From the diterpenic fraction of the wood of Juniperus rigida there were isolated: ferruginol, cryptojaponol, sugiol, δ⁶-dehydroferruginol, xanthoperol, and new diterpenes, 12-hydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial, 6,12-dihydroxy-5,8,11,13-abietatetraen-7-one, 12-rnethoxy-8,11,13-abietatriene-7β,11-diol, 12-methoxy-6,8,11,13-abietatetraen-11-ol, 7β,12-dimethoxy-8,11,13-abietatrien-11-ol and 7β-ethoxy-12-methoxy-8,11,13-abietatrien-11-ol.

   Three triterpenes, named gracilol-A, -B and -C, having dammarane skeleton, have been isolated as main constituents from Dipterocarpus gracilis. The structure of gracilol-A, -B and -C were 25-hydroxy-dammar-20(22)-ene-3-one (II), 20,25-dihydroxy-dammar-3-one (IX) and 3β,25-dihydroxy-dammarane (XI), respectively, which were derived on the basis of the partial synthesis from dipterocarpol (V) and spectroscopic evidences.

   Unusually low brightness and intense colour reversion are the characteristic feature of the bleached sulphate pulps (BKP) prepared from the woods especially the heartwoods of Sugi (Cryptomeria japonica D. Don.). These unfavourable properties, however, can be completely improved by extraction of either the wood chips or the unbleached sulphate pulps (UKP) with methanol prior to the following treatments, namely cooking or bleaching, respectively. The facts may be ascribed to the occurrence of a new type of pitch troubles. The major cause for the low brightness and the intense colour reversion was shown to be a diterpenoid phenol, ferruginol present as a part of the resin particles spreading on the fiber surface. Colouring and condensation of the extractives accompanied by insolubilization to organic solvents were proved both chemically and microscopically to occur by the treatment with chlorine dioxide in the five-stage bleaching.

   An explanation of the chemical components of the heartwood of Agathis is given. The methanol extract comprised 80% of the total weight of the extracts (hexane, ether, and methanol) and included several compounds as main constituents as determined by gas chromatography (GC) analysis. As phenolic compounds, hinokiresinol (S3) and monomethoxyhinokiresinol (S2) were identified. As terpenoids, araucarol (S4) was identified, and two other tricyclic diterpentriols (S6) and (S7) were identified tentatively. The existence of polyphenolic compounds in the methanol extract also is explained. These compounds comprise about 80% of the total extracts. ¹³CNMR (nuclear magnetic resonance) of whole methanol extract showed a reasonable spectrum for the above results.

   Interactions between the inorganics and MeOH extractives and fractions from pokasa were found by the determination of the changes both in turbidity and in amounts of inorganics adsorbed in the aggregates. Results showed that Ca++ among the inorganics was the main factor for the speck formation. The acidic fraction (Fr.A) in the extractives was shown to have the greatest potential to form aggregates with Ca⁺⁺, but in smallest amounts. Moreover, the co-existence of Fr.A with either the neutrals (Fr.N) or the phenols (Fr.P), namely N + A and N + P + A, resulted in a large synergistic effect on the aggregate formation. Therefore, each and every fraction played an important role.
   On the other hand, the presence of thirteen triterpenoids and three steroids in Frs. II, III, IV, and V, besides series of n- and iso-alkane in Fr.I, and alkanol in Fr.Ill were confirmed. Among them, lupenyl formate was shown to be a new compound. It is suggested that triterpenes and steroids were the major organic components, both in large quantities and characteristic properties, responsible for the formation of ink-repellent specks.

   Bark extractives of shirakamba (Betula platyphylla Sukatchev var. japonica Hara) were investigated for their conversion into useful compounds.
   The outer bark contained about four times as much extractives as the inner bark, and they were composed mainly of triterpenoids. Form dichloromethane extractives of the outer bark, betulin, lupeol, oleanolic acid, acetyl oleanolic acid, β-sitosterol, betulin 3-caffeate, betulinic acid 3-caffeate, and five straight-chain hydrocarbons (hexadecane, octadecane, eicosane, docosane, and tetracosane) were separated and identified. Betulinic acid 3-caffeate is a new compound as a component of the bark of Betula species. The predominant triterpenoid in the outer bark was betulin, and the yield amounted to 76% of the dichloromethane extractives. Thus it may be available as a raw material for chemical utilization.

   Forteen triterpenoids, four steroids, and two fatty alcohols were isolated from the extractives of white lauan (Dryobalanops sp.) sulfate pulp by high-performance liquid chromatography using a combination of gel-permeation, reversed phase, and silica-gel columns. Typical triterpenoids were homologues of those having dammarane skeletons. Carbon 13 nuclear magnetic resonance (¹³C-NMR) spectroscopy was effectively employed in their structural explanation, and assignments of complete signals were conducted successfully by the several-pulse methods.

