kevin Hsu Research Fund (to YCK)

and Commonwealth Science Council (to PPHB). The staff of the Singapore Botanic Gardens

and the Forest Research Institute of Malaysia are thanked for their assistance in collecting plant

material.

Key words: Chemotaxonomy, yuehchukene, 8-prenylated coumarin, Clauseneae, Murraya

毕培曦, 江润祥, 李钳, 张宏达, Chang Kiaw-Lan, Wong Khoon-Meng, Gray Alexander I., Waterman Peter G.. 芸香科九里香属及美栌木属的化学分类[J]. 中国科学院大学学报.

But Paul Pui-Hay, Kong Yun-Cheung, Li Qian, Chang Hong-Ta, Chang Kiaw-Lan, Wong Khoon-Meng, Gray Alex,er I., Waterman Peter G.. Chemotaxonomic Relationship Between Murraya and Merrillia (Rutaceae)[J]. .

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芸香科九里香属及美栌木属的化学分类

Chemotaxonomic Relationship Between Murraya and Merrillia (Rutaceae)

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