   The methanol extractives and the essential oil from the bark of Abies mariesii Masters were studied. Three triterpenes were isolated from the methanol extractives. In addition to two known lanostane-type triterpenes, abieslactone (I) [(23R)-3α-methoxy-5α,9β]-lanosta-7,24-dien-26,23-olide] and demethyl-abieslactone (III) [(23R)-3a-hydroxy-5a,9β-lanosta-7,24-dien-26,23-olide], one new triterpene, (II) [(23R)-3α-methoxy-5α,9β-lanosta-8,24-dien-26,23-olide] which is an isomer of I was isolated and was named neoabieslactone. Steroidal compound, β-sitosteryl-palmitate (IV) and an unsaturated fatty acid methyl ester, methyl- (Z) -9-octadecenoate (V) also were isolated from the methanol extractives. From the essential oil, twenty monoterpenoids and one sesquiterpenoid were identified by GC/MS.

   Ten samples of sugi (Cryptomeria japonica D. Don) wood from different localities were extracted with acetone, and the hexane or ether soluble parts of the extracts were compared. The obisugi variety yielded more extracts and components than those of any other locality. Commonly, sesquiterpene alcohols were minor components, and cubenol and/or epicubenol in addition to an unidentified secondary alcohol were present. However, the obisugi variety contained additionally, much cubebol, 4-epicubebol, in addition to elemol, cedrol, eudesmols and so forth. 2,7(14),10-bisabolatrien-1-ol-4-one (50) and 1,3,5,7(14),10-bisabolapentaen-2-ol (51b) were found as new compounds.
   The main acidic component was sandaracopimaric acid. The ratio of isopimaric acid to sandaracopimaric acid varied with samples and was very low in the obisugi variety. A race which contain much myrtenic acid was discovered.
   Extract from the part stained by Guignardia dieback yielded much extract in which the sesquiterpene alcohols increased. Extract from sapwood was small, and the composition was different from that of heartwood.

   Some betulin glycosides were synthesized to utilize betulin as a biologically active compound and to clarify the correlation between the chemical structures, and the biological activities of triterpene glycosides. Betulin-3-yl β-D-cellobioside was synthesized by coupling 28-O-acetylbetulin with hepta-O-acetyl α-D-cellobiosyl bromide by means of a Koenigs-Knorr type condensation followed by deacetylation. Furthermore, some betulin oligoglycosides with α-glycosidic linkages were synthesized from α-cyclodextrin as a donor and betulin-3-yl β-D-cellobioside as an acceptor by the transglycosylation of cyclodextrin glycosyltransferase (CGTase) from Bacillius macerans. The addition of a small amount of surfactant made the enzymic reaction efficient. The nuclear magnetic resonance (NMR) chemical shift assignments determined by a variety of two dimensional experiments resulted in the conclusion that the main products of the enzymic reaction were betulin-3-yl β-D-(4-O-β-D-maltosyl)-glucoside and betulin-3-yl β-D-(4-O-β-D-maltotriosyl)-glucoside.

   The dichloromethane extractives from the bark of Abies sachalinensis Mast, were studied. Three diterpenoids, cis-abienol (I), 13-epi-mannol (II), and dehydroabietic acid (III), and two triterpenoids, β-sitosterol (IV) and β-sitostenone (V), were isolated from its bark.
   A rapid and quantitative analysis method for cis-abienol was studied by using the HPLC system to develop an efficient extraction method. Efficient extractions of cis-abienol from the bark have been studied by means of organic solvents and supercritical carbon dioxide. Consequently, it was revealed that supercritical carbon dioxide extraction under 100 kgf/cm² at 40°C was the most efficient method for extracting cis-abienol from the bark. Under the above conditions, the content of cis-abienol was 13.60% in extractives (0.023% on an oven-dried bark basis).

   The biotransformation of dehydroabietic acid (1) by a series of fungal preparations was studied. In cubation of 1 with Chaetomium cochliodes IFO 30576 gave five metabolites. On the basis of chemical and spectral data, their structures were established to be 15-hydroxy-8,11,13-abietatrien-18-oic acid (2), (15R)-16-hydroxy-8,11,13-abietatrien-18-oic acid (3), 15,16-dihydroxy-8,11,13-abietatrien-18-oic acid (5), 7β,15-dihydroxy-8,11,13-abietatrien-18-oic acid (7), and 7β,16-dihydroxy-8,11,13-abietatrien-18-oic acid (10). A biotransformation pathway of 1 by C. cochliodes was proposed.

   Terpenoids of two elite clones of sugi (Cryptomeria japonica D. Don) wood growing in three different habitats were analyzed. There were clear differences in heartwood constituents between two of the clones but the difference among habitats was trivial in the same clone. The Fukuokasho-2 clone (race Akaba) seemed to be a race near to the Obisugi variety. The Higashiusuki-5 clone (race Kitagou-arakawa) belongs to the Obisugi variety but differs from those of Tanoaka and Hidarimaki, both members of the Obisugi variety. The sapwood extracts were in small amounts and seemed to be affected by the habitats.

   In the course of our studies on the microbial transformation of terpenoids, the bioconversion of (−)-caryophyllene 1 in Chaetomium cochiliodes IFO 30576 was studied. Substrate 1 was first epoxidized at the C-C double bond, producing (−)-caryophyllene-4,5-oxide 2, which then was hydroxylated at the gem-dimethyl group and C-7 position. Two major metabolites produced from 1 were isolated newly from the culture broth by liquid chromatography. On the basis of 1-D and 2-D NMR spectral data their structures were established to be (11S)-(−)-12β-hydroxycaryophyllene-4,5-oxide 3 and (11S)-(−)-caryophyllene-4,5-oxide-7β,12β-diol 5, respectively.
   (−)-Caryophyllene-4,5-oxide 2, which was found to be an intermediate for metabolites 3 and 5, has been demonstrated to have great antimite activities, whereas metabolites 3 and 5 has smaller antimite activities than 2.

   The biotransformation of dehydroabietic acid 1 by Chaetomium cochliodes IFO 30576 in the presence of various metabolic inhibitors was studied. The addition of α,α'-dipyridyl to the culture broth, 7-oxo-8,11,13-abietatrien-18-oic acid 3 having antifungal activities, was accumulated in the fungal culture as a major metabolite. On the other hand, four matabolic inhibitors except α,α'- dipyridyl, [thiourea, NaF, ICH₂COOH, and ethylenediaminetetraacetic acid (EDTA) ] were ineffective in the accumulation of compound 3.
   The results suggest that because the addition of α,α'-dipyridyl accumulated predominantly 7-oxo-8,11,13-abietatrien-18-oic acid 3, the selective production of antifungal metabolites may be possible by selecting suitable incubating conditions with the specific metabolic inhibitors.

   In order to determine the absolute configuration of the C-15 position in 15,16-dihydroxy-8,11,13-abietatrien-18-oic acid 1, a metabolite of (+)-dehydroabietic acid 2 by Chaetomium cochliodes IFO 30576, metabolite 1 was converted into the known absolute configuration at the C-15 position, in 16-hydroxy-8,11,13-abietatrien-18-oic acid. Consequentry, methylated metabolite 1' was transformed into methyl (15R)-16-hydroxy-8,11,13-abietatrien-18-oate 6. Thus, the absolute configuration of the C-15 position in metabolite 1 was determined to be an R-configuration.

   Leaf oil terpenoids of ganso (founder) ate and Horyuzan-jisei (wild grow) ate were examined and compaired with other ates, hiba of Aomori Prefecture, and asunaro of the Kiso District of Nagano Prefecture. Trans-Communic acid is effective as a criterion of the chemotaxonomy of varieties of Thujopsis species. According to this criterion, kusaate belongs to Thujopsis dolabrata S. and Z. var. hondae Makino and maate, kanaate and jisei-ate belong to Th. dolabrata var. dolabrata, but they may be distinguished as the Noto-type from var. dolabrata of Kiso. Ganso-ate seems to be a hybrid of Th. dolabrata var. dolabrata and Th. dalabrata var. hondae. and was difficult to believe it as an ancestor of kusaate.

   Terpenoids of four samples of yakusugi (Cryptomeria japonica D. Don grown in Yakushima island) wood were analyzed. Eight new bisabolanoids were separated from ether soluble parts of acetone extracts of one sample. They were 7(14),10-bisaboladien-2-one (28), 7(14),10-bisaboladien-2-ol (32), 2β-acetoxy-7(14)-bisabolen-11-ol (43b), bisabolane-2β,11-diol (45), 7(14)-bisabolene-2β,11- diol (47b), bisabolane-2α,11-diol (47c), 7-bisabolene-2β,11-diol (48b), 7(14)-bisabolene-2α,11-diol (48c). Six of new compounds had hydroxyl groups at C-11, which were not found in samples grown on Kyushu Island and seemed characteristic to a part of yakusugi